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Abstract

The marine flora and animal world are a rich source of biologically active compounds. A large number of sometimes highly toxic metabolites has been isolated inter alia from protozoans, sponges, coelenter- ates, echinoderms, molluscs, nemertines, sea snakes, and fishes (1–4) and the great interest in these chemically varied compounds has resulted in extensive publications (5–13). Among the best known of the toxic substances are tetrodotoxin, saxitoxin, and the polypeptides from sea anemones, but they will not be the main subject of this report.

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References

  1. Halstead, B.W.: Current Status of Marine Biotoxicology - An Overview. Clinical Toxicology 18, 1 (1981).

    CAS  Google Scholar 

  2. Bakus, G.J.: Chemical Defense Mechanism on the Great Barrier Reef, Australia. Science 21b1, 497 (1981).

    Google Scholar 

  3. Endean, R., and A.M. Cameron: Toxins in Coral Reef Organisms. Toxicon Suppl. 3, 105 (1983).

    Google Scholar 

  4. Bakus, G.J., T. Evans, B. Mading, and P. Kouros: The Use of Natural and Synthetic Toxins as Shark Repellents and Antifouling Agents. Toxicon Suppl. 3, 25 (1983).

    Google Scholar 

  5. a)Halstead, B.W.: Poisonous and Venomous Marine Animals of the World. Vols. 1-3. Washington, D.C.: U.S. Government Printing Office. 1965-1970. b) Rev. ed. Princeton, N.J.: Darwin Press. 1978.

    Google Scholar 

  6. Hashimoto, Y.: Marine Toxins and Other Bioactive Marine Metabolites. Tokyo: Japan Scientific Societies Press. 1979.

    Google Scholar 

  7. a) Habermehl, G.: Gift-Tiere und ihre Waffen, 3. Auflage. Berlin-Heidelberg-New York: Springer 1983. b) Venomous Animals and Their Toxins. Berlin-Heidelberg- New York: Springer. 1981.

    Google Scholar 

  8. Scheuer, P.J., ed.: Marine Natural Products. Chemical and Biological Perspectives, Vols. I-V. New York: Academic Press. 1978-1983.

    Google Scholar 

  9. Okuda, R.K., D. Klein, R.B. Kinnel, M. Li, and P.J. Scheuer: Marine Natural Products: The Past Twenty Years and Beyond. Pure and Appl. Chem. 54, 1907 (1982).

    CAS  Google Scholar 

  10. Fenical, W.: Natural Products Chemistry in the Marine Environment. Science 215, 923 (1982).

    CAS  Google Scholar 

  11. Kashman, Y., A. Groweiss, S. Carmely, Z. Kinamoni, D. Czarkie, and M. Rotem: Recent Research in Marine Natural Products from the Red Sea. Pure and Appl. Chem. 54, 1995 (1982).

    CAS  Google Scholar 

  12. Faulkner, D.J.: Marine Natural Products: Metabolites of Marine Algae and Herbivorous Marine Molluscs. Nat. Prod. Rep. 1984, 251.

    Google Scholar 

  13. Faulkner, D.J.: Marine Natural Products: Metabolites of Marine Invertebrates. Nat. Prod. Rep. 1984, 551.

    Google Scholar 

  14. Rinehart, Jr., K.L., P.D. Shaw, L.S. Shield, J.B. Gloer, G.C. Harbour, M.E.S. Koker, D. Samain, R.E. Schwartz, A.A. Tymiak, D.L. Weller, G.T. Carter, M.H.G. Munro, R.G. Hughes, Jr., H. E. Renis, E.B. Swynenberg, D.A. Stringfel- low, J.J. Vavra, J.H. Coats, G.E. Zurenko, S.L. Kuentzel, L.H. Li, G.J. Bakus, R.C. Brusca, L.L. Craft, D.N. Young, and J.L. Connor: Marine Natural Products as Sources of Antiviral, Antimicrobial, and Antineoplastic agents. Pure and Appl. Chem. 53, 795 (1981).

    CAS  Google Scholar 

  15. Jacobs, R.S., S. White, and L. Wilson: Selective Compounds Derived from Marine Organisms: Effects on Cell Division in Fertilized Sea Urchin Eggs. Fed. Proc. 40, 26 (1981).

    CAS  Google Scholar 

  16. Berlepsch, K.: Drug from Marine Organisms. The Target of the Roche Research Institute of Marine Pharmacology in Australia. Naturwissenschaften 67, 338 (1980).

    Google Scholar 

  17. Kaul, P.N.: Biomedical Potential of the Sea. Pure and Appl. Chem. 54, 1963 (1982).

    CAS  Google Scholar 

  18. Kaul, P.N.: Compounds from the Sea with Actions on the Cardiovascular and Central Nervous Systems. Fed. Proc. 40, 10 (1981).

    CAS  Google Scholar 

  19. Jacobs, R.S., P. Culver, R. Langdon, T. O’Brien, and S. White: Some Pharmaco­logical Observations on Marine Natural Products. Tetrahedron 41, 981 (1985).

    CAS  Google Scholar 

  20. Shimizu, Y.: Bioactive Marine Natural Products, with Emphasis on Handling of Water-Soluble Compounds. J. Nat. Prod. 48, 223 (1985).

    CAS  Google Scholar 

  21. Djerassi, C.: Recent Studies in the Marine Sterol Field. Pure and Appl. Chem. 53, 873 (1981).

    CAS  Google Scholar 

  22. Goad, L J.: Sterol Biosynthesis and Metabolism in Marine Invertebrates. Pure and Appl. Chem. 51, 837 (1981).

    Google Scholar 

  23. Catalan, C.A.N., J.E. Thompson, W.C.M.C. Kokke, and C. Djerassi: Biosynthetic Studies of Marine Lipids - 3. Experimental Demonstration of the Course of Side Chain Extension in Marine Sterols. Tetrahedron 41, 1073 (1985).

    CAS  Google Scholar 

  24. Withers, N.W., W.C.M.C. Kokke, W. Fenical, and C. Djerassi: Sterol Patterns of Cultured Zooxanthellae Isolated from Marine Invertebrates: Synthesis of Gorgo- sterol and 23-Desmethylgorgosterol by Aposymbiotic Algae. Proc. Natl. Acad. Sci. U.S.A. 79, 3764 (1982).

    CAS  Google Scholar 

  25. Blanc, P.-A., and C. Djerassi: Isolation and Structure Elucidation of 22(5),23(S)- Methylenecholesterol. Evidence for Direct Bioalkylation of 22-Dehydrocholesterol. J. Am. Chem. Soc. 102, 7113 (1980). Erratum: J. Am. Chem. Soc. 103, 7036 (1981).

    Google Scholar 

  26. Zielinski, J., W.C.M.C. Kokke, T.B. T. Ha, A.Y.L. Shu, W.L. Duax, and C. Djerassi: Isolation, Partial Synthesis, and Structure Determination of Sterols with the Four Possible 23,24-Dimethyl-Substituted Side Chains. J. Org. Chem. 48, 3471 (1983).

    CAS  Google Scholar 

  27. Sargent, J.R., R.R. Gatten, and R.J. Henderson: Marine Wax Esters. Pure and Appl. Chem. 53, 867 (1981).

    CAS  Google Scholar 

  28. Kokke, W.C.M.C., S. Epstein, S.A. Look, G.H. Rau, W. Fenical, and C. Djerassi: On the Origin of Terpenes in Symbiotic Associations between Marine Invertebrates and Algae (Zooxanthellae). Culture Studies and an Application of 13C/12C Isotope Ratio Mass Spectrometry. J. Biol. Chem. 259, 8168 (1984).

    CAS  Google Scholar 

  29. Crews, P., S. Naylor, F.J. Hanke, E.R. Hogue, E. Kho, and R. Braslau: Halogen Regiochemistry and Substituent Stereochemistry Determination in Marine Monoter- penes by 13C NMR. J. Org. Chem. 49, 1371 (1984).

    CAS  Google Scholar 

  30. Colwell, R.R.: Biotechnology in the Marine Sciences. Science 222, 19 (1983).

    CAS  Google Scholar 

  31. Okami, Y.: Potential Use of Marine Microorganisms for Antibiotics and Enzyme Production. Pure and Appl. Chem. 54, 1951 (1982).

    CAS  Google Scholar 

  32. Shimizu, Y.: Paralytic Shellfish Poisons. Fortschritte d. Chem. organ. Naturstoffe (W. Herz, H. Grisebach, G.W. Kirby, and C. Tamm, eds.), Vol. 45, p. 235. Wien- New York: Springer. 1984.

    Google Scholar 

  33. Bergquist, P.R., and R.J. Wells: Chemotaxonomy of the Porifera: The Develop­ment and Current Status of the Field. In: Marine Natural Products. Chemical and Biological Perspectives (P. Scheuer, ed.), Vol. V, p. 1. New York-San Francisco- London: Academic Press. 1983.

    Google Scholar 

  34. McCaffrey, E.J.: Biologically Active Material from a Marine Sponge. Toxicon Suppl. 3, 277 (1983).

    Google Scholar 

  35. Sevcik, C., and C.A. Barboza: The Presynaptic Effect of Fractions Isolated from the Sponge Tedaniaignis. Toxicon 21, 191 (1983).

    CAS  Google Scholar 

  36. Mebs, D.: Lack of Toxins in Alcoholic Extracts of the Sponge Tedania ignis. Toxicon 22, 821 (1984).

    CAS  Google Scholar 

  37. Bohlin, L., H.P. Gehrken, P.J. Scheuer, and C. Djerassi: Minor and Trace Sterols in Marine Invertebrates XVI. 3ξ-Hydroxymethyl-A-nor-5α-gorgostane, a Novel Sponge Sterol. Steroids 35, 295 (1980).

    CAS  Google Scholar 

  38. Khalil, M.W., L.J. Durham, C. Djerassi, and D. Sica: Ficisterol (23-Ethyl-24- methyl-27-norcholesta-5,25-dien-3β-ol). A Biosynthetically Unprecedented Sterol from the Marine Sponge Petrosia ficiformis. J. Am. Chem. Soc. 102, 2133 (1980).

    CAS  Google Scholar 

  39. Karpf, M., and C. Djerassi: Synthesis of Ficisterol - The First Natural Sterol with 23-Ethyl Substitution. Tetrahedron Lett. 21, 1603 (1980).

    CAS  Google Scholar 

  40. Bergquist, P.R., W. Hofheinz, and G. Oesterhelt: Sterol Composition and the Classification of the Demospongiae. Biochem. Syst. Ecol. 8, 423 (1980).

    CAS  Google Scholar 

  41. Khalil, M.W., C. Djerassi, and D. Sica: Minor and Trace Sterols in Marine Invertebrates XVII. (24R)-24,26-Dimethylcholesta-5,26-dien-3β-ol, a New Sterol from the Sponge Petrosia ficiformis. Steroids 35, 707 (1980).

    CAS  Google Scholar 

  42. Li, L.N., U. Sjöstrand, and C. Djerassi: Minor and Trace Sterols in Marine Inverte­brates. 19. Isolation, Structure Elucidation, and Partial Synthesis of 24-Methylene- 25-ethylcholesterol (Mutasterol): First Example of Sterol Side-Chain Bioalkylation at Position 25. J. Am. Chem. Soc. 103, 115 (1981).

    CAS  Google Scholar 

  43. Bohlin, L., U. Sjöstrand, C. Djerassi, and B.W. Sullivan: Minor and Trace Sterols in Marine Invertebrates. Part 20. 3ξ-Hydroxymethyl-A-nor-patinosterol and 3ξ-Hydroxymethyl-A-Hordinosterol. Two New Sterols with Modified Nucleus and Side-chain from the Sponge Teichaxinella morchella. J. Chem. Soc., Perkin Trans. I 1981, 1023.

    Google Scholar 

  44. Kho, E., D.K. Imagawa, M. Rohmer, Y. Kashman, and C. Djerassi: Sterols in Marine Invertebrates. 22. Isolation and Structure Elucidation of Conicasterol and Theonellasterol, Two New 4-Methylene Sterols from the Red Sea Sponges Theonella conica and Theonella swinhoei. J. Org. Chem. 46, 1836 (1981).

    CAS  Google Scholar 

  45. Li, L.N., and C. Djerassi: Minor and Trace Sterols in Marine Invertebrates. 23. Xes- tospongesterol and Isoxestospongesterol - First Examples of Quadruple Biomethylation of the Sterol Side Chain. J. Am. Chem. Soc. 103, 3606 (1981).

    CAS  Google Scholar 

  46. Zielinski, J., H. Li, T.S. Milkova, S. Popov, N.L. Marekov, and C. Djerassi: Isolation of 22-Methylenecholesterol. Further Evidence for Direct Bioalkylation of 22-Dehydrocholesterol. Tetrahedron Lett. 22, 2345 (1981).

    CAS  Google Scholar 

  47. Li, L.N., U. Sjöstrand, and C. Djerassi: Minor and Trace Sterols in Marine Inverte­brates. 27. Isolation, Structure Elucidation, and Partial Synthesis of 25-Methylxesto- sterol, a New Sterol Arising from Quadruple Biomethylation in the Side Chain. J. Org. Chem. 46, 3867 (1981).

    CAS  Google Scholar 

  48. Sjöstrand, U., J.M. Kornprobst, and C. Djerassi: Minor and Trace Sterols from Marine Invertebrates. 29. (22E)-Ergosta-5,22,25-trien-3β-ol and (22E,24R)-24,26- Dimethylcholesta-5,22,25(27)-trien-3β-ol. Two New Marine Sterols from the Sponge Pseudaxinella lunacharta. Steroids 38, 355 (1981).

    Google Scholar 

  49. Li, L.N., and C. Djerassi: Minor and Trace Sterols in Marine Invertebrates. 30. Iso­lation Structure Elucidation and Partial Synthesis of 26-Methylstrongylosterol and 28-Methylxestosterol - Two Marine Sterols Arising by a Novel Quadruple Biomethy­lation Sequence. Tetrahedron Lett. 22, 4639 (1981).

    CAS  Google Scholar 

  50. Li, L.N., H. Li, R.W. Lang, T. Itoh, D. Sica, and C. Djerassi: Minor and Trace Sterols in Marine Invertebrates. 31. Isolation and Structure Elucidation of 23 H- Isocalysterol, a Naturally Occurring Cyclopropene. Some Comparative Observations on the Course of Hydrogenolytic Ring Opening of Steroidal Cyclopropenes and Cyclopropanes. J. Am. Chem. Soc. 104, 6726 (1982).

    CAS  Google Scholar 

  51. Zielinski, J., T. Milkova, S. Popov, N. Marekov, and C. Djerassi: Minor and Trace Sterols in Marine Invertebrates. 34. Isolation and Structure Elucidation of 24-Methyl-5a-cholesta-7,9(11),24(28)-trien-3β-ol, the First Naturally Occurring Δ7,9(11) Unsaturated Marine Sterol. Steroids 39, 675 (1982).

    CAS  Google Scholar 

  52. Eggersdorfer, M.L., W.C.M.C. Kokke, C.W. Crandell, J.E. Hochlowski, and C. Djerassi: Sterols in Marine Invertebrates. 32. Isolation of 3 β-(Hydroxymethyl)- A-nor-5α-cholest-15-ene, the First Naturally Occurring Sterol with a 15-16 Double Bond. J. Org. Chem. 47, 5304 (1982).

    CAS  Google Scholar 

  53. Bohlin, L., U. Sjöstrand, G. Sodano, and C. Djerassi: Sterols in Marine Inverte­brates. 33. Structures of Five New 3 β-(Hydroxymethyl)-A-nor Steranes: Indirect Evidence for Transformation of Dietary Precursors in Sponges. J. Org. Chem. 47, 5309 (1982).

    CAS  Google Scholar 

  54. Itoh, T., D. Sica, and C. Djerassi: Minor and Trace Sterols in Marine Invertebrates. 36. (24 S)-24 H-Isocalysterol: A New Steroidal Cyclopropene from the Marine Sponge Calyx niceaensis. J. Org. Chem. 48, 890 (1983).

    CAS  Google Scholar 

  55. Di Giacomo, G., A. Dini, B. Falco, A. Marino, and D. Sica: Sterols from the Sponge Agelas oroides. Comp. Biochem. Physiol. 74B, 499 (1983).

    Google Scholar 

  56. Catalan, C.A.N., V. Lakshmi, F.J. Schmitz, and C. Djerassi: Minor and Trace Sterols in Marine Invertebrates. 39. 24ξ,25ξ-24,26-Cyclocholest-5-en-3β-ol, a Novel Cyclopropyl Sterol. Steroids 40, 455 (1982).

    CAS  Google Scholar 

  57. Crist, B.V., X. Li, P.R. Bergquist, and C. Djerassi: Sterols of Marine Invertebrates. 44. Isolation, Structure Elucidation, Partial Synthesis, and Determination of Absolute Configuration of Pulchrasterol. The First Example of Double Bioalkylation of the Sterol Side Chain at Position 26. J. Org. Chem. 48, 4472 (1983).

    CAS  Google Scholar 

  58. Crist, B.V., and C. Djerassi: Minor and Trace Sterols in Marine Invertebrates. 47. A Re-investigation of the 19-Nor Stanols Isolated from the Sponge Axinella polypoides. Steroids 42, 331 (1983).

    CAS  Google Scholar 

  59. Proudfoot, J.R., X. Li, and C. Djerassi: Minor and Trace Sterols from Marine Invertebrates. 50. Stereostructure and Synthesis of Nicasterol, a Novel Cyclopropane-Containing Sponge Sterol. J. Org. Chem. 50, 2026 (1985).

    CAS  Google Scholar 

  60. Li, X., and C. Djerassi: Minor and Trace Sterols in Marine Invertebrates. 40. Structure and Synthesis of Axinyssasterol, 25-Methylfucosterol and 24-Ethyl-24-methyl- cholesterol - Novel Sponge Sterols with Highly Branched Side Chains. Tetrahedron Lett. 24, 665 (1983).

    CAS  Google Scholar 

  61. Itoh, T., D. Sica, and C. Djerassi: Minor and Trace Sterols in Marine Invertebrates. Part 35. Isolation and Structure Elucidation of Seventyfour Sterols from the Sponge Axinella cannabina. J. Chem. Soc., Perkin Trans. I 1983, 147.

    Google Scholar 

  62. Shubina, L.K., T.N. Makarieva, V.M. Boguslavskii, and V.A. Stonik: Steroid Compounds of Marine Sponges. 1. Sterols of Esperiopsis digitata. Khim. Prir. Soedin. 1983, 740.

    Google Scholar 

  63. Koch, P., C. Djerassi, V. Lakshmi, and F.J. Schmitz: 240. Identification de stérols à chaîne latérale oxygénée dans une éponge de l’espèce Hyrtios. Helv. Chim. Acta 66, 2431 (1983).

    CAS  Google Scholar 

  64. Cafieri, F., P. Ciminiello, M.V. D’Auria, and C. Santacroce: Sterol Composition of the Marine Sponge Crambe crambe. Biochem. Syst. Ecol. 12, 203 (1984).

    CAS  Google Scholar 

  65. Makarieva, T.N., L.K. Shubina, A.I. Kalinovsky, V.A. Stonik, and G.B. Elyakov: Steroids in Porifera. II. Steroid Derivatives from two Sponges of the Family Halichondriidae. Sokotrasterol sulfate, a Marine Steroid with a New Pattern of Side Chain Alkylation. Steroids 42, 267 (1983).

    CAS  Google Scholar 

  66. Shubina, L.K., T.N. Makarieva, and V.A. Stonik: Steroid Compounds of Marine Sponges. III. 24-Ethyl-25-methylcholesta-5,22-dien-3β-ol - A New Marine Sterol from the Sponge Halichondria sp. Khim.Prir. Soedin. 1984, 464.

    Google Scholar 

  67. Kitagawa, I., M. Kobayashi, K. Kitanaka, M. Kido, and Y. Kyogoku: Marine Natural Products. XII. On the Chemical Constituents of the Okinawan Marine Sponge Hymeniacidon aldis. Chem. Pharm. Bull. (Japan) 31, 2321 (1983).

    CAS  Google Scholar 

  68. De Stefano, A., and G. Sodano: Metabolism in Porifera. XII. Further Informations on the Biosynthesis of 3 β-Hydroxymethyl-A-nor-steranes in the Sponge Axinella verrucosa. Experientia 36, 630 (1980).

    Google Scholar 

  69. Gunatilaka, A.A.L., Y. Gopichand, F.J. Schmitz, and C. Djerassi: Minor and Trace Sterols in Marine Invertebrates. 26. Isolation and Structure Elucidation of Nine New 5α,8α-Epidioxy Sterols from Four Marine Organisms. J. Org. Chem. 46, 3860 (1981).

    CAS  Google Scholar 

  70. Fusetani, N., S. Matsunaga, and S. Konosu: Bioactive Marine Metabolites. II. Halistanol sulfate, an Antimicrobial Novel Steroid Sulfate from the Marine Sponge Halichondria CF. moorei Bergquist. Tetrahedron Lett. 22, 1985 (1981).

    Google Scholar 

  71. Nakatsu, T., R.P. Walker, J.E. Thompson, and D.J. Faulkner: Biologically Active Sterol Sulfates from the Marine Sponge Toxadocia zumi. Experientia 39, 759 (1983).

    CAS  Google Scholar 

  72. Gunasekera, S.P., and F.J. Schmitz: Marine Natural Products: 9α,11α-Epoxycholest-7-ene-3β,5α,6β,19-tetrol 6-Acetate from a Sponge, Dysidea sp. J. Org. Chem. 48, 885 (1983).

    CAS  Google Scholar 

  73. Rosser, R.M., and D.J. Faulkner: Two Steroidal Alkaloids from a Marine Sponge, Plakina sp. J. Org. Chem. 49, 5157 (1984).

    CAS  Google Scholar 

  74. Cariello, L., M. De Nicola Giudici, and L. Zanetti: Developmental Aberrations in Sea-Urchin Eggs Induced by Avarol and Two Cogeners. The Main Sesquiterpenoid Hydroquinones from the Marine Sponge, Dysidea avara. Comp. Biochem. Physiol. 65C, 37 (1980).

    Google Scholar 

  75. Cariello, L., L. Zanetti, V. Cuomo, and F. Vanzanella: Antimicrobial Activity of Avarol, a Sesquiterpenoid Hydroquinone from the Marine Sponge, Dysidea avara. Comp. Biochem. Physiol. 71B, 281 (1982).

    CAS  Google Scholar 

  76. Schulte, G., P.J. Scheuer, and O.J. McConnell: 227. Two Furanosesquiterpene Marine Metabolites with Antifeedant Properties. Helv. Chim. Acta 63, 2159 (1980).

    CAS  Google Scholar 

  77. Guella, G., A. Guerriero, P. Traldi, and F. Pietra: Penlanfuran, a New Furanoid Sesquiterpene from the Marine Sponge Dysidea fragilis (Mont.) of Brittany. A Strik­ing Difference with the Same Hawaiian Species. Tetrahedron Lett. 24, 3897 (1983).

    CAS  Google Scholar 

  78. Guella, G., A. Guerriero, and F. Pietra: 4. Sesquiterpenoids of the Sponge Dysi­dea fragilis of the North-Brittany Sea. Helv. Chim. Acta 68, 39 (1985).

    CAS  Google Scholar 

  79. Guella, G., I. Mancini, A. Guerriero, and F. Pietra: 140. New Furanosesquiter- penoids from Mediterranean Sponges. Helv. Chim. Acta 68, 1276 (1985).

    CAS  Google Scholar 

  80. Walker, R.P., R.M. Rosser, D.J. Faulkner, L.S. Bass, H. Cun-heng, and J. Clardy: Two New Metabolites of the Sponge Dysidea amblia and Revision of the Structure of Ambliol B. J. Org. Chem. 49, 5160 (1984).

    CAS  Google Scholar 

  81. Hochlowski, J.E., R.P. Walker, C. Ireland, and D.J. Faulkner: Metabolites of Four Nudibranchs of the Genus Hypselodoris. J. Org. Chem. 47, 88 (1982).

    CAS  Google Scholar 

  82. Dunlop, R.W., R. Kazlauskas, G. March, P.T. Murphy, and R.J. Wells: New Furano-Sesquiterpenes from the Sponge Dysidea herbacea. Aust. J. Chem. 35, 95 (1982).

    CAS  Google Scholar 

  83. Grode, S.H., and J.H. Cardellina II: Sesquiterpenes from the Sponge Dysidea etheria and the Nudibranch Hypselodoris zebra. J. Nat. Prod. 47, 76 (1984).

    CAS  Google Scholar 

  84. Sullivan, B., D.J. Faulkner, and L. Webb: Siphonodictidine, a Metabolite of the Burrowing Sponge Siphonodictyon sp. That Inhibits Coral Growth, Science 221, 1175 (1983).

    CAS  Google Scholar 

  85. Schulte, G., P.J. Scheuer, and O.J. McConnell: Upial, a Sesquiterpenoid Bicy- clo[3.3.1]nonane Aldehyde Lactone from the Marine Sponge Dysidea fragilis. J. Org. Chem. 45, 552 (1980).

    CAS  Google Scholar 

  86. Taschner, M.J., and A. Shahripour: Total Synthesis of (–)-Upial. J. Am. Chem. Soc. 107, 5570 (1985).

    CAS  Google Scholar 

  87. Sullivan, B., P. Djura, D.E. McIntyre, and D.J. Faulkner: Antimicrobial Con­stituents of the Sponge Siphonodictyon coralliphagum. Tetrahedron 37, 979 (1981).

    CAS  Google Scholar 

  88. Schmitz, F.J., V. Lakshmi, D.R. Powell, and D. van der Helm: Arenarol and Arenarone: Sesquiterpenoids with Rearranged Drimane Skeletons from the Marine Sponge Dysidea arenaria. J. Org. Chem. 49, 241 (1984).

    CAS  Google Scholar 

  89. Carté, B., C.B. Rose, and D.J. Faulkner: 5-epi-Ilimaquinone, a Metabolite of the Sponge Fenestraspongia Sp. J. Org. Chem. 50, 2785 (1985).

    Google Scholar 

  90. Amade, P., L. Chevolot, H.P. Perzanowski, and P.J. Scheuer: 161. A Dimer of Puupehenone. Helv. Chim. Acta 66, 1672 (1983). Erratum: Helv. Chim. Acta 67, 927 (1984).

    Google Scholar 

  91. Djura, P., D.B. Stierle, B. Sullivan, D.J. Faulkner, E. Arnold, and J. Clardy: Some Metabolites of the Marine Sponges Smenospongia aurea and Smenospongia (= Polyfibrospongia) echina. J. Org. Chem. 45, 1435 (1980).

    CAS  Google Scholar 

  92. Capon, R.J., E.L. Ghisalberti, and P.R. Jefferies: New Aromatic Sesquiterpenes from a Halichondria sp. Aust. J. Chem. 35, 2583 (1982).

    CAS  Google Scholar 

  93. Ciminiello, P., E. Fattorusso, S. Magno, and L. Mayol: New Nitrogenous Sesqui­terpenes from the Marine Sponge Axinella cannabina. J. Org. Chem. 49, 3949 (1984).

    CAS  Google Scholar 

  94. Ciminiello, P., E. Fattorusso, S. Magno, and L. Mayol: Sesquiterpenoids Based on the epi-Maaliane Skeleton from the Marine Sponge Axinella cannabina. J. Nat. Prod. 48, 64 (1985).

    CAS  Google Scholar 

  95. Nakamura, H., J. Kobayashi, Y. Ohizumi, and Y. Hirata: Novel Bisabolene-Type Sesquiterpenoids with a Conjugated Diene Isolated from the Okinawan Sea Sponge Theonella cf. swinhoei. Tetrahedron Lett. 25, 5401 (1984).

    CAS  Google Scholar 

  96. Nakamura, H., H. Wu, J. Kobayashi, Y. Ohizumi, Y. Hirata, T. Higashijima, and T. Miyazawa: Agelasidine-A, a Novel Sesquiterpene Possessing Antispasmodic Activity from the Okinawa Sea Sponge Agelas sp. Tetrahedron Lett. 24, 4105 (1983).

    CAS  Google Scholar 

  97. Capon, R.J., and D.J. Faulkner: Antimicrobial Metabolites from a Pacific Sponge, Agelas sp. J. Am. Chem. Soc. 106, 1819 (1984).

    CAS  Google Scholar 

  98. Walker, R.P., and D.J. Faulkner: Diterpenes from the Sponge Dysidea amblia. J. Org. Chem. 46, 1098 (1981).

    CAS  Google Scholar 

  99. Sullivan, B., and D.J. Faulkner: Metabolites of the Marine Sponge Dendrilla sp. J. Org. Chem. 49, 3204 (1984).

    CAS  Google Scholar 

  100. Capelle, N., J.C. Braekman, D. Daloze, and B. Tursch: Chemical Studies of Marine Invertebrates. XLIV. Three New Spongian Diterpenes from Spongia officinalis. Bull. Soc. Chim. Belg. 89, 399 (1980).

    CAS  Google Scholar 

  101. Cimino, G., R. Morrone, and G. Sodano: New Diterpenes from Spongia officinalis. Tetrahedron Lett. 23, 4139 (1982).

    CAS  Google Scholar 

  102. Gonzalez, A.G., D.M. Estrada, J.D. Martin, V.S. Martin, C. Perez, and R. Perez: New Antimicrobial Diterpenes from the Sponge Spongia officinalis. Tetrahe­dron 40, 4109 (1984).

    CAS  Google Scholar 

  103. Nakano, T., and M.I. Hernandez: Stereoselective Total Syntheses of (±)-Isoagatho- lactone and (±)-12a-Hydroxyspongia-13(16),14-diene, Two Marine Sponge Metabolites. J. Chem. Soc., Perkin Trans. I 1983, 135.

    Google Scholar 

  104. Schmitz, F.J., J.S. Chang, M.B. Hossain, and D. van der Helm: Marine Natural Products: Spongiane Derivatives from the Sponge Igernella notabilis. J. Org. Chem. 50, 2862 (1985).

    CAS  Google Scholar 

  105. Schmitz, F.J., D.J. Vanderah, K.H. Hollenbeak, C.E.L. Enwall, Y. Gopichand, P.K. SenGupta, M.B. Hossain, and D. van der helm: Metabolites from the Marine Sponge Tedania ignis. A New Atisanediol and Several Known Diketopiperazines. J. Org. Chem. 48, 3941 (1983).

    Google Scholar 

  106. Mayol, L., V. Piccialli, and D. Sica: Gracilin A, an Unique Nor-Diterpene Metabolite from the Marine Sponge Spongionella gracilis. Tetrahedron Lett. 26, 1357 (1985).

    CAS  Google Scholar 

  107. Mayol, L., V. Piccialli, and D. Sica: Application of 2D-NMR Spectroscopy in the Structural Determination of Gracilin B, a Bis-nor-diterpene from the Sponge Spongionella gracilis. Tetrahedron Lett. 26, 1253 (1985).

    CAS  Google Scholar 

  108. Hochlowski, J.E., D.J. Faulkner, G.K. Matsumoto, and J. Clardy: Norrisolide, a Novel Diterpene from the Dorid Nudibranch Chromodoris norrisi. J. Org. Chem. 48, 1141 (1983).

    CAS  Google Scholar 

  109. Karuso, P., B.W. Skelton, W.C. Taylor, and A.H. White: The Constituents of Marine Sponges. I. The Isolation from Aplysilla sulphurea (Dendroceratida) of (1 R *,1’S*, 1”R *,3 R *)-l-Acetoxy-4-ethyl-5-(l,3,3-trimethylcyclohexyl)-l,3-dihydro- isobenzofuran-1’(4),3-carbolactone and the Determination of its Crystal Structure. Aust. J. Chem. 37, 1081 (1984).

    CAS  Google Scholar 

  110. Nakamura, H., H. Wu, Y. Ohizumi, and Y. Hirata: Agelasine-A, -B, -C, and -D, Novel Bicyclic Diterpenoids with a 9-Methyladeninium Unit Possessing Inhibito­ry Effects on Na,K-ATPase from the Okinawan Sea Sponge Agelas sp. Tetrahedron Lett. 25, 2989 (1984).

    CAS  Google Scholar 

  111. Wu, H., H. Nakamura, J. Kobayashi, Y. Ohizumi, and Y. Hirata: Agelasine-E and -F, Novel Monocyclic Diterpenoids with a 9-Methyladeninium

    Google Scholar 

  112. Unit Possessing Inhibitory Effects on Na,K-ATPase Isolated from the Okinawan Sea Sponge Agelas nakamurai Hoshino. Tetrahedron Lett. 25, 3719 (1984).

    Google Scholar 

  113. Nakatsu, T., D.J. Faulkner, G.K. Matsumoto, and J. Clardy: Structure of the Diterpene Portion of a Novel Base from the Sponge Agelas mauritiana. Tetrahedron Lett. 25, 935 (1984).

    CAS  Google Scholar 

  114. Chang, C.W.J., A. Patra, D.M. Roll, P.J. Scheuer, G.K. Matsumoto, and J. Clardy: Kalihinol-A, a Highly Functionalized Diisocyano Diterpenoid Antibiotic from a Sponge. J. Am. Chem. Soc. 106, 4644 (1984).

    CAS  Google Scholar 

  115. Patra, A., C.W.J. Chang, P.J. Scheuer, G.D. van Duyne, G.K. Matsumoto, and J. Clardy: An Unprecedented Triisocyano Diterpenoid Antibiotic from a Sponge. J. Am. Chem. Soc. 106, 7981 (1984).

    CAS  Google Scholar 

  116. Kazlauskas, R., P.T. Murphy, R.J. Wells, and F.J. Blount: New Diterpene Isocyanides from a Sponge. Tetrahedron Lett. 21, 315 (1980).

    CAS  Google Scholar 

  117. Manes, L.V., G.J. Bakus, and P. Crews: Bioactive Marine Sponge JVorditerpene and Aforsesterterpene Peroxides. Tetrahedron Lett. 25, 931 (1984).

    CAS  Google Scholar 

  118. Capon, R.J., and J.K. Macleod: Structural and Stereochemical Studies on Marine Aforterpene Cyclic Peroxides. Tetrahedron 41, 3391 (1985).

    CAS  Google Scholar 

  119. Nakamura, H., H. Wu, J. Kobayashi, M. Kobayashi, Y. Ohizumi, and Y. Hirata: Agelasidines. Novel Hypotaurocyamine Derivatives from the Okinawan Sea Sponge Agelas nakamurai Hoshino. J. Org. Chem. 50, 2494 (1985).

    CAS  Google Scholar 

  120. Crews, P., and S. Naylor: Sesterterpenes: An Emerging Group of Metabolites from Marine and Terrestrial Organisms. Fortschr. Chem. Organ. Naturstoffe (W. Herz, H. Grisebach, G.W. Kirby, and Ch. Tamm, eds.) 48, p. 203. Wien-New York: Springer. 1985.

    Google Scholar 

  121. González, A.G., M.L. Rodríguez, and A.S.M. Barrientos: On the Stereochem­istry and Biogenesis of C21 Linear Furanoterpenes in Ircinia sp. J. Nat. Prod. 46, 256 (1983).

    Google Scholar 

  122. Kazlauskas, R., P.T. Murphy, and R.J. Wells: Furodendin, a C22 Degraded Terpene from the Sponge Phyllospongia dendyi. Experientia 36, 814 (1980).

    CAS  Google Scholar 

  123. Kashman, Y., and M. Zviely: Furospongolide, a New C21 Furanoterpene from a Marine Organism. Experientia 36, 1279 (1980).

    CAS  Google Scholar 

  124. Capon, R.J., E.L. Ghisalberti, and P.R. Jefferies: A New Furanoterpene from a Spongia sp. Experientia 38, 1444 (1982).

    CAS  Google Scholar 

  125. Walker, R.P., J.E. Thompson, and D.J. Faulkner: Sesterterpenes from Spongia idia. J. Org. Chem. 45, 4976 (1980).

    CAS  Google Scholar 

  126. Fusetani, N., Y. Kato, S. Matsunaga, and K. Hashimoto: Bioactive Marine Me­tabolites. V. Two New Furanosesterterpenes, Inhibitors of Cell Division of the Ferti­lized Starfish Eggs, from the Marine Sponge Cacospongia scalaris. Tetrahedron Lett. 25, 4941 (1984).

    CAS  Google Scholar 

  127. De Silva, E.D., and P.J. Scheuer: Manoalide, an Antibiotic Sesterterpenoid from the Marine Sponge Luffariella variabilis (Polejaeff). Tetrahedron Lett. 21, 1611 (1980).

    Google Scholar 

  128. De Silva, E.D., and P.J. Scheuer: Three New Sesterterpenoid Antibiotics from the Marine Sponge Luffariella varia­bilis (Polejaeff). Tetrahedron Lett. 22, 3147 (1981).

    Google Scholar 

  129. Blankemeier, L.A., and R.S. Jacobs: Biochemical Analysis of the Inhibition of Purified Phospholipase A2 by the Marine Natural Product, Manoalide. Fed. Proc. 42, 374 (1983).

    Google Scholar 

  130. De Freitas, J.C., and R.S. Jacobs: Antagonism of the Neurotoxic Action of the P-Bungarotoxin on the Rat Phrenic Nerve-Hemidiaphragm by the Marine Natural Product, Manoalide. Fed. Proc. 42, 374 (1983).

    Google Scholar 

  131. Braekman, J.C., D. Daloze, R. Bertau, and P. Macedo de Abreu: Cavernosine, a Novel Ichthyotoxic Terpenoid Lactone from the Sponge Fasciospongia cavernosa. Bull. Soc. Chim. Belg. 91, 791 (1982).

    CAS  Google Scholar 

  132. Sullivan, B., and D.J. Faulkner: An Antimicrobial Sesterterpene from a Palauan Sponge. Tetrahedron Lett. 23, 907 (1982).

    CAS  Google Scholar 

  133. Yasuda, F., and H. Tada: Desacetylscalaradial, a Cytotoxic Metabolite from the Sponge Cacospongia scalaris. Experientia 37, 110 (1981).

    CAS  Google Scholar 

  134. Kazlauskas, R., P.T. Murphy, R.J. Wells, and J.J. Daly: Terpenoid Constituents from Two Phyllospongia spp. Aust. J. Chem. 33, 1783 (1980).

    CAS  Google Scholar 

  135. Kikuchi, H., Y. Tsukitani, I. Shimizu, M. Kobayashi, and I. Kitagawa: Foliaspongin, an Antiinflammatory Bishomosesterterpene from the Marine Sponge Phyllospongia foliascens (Pallas). Chem. Pharm. Bull. (Japan) 29, 1492 (1981).

    CAS  Google Scholar 

  136. Kikuchi, H., Y. Tsukitani, I. Shimizu, M. Kobayashi, and I. Kitagawa: Marine Natural Products. XI. An Antiinflammatory Scalarane-type Bishomosesterterpene, Foliaspongin, from the Okinawan Marine Sponge Phyllospongia foliascens (Pallas). Chem. Pharm. Bull. (Japan) 31, 552 (1983).

    CAS  Google Scholar 

  137. Kashman, Y., and M. Zviely: New Alkylated Scalarins from the Sponge Dysidea herbacea. Tetrahedron Lett. 40, 3879 (1979).

    Google Scholar 

  138. Kazlauskas, R., P.T. Murphy, and R.J. Wells: Five New C26 Tetracyclic Terpenes from a Sponge (.Lendenfeldia sp.). Aust. J. Chem. 35, 51 (1982).

    CAS  Google Scholar 

  139. Croft, K.D., E.L. Ghisalberti, B.W. Skelton, and A.H. White: Structural Study of a New Dialkylated Scalarane from a Carteriospongia sp. J. Chem. Soc., Perkin Trans. I 1983, 155.

    Google Scholar 

  140. Cimino, G., S. de Rosa, and S. de Stefano: Scalarobutenolide, a New Sesterterpenoid from the Marine Sponge Spongia nitens. Experientia 37, 214 (1981).

    CAS  Google Scholar 

  141. Gregson, R.P., and D. Ouvrier: Wistarin, a Tetracyclic Furanosesterterpene from the Marine Sponge Ircinia wistarii. J. Nat. Prod. 45, 412 (1982).

    CAS  Google Scholar 

  142. Albericci, M., J.C. Braekman, D. Daloze, and B. Tursch: Chemical Studies of Marine Invertebrates - XLV. The Chemistry of Three Aforsesterterpene Peroxides from the Sponge Sigmosceptrella laevis. Tetrahedron 38, 1881 (1982).

    CAS  Google Scholar 

  143. Sokoloff, S., S. Halevy, V. Usieli, A. Colorni, and S. Sarel: Prianicin A and B, Nor-sesterterpenoid Peroxide Antibiotics from Red Sea Sponges. Experientia 38, 337 (1982).

    CAS  Google Scholar 

  144. Kashman, Y., and M. Rotem: Muqubilin, a New C24-Isopenoid from a Marine Sponge. Tetrahedron Lett. 19, 1707 (1979).

    Google Scholar 

  145. Manes, L.V., S. Naylor, P. Crews, and G.J. Bakus: Suvanine, a Novel Sesterter­pene from an Ircinia Marine Sponge. J. Org. Chem. 50, 284 (1985).

    CAS  Google Scholar 

  146. Shmueli, U., S. Carmely, A. Groweiss, and Y. Kashman: Sipholenol and Siphole- none, Two New Triterpenes from the Marine Sponge Siphonochalina siphonella (Levi). Tetrahedron Lett. 22, 709 (1981).

    CAS  Google Scholar 

  147. Carmely, S., and Y. Kashman: The Sipholanes: A Novel Group of Triterpenes from the Marine Sponge Siphonochalina siphonella. J. Org. Chem. 48, 3517 (1983).

    CAS  Google Scholar 

  148. Carmely, S., Y. Loya, and Y. Kashman: Siphonellinol, a New Triterpene from the Marine Sponge Siphonochalina siphonella. Tetrahedron Lett. 24, 3673 (1983).

    CAS  Google Scholar 

  149. Ravi, B.N., R.J. Wells, and K.D. Croft: Malabaricane Triterpenes from a Fijian Collection of the Sponge Jaspis stellifera. J. Org. Chem. 46, 1998 (1981).

    Google Scholar 

  150. Ravi, B.N., and R.J. Wells: Malabaricane Triterpenes from a Great Barrier Reef Collection of the Sponge Jaspis stellifera. Aust. J. Chem. 35, 39 (1982).

    CAS  Google Scholar 

  151. McCabe, T., J. Clardy, L. Minale, C. Pizza, F. Zollo, and R. Riccio: A Triterpenoid Pigment with the Isomalabaricane Skeleton from the Marine Sponge Stelletta sp. Tetrahedron Lett. 23, 3307 (1982).

    CAS  Google Scholar 

  152. Liaaen-Jensen, S., B. Renstrom, T. Ramdahl, M. Hallenstvet, and P. Bergquist: Carotenoids of Marine Sponges. Biochem. Syst. Ecol. 10, 167 (1982).

    CAS  Google Scholar 

  153. Litchfield, C., and S. Liaaen-Jensen: Carotenoids of the Marine Sponge Microciona prolifera. Comp. Biochem. Physiol. 66B, 359 (1980).

    Google Scholar 

  154. Hertzberg, S., T. Ramdahl, J.E. Johansen, and S. Liaaen-Jensen: Carotenoid Sulfates. 2. Structural Elucidation of Bastaxanthin. Acta Chem. Scand. B37, 267 (1983).

    Google Scholar 

  155. Djura, P., and D.J. Faulkner: Metabolites of the Marine Sponge Dercitus sp. J. Org. Chem. 45, 735 (1980).

    CAS  Google Scholar 

  156. Taylor, K.M., J.A. Baird-Lambert, P.A. Davis, and I. Spence: Methylaplysinopsin and Other Marine Natural Products Affecting Neurotransmission. Fed. Proc. 40, 15 (1981).

    Google Scholar 

  157. Tymiak, A.A., K.L. Rinehart, Jr., and G. J. Bakus: Constituents of Morphologically Similar Sponges Aplysina and Smenospongia Species. Tetrahedron 41, 1039 (1985).

    CAS  Google Scholar 

  158. Dellar, G., P. Djura, and M.V. Sargent: Structure and Synthesis of a New Bromoindole from a Marine Sponge. J. Chem. Soc., Perkin Trans. I 1981, 1679.

    Google Scholar 

  159. Makarieva, T.N., V.A. Stonik, P. Alcolado, and Y.B. Elyakov: Comparative Study of the Halogenated Tyrosine Derivatives from Demospongiae (Porifera). Comp. Biochem. Physiol. 68B, 481 (1981).

    Google Scholar 

  160. Gorshkov, B.A., I.A. Gorshkova, T.N. Makarieva, and V.A. Stonik: Inhibiting Effect of Cytotoxic Bromine-Containing Compounds from Sponges (Aplysinidae) on Na+-K+-ATPase Activity. Toxicon 20, 1092 (1982).

    CAS  Google Scholar 

  161. Gorshkov, B.A., I.A. Gorshkova, and T.N. Makarieva: Inhibitory Characteristics of 3,5-Dibromo-l-acetoxy-4-oxo-2,5-cyclohexadien-l-acetonitrile, a Semisynthetic Derivative of Aeroplysinin-1 from Sponges (Aplysinidae), on Na+-K+-ATPase. Tox­icon 22, 441 (1984).

    CAS  Google Scholar 

  162. D’Ambrosio, M., A. Guerriero, and F. Pietra: 168. Novel, Racemic or Nearly- Racemic Antibacterial Bromo- and Chloroquinols and γ-Lactams of the Verongia- quinol and the Cavernicolin Type from the Marine Sponge Aplysina (= Verongia) cavernicola. Helv. Chim. Acta 67, 1484 (1984).

    Google Scholar 

  163. D’Ambrosio, M., A. Guerriero, R. de Clauser, G. de Stanchina, and F. Pietra: Dichloroverongiaquinol, a New Marine Antibacterial Compound from Aplysina cavernicola. Isolation and Synthesis. Experientia 39, 1091 (1983).

    Google Scholar 

  164. D’Ambrosio, M., A. Guerriero, P. Traldi, and F. Pietra: Cavernicolin-1 and Cavernicolin-2, Two Epimeric Dibromolactams from the Mediterranean Sponge Aplysina (Verongia) cavernicola. Tetrahedron Lett. 23, 4403 (1982).

    Google Scholar 

  165. Guerriero, A., M. D’Ambrosio, P. Traldi, and F. Pietra: On the First Marine Natural Product Having Low Enantiomeric Purity. Naturwissenschaften 71, 425 (1984).

    CAS  Google Scholar 

  166. Tymiak, A.A., and K.L. Rinehart, Jr.: Biosynthesis of Dibromotyrosine-Derived Antimicrobial Compounds by the Marine Sponge Aplysina fistularis (Verongia aurea). J. Am. Chem. Soc. 103, 6763 (1981).

    CAS  Google Scholar 

  167. Rotem, M., S. Carmely, Y. Kashman, and Y. Loya: Two New Antibiotics from the Red Sea Sponge Psammaplysilla purpurea. Total 13C-NMR Line Assignment of Psammaplysins A and B and Aerothionin. Tetrahedron 39, 667 (1983).

    CAS  Google Scholar 

  168. McMillan, J.A., I.C. Paul, Y.M. Goo, K.L. Rinehart, Jr., W.C. Krueger, and L.M. Pschigoda: An X-Ray Study of Aerothionin from Aplysina fistularis (Pallas). Tetrahedron Lett. 22, 39 (1981).

    CAS  Google Scholar 

  169. Cimino, G., S. de Rosa, S. de Stefano, R. Self, and G. Sodano: The Bromo- Compounds of the True Sponge Verongia aerophoba. Tetrahedron Lett. 24, 3029 (1983).

    CAS  Google Scholar 

  170. Kazlauskas, R., R.O. Lidgard, P.T. Murphy, and R.J. Wells: Brominated Tyro- sine-Derived Metabolites from the Sponge Ianthella basta. Tetrahedron Lett. 21, 2277 (1980).

    CAS  Google Scholar 

  171. Kazlauskas, R., R.O. Lidgard, P.T. Murphy, R.J. Wells, and J.F. Blount: Brominated Tyrosine-Derived Metabolites from the Sponge Ianthella basta. Aust. J. Chem. 34, 765 (1981).

    CAS  Google Scholar 

  172. Roll, D.M., C.W.J. Chang, P.J. Scheuer, G.A. Gray, J.N. Shoolery, G.K. Matfdsumoto, G.D. van Duyne, and J. Clardy: Structure of the Psammaplysins. J. Am. Chem. Soc. 107, 2916 (1985).

    CAS  Google Scholar 

  173. Nakamura, H., H. Wu, J. Kobayashi, Y. Nakamura, Y. Ohizumi, and Y. Hirata: Purealin, a Novel Enzyme Activator from the Okinawan Marine Sponge Psammaply- silla purea. Tetrahedron Lett. 26, 4517 (1985).

    CAS  Google Scholar 

  174. Charles, C., J.C. Braekman, D. Daloze, and B. Tursch: Chemical Studies of Marine Invertebrates - XLII. The Relative and Absolute Configuration of Dysidenin. Tetrahedron 36, 2133 (1980).

    CAS  Google Scholar 

  175. Charles, C., J.C. Braekman, D. Daloze, B. Tursch, and R. Karlsson: Chemical Studies of Marine Invertebrates. XXXII. Isodysidenin, a Further Hexachlorinated Metabolite from the Sponge Dysidea herbacea. Tetrahedron Lett. 17, 1519 (1978).

    Google Scholar 

  176. Biskupiak, J.E., and C.M. Ireland: Revised Absolute Configuration of Dysidenin and Isodysidenin. Tetrahedron Lett. 25, 2935 (1984).

    CAS  Google Scholar 

  177. Erickson, K.L., and R.J. Wells: New Polychlorinated Metabolites from a Barrier Reef Collection of the Sponge Dysidea herbacea. Aust. J. Chem. 35, 31 (1982).

    CAS  Google Scholar 

  178. De Laszlo, S.E., and P.G. Williard: Total Synthesis of (+)-Demethyldysidenin and (–)-Demethylisodysidenin, Hexachlorinated Amino Acids from the Marine Sponge Dysideaherbacea. Assignment of Absolute Stereochemistry. J. Am. Chem. Soc. 107, 199 (1985).

    Google Scholar 

  179. Williard, P.G., and S.E. de Laszlo: Total Synthesis of (±)-Dysidin, a Marine Metabolite Containing an N-Acyl-O-methyltetramic Acid. J. Org. Chem. 49, 3489 (1984).

    CAS  Google Scholar 

  180. Stonard, R.J., and R.J. Andersen: Celenamides A and B, Linear Peptide Alkaloids from the Sponge Cliona celata. J. Org. Chem. 45, 3687 (1980).

    CAS  Google Scholar 

  181. Stonard, R.J., and R.J. Andersen: Linear Peptide Alkaloids from the Sponge Cliona celata (Grant). Celenamides C and D. Can. J. Chem. 58, 2121 (1980).

    CAS  Google Scholar 

  182. Schmidt, U., and J. Wild: Totalsynthese von Hexaacetylcelenamid A. Angew. Chem. 96, 996 (1984).

    CAS  Google Scholar 

  183. Matsunaga, S., N. Fusetani, and S. Konosu: Bioactive Marine Metabolites, IV. Isolation and the Amino Acid Composition of Discodermin A, an Antimicrobial Peptide, from the Marine Sponge Discodermia kiiensis. J. Nat. Prod. 48, 236 (1985).

    CAS  Google Scholar 

  184. Matsunaga, S., N. Fusetani, and S. Konosu: Bioactive Marine Metabolites VI. Structure Elucidation of Discodermin A, an Antimicrobial Peptide from the Marine Sponge Discodermia kiiensis. Tetrahedron Lett. 25, 5165 (1984).

    CAS  Google Scholar 

  185. Matsunaga, S., N. Fusetani, and S. Konosu: Bioactive Marine Metabolites VII. Structures of Discodermins B, C, and D, Antimicrobial Peptides from the Marine Sponge Discodermia kiiensis. Tetrahedron Lett. 26, 855 (1985).

    CAS  Google Scholar 

  186. Pettit, G.R., J.A. Rideout, and J.A. Hasler: Isolation of Geodiastatins 1 and 2 from the Marine Sponge Geodia mesotriaena. J. Nat. Prod. 44, 588 (1981).

    CAS  Google Scholar 

  187. Müller, W.E.G., A. Bernd, R.K. Zahn, B. Kurelec, K. Dawes, I. Müller, and G. Uhlenbruck: Xenograft Rejection in Marine Sponges. Isolation and Purification of an Inhibitory Aggregation Factor from Geodia cydonium. Eur. J. Biochem. 116, 573 (1981).

    Google Scholar 

  188. Quinn, R.J., R.P. Gregson, A.F. Cook, and R.T. Bartlett: Isolation and Synthesis of 1-Methylisoguanosine, a Potent Pharmacologically Active Constituent from the Marine Sponge Tedania digitata. Tetrahedron Lett. 21, 567 (1980).

    CAS  Google Scholar 

  189. Cook, A.F., R.T. Bartlett, R.P. Gregson, and R.J. Quinn: 1-Methylisoguanosine, a Pharmacologically Active Agent from a Marine Sponge. J. Org. Chem. 45, 4020 (1980).

    CAS  Google Scholar 

  190. Baird-Lambert, J., J.F. Marwood, L.P. Davies, and K.M. Taylor: 1-Methyliso- guanosine: An Orally Active Marine Natural Product with Skeletal Muscle and Cardiovascular Effects. Life Sci. 26, 1069 (1980).

    CAS  Google Scholar 

  191. Davies, L.P., K.M. Taylor, R.P. Gregson, and R.J. Quinn: Stimulation of Guinea- Pig Brain Adenylate Cyclase by Adenosine Analogues with Potent Pharmacological Activity in vivo. Life Sci. 26, 1079 (1980).

    CAS  Google Scholar 

  192. Davies, L.P., A.F. Cook, M. Poonian, and K.M. Taylor: Displacement of [3H] Diazepam Binding in Rat Brain by Dipyridamole and by 1-Methylisoguanosine, a Marine Natural Product with Muscle Relaxant Activity. Life Sci. 26, 1089 (1980).

    CAS  Google Scholar 

  193. Kato, Y., N. Fusetani, S. Matsunaga, and K. Hashimoto: Bioactive Marine Metabolites. IX. Mycalisines A and B, Novel Nucleosides which Inhibit Cell Division of Fertilized Starfish Eggs, from the Marine Sponge Mycale Sp. Tetrahedron Lett. 26, 3483 (1985).

    CAS  Google Scholar 

  194. Weber, J.F., F.A. Fuhrman, G.J. Fuhrman, and H.S. Mosher: Isolation of Allantoin and Adenosine from the Marine Sponge Tethya aurantia. Comp. Biochem. Physiol. 70B, 799 (1981).

    Google Scholar 

  195. Kazlauskas, R., P.T. Murphy, R.J. Wells, J.A. Baird-Lambert, and D.D. Jamie- son: Halogenated Pyrrolo[2,3-d]pyrimidine Nucleosides from Marine Organisms. Aust. J. Chem. 36, 165 (1983).

    CAS  Google Scholar 

  196. Stierle, D.B., and D.J. Faulkner: Metabolites of the Marine Sponge Laxosuberites sp. J. Org. Chem. 45, 4980 (1980).

    CAS  Google Scholar 

  197. Nakamura, H., Y. Ohizumi, J. Kobayashi, and Y. Hirata: Keramadine, a Novel Antagonist of Serotonergic Receptors Isolated from the Okinawan Sea Sponge Agelas sp. Tetrahedron Lett. 25, 2475 (1984).

    CAS  Google Scholar 

  198. Walker, R.P., D.J. Faulkner, D. van Engen, and J. Clardy: Sceptrin, an Antimi­crobial Agent from the Sponge Agelas sceptrum. J. Am. Chem. Soc. 103, 6772 (1981).

    CAS  Google Scholar 

  199. Sharma, G.M., J.S. Buyer, and M.W. Pomerantz: Characterization of a Yellow Compound Isolated from the Marine Sponge Phakellia flabellata. J. Chem. Soc., Chem. Comm. 1980, 435.

    Google Scholar 

  200. Cimino, G., S. de Rosa, S. de Stefano, L. Mazzarella, R. Puliti, and G. Sodano: Isolation and X-Ray Crystal Structure of a Novel Bromo-Compound from Two Marine Sponges. Tetrahedron Lett. 23, 767 (1982).

    CAS  Google Scholar 

  201. Schmitz, F.J., S.P. Gunasekera, V. Lakshmi, and L.M.V. Tillekeratne: Marine Natural Products: Pyrrololactams from Several Sponges. J. Nat. Prod. 48, 47 (1985).

    CAS  Google Scholar 

  202. Harbour, G.C., A.A. Tymiak, K.L. Rinehart, Jr., P.D. Shaw, R.G. Hughes, Jr., S.A. Mizsak, J.H. Coats, G.E. Zurenko, L.H. Li, and S.L. Kuentzel: Ptilocaulin and Isoptilocaulin, Antimicrobial and Cytotoxic Cyclic Guanidines from the Caribbean Sponge Ptilocaulis aff. P. spiculifer (Lamarck, 1814). J. Am. Chem. Soc. 103, 5604 (1981).

    CAS  Google Scholar 

  203. Snider, B.B., and W.C. Faith: The Total Synthesis of (±)-Ptilocaulin. Tetrahedron Lett. 24, 861 (1983).

    CAS  Google Scholar 

  204. Snider, B.B., and W.C. Faith: Total Synthesis of (±)- and (-)-Ptilocaulin. J. Am. Chem. Soc. 106, 1443 (1984).

    CAS  Google Scholar 

  205. Roush, W.R., and A.E. Walts: Total Synthesis of (-)-Ptilocaulin. J. Am. Chem. Soc. 106, 721 (1984).

    CAS  Google Scholar 

  206. Walts, A.E., and W.R. Roush: A Stereorational Total Synthesis of (-)-Ptilocaulin. Tetrahedron 41, 3463 (1985).

    CAS  Google Scholar 

  207. Cimino, G., S. de Rosa, S. de Stefano, A. Spinella, and G. Sodano: The Zoo- chrome of the Sponge Verongia aerophoba (“Uranidine”). Tetrahedron Lett. 25, 2925 (1984).

    CAS  Google Scholar 

  208. Cardellina II, J.H., and J. Meinwald: Leucettidine, a Novel Pteridine from the Calcareous Sponge Leucetta microraphis. J. Org. Chem. 46, 4782 (1981).

    CAS  Google Scholar 

  209. Cimino, G., A. de Giulio, S. de Rosa, S. de Stefano, R. Puliti, C.A. Mattia, and L. Mazzarella: Isolation and X-ray Crystal Structure of a Novel 8-Oxopurine Compound from a Marine Sponge. J. Nat. Prod. 48, 523 (1985).

    CAS  Google Scholar 

  210. Nakamura, H., J. Kobayashi, Y. Ohizumi, and Y. Hirata: Isolation and Structure of Aaptamine, a Novel Heteroaromatic Substance Possessing α-Blocking Activity from the Sea Sponge Aaptos aaptos. Tetrahedron Lett. 23, 5555 (1982).

    CAS  Google Scholar 

  211. Schmitz, F.J., S.K. Agarwal, S.P. Gunasekera, P.G. Schmidt, and J.N. Shoolery: Amphimedine, New Aromatic Alkaloid from a Pacific Sponge, Amphimedon sp. Carbon Connectivity Determination from Natural Abundance 13C-13C Coupling Constants. J. Am. Chem. Soc. 105, 4835 (1983).

    CAS  Google Scholar 

  212. Braekman, J.C., D. Daloze, P. Macedo de Abreu, C. Piccinni-Leopardi, G. Ger­main, and M. van Meerssche: A Novel Type of Bis-Quinolizidine Alkaloid from the Sponge Petrosia seriata. Tetrahedron Lett. 23, 4277 (1982).

    CAS  Google Scholar 

  213. Braekman, J.C., D. Daloze, N. Defay, and D. Zimmermann: Petrosin-A and -B, Two New Bis-Quinolizidine Alkaloids from the Sponge Petrosia seriata. Bull. Soc. Chim. Belg. 93, 941 (1984).

    CAS  Google Scholar 

  214. Nakagawa, M., M. Endo, N. Tanaka, and L. Gen-Pei: Structures of Xestospongin A, B, C and D, Novel Vasodilative Compounds from Marine Sponge, Xestospon- gia exigua. Tetrahedron Lett. 25, 3227 (1984).

    CAS  Google Scholar 

  215. Frincke, J.M., and D.J. Faulkner: Antimicrobial Metabolites of the Sponge Reniera sp. J. Am. Chem. Soc. 104, 265 (1982).

    CAS  Google Scholar 

  216. Kashman, Y., A. Groweiss, and U. Shmueli: Latrunculin, a New 2-Thiazolidinone Macrolide from the Marine Sponge Latrunculia magnifica. Tetrahedron Lett. 21, 3629 (1980).

    CAS  Google Scholar 

  217. Groweiss, A., U. Shmueli, and Y. Kashman: Marine Toxins of Latrunculia magnifica. J. Org. Chem. 48, 3512 (1983).

    CAS  Google Scholar 

  218. Kashman, Y., A. Groweiss, R. Lidor, D. Blasberger, and S. Carmely: Latrunculins: NMR Study, Two New Toxins and a Synthetic Approach. Tetrahedron 41, 1905 (1985).

    CAS  Google Scholar 

  219. Spector, I., N.R. Shochet, Y. Kashman, and A. Groweiss: Latrunculins: Novel Marine Toxins That Disrupt Microfilament Organization in Cultured Cells. Science 219, 493 (1983).

    CAS  Google Scholar 

  220. Carmely, S., and Y. Kashman: Structure of Swinholide-A, a New Macrolide from the Marine Sponge Theonella swinhoei. Tetrahedron Lett. 26, 511 (1985).

    CAS  Google Scholar 

  221. Schmitz, F.J., S.P. Gunasekera, G. Yalamanchili, M.B., Hossain, and D. van der Helm: Tedanolide: A Potent Cytotoxic Macrolide from the Caribbean Sponge Tedaniaignis. J. Am. Chem. Soc. 106, 7251 (1984).

    CAS  Google Scholar 

  222. Uemura, D., K. Takahashi, T. Yamamoto, C. Katayama, J. Tanaka, Y. Okumura, and Y. Hirata: Norhalichondrin A: An Antitumor Polyether Macrolide from a Marine Sponge. J. Am. Chem. Soc. 107, 4796 (1985).

    CAS  Google Scholar 

  223. Carté, B., and D.J. Faulkner: Polybrominated Diphenyl Ethers from Dysidea herbacea, Dysidea chlorea and Phyllospongia foliascens. Tetrahedron 37, 2335 (1981).

    Google Scholar 

  224. Norton, R.S., K.D. Croft, and R.J. Wells: Polybrominated Oxydiphenol Deriva­tives from the Sponge Dysidea herbacea. Structure Determination by Analysis of 13C Spin-Lattice Relaxation Data for Quaternary Carbons and 13C-1H Coupling Constants. Tetrahedron 37, 2341 (1981).

    CAS  Google Scholar 

  225. Norton, R.S., and R.J. Wells: Use of 13C Spin-Lattice Relaxation Measurements to Determine the Structure of a Tetrabromo Diphenyl Ether from the Sponge Dysidea herbacea. Tetrahedron Lett. 21, 3801 (1980).

    CAS  Google Scholar 

  226. Capon, R., E.L. Ghisalberti, P.R. Jefferies, B.W. Skelton, and A.H. White: Structural Studies of Halogenated Diphenyl Ethers from a Marine Sponge. J. Chem. Soc., Perkin Trans. I 1981, 2464.

    Google Scholar 

  227. Wratten, S.J., and J. Meinwald: Antimicrobial Metabolites of the Marine Sponge Axinella polycapella. Experientia 37, 13 (1981).

    CAS  Google Scholar 

  228. Bergquist, P.R., M.P. Lawson, A. Lavis, and R.C. Cambie: Fatty Acid Composition and the Classification of the Porifera. Biochem. Syst. Ecol. 12, 63 (1984).

    CAS  Google Scholar 

  229. Lawson, M.P., P.R. Bergquist, and R.C. Cambie: Fatty Acid Composition and the Classification of the Porifera. Biochem. Syst. Ecol. 12, 375 (1984).

    CAS  Google Scholar 

  230. Litchfield, C., J. Tyszkiewics, and V. Dato: 5,9,23-Triacontatrienoic Acid, Principal Fatty Acid of the Marine Sponge Chondrilla nucula. Lipids 15, 200 (1980).

    CAS  Google Scholar 

  231. Walkup, R.D., G.C. Jamieson, M.R. Ratcliff, and C. Djerassi: Phospholipid Studies of Marine Organisms: 2. Phospholipids, Phospholipid-Bound Fatty Acids and Free Sterols of the Sponge Aplysina fistularis (Pallas) Forma fulva (Pallas) (= Verongia thiona). Isolation and Structure Elucidation of Unprecedented Branched Fatty Acids. Lipids 16, 631 (1981).

    CAS  Google Scholar 

  232. Ayanoglu, E., R.D. Walkup, D. Sica, and C. Djerassi: Phospholipid Studies of Marine Organisms: III. New Phospholipid Fatty Acids from Petrosia ficiformis. Lipids 17, 617 (1982).

    CAS  Google Scholar 

  233. Ayanoglu, E., J.M. Kornprobst, A. Aboud-Bichara, and C. Djerassi: Phospho­lipid Studies of Marine Organisms 4. (2R,21Z)-2-Methoxy-21-octacosenoic Acid, the First Naturally Occurring a-Methoxy Acid from a Phospholipid. Tetrahedron Lett. 24, 1111 (1983).

    CAS  Google Scholar 

  234. Ayanoglu, E., S. Popov, J.M. Kornprobst, A. Aboud-Bichara, and C. Djerassi: Phospholipid Studies of Marine Organisms: V. New α-Methoxy Acids from Higgin- sia tethyoides. Lipids 18, 830 (1983).

    CAS  Google Scholar 

  235. Lankelma, J., E. Ayanoglu, and C. Djerassi: Double-Bond Location in Long- Chain Polyunsaturated Fatty Acids by Chemical Ionization-Mass Spectrometry. Lipids 18, 853 (1983).

    CAS  Google Scholar 

  236. Dasgupta, A., E. Ayanoglu, and C. Djerassi: Phospholipid Studies of Marine Organisms: New Branched Fatty Acids from Strongylophora durissima. Lipids 19, 768 (1984).

    CAS  Google Scholar 

  237. Cimino, G., A. Crispino, S. de Rosa, S. de Stefano, and G. Sodano: Polyacetylenes from the Sponge Petrosia ficiformis Found in Dark Caves. Experientia 37, 924 (1981).

    CAS  Google Scholar 

  238. Wijekoon, W.M.D., E. Ayanoglu, and C. Djerassi: Phospholipid Studies of Marine Organisms 9. New Brominated Demospongic Acids from the Phospholipids of Two Petrosia Species. Tetrahedron Lett. 25, 3285 (1984).

    CAS  Google Scholar 

  239. Quinn, R.J., and D.J. Tucker: A Brominated Bisacetylenic Acid from the Marine Sponge Xestospongia testudinaria. Tetrahedron Lett. 26, 1671 (1985).

    CAS  Google Scholar 

  240. Schmitz, F.J., R.S. Prasad, Y. Gopichand, M.B. Hossain, D. van der Helm, and P. Schmidt: Acanthifolicin, a New Episulfide-Containing Polyether Carboxylic Acid from Extracts of the Marine Sponge Pandaros acanthifolium. J. Am. Chem. Soc. 103, 2467 (1981).

    CAS  Google Scholar 

  241. Tachibana, K., P.J. Scheuer, Y. Tsukitani, H. Kikuchi, D. van Engen, J. Clardy, Y. Gopichand, and F.J. Schmitz: Okadaic Acid, a Cytotoxic Polyether from Two Marine Sponges of the Genus Halichondria. J. Am. Chem. Soc. 103, 2469 (1981).

    CAS  Google Scholar 

  242. Shibata, S., Y. Ishida, H. Kitano, Y. Ohizumi, J. Habon, Y. Tsukitani, and H. Kikuchi: Contractile Effects of Okadaic Acid, a Novel Ionophore-Like Substance from Black Sponge, on Isolated Smooth Muscles Under the Condition of Ca Deficiency. J. Pharmacol. Exp. Ther. 223, 135 (1982).

    CAS  Google Scholar 

  243. Stierle, D.B., and D.J. Faulkner: Metabolites of Three Marine Sponges of the Genus Plakortis. J. Org. Chem. 45, 3396 (1980).

    CAS  Google Scholar 

  244. Phillipson, D.W., and K.L. Rinehart, Jr.: Antifungal Peroxide-Containing Acids from Two Caribbean Sponges. J. Am. Chem. Soc. 105, 7735 (1983).

    CAS  Google Scholar 

  245. Cimino, G., A. de Giulio, S. de Rosa, S. de Stefano, and G. Sodano: Further High Molecular Weight Polyacetylenes from the Sponge Petrosia ficiformis. J. Nat. Prod. 48, 22 (1985).

    CAS  Google Scholar 

  246. Fusetani, N., Y. Kato, S. Matsunaga, and K. Hashimoto: Bioactive Marine Me­tabolites III. A Novel Polyacetylene Alcohol, Inhibitor of Cell Division in Fertilized Sea Urchin Eggs, from the Marine Sponge Tetrosia sp. Tetrahedron Lett. 24, 2771 (1983).

    CAS  Google Scholar 

  247. Castiello, D., G. Cimino, S. de Rosa, S. de Stefano, and G. Sodano: High Molecu­lar Weight Polyacetylenes from the Nudibranch Peltodoris atromaculata and the Sponge Petrosia ficiformis. Tetrahedron Lett. 21, 5047 (1980).

    CAS  Google Scholar 

  248. Cardellina II, J.H., C. J. Graden, B.J. Greer, and J.R. Kern: 17Z-Tetracosenyl 1-Glycerol Ether from the Sponges Cinachyra alloclada and Ulosa ruetzleri. Lipids 18, 107 (1983).

    CAS  Google Scholar 

  249. Myers, B.L., and P. Crews: Chiral Ether Glycerides from a Marine Sponge. J. Org. Chem. 48, 3583 (1983).

    CAS  Google Scholar 

  250. Do, M.N., and K.L. Erickson: Branched Chain Mono-Glycerol Ethers from a Taiwanese Marine Sponge of the Genus Aaptos. Tetrahedron Lett. 24, 5699 (1983).

    CAS  Google Scholar 

  251. Roll, D.M., P.J. Scheuer, G.K. Matsumoto, and J. Clardy: Halenaquinone, a Pentacyclic Polyketide from a Marine Sponge. J. Am. Chem. Soc. 105, 6177 (1983).

    CAS  Google Scholar 

  252. Kobayashi, M., N. Shimizu, I. Kitagawa, Y. Kyogoku, N. Harada, and H. Uda: Absolute Stereostructures of Halenaquinol and Halenaquinol Sulfate, Pentacyclic Hydroquinones from the Okinawan Marine Sponge Xestospongia sapra, as Determined by Theoretical Calculation of CD Spectra. Tetrahedron Lett. 26, 3833 (1985).

    CAS  Google Scholar 

  253. Capon, R.J., E.L. Ghisalberti, and P.R. Jefferies: New Tetrahydropyrans from a Marine Sponge. Tetrahedron 38, 1699 (1982).

    CAS  Google Scholar 

  254. Hagadone, M.R., P.J. Scheuer, and A. Holm: On the Origin of the Isocyano Function in Marine Sponges. J. Am. Chem. Soc. 106, 2447 (1984).

    CAS  Google Scholar 

  255. Faulkner, D.J., and B.N. Ravi: Metabolites of the Marine Sponge Plakortis zygompha. Tetrahedron Lett. 21, 23 (1980).

    CAS  Google Scholar 

  256. Beress, L.: Biologically Active Compounds from Coelenterates. Pure and Appl. Chem. 54, 1981 (1982).

    CAS  Google Scholar 

  257. Neeman, I., G.J. Calton, and J.W. Burnett: Purification and Characterization of the Endonuclease Present in Physalia physalis Venom. Comp. Biochem. Physiol. 67B, 155 (1980).

    Google Scholar 

  258. Lal, D.M., G.J. Calton, I. Neeman, and J.W. Burnett: Characterization of Physalia physalis (Portuguese Man-O’War) Nematocyst Venom Collagenase. Comp. Biochem. Physiol. 70B, 635 (1981).

    Google Scholar 

  259. Neeman, I., G.J. Calton, and J.W. Burnett: Purification of an Endonuclease Present in Chrysaora quinquecirrha Venom (41077). Proceedings of the Society for Experimental Biology and Medicine 166, 374 (1981).

    CAS  Google Scholar 

  260. Lal, D.M., G.J. Calton, I. Neeman, and J.W. Burnett: Characterization of Chrysaora quinquecirrha (Sea Nettle) Nematocyst Venom Collagenase. Comp. Biochem. Physiol. 69B, 529 (1981).

    Google Scholar 

  261. Calton, G.J., and J.W. Burnett: Partial Purification and Characterization of the Acid Protease of Sea Nettle (Chrysaora quinquecirrha) Nematocyst Venom. Comp. Biochem. Physiol. 72B, 93 (1982).

    CAS  Google Scholar 

  262. Calton, G.J., and J.W. Burnett: Partial Purification and Characterization of the Alkaline Protease of Sea Nettle (Chrysaora quinquecirrha) Nematocyst Venom. Comp. Biochem. Physiol. 74C, 361 (1983).

    Google Scholar 

  263. Tamkun, M.M., and D.A. Hessinger: Isolation and Partial Characterization of a Hemolytic and Toxic Protein from the Nematocyst Venom of the Portuguese Man-of-War, Physalia physalis. Biochim. Biophys. Acta 667, 87 (1981).

    CAS  Google Scholar 

  264. Watrous, J., and K. Thompson: Chrysaora quinquecirrha (Sea Nettle) Toxin: A Comparison Between a Commercial and Our Own Preparation. Toxicon 19, 319 (1981).

    CAS  Google Scholar 

  265. Cobbs, C.S., P. Gold, G.J. Calton, and J.W. Burnett: Sea Nettle (Chrysaora quinquecirrha) Nematocyst Venom Hemagglutinins. Comp. Biochem. Physiol. 74C, 225 (1983).

    CAS  Google Scholar 

  266. Kelman, S.N., G.J. Calton, and J.W. Burnett: Isolation and Partial Characterization of a Lethal Sea Nettle (Chrysaora quinquecirrha) Mesenteric Toxin. Toxicon 22, 139 (1984).

    CAS  Google Scholar 

  267. Hartman, K.R., G.J. Calton, and J.W. Burnett: The Utilization of the Bradykinin Radioimmunoassay for the Study of a Kinin-Like Factor in Jellyfish Toxin. Comp. Biochem. Physiol. 66C, 163 (1980).

    Google Scholar 

  268. Hartman, K.R., G.J. Calton, and J.W. Burnett: A Comparison of the Kinin-Like Factor in the Sea Nettle Fishing and Mesen­teric Tentacles. Comp. Biochem. Physiol. 68C, 235 (1981).

    Google Scholar 

  269. Gaur, P.K., G.J. Calton, and J.W. Burnett: Enzyme-Linked Immunosorbent Assay to Detect Anti-Sea Nettle Venom Antibodies. Experientia 37, 1005 (1981).

    CAS  Google Scholar 

  270. Gaur, P.K., R.L. Anthony, G.J. Calton, and J.W. Burnett: Isolation of Hybridomas Secreting Monoclonal Antibodies Against Physalia physalis (Portuguese Man- O’War) Nematocyst Venom. Toxicon 20, 419 (1982).

    CAS  Google Scholar 

  271. Cobbs, C.S., P.K. Gaur, A.J. Russo, J.E. Warnick, G.J. Calton, and J.W. Bur­nett: Immunosorbent Chromatography of Sea Nettle (Chrysaora quinquecirrha) Venom and Characterization of Toxins. Toxicon 21, 385 (1983).

    CAS  Google Scholar 

  272. Olson, C.E., D.G. Cargo, G.J. Calton, and J.W. Burnett: Immunochromatography and Cardiotoxicity of Sea Nettle (Chrysaora quinquecirrha) Polyps and Cysts. Toxicon 23, 127 (1985).

    CAS  Google Scholar 

  273. Warnick, J.E., D. Weinreich, and J.W. Burnett: Sea Nettle (Chrysaora quinquecirrha) Toxin on Electrogenic and Chemosensitive Properties of Nerve and Muscle. Toxicon 19, 361 (1981).

    CAS  Google Scholar 

  274. Neeman, I., G.J. Calton, and J.W. Burnett: Cytotoxicity and Dermonecrosis of Sea Nettle (Chrysaora quinquecirrha) Venom. Toxicon 18, 55 (1980).

    CAS  Google Scholar 

  275. Neeman, I., G.J. Calton, and J.W. Burnett: An Ultrastructural Study of the Cytotoxic Effect of the Venoms from the Sea Nettle (Chrysaora quinquecirrha) and Portuguese Man-of-War (Physalia physalis) on Cultured Chinese Hamster Ovary K-l Cells. Toxicon 18, 495 (1980).

    CAS  Google Scholar 

  276. Shryock, J.C., and C.P. Bianchi: Sea Nettle (Chrysaora quinquecirrha) Nematocyst Venom: Mechanism of Action on Muscle. Toxicon 21, 81 (1983).

    CAS  Google Scholar 

  277. Cobbs, C.S., R.E. Drzymala, A.E. Shamoo, G.J. Calton, and J.W. Burnett: Sea Nettle (Chrysaora quinquecirrha) Lethal Factor: Effect on Black Lipid Mem­branes. Toxicon 21, 558 (1983).

    CAS  Google Scholar 

  278. Burnett, J.W., G.J. Calton, C.S. Cobbs, and S.N. Kelman: Sea Nettle and Portu­guese Man-O’War Nematocyst Venoms: Studies with Monoclonal Antibodies and Affinity Chromatography. Toxicon Suppl. 3, 49 (1983).

    Google Scholar 

  279. Flowers, A.L., and D.A. Hessinger: Mast Cell Histamine Release Induced by Portuguese Man-of-War (Physalia) Venom. Biochem. Biophys. Res. Commun. 103, 1083 (1981).

    CAS  Google Scholar 

  280. Behrens-Baumann, W.: Zur Bedeutung der Quallen und deren Giftwirkung auf den Menschen. Dermatosen 29, 121 (1981).

    CAS  Google Scholar 

  281. Endean, R., and J. Rifkin: Envenomation Involving Nematocysts of the Box Jelly­fish Chironex fleckeri. Toxicon Suppl. 3, 115 (1983).

    Google Scholar 

  282. Olson, C.E., E.E. Pockl, G.J. Calton, and J.W. Burnett: Immunochromato- graphic Purification of a Nematocyst Toxin from the Cnidarian Chironex fleckeri (Sea Wasp). Toxicon 22, 733 (1984).

    CAS  Google Scholar 

  283. Cimino, G., S. de Rosa, S. de Stefano, and G. Sodano: Cholest-4-en-4,16ß,18,22R-tetrol-3-one 16,18-diacetate, a Novel Polyhydroxylated Steroid from the Hydroid Eudendrium sp. Tetrahedron Lett. 21, 3303 (1980).

    CAS  Google Scholar 

  284. Fattorusso, E., V. Lanzotti, S. Magno, and E. Novellino: Cholest-5-ene- 2α,3α,7β,15β,18-pentol 2,7,15,18-Tetraacetate, a Novel Highly Hydroxylated Sterol from the Marine Hydroid Eudendrium glomeratum. J. Org. Chem. 50, 2868 (1985).

    CAS  Google Scholar 

  285. Fattorusso, E., V. Lanzotti, S. Magno, and E. Novellino: Two New Polyoxygenated Sterols from the Marine Hydroid Eudendrium glomeratum. J. Nat. Prod. 48, 784 (1985).

    CAS  Google Scholar 

  286. De Napoli, L., E. Fattorusso, S. Magno, and L. Mayol: Acyclic Polyhalogenated Monoterpenes from Four Marine Hydroids. Biochem. Syst. Ecol. 12, 321 (1984).

    Google Scholar 

  287. Fahy, E., R.J. Andersen, H. Cun-heng, and J. Clardy: Garveatin A, an Antimicro­bial l(4H)-Anthracenone Derivative from the Hydroid Garveia annulata. J. Org. Chem. 50, 1149 (1985).

    CAS  Google Scholar 

  288. Lubbock, R.: Why are Clownfishes not Stung by Sea Anemones ? Proc. R. Soc. Lond. B 207, 35 (1980).

    CAS  Google Scholar 

  289. Maretic, Z., and F.E. Russell: Some Epidemiological and Clinical Aspects of Stings by the Sea Anemone Anemonia sulcata. Toxicon 20, 360 (1982).

    Google Scholar 

  290. Scheffler, J.-J., A. Tsugita, G. Linden, H. Schweitz, and M. Lazdunski: The Amino Acid Sequence of Toxin V from Anemonia sulcata. Biochem. Biophys. Res. Commun. 107, 272 (1982).

    CAS  Google Scholar 

  291. Blumenthal, K.M., and W.R. Kem: Primary Structure of Stoichactis helianthus Cytolysin III. J. Biol. Chem. 258, 5574 (1983).

    CAS  Google Scholar 

  292. Krebs, H.C., G. Habermehl, and E. Wachter: Biologic Active Substances from the Sea Anemone Metridium senile. Third International Symposium on Marine Natural Products, Brussels, Belgium, 1980.

    Google Scholar 

  293. Mebs, D., and E. Gebauer: Isolation of Proteinase Inhibitory, Toxic and Hemolytic Polypeptides from a Sea Anemone, Stoichactis sp. Toxicon 18, 97 (1980).

    CAS  Google Scholar 

  294. Samejima, Y., and D. Mebs: Structural Studies on a Proteinase Inhibitor from the Sea Anemone Stoichactis sp. Toxicon 20, 335 (1982).

    Google Scholar 

  295. Schweitz, H., J.-P. Vincent, J. Barhanin, C. Frelin, G. Linden, M. Hugues, and M. Lazdunski: Purification and Pharmacological Properties of Eight Sea Anem­one Toxins from Anemonia sulcata, Anthopleura xanthogrammica, Stoichactis gigan- teus, and Actinodendron plumosum. Biochemistry 20, 5245 (1981).

    CAS  Google Scholar 

  296. Schweitz, H., J.-P. Vincent, J. Barhanin, C. Frelin, G. Linden, M. Hugues, and M. Lazdunski: Purification and Pharmacological Properties of Eight Sea Anemone Toxins from Anemonia sulcata, Anthopleura xanthogrammica, Stoichactis giganteus, and Actinodendron plumosum. Toxicon 20, 77 (1982).

    Google Scholar 

  297. Norton, T.R.: Cardiotonic Polypeptides from Anthopleura xanthogrammica (Brandt) and A. elegantissima (Brandt). Fed. Proc. 40, 21 (1981).

    CAS  Google Scholar 

  298. Aldeen, S.I., R.C. Elliott, and M. Sheardown: The Partial Purification and Bioassay of a Toxin Present in Extracts of the Sea Anemone, Tealia felina (L.). Br. J. Pharmac. 72, 211 (1981).

    CAS  Google Scholar 

  299. Bernheimer, A.W., L.S. Avigad, and C.Y. Lai: Purification and Properties of a Toxin from the Sea Anemone Condylactis gigantea. Arch. Biochem. Biophys. 214, 840 (1982).

    CAS  Google Scholar 

  300. Măcek, P., L. Senčič, and D. Lebez: Isolation and Partial Characterization of Three Lethal and Hemolytic Toxins from the Sea Anemone Actinia cari. Toxicon 20, 181 (1982).

    Google Scholar 

  301. Bernheimer, A.W., and L.S. Avigad: Toxins of the Sea Anemone Epiactisprolifera. Arch. Biochem. Biophys. 217, 174 (1982).

    CAS  Google Scholar 

  302. Ferlan, I., and K.W. Jackson: Partial Amino Acid Sequence of Equinatoxin. Toxicon Suppl. 3, 141 (1983).

    Google Scholar 

  303. Nabiullin, A.A., S.E. Odinokov, E.P. Kozlovskaya, and G.B. Elyakov: Secondary Structure of Sea Anemone Toxins. Circular Dichroism, Infrared Spectroscopy and Chou-Fasman Calculations. Febs Lett. 141, 124 (1982).

    CAS  Google Scholar 

  304. Mebs, D., M. Liebrich, A. Reul, and Y. Samejima: Hemolysins and Proteinase Inhibitors from Sea Anemones of the Gulf of Aqaba. Toxicon 21, 257 (1983).

    CAS  Google Scholar 

  305. Mebs, D., M. Liebrich, and A. Reul: Biologically Active Polypeptides from Sea Anemones of the Red Sea. Toxicon Suppl. 3, 289 (1983).

    Google Scholar 

  306. Beress, L., and J. Zwick: Purification of Two Crab-Paralysing Polypeptides from the Sea Anemone Bolocera tuediae. Mar. Chem. 8, 333 (1980).

    CAS  Google Scholar 

  307. Bernheimer, A.W., L.S. Avigad, G. Branch, E. Dowdle, and C.Y. Lai: Purification and Properties of a Toxin from the South African Sea Anemone, Pseudactinia varia. Toxicon 22, 183 (1984).

    CAS  Google Scholar 

  308. Bernheimer, A.W., and L.S. Avigad: New Cytolysins in Sea Anemones from the West Coast of the United States. Toxicon 19, 529 (1981).

    CAS  Google Scholar 

  309. Norton, R.S., J. Zwick, and L. Beress: Natural-Abundance 13C Nuclear-Magnetic- Resonance Study of Toxin II from Anemonia sulcata. Eur. J. Biochem. 113, 75 (1980).

    CAS  Google Scholar 

  310. Romey, G., J.F. Renaud, M. Fosset, and M. Lazdunski: Pharmacological Proper­ties of the Interaction of a Sea Anemone Polypeptide Toxin with Cardiac Cells in Culture. J. Pharmacol. Exp. Ther. 213, 607 (1980).

    CAS  Google Scholar 

  311. Elliott, R.C., and M.J. Sheardown: The Action of an Extract of the Sea Anemone Tealia felina on Neuromuscular Transmission Studied in vitro. Br. J. Pharmac. 69, 293 P (1980).

    Google Scholar 

  312. Alsen, C., and A. Kampen: Induction of Spontaneous Contractions of Left Guinea Pig Atria by ATX II (Anemonia sulcata). Naunyn Schmiedebergs Arch. Pharmacol. 311 (Suppl. R), R 39 (1980).

    Google Scholar 

  313. Stengelin, S., and F. Hucho: Radioactive Labelling of Toxin I from Anemonia sulcata and Binding to Crayfish Nerve in vitro. Hoppe-Seyler’s Z. Physiol. Chem. 361, 577 (1980).

    CAS  Google Scholar 

  314. Neumcke, B., W. Schwarz, and R. Stampfli: Modification of Sodium Inactivation in Myelinated Nerve by Anemonia Toxin II and Iodate. Analysis of Current Fluctuations and Current Relaxations. Biochim. Biophys. Acta 600, 456 (1980).

    CAS  Google Scholar 

  315. Ohizumi, Y., and S. Shibata: Possible Mechanism of the Dual Action of the New Polypeptide (Anthopleurin-B) from Sea Anemone in the Isolated Ileum and Taenia Caeci of the Guinea-Pig. Br. J. Pharmac. 72, 239 (1981).

    CAS  Google Scholar 

  316. Kudo, Y., and S. Shibata: The Potent Excitatory Effect of a Novel Polypeptide, Anthopleurin-B, Isolated from a Sea Anemone (.Anthopleura xanthogrammica) on the Frog Spinal Cord. J. Pharmacol. Exp. Ther. 214, 443 (1980).

    CAS  Google Scholar 

  317. Hashimoto, K., R. Ochi, K. Hashimoto, J. Inui, and Y. Miura: The Ionic Mecha­nism of Prolongation of Action Potential Duration of Cardiac Ventricular Muscle by Anthopleurin-A and Its Relationship to the Inotropic Effect. J. Pharmacol. Exp. Ther. 215, 479 (1980).

    CAS  Google Scholar 

  318. Vincent, J.P., M. Balerna, J. Barhanin, M. Fosset, and M. Lazdunski: Binding of Sea Anemone Toxin to Receptor Sites Associated with Gating System of Sodium Channel in Synaptic Nerve Endings in vitro. Proc. natl. Acad. Sci. U.S.A. 77, 1646 (1980).

    CAS  Google Scholar 

  319. Bailey, L.E., S. Shibata, D.G. Seriguchi, and P.E. Dresel: Inhibition of the Posi­tive Inotropic Effect of Anthopleurin-A (AP-A) by Dantrolene. Life Sci. 26, 1061 (1980).

    CAS  Google Scholar 

  320. Norton, T.R., Y. Ohizumi, and S. Shibata: Excitatory Effect of a New Polypeptide (Anthopleurin-B) from Sea Anemone on the Guinea-Pig Vas Deferens. Br. J. Pharmac. 74, 23 (1981).

    CAS  Google Scholar 

  321. Lemeignan, M., J. Molgo, and F. Tazieff-Depierre: Effects of Sea Anemonia sul­cata Toxin II on Normal and Chronically Denervated Mammalian Neuromuscular Junctions. Br. J. Pharmac. 72, 546 P (1981).

    Google Scholar 

  322. Alsen, C., J.B. Harris, and I. Tesseraux: Mechanical and Electrophysiological Effects of Sea Anemone (Anemonia sulcata) Toxins on Rat Innervated and Denervated Skeletal Muscle. Br. J. Pharmac. 74, 61 (1981).

    CAS  Google Scholar 

  323. Stengelin, S., W. Rathmayer, G. Wunderer, L. Beress, and F. Hucho: Radioac­tive Labeling of Toxin II from Anemonia sulcata. Analytical Biochemistry 113, 277 (1981).

    CAS  Google Scholar 

  324. Norton, R.S., T.R. Norton, R.W. Sleigh, and D.G. Bishop: Interaction of the Polypeptide Cardiac Stimulant Anthopleurin-A with H+, Ca2+, and Membrane Lipids. Arch. Biochem. Biophys. 213, 87 (1982).

    CAS  Google Scholar 

  325. Hucho, F., and L. Lauffer: Interaction of Anemone Toxin I with Crayfish Nerve Membranes. Toxicon 20, 70 (1982).

    Google Scholar 

  326. Laufer, J., and M. Pelhate: Action of Anthopleurin-A on the Isolated Cockroach Axon. Toxicon 20, 72 (1982).

    Google Scholar 

  327. Schmidtmayer, J., M. Stoye-Herzog, and W. Ulbricht: Rate of Action of Anemonia sulcata Toxin II on Sodium Channels in Myelinated Nerve Fibres. Pflügers Arch. 394, 313 (1982).

    CAS  Google Scholar 

  328. Alsen, C., T. Peters, and E. Scheufler: Studies on the Mechanism of the Positive Inotropic Effect of ATX II (Anemonia sulcata) on the Isolated Guinea Pig Atria. J. Cardiovasc. Pharmacol. 4, 63 (1982).

    CAS  Google Scholar 

  329. Alsen, C.: Biological Significance of Peptides from Anemonia sulcata. Fed. Proc. 42, 101 (1983).

    CAS  Google Scholar 

  330. Fujita, S., A. Warashina, and M. Satake: Binding Characteristics of a Sea Anemone Toxin from Parasicyonis actinostoloides with Crayfish Leg Nerves. Comp. Biochem. Physiol. 76C, 25 (1983).

    CAS  Google Scholar 

  331. Beress, L., R. Ritter, and U. Ravens: The Influence of the Rate of Electrical Stimulation on the Effects of the Anemonia sulcata Toxin ATX II in Guinea Pig Papillary Muscle. Eur. J. Pharmac. 79, 265 (1982).

    CAS  Google Scholar 

  332. Härtung, K., and W. Rathmayer: Effects of Three Anemone Toxins on Sodium Currents in a Crayfish Neurone. Naunyn-Schmiedebergs Arch. Pharmacol. 322, R 66 (1983).

    Google Scholar 

  333. Miyake, M., and S. Shibata: A Novel Mode of Neurotoxin Action. A Polypeptide Toxin Isolated from Anemonia sulcata Shifts the Voltage Dependence of the Maximal Rate of Rise of Na+ Action Potentials in a Mouse Neuronal Clone. Mol. Pharmac. 20, 453 (1981).

    CAS  Google Scholar 

  334. Ravens, U., and E. Schöllhorn: The Effects of a Toxin (ATX II) from the Sea Anemone Anemonia sulcata on the Electrical and Mechanical Activity of Denervated Hemidiaphragm of the Rat. Toxicon 21, 131 (1983).

    CAS  Google Scholar 

  335. Ulbricht, W., and J. Schmidtmayer: Modification of Sodium Channels in Myelin­ated Nerve by Anemonia sulcata Toxin II. J. Physiol., Paris 77, 1103 (1981).

    CAS  Google Scholar 

  336. Warashina, A., and S. Fujita: Effect of Sea Anemone Toxin on the Sodium Inactivation Process in Crayfish Axons. J. Gen. Physiol. 81, 305 (1983).

    CAS  Google Scholar 

  337. Lafranconi, W.M., I. Ferlan, F.E. Russell and R.J. Huxtable: The Action of Equinatoxin, a Peptide from the Venom of the Sea Anemone, Actinia equina, on the Isolated Lung. Toxicon 22, 347 (1984).

    CAS  Google Scholar 

  338. Erxleben, C., and W. Rathmayer: Effects of the Sea Anemone Anemonia sulcata Toxin II on Skeletal Muscle and on Neuromuscular Transmission. Toxicon 22, 387 (1984).

    CAS  Google Scholar 

  339. Varanda, W., and A. Finkelstein: Ion and Nonelectrolyte Permeability Properties at Channels Formed in Planar Lipid Bilayer Membranes by the Cytolytic Toxin from the Sea Anemone Stoichactis helianthus. J. Membrane Biol. 55, 203 (1980).

    CAS  Google Scholar 

  340. Schmidtmayer, J., M. Stoye-Herzog, and W. Ulbricht: Kinetic and Equilibrium Effects of Different Concentrations of Anemonia sulcata Toxin II (ATX). Pflügers Arch. ges. Physiol. 293, R 32 (1982).

    Google Scholar 

  341. Rack, M., H. Meves, L. Beress, and H.H. Grünhagen: Preparation and Properties of Fluorescence Labeled Neuro- and Cardiotoxin II from the Sea Anemone (Ane- monia sulcata). Toxicon 21, 231 (1983).

    CAS  Google Scholar 

  342. Macek, P., and D. Lebez: Kinetics of Hemolysis Induced by Equinatoxin, a Cytolytic Toxin from the Sea Anemone Actinia equina. Effect of Some Ions and pH. Toxicon 19, 233 (1981).

    CAS  Google Scholar 

  343. Barhanin, J., M. Hugues, H. Schweitz, J.-P. Vincent, and M. Lazdunski: Structure Function Relationships of Sea Anemone Toxin II from Anemonia sulcata. J. Biol. Chem. 256, 5764 (1981).

    CAS  Google Scholar 

  344. Barhanin, J., M. Hugues, H. Schweitz, J.-P. Vincent, and M. Lazdunski: Structure-Function Relationships of Sea Anemone Toxin II from Anemonia sulcata. Toxicon 20, 59 (1982).

    Google Scholar 

  345. Sedmak, B., J. Skrk, V. Kodelja, and D. Lebez: The Influence of Cytolysin from the Sea Anemone Condylactis aurantiaca on the Survival of Mice Bearing Ehrlich Ascites Tumor. Toxicon 20, 207 (1982).

    Google Scholar 

  346. Burcham, J.M., G.E. Dearlove, and S.H. Bishop: Phosphonomonoesterase Activity in Metridium senile L. Comp. Biochem. Physiol. 67B, 147 (1980).

    Google Scholar 

  347. Findlay, J.A., and A.D. Patil: A Novel Sterol Peroxide from the Sea Anemone Metridium senile. Steroids 44, 261 (1984).

    CAS  Google Scholar 

  348. Milkova, T.S., S.S. Popov, N.L. Marekov, and S.N. Andreev: Sterols from Black Sea Invertebrates - I. Sterols from Scyphozoa and Anthozoa (Coelenterata). Comp. Biochem. Physiol. 67B, 633 (1980).

    Google Scholar 

  349. Milkova, T., S. Popov, N. Marekov, I. Stoilov, S. Andreev, and G. Kovachev: Sterols from Black Sea Coelenterata and Mollusca. Bull. Soc. Chim. Belg. 89, 1081 (1980).

    CAS  Google Scholar 

  350. Moore, R.E.: The Structure of Palytoxin. Fortschr. Chem. Organ. Naturstoffe (W. Herz, H. Grisebach, G.W. Kirby, and Ch. Tamm, eds.), Vol. 48, p. 81. Wien-New York: Springer 1985.

    Google Scholar 

  351. Beress, L., J. Zwick, H.J. Kolkenbrock, P.N. Kaul, and O. Wassermann: A Method for the Isolation of the Caribbean Palytoxin (C-PTX) from the Coelenterate (Zooanthid) Palythoa caribaeorum. Toxicon 21, 285 (1983).

    CAS  Google Scholar 

  352. Macfarlane, R.D., D. Uemura, K. Ueda, and Y. Hirata: 252Cf Plasma Desorption Mass Spectrometry of Palytoxin. J. Am. Chem. Soc. 102, 875 (1980).

    CAS  Google Scholar 

  353. Uemura, D., K. Ueda, Y. Hirata, C. Katayama, and J. Tanaka: Structural Studies on Palytoxin, a Potent Coelenterate Toxin. Tetrahedron Lett. 21, 4857 (1980).

    CAS  Google Scholar 

  354. Uemura, D., K. Ueda, Y. Hirata, C. Katayama, and J. Tanaka: Structures of Two Oxidation Products Obtained from Palytoxin. Tetrahe­dron Lett. 21, 4861 (1980).

    CAS  Google Scholar 

  355. Moore, R.E., F.X. Woolard, and G. Bartolini: Periodate Oxidation of N-(p- Bromobenzoyl)palytoxin. J. Am. Chem. Soc. 102, 7370 (1980).

    CAS  Google Scholar 

  356. Moore, R.E., and G. Bartolini: Structure of Palytoxin. J. Am. Chem. Soc. 103, 2491 (1981).

    CAS  Google Scholar 

  357. Uemura, D., K. Ueda, Y. Hirata, H. Naoki, and T. Iwashita: Further Studies on Palytoxin. I. Tetrahedron Lett. 22, 1909 (1981).

    CAS  Google Scholar 

  358. Klein, L.L., W.W. McWhorter, Jr., S.S. Ko, K.-P. Pfaff, Y. Kishi, D. Uemura, and Y. Hirata: Stereochemistry of Palytoxin. 1. C85-C115 Segment. J. Am. Chem. Soc. 104, 7362 (1982).

    CAS  Google Scholar 

  359. Ko, S.S., J.M. Finan, M. Yonaga, Y. Kishi, D. Uemura, and Y. Hirata: Stereo­chemistry of Palytoxin. 2. C1-C6, C47-C74, and C77-C83 Segments. J. Am. Chem. Soc. 104, 7364 (1982).

    CAS  Google Scholar 

  360. Fujioka, H., W.J. Christ, J.K. Cha, J. Leder, Y. Kishi, D. Uemura, and Y. Hirata: Stereochemistry of Palytoxin. 3. C7-C51 Segment. J. Am. Chem. Soc. 104, 7367 (1982).

    CAS  Google Scholar 

  361. Uemura, D., K. Ueda, Y. Hirata, H. Naoki, and T. Iwashita: Further Studies on Paly toxin, II. Structure of Palytoxin. Tetrahedron Lett. 22, 2781 (1981).

    CAS  Google Scholar 

  362. Moore, R.E., G. Bartolini, J. Barchi, A.A. Bothner-By, J. Dadok, and J. Ford: Absolute Stereochemistry of Palytoxin. J. Am. Chem. Soc. 104, 3776 (1982).

    CAS  Google Scholar 

  363. Cha, J.K., W.J. Christ, J.M. Finan, H. Fujioka, Y. Kishi, L.L. Klein, S.S. Ko, J. Leder, W.W. McWhorter, Jr., K.-P. Pfaff, M. Yonaga, D. Uemura, and Y. Hirata: Stereochemistry of Palytoxin. 4. Complete Structure. J. Am. Chem. Soc. 104, 7369 (1982).

    CAS  Google Scholar 

  364. Uemura, D., Y. Hirata, T. Iwashita, and H. Naoki: Studies on Palytoxins. Tetrahedron 41, 1007 (1985).

    CAS  Google Scholar 

  365. Still, W.C., and I. Galynker: Stereospecific Synthesis of the C30-C43 Segment of Palytoxin by Macrocyclically Controlled Remote Asymmetric Induction. J. Am. Chem. Soc. 104, 1774 (1982).

    CAS  Google Scholar 

  366. Ko, S.S., L.L. Klein, K.-P. Pfaff, and Y. Kishi: Synthetic Studies on Palytoxin. Stereocontrolled, Practical Synthesis of the C.101-C.115 Segment. Tetrahedron Letters 23, 4415 (1982).

    CAS  Google Scholar 

  367. Leder, J., H. Fujioka, and Y. Kishi: Synthetic Studies on Palytoxin. Stereocon­trolled Practical Synthesis of the C.23-C.37 Segment. Tetrahedron Lett. 24, 1463 (1983).

    CAS  Google Scholar 

  368. Kudo, Y., and S. Shibata: The Potent Depolarizing Action of Palytoxin Isolated from Palythoa tubercurosa on the Isolated Spinal Cord of the Frog. Br. J. Pharmac. 71, 575 (1980).

    CAS  Google Scholar 

  369. Ohizumi, Y., and S. Shibata: Mechanism of the Excitatory Action of Palytoxin and N-Acetylpalytoxin in the Isolated Guinea-Pig Vas Deferens. J. Pharmacol, exp. Ther. 214, 209 (1980).

    CAS  Google Scholar 

  370. Habermann, E., G.S. Chhatwal, and H.J. Hessler: Palytoxin Raises the Nonspe­cific Permeability of Erythrocytes in an Ouabain-Sensitive Manner. Naunyn-Schmie- deberg’s Arch. Pharmacol. 317, P 374 (1981).

    Google Scholar 

  371. Habermann, E., G. Ahnert-Hilger, G.S. Chhatwal, and L. Beress: Delayed Haemolytic Action of Palytoxin. General Characteristics. Biochim. Biophys. Acta 649, 481 (1981).

    CAS  Google Scholar 

  372. Habermann, E., and G.S. Chhatwal: Ouabain Inhibits the Increase Due to Palytoxin of Cation Permeability of Erythrocytes. Naunyn-Schmiedeberg’s Arch. Pharmacol. 319, 101 (1982).

    CAS  Google Scholar 

  373. Chhatwal, G.S., G. Ahnert-Hilger, L. Beress, and E. Habermann: Palytoxin Induces As Well As Inhibits the Release of Histamine from Rat Mast Cells. Int. Archs. Allergy appl. Immun. 68, 97 (1982).

    CAS  Google Scholar 

  374. Ito, K., N. Urakawa, and H. Koike: Cardiovascular Toxicity of Palytoxin in Anesthetized Dogs. Arch. int. Pharmacodyn. 258, 146 (1982).

    CAS  Google Scholar 

  375. Pichon, Y.: Effects of Palytoxin on Sodium and Potassium Permeabilities in Unmyelinated Axons. Toxicon 20, 41 (1982).

    CAS  Google Scholar 

  376. Chhatwal, G.S., G. Ahnert-Hilger, L. Beress, and E. Habermann: Palytoxin: Its Action on Erythrocytes and Rat Mast Cells. Toxicon 20, 62 (1982).

    Google Scholar 

  377. Draijer, F., P. Suvanto, I. Tesseraux, and L. Beress: Mechanical Studies About the Action of Palytoxin (Palythoa caribaeorum) on Innervated and Denervated Rat Diaphragms. Toxicon 20, 65 (1982).

    Google Scholar 

  378. Alsen, C., G. Agena, and L. Beress: The Action of Palytoxin (Palythoa caribaeorum) on Isolated Atria of Guinea Pig Hearts. Toxicon 20, 57 (1982).

    Google Scholar 

  379. Ishida, Y., K. Takagi, M. Takahashi, N. Satake, and S. Shibata: Palytoxin Iso­lated from Marine Coelenterates. The Inhibitory Action on (Na,K)-ATPase. J. Biol. Chem. 258, 7900 (1983).

    CAS  Google Scholar 

  380. Pettit, G.R., Y. Fujii, J.A. Hasler, J.M. Schmidt, and C. Michel: Antineoplastic Agents. 78. Isolation of Palystatins 1-3 from the Indian Ocean Palythoa liscia. J. Nat. Prod. 45, 263 (1982).

    CAS  Google Scholar 

  381. Pettit, G.R., Y. Fujii, J. A. Hasler, and J.M. Schmidt: Isolation and Characteriza­tion of Palystatins A-D. J. Nat. Prod. 45, 272 (1982).

    CAS  Google Scholar 

  382. Pettit, G.R., and Y. Fujii: Antineoplastic Agents. 81. The Glycerol Ethers of Palythoa liscia. J. Nat. Prod. 45, 640 (1982).

    CAS  Google Scholar 

  383. Kelecom, A., and A.M. Sole-Cava: Comparative Study of Zoanthid Sterols, the Genus Palythoa (Hexacorallia, Zoanthidea). Comp. Biochem. Physiol. 72B, 677 (1982).

    Google Scholar 

  384. Kelecom, A.: Studies of Brazilian Marine Invertebrates. VIII. Zoanthosterol, a New Sterol from the Zoanthid Zoanthus sociatus (Hexacorallia, Zoanthidae). Bull. Soc. Chim. Belg. 90, 971 (1981).

    CAS  Google Scholar 

  385. Sturaro, A., A. Guerriero, R. de Clauser, and F. Pietra: A New, Unexpected Marine Source of a Molting Hormone. Isolation of Ecdysterone in Large Amounts from the Zoanthid Gerardia savaglia. Experientia 38, 1184 (1982).

    CAS  Google Scholar 

  386. Komoda, Y., M. Shimizu, S. Kaneko, M. Yamamoto, and M. Ishikawa: Chemistry of Paragracine, a Biologically Active Marine Base from Parazoanthus gracilis (Lwowsky). Chem. Pharm. Bull. (Japan) 30, 502 (1982).

    CAS  Google Scholar 

  387. Rao, C.B., A.S.R. Anjaneyulu, N.S. Sarma, Y. Venkateswarlu, R.M. Rosser, D.J. Faulkner, M.H.M. Chen, and J. Clardy: Zoanthamine: A Novel Alkaloid from a Marine Zoanthid. J. Am. Chem. Soc. 106, 7983 (1984).

    Google Scholar 

  388. Rao, C.B., A.S.R. Anjaneyulu, N.S. Sarma, Y. Venkateswarlu, R.M. Rosser, and D.J. Faulkner: Alkaloids from a Marine Zoanthid. J. Org. Chem. 50, 3757 (1985)

    CAS  Google Scholar 

  389. Kokke, W.C.M.C., W. Fenical, L. Bohlin, and C. Djerassi: Sterol Synthesis by Cultured Zooxanthellae; Implications Concerning Sterol Metabolism in the Host- Symbiont Association in Caribbean Gorgonians. Comp. Biochem. Physiol. 68B, 281 (1981).

    Google Scholar 

  390. Kelecom, A., A.M. Solé Cava, and G.J. Kannengiesser: Occurrence of 23,24ξ- Dimethylcholesta-5,22-dien-3β-ol in the Brazilian Gorgonian Phyllogorgia dilatata (Octocorallia, Gorgonacea) and in its Associated Zooxanthella. Bull. Soc. Chim. Belg. 89, 1013 (1980).

    CAS  Google Scholar 

  391. Kokke, W.C.M.C., L. Bohlin, W. Fenical, and C. Djerassi: Novel Dinoflagellate 4a-Methylated Sterols from Four Caribbean Gorgonians. Phytochemistry 21, 881 (1982).

    CAS  Google Scholar 

  392. Kobayashi, M., T. Ishizaka, and H. Mitsuhashi: Marine Sterols X. Minor Constit­uents of the Sterols of the Soft Coral Sarcophyton glaucum. Steroids 40, 209 (1982).

    CAS  Google Scholar 

  393. Bonini, C., R.B. Kinnel, M. Li, P.J. Scheuer, and C. Djerassi: Minor and Trace Sterols in Marine Invertebrates 38: Isolation, Structure Elucidation and Partial Synthesis of Papakusterol, a New Biosynthetically Unusual Marine Sterol with a Cyclo- propyl-Containing Side Chain. Tetrahedron Lett. 24, 277 (1983).

    CAS  Google Scholar 

  394. Kobayashi, M., and H. Mitsuhashi: Marine Sterols. XII. Glaucasterol, a Novel C27 Sterol with a Unique Side Chain, from the Soft Coral Sarcophyton glaucum. Steroids 40, 665 (1982).

    Google Scholar 

  395. Kobayashi, M., T. Ishizaka, and H. Mitsuhashi: Isolation of 5α,6-Dihydroglauca- sterol, a New Marine C27 Sterol with a 24,26-Cyclized Side Chain, from the Soft Coral Sarcophyton glaucum. Chem. Pharm. Bull. (Japan) 31, 1803 (1983).

    CAS  Google Scholar 

  396. Popov, S., R.M.K. Carlson, and C. Djerassi: Occurrence and Seasonal Variation of 19-Norcholest-4-en-3-one and 3 β-Monohydroxy Sterols in the Californian Gor­gonian, Muricea californica. Steroids 41, 537 (1983).

    CAS  Google Scholar 

  397. Kashman, Y., and S. Carmely: Four Novel C28 Sterols from Lobophytum depressum. Tetrahedron Lett. 21, 4939 (1980).

    CAS  Google Scholar 

  398. Carmely, S., and Y. Kashman: Isolation and Structure Elucidation of Lobophyto- sterol, Depresosterol and Three Other Closely Related Sterols. Tetrahedron 37, 2397 (1981).

    CAS  Google Scholar 

  399. Yamada, Y., S. Suzuki, K. Iguchi, H. Kikuchi, Y. Tsukitani, H. Horiai, and H. Nakanishi: Studies on Marine Natural Products. II. New Polyhydroxylated Sterols from the Soft Coral Lobophytum pauciflorum (Ehrenberg). Chem. Pharm. Bull. (Japan) 28, 473 (1980).

    CAS  Google Scholar 

  400. Kobayashi, M., T. Hayashi, K. Hayashi, M. Tanabe, T. Nakagawa, and H. Mitsuhashi: Marine Sterols. XI. Polyhydroxysterols of the Soft Coral Sarcophyton glau- cum: Isolation and Synthesis of 5α-Cholestane-l β,3 β,5,6 β-tetrol. Chem. Pharm. Bull. (Japan) 31, 1848 (1983).

    CAS  Google Scholar 

  401. Kobayashi, M., and H. Mitsuhashi: Marine Sterols. XIV. Isolation of (24S)-24- Methyl-5a-cholestane-3 β,5,6 β,25ξ,26-pentol from the Soft Coral Sarcophyton glaucum. Chem. Pharm. Bull. (Japan) 31, 4127 (1983).

    CAS  Google Scholar 

  402. Ksebati, M.B., and F.J. Schmitz: 24 £-Methyl-5a-cholestane-3 β,5,6 β,22 R,24-pentol 6-Acetate: New Polyhydroxylated Sterol from the Soft Coral Asterospicularia randalli. Steroids 43, 639 (1984).

    CAS  Google Scholar 

  403. Kobayashi, M., and H. Mitsuhashi: Marine Sterols XIII. Isolation and Synthesis of 1 β,3 β,5,6 (3-Tetrahydroxy-5α-androstan-17-one from the Soft Coral Sarcophyton glaucum. Steroids 40, 673 (1982).

    Google Scholar 

  404. Jagodzinska, B.M., J.S. Trimmer, W. Fenical, and C. Djerassi: Sterols in Marine Invertebrates. 49. Isolation and Structure Elucidation of Eight New Polyhydroxyl­ated Sterols from the Soft Coral Sinularia dissecta. J. Org. Chem. 50, 1435 (1985).

    CAS  Google Scholar 

  405. Kobayashi, M., N.K. Lee, B.W. Son, K. Yanagi, Y. Kyogoku, and I. Kitagawa: Stoloniferone-A, -B, -C, and -D, Four New Cytotoxic Steroids from the Okinawan Soft Coral Clavularia viridis. Tetrahedron Lett. 25, 5925 (1984).

    CAS  Google Scholar 

  406. Cimino, G., S. de Rosa, S. de Stefano, G. Scognamiglio, and G. Sodano: Cholest- 4,14-dien-15,2ξ-diol-3,16-dione, a Novel Polyoxygenated Marine Steroid which Easily Loses the Side Chain. Tetrahedron Lett. 22, 3013 (1981).

    CAS  Google Scholar 

  407. Benvegnu, R., G. Cimino, S. de Rosa, and S. de Stefano: Guggulsterol-Like Steroids from the Mediterranean Gorgonian Leptogorgia sarmentosa. Experientia 38, 1443 (1982).

    CAS  Google Scholar 

  408. Kingston, J.F., and A.G. Fallis: Marine Natural Products: Highly Functionalized Steroids (12 β-Hydroxy-24-norcholesta-l,4,22-trien-3-one and 12β-Acetoxy-24-nor- cholesta-l,4,22-trien-3-one) from the Sea Raspberry, Gersemia rubiformis. Can. J. Chem. 60, 820 (1982).

    CAS  Google Scholar 

  409. Sjöstrand, U., L. Bohlin, L. Fisher, M. Colin, and C. Djerassi: Minor and Trace Sterols from Marine Invertebrates. 28. A Novel Polyhydroxylated Sterol from the Soft Coral Anthelia glauca. Steroids 38, 347 (1981).

    Google Scholar 

  410. Tanaka, J., T. Higa, K. Tachibana, and T. Iwashita: Gorgost-5-ene-3 β,7α,11α, 12 β-tetraol 12-Monoacetate, a New Marine Sterol from the Gorgonian Isis hippuris. Chem. Lett. 1982, 1295.

    Google Scholar 

  411. Higa, T., J. Tanaka, and K. Tachibana: 18-Oxygenated Polyfunctional Steroids from the Gorgonian Isis hippuris. Tetrahedron Lett. 22, 2777 (1981).

    CAS  Google Scholar 

  412. Higa, T., J. Tanaka, Y. Tsukitani, and H. Kikuchi: Hippuristanols, Cytotoxic Polyoxygenated Steroids from the Gorgonian Isis hippuris. Chem. Lett. 1981, 1647.

    Google Scholar 

  413. Stonard, R.J., J.C. Petrovich, and R.J. Andersen: New C26 Sterol Peroxide from the Opisthobranch Mollusk Adalaria sp. and the Sea Pen Virgularia sp. Steroids 36, 81 (1980).

    CAS  Google Scholar 

  414. Kazlauskas, R., P.T. Murphy, B.N. Ravi, R.L. Sanders, and R.J. Wells: Spermidine Derivatives and 9,11-Secosteroids from a Soft Coral (Sinularia sp.). Aust. J. Chem. 35, 69 (1982).

    CAS  Google Scholar 

  415. Bonini, C., C.B. Cooper, R. Kazlauskas, R.J. Wells, and C. Djerassi: Minor and Trace Sterols in Marine Invertebrates. 41. Structure and Stereochemistry of Naturally Occurring 9,11-Seco Sterols. J. Org. Chem. 48, 2108 (1983).

    CAS  Google Scholar 

  416. Kobayashi, M., Y. Kiyota, S. Orito, Y. Kyogoku, and I. Kitagawa: Five New Steroidal Glycosides, Pregnedioside-A, -B, and their Three Monoacetates, from an Okinawan Soft Coral of Alcyonium sp. Tetrahedron Lett. 25, 3731 (1984).

    CAS  Google Scholar 

  417. Bandurraga, M.M., and W. Fenical: Isolation of the Muricins. Evidence of a Chemical Adaptation Against Fouling in the Marine Octocoral Muricea fruticosa (Gorgonacea). Tetrahedron 41, 1057 (1985).

    CAS  Google Scholar 

  418. Coll, J.C., and P.W. Sammarco: Terpenoid Toxins of Soft Corals (Cnidaria, Octocorallia): Their Nature, Toxicity, and Ecological Significance. Toxicon Suppl. 3, 69 (1983).

    Google Scholar 

  419. Coll, J.C., B.F. Bowden, D.M. Tapiolas, R.H. Willis, P. Djura, M. Streamer, and L. Trott: Studies of Australian Soft Corals - XXXV. The Terpenoid Chemistry of Soft Corals and Its Implications. Tetrahedron 41, 1085 (1985).

    CAS  Google Scholar 

  420. Webb, L., and J.C. Coll: Effects of Alcyonarian Coral Terpenes on Scleractinian Coral Photosynthesis and Respiration. Toxicon Suppl. 3, 485 (1983).

    Google Scholar 

  421. Bowden, B.F., J.C. Coll, and D.M. Tapiolas: Studies of Australian Soft Corals. XXX. A Novel Trisworsesquiterpene from a Cespitularia Species and the Isolation of Guaiazulene from a Small Blue Alcyonium Species. Aust. J. Chem. 36, 211 (1983).

    CAS  Google Scholar 

  422. Kobayashi, M., B.W. Son, M. Kido, Y. Kyogoku, and I. Kitagawa: Clavukerin A, a New Trinor-guaiane Sesquiterpene from the Okinawan Soft Coral Clavularia koellikeri. Chem. Pharm. Bull. (Japan) 31, 2160 (1983).

    CAS  Google Scholar 

  423. Kobayashi, M., B.W. Son, Y Kyogoku, and I. Kitagawa: Clavukerin C, a New Trircor-guaiane Sesquiterpene Having a Hydroperoxy Function, from the Okinawan Soft Coral Clavularia koellikeri. Chem. Pharm. Bull. (Japan) 32, 1667 (1984).

    CAS  Google Scholar 

  424. Izac, R.R., W. Fenical, and J.M. Wright: Inflatene, an Ichthyotoxic C12 Hydro­carbon from the Stoloniferan Soft Coral Clavularia inflata var. luzoniana. Tetrahedron Lett. 25, 1325 (1984).

    CAS  Google Scholar 

  425. Kashman, Y., M. Bodner, J.S. Finer-Moore, and J. Clardy: Δ9(15)-Africanene, a New Sesquiterpene Hydrocarbon from the Soft Coral Sinularia erecta. Experientia 36, 891 (1980).

    CAS  Google Scholar 

  426. Braekman, J.C., D. Daloze, B. Tursch, S.E. Hull, J.P. Declercq, G. Germain, and M. van Meerssche: Chemical Studies of Marine Invertebrates. XXXVIII. Δ9(15)-Africanene, a New Sesquiterpene Hydrocarbon from Sinularia polydactyla (Coelenterata, Octocorallia, Alcyonaceae). Experientia 36, 893 (1980).

    CAS  Google Scholar 

  427. Bowden, B.F., J.C. Coll, and S.J. Mitchell: Studies of Australian Soft Corals. XXI. A New Sesquiterpene from Nephthea chabrolii and an Investigation of the Common Clam Tridacna maxima. Aust. J. Chem. 33, 1833 (1980).

    CAS  Google Scholar 

  428. Fusetani, N., S. Matsunaga, and S. Konosu: Bioactive Marine Metabolites. I. Isolation of Guaiazulene from the Gorgonian Euplexaura erecta. Experientia 37, 680 (1981).

    CAS  Google Scholar 

  429. Li, M.K.W., and P.J. Scheuer: Halogenated Blue Pigments of a Deep Sea Gorgon­ian. Tetrahedron Lett. 25, 587 (1984).

    CAS  Google Scholar 

  430. Li, M.K.W., and P.J. Scheuer: N,N-Dimethylamino-3-guaiazulenylmethane from a Deep Sea Gorgonian. Te­trahedron Lett. 25, 4707 (1984).

    CAS  Google Scholar 

  431. Imre, S., R.H. Thomson, and B. Yalhi: Linderazulene, a New Naturally Occurring Pigment from the Gorgonian Paramuricea chamaeleon. Experientia 37, 442 (1981).

    CAS  Google Scholar 

  432. Li, M.K.W., and P.J. Scheuer: A Guaianolide Pigment from a Deep Sea Gorgonian. Tetrahedron Lett. 25, 2109 (1984).

    CAS  Google Scholar 

  433. Alpertunga, B., S. Imre, H.J. Cowe, P.J. Cox, and R.H. Thomson: A Photo Artefact from Linderazulene. Tetrahedron Lett. 24, 4461 (1983).

    CAS  Google Scholar 

  434. Gopichand, Y., F.J. Schmitz, and P.G. Schmidt: Marine Natural Products: Two New Acyclic Sesquiterpene Hydrocarbons from the Gorgonian Plexaurella grisea. J. Org. Chem. 45, 2523 (1980).

    CAS  Google Scholar 

  435. Bowden, B.F., J.C. Coll, E.D. de Silva, M.S.L. de Costa, P. J. Djura, M. Mahendran, and D.M. Tapiolas: Studies of Australian Soft Corals. XXXI. Novel Furano- sesquiterpenes from Several Sinularian Soft Corals (Coelenterata, Octocorallia, Al- cyonacea). Aust. J. Chem. 36, 371 (1983).

    CAS  Google Scholar 

  436. Cimino, G., S. de Rosa, S. de Stefano, and G. Sodano: A New Furanosesquiterpene from the Mediterranean Alcyonacean Alcyonum palmatum. J. Nat. Prod. 47, 877 (1984).

    CAS  Google Scholar 

  437. Bowden, B.F., J.C. Braekman, J.C. Coll, and S.J. Mitchell: Studies of Australian Soft Corals. XX. A New Sesquiterpene Furan from Soft Corals of the Family Xeniidae and an Examination of Clavularia inflata from North Queensland Waters. Aust. J. Chem. 33, 927 (1980).

    CAS  Google Scholar 

  438. Izac, R.R., M.M. Bandurraga, J.M. Wasylyk, F.W. Dunn, and W. Fenical: Germacrene Derivatives from Diverse Marine Soft-Corals (Octocorallia). Tetrahedron 38, 301 (1982).

    CAS  Google Scholar 

  439. Bowden, B.F., J.C. Coll, S.J. Mitchell, J.L.E. Nemorin, and S. Sternhell: Studies of Australian Soft Corals. XXIII. The Co-occurrence of Bicyclogermacrene and Lemnacarnol Derivatives in Parerythropodium fulvum. Tetrahedron Lett. 21, 3105 (1980).

    CAS  Google Scholar 

  440. Kobayashi, M., T. Yasuzawa, Y. Kyogoku, M. Kido, and I. Kitagawa: Three New ent-Valerenane Sesquiterpenes from an Okinawan Soft Coral. Chem. Pharm. Bull. (Japan) 30, 3431 (1982).

    CAS  Google Scholar 

  441. Izac, R.R., S.E. Poet, W. Fenical, D. van Engen, and J. Clardy: The Structure of Pacifigorgiol, an Ichthyotoxic Sesquiterpenoid from the Pacific Gorgonian Coral Pacifigorgia cf. adamsii. Tetrahedron Lett. 23, 3743 (1982).

    CAS  Google Scholar 

  442. Martin, M., and J. Clardy: The Synthesis of Pacifigorgiol. Pure & Appl. Chem. 54, 1915 (1982).

    CAS  Google Scholar 

  443. Bowden, B.F., J.C. Coll, and S.J. Mitchell: Studies of Australian Soft Corals. XVI. Two New Sesquiterpenes from Lemnalia humesi. Aust. J. Chem. 33, 681 (1980).

    CAS  Google Scholar 

  444. Do, M.N., and K.L. Erickson: An Aristolane Sesquiterpenoid from the Sea Pen Scytalium splendens. J. Org. Chem. 48, 4410 (1983).

    CAS  Google Scholar 

  445. Bowden, B.F., J.C. Coll, and S.J. Mitchell: Studies of Australian Soft Corals. XIX. Two New Sesquiterpenes with the Nardosinane Skeleton from a Paralemnalia Species. Aust. J. Chem. 33, 885 (1980).

    CAS  Google Scholar 

  446. Bowden, B.F., J.C. Coll, S.J. Mitchell, B.W. Skelton, and A.H. White: Studies of Australian Soft Corals. XXII. The Structures of Two Novel Sesquiterpenes and a Nor Sesquiterpene from Lemnalia africana, Confirmed by a Single-Crystal X-Ray Study. Aust. J. Chem. 33, 2737 (1980).

    CAS  Google Scholar 

  447. Izac, R.R., P. Schneider, M. Swain, and W. Fenical: New Aforsesquiterpenoids of Apparent Nardosinane Origin from the Pacific Soft-Coral Paralemnalia thyrsoides. Tetrahedron Lett. 23, 817 (1982).

    CAS  Google Scholar 

  448. Izac, R.R., W. Fenical, B. Tagle, and J. Clardy: Neolemnane and Eremophilane Sesquiterpenoids from the Pacific Soft Coral Lemnalia africana. Tetrahedron 37, 2569 (1981).

    CAS  Google Scholar 

  449. Braekman, J.C., D. Daloze, A. Dupont, B. Tursch, J.P. Declercq, G. Germain, and M. van Meerssche: Chemical Studies of Marine Invertebrates-XLIII. Novel Sesquiterpenes from Clavularia inflata and Clavularia koellikeri (Coelenterata, Octocorallia, Stolonifera). Tetrahedron 37, 179 (1981).

    CAS  Google Scholar 

  450. Kikuchi, H., Y. Tsukitani, Y. Yamada, K. Iguchi, S.A. Drexler, and J. Clardy: Lemnalol, a New Sesquiterpenoid from the Soft Coral Lemnalia tenuis Verseveldt. Tetrahedron Lett. 23, 1063 (1982).

    CAS  Google Scholar 

  451. Kikuchi, H., T. Manda, K. Kobayashi, Y. Yamada, and K. Iguchi: Anti-Tumor Activity of Lemnalol Isolated from the Soft Coral Lemnalia tenuis Verseveldt. Chem. Pharm. Bull. (Japan) 31, 1086 (1983).

    CAS  Google Scholar 

  452. Kaisin, M., J.C. Braekman, D. Daloze, and B. Tursch: Novel Acetoxycapnellenes from the Alcyonacean Capnella imbricata. Tetrahedron 41, 1067 (1985).

    CAS  Google Scholar 

  453. Sheikh, Y.M., G. Singy, M. Kaisin, H. Eggert, C. Djerassi, B. Tursch, D. Daloze, and J.C. Braekman: Terpenoids - LXXI. Chemical Studies of Marine Invertebrates - XIV. Four Representatives of a Novel Sesquiterpene Class - The Capnellane Skeleton. Tetrahedron 32, 1171 (1976).

    CAS  Google Scholar 

  454. Groweiss, A., W. Fenical, H. Cun-heng, J. Clardy, W. Zhongde, Y. Zhongnian, and L. Kanghou: Subergorgic Acid, a Novel Tricyclopentanoid Cardiotoxin from the Pacific Gorgonian Coral Subergorgia suberosa. Tetrahedron Lett. 26, 2379 (1985).

    CAS  Google Scholar 

  455. Fenical, W., R.K. Okuda, M.M. Bandurraga, P. Culver, and R.S. Jacobs: Lophotoxin: A Novel Neuromuscular Toxin from Pacific Sea Whips of the Genus Lophogorgia. Science 212, 1512 (1981).

    CAS  Google Scholar 

  456. Bandurraga, M.M., B. McKittrick, W. Fenical, E. Arnold, and J. Clardy: Diketone Cembrenolides from the Pacific Gorgonian Lophogorgia alba. Tetrahedron 38, 305 (1982).

    CAS  Google Scholar 

  457. Culver, P., and R.S. Jacobs: Lophotoxin: A Neuromuscular Acting Toxin from the Sea Whip (Lophogorgia rigida). Toxicon 19, 825 (1981).

    CAS  Google Scholar 

  458. Kazlauskas, R., J.A. Baird-Lambert, P.T. Murphy, and R.J. Wells: Two New Cembrane Diterpenes from a Soft Coral (Sarcophyton Species). Aust. J. Chem. 35, 61 (1982).

    CAS  Google Scholar 

  459. Kobayashi, J., Y. Ohizumi, H. Nakamura, T. Yamakado, T. Matsuzaki, and Y. Hirata: Caantagonistic Substance from Soft Coral of the Genus Sarcophyton. Experientia 39, 67 (1983).

    CAS  Google Scholar 

  460. Bowden, B.F., J.C. Coll, and S.J. Mitchell: Studies of Australian Soft Corals. XVIII. Further Cembranoid Diterpenes from Soft Corals of the Genus Sarcophyton. Aust. J. Chem. 33, 879 (1980).

    CAS  Google Scholar 

  461. Uchio, Y., J. Toyota, H. Nozaki, M. Nakayama, Y. Nishizono, and T. Hase: Lobohedleolide and (7 Z)-Lobohedleolide, New Cembranolides from the Soft Coral Lobophytum hedleyi Whitelegge. Tetrahedron Lett. 22, 4089 (1981).

    CAS  Google Scholar 

  462. Norton, R.S., and R. Kazlauskas: 13C NMR-Study of Flexibilide, an Anti-Inflam­matory Agent from a Soft Coral. Experientia 36, 276 (1980).

    CAS  Google Scholar 

  463. Mori, K., S. Suzuki, K. Iguchi, and Y. Yamada: 8,11-Epoxy Bridged Cembranolide Diterpene from the Soft Coral Sinularia flexibilis. Chem. Lett. 1983, 1515.

    Google Scholar 

  464. Uchio, Y., S. Eguchi, J. Kuramoto, M. Nakayama, and T. Hase: Denticulatolide, an Ichthyotoxic Peroxide-Containing Cembranolide from the Soft Coral Lobophytum denticulatum. Tetrahedron Lett. 26, 4487 (1985).

    CAS  Google Scholar 

  465. Kashman, Y., S. Carmely, and A. Groweiss: Further Cembranoid Derivatives from the Red Sea Soft Corals Alcyonium flaccidum and Lobophytum crassum. J. Org. Chem. 46, 3592 (1981).

    CAS  Google Scholar 

  466. Poet, S.E., and B.N. Ravi: Three New Diterpenes from a Soft Coral Nephthea Species. Aust. J. Chem. 35, 77 (1982).

    CAS  Google Scholar 

  467. Blackman, A.J., B.F. Bowden, J.C. Coll, B. Frick, M. Mahendran, and S.J. Mitchell: Studies of Australian Soft Corals. XXIX’ Several New Cembranoid Di­terpenes from Nephthea brassica and Related Diterpenes from a Sarcophyton Species. Aust. J. Chem. 35, 1873 (1982).

    CAS  Google Scholar 

  468. Kinamoni, Z., A. Groweiss, S. Carmely, Y. Kashman, and Y Loya: Several New Cembranoid Diterpenes from Three Soft Corals of the Red Sea. Tetrahedron 39, 1643 (1983).

    CAS  Google Scholar 

  469. Bowden, B.F., J.C. Coll, and D.M. Tapiolas: Studies of Australian Soft Corals. XXXIII. New Cembranoid Diterpenes from a Lobophytum Species. Aust. J. Chem. 36, 2289 (1983).

    CAS  Google Scholar 

  470. Nakagawa, T., M. Kobayashi, K. Hayashi, and H. Mitsuhashi: Marine Terpenes and Terpenoids. II. Structures of Three Cembrane-type Diterpenes, Sarcophytol-C, Sarcophytol-D, and Sarcophytol-E, from the Soft Coral, Sarcophyton glaucum Q. et G. Chem. Pharm. Bull. (Japan) 29, 82 (1981).

    CAS  Google Scholar 

  471. Uchio, Y., H. Nabeya, M. Nakayama, S. Hayashi, and T. Hase: Cembrenene and Mayol, Two New Cembranoid Diterpenes from the Soft Coral Sinularia mayi. Tetrahedron Lett. 22, 1689 (1981).

    CAS  Google Scholar 

  472. Bowden, B.F., J.C. Coll, S.J. Mitchell, and R. Kazlauskas: Studies of Australian Soft Corals. XXIV. Two Cembranoid Diterpenes from the Soft Coral Sinularia facile. Aust. J. Chem. 34, 1551 (1981).

    CAS  Google Scholar 

  473. Carmely, S., A. Groweiss, and Y. Kashman: Decaryiol, a New Cembrane Diterpene from the Marine Soft Coral Sarcophyton decaryi. J. Org. Chem. 46, 4279 (1981).

    CAS  Google Scholar 

  474. Uchio, Y., M. Nitta, H. Nozaki, M. Nakayama, T. Iwagawa, and T. Hase: 10-Oxo-, 10-Hydroxy-, and 10-Methoxycembrenes from the Soft Coral Sarcophyta elegans. Chem. Lett. 1983, 1719.

    Google Scholar 

  475. Uchio, Y., S. Eguchi, M. Nakayama, and T. Hase: The Isolation of Two Simple γ-Lactonic Cembranolides from the Soft Coral Sinularia mayi. Chem. Lett. 1982, 277.

    Google Scholar 

  476. Yamada, Y., S. Suzuki, K. Iguchi, H. Kikuchi, Y. Tsukitani, H. Horiai, and F. Shibayama: Studies on Marine Natural Products. IV. The Stereochemistry of 13-Membered Carbocyclic Cembranolide Diterpenes from the Soft Coral Lobophy- tum pauciflorum (Ehrenberg). Tetrahedron Lett. 21, 3911 (1980).

    CAS  Google Scholar 

  477. Frincke, J.M., D.E. McIntyre, and D.J. Faulkner: Deoxosarcophine from a Soft Coral, Sarcophyton sp. Tetrahedron Lett. 21, 735 (1980).

    CAS  Google Scholar 

  478. Yamada, Y., S. Suzuki, K. Iguchi, H. Kikuchi, Y. Tsukitani, and H. Horiai: Studies on Marine Natural Products. III. Two New Cembranolides from the Soft Coral Lobophytum pauciflorum (Ehrenberg). Chem. Pharm. Bull. (Japan) 28, 2035 (1980).

    CAS  Google Scholar 

  479. Burns, K.P., R. Kazlauskas, P.T. Murphy, R.J. Wells, and P. Schonholzer: Two Cembranes from Cespitularia Species (Soft Coral). Aust. J. Chem. 35, 85 (1982).

    CAS  Google Scholar 

  480. Gopichand, Y., L.S. Ciereszko, F.J. Schmitz, D. Switzner, A. Rahman, M.B. Hossain, and D. van der Helm: Further Studies of the Terpenoid Content in the Gorgonian Eunicea succinea: 12,13-Bisepieupalmerin, a New Cembranolide. J. Nat. Prod. 47, 607 (1984).

    CAS  Google Scholar 

  481. Toth, J.A., B.J. Burreson, P.J. Scheuer, J. Finer-Moore, and J. Clardy: Emblide, a New Polyfunctional Cembranolide from the Soft Coral Sarcophyton glaucum. Tetrahedron 36, 1307 (1980).

    CAS  Google Scholar 

  482. Bowden, B.F., J.C. Coll, and R.H. Willis: Studies of Australian Soft Corals. XXVII. Two Novel Diterpenes from Sarcophyton glaucum. Aust. J. Chem. 35, 621 (1982).

    CAS  Google Scholar 

  483. Uchio, Y., M. Nitta, M. Nakayama, T. Iwagawa, and T. Hase: Ketoemblide and Sarcophytolide, Two New Cembranolides with ε-Lactone Function from the Soft Coral Sarcophyta elegans. Chem. Lett. 1983, 613.

    Google Scholar 

  484. Estrella, D.J., and R.S. Jacobs: Deoxosarcophine (DXS), a Potentiator of Skeletal Muscle Contraction. Fed. Proc. 43, 586 (1984).

    Google Scholar 

  485. Bandurraga, M.M., W. Fenical, S.F. Donovan, and J. Clardy: Pseudopterolide, an Irregular Diterpenoid with Unusual Cytotoxic Properties from the Caribbean Sea Whip Pseudopterogorgia acerosa (Pallas) (Gorgonacea). J. Am. Chem. Soc. 104, 6463 (1982).

    CAS  Google Scholar 

  486. Look, S.A., W. Fenical, Z. Qi-tai, and J. Clardy: Calyculones, New Cubitane Diterpenoids from the Caribbean Gorgonian Octocoral Eunicea calyculata. J. Org. Chem. 49, 1417 (1984).

    CAS  Google Scholar 

  487. Look, S.A., and W. Fenical: New Bicyclic Diterpenoids from the Caribbean Gor- gonian Octocoral Eunicea calyculata. J. Org. Chem. 47, 4129 (1982).

    CAS  Google Scholar 

  488. Kobayashi, M., B.W. Son, T. Fujiwara, Y. Kyogoku, and I. Kitagawa: Neodolabelline, a Methyl Migrated Dolabellane-Type Diterpene from the Okinawan Soft Coral Clavularia koellikeri. Tetrahedron Lett. 25, 5543 (1984).

    CAS  Google Scholar 

  489. Look, S.A., W. Fenical, D. van Engen, and J. Clardy: Erythrolides: Unique Marine Diterpenoids Interrelated by a Naturally Occurring Di-π-methane Rearrangement. J. Am. Chem. Soc. 106, 5026 (1984).

    CAS  Google Scholar 

  490. Grode, S.H., T.R. James, Jr., J.H. Cardellina II, and K.D. Onan: Molecular Structures of the Briantheins, New Insecticidal Diterpenes from Briareum polyanthes. J. Org. Chem. 48, 5203 (1983).

    CAS  Google Scholar 

  491. Grode, S.H., T.R. James, and J.H. Cardellina II: Brianthein Z, a New Polyfunctional Diterpene from the Gorgonian Briareum polyanthes. Tetrahedron Lett. 24, 691 (1983).

    CAS  Google Scholar 

  492. Cardellina II, J.H., T.R. James, Jr., M.H.M. Chen, and J. Clardy: Structure of Brianthein W, from the Soft Coral Briareum polyanthes. J. Org. Chem. 49, 3398 (1984).

    CAS  Google Scholar 

  493. Clastres, A., A. Ahond, C. Poupat, P. Potier, and S.K. Kan: Invertébrés Marins Du Lagon Néo-Calédonien, II. Étude Structurale De Trois Nouveaux Diterpènes Isolés Du Pennatulaire Pteroides laboutei. J. Nat. Prod. 47, 155 (1984).

    CAS  Google Scholar 

  494. Clastres, A., P. Laboute, A. Ahond, C. Poupat, and P. Potier: Invertébrés Marins Du Lagon Néo-Calédonien, III. Étude Structurale De Trois Nouveaux Diterpènes Isolés Du Pennatulaire, Cavernulina grandiflora. J. Nat. Prod. 47, 162 (1984).

    CAS  Google Scholar 

  495. Ravi, B.N., J.F. Marwood, and R.J. Wells: Three New Diterpenes from the Sea Pen Scytalium tentaculatum. Aust. J. Chem. 33, 2307 (1980).

    CAS  Google Scholar 

  496. Kashman, Y.: A New Diterpenoid Related to Eunicellin and Cladiellin from a Muricella sp. Tetrahedron Lett. 21, 879 (1980).

    CAS  Google Scholar 

  497. Hochlowski, J.E., and D.J. Faulkner: A Diterpene Related to Cladiellin from a Pacific Soft Coral. Tetrahedron Lett. 21, 4055 (1980).

    CAS  Google Scholar 

  498. Stierle, D.B., B. Carte, D.J. Faulkner, B. Tagle, and J. Clardy: The Asbestinins, a Novel Class of Diterpenes from the Gorgonian Briareum asbestinum. J. Am. Chem. Soc. 102, 5088 (1980).

    CAS  Google Scholar 

  499. Selover, S.J., P. Crews, B. Tagle, and J. Clardy: New Diterpenes from the Com­mon Caribbean Gorgonian Briareum asbestinum (Pallus). J. Org. Chem. 46, 964 (1981).

    CAS  Google Scholar 

  500. Kashman, Y., and A. Groweiss: New Diterpenoids from the Soft Corals Xenia macrospiculata and Xenia obscuronata. J. Org. Chem. 45, 3814 (1980).

    CAS  Google Scholar 

  501. Vanderah, D.J., P.A. Steudler, L.S. Ciereszko, F. J. Schmitz, J.D. Ekstrand, and D. van der Helm: Marine Natural Products. Xenicin: a Diterpenoid Possessing a Nine-Membered Ring from the Soft Coral Xenia elongata. J. Am. Chem. Soc. 99, 5780 (1977).

    CAS  Google Scholar 

  502. Bowden, B.F., J.C. Coll, E. Ditzel, S.J. Mitchell, and W.T. Robinson: Studies of the Australian Soft Corals. XXVIII. The Structure Determination of Two New Diterpenes from the Genus Xenia (Alcyonacea). Aust. J. Chem. 35, 997 (1982).

    CAS  Google Scholar 

  503. Groweiss, A., and Y. Kashman: Eight New Xenia Diterpenoids from Three Soft Corals of the Red Sea. Tetrahedron 39, 3385 (1983).

    CAS  Google Scholar 

  504. Ahond, A., B.F. Bowden, J.C. Coll, J.-D. Fourneron, and S.J. Mitchell: Studies of Australian Soft Corals. XXV. Several Caryophyllene-Based Diterpenes from a Nephthea Species. Aust. J. Chem. 34, 2657 (1981).

    CAS  Google Scholar 

  505. Coval, S.J., P.J. Scheuer, G.K. Matsumoto, and J. Clardy: Two New Xenicin Diterpenoids from the Octocoral Anthelia edmondsoni. Tetrahedron 40, 3823 (1984).

    CAS  Google Scholar 

  506. Schwartz, R.E., P.J. Scheuer, V. Zabel, and W.H. Watson: The Coraxeniolides, Constituents of Pink Coral, Corallium sp. Tetrahedron 37, 2725 (1981).

    CAS  Google Scholar 

  507. Burns, K.P., G. Englert, R. Kazlauskas, P.T. Murphy, P. Schönholzer, and R.J. Wells: The Structure of a Diterpene with a New Carbocyclic Ring Skeleton from the Soft Coral Efflatounaria sp. nov. Aust. J. Chem. 36, 171 (1983).

    CAS  Google Scholar 

  508. Kobayashi, M., T. Yasuzawa, Y. Kobayashi, Y. Kyogoku, and I. Kitagawa: Alcyonolide, a Novel Diterpenoid from a Soft Coral. Tetrahedron Lett. 22, 4445 (1981).

    CAS  Google Scholar 

  509. Bowden, B.F., J.C. Coll, V.A. Patrick, D.M. Tapiolas, and A.H. White: Studies of Australian Soft Corals. XXXII. The Structure Determination of Degraded Xenicin-Type Diterpenes from Several Efflatounaria Species. Aust. J. Chem. 36, 2279 (1983).

    CAS  Google Scholar 

  510. Baird-Lambert, J., R.W. Dunlop, and D.D. Jamieson: Anticonvulsant Activity of a Novel Diterpene Isolated from a Soft Coral of the Genus Lobophytum. Arzneim. Forsch./Drud Res. 30 (I), 964 (1980).

    CAS  Google Scholar 

  511. Ravi, B.N., and R.J. Wells: Lipid and Terpenoid Metabolites of the Gorgonian Plexaura flava. Aust. J. Chem. 35, 105 (1982).

    CAS  Google Scholar 

  512. Bowden, B.F., and J.C. Coll: Studies of Australian Soft Corals. XXVI. Tetraprenyl- benzoquinone Derivatives from a Nephthea Species of Soft Coral (Octocorallia, Al- cyonacea). Aust. J. Chem. 34, 2677 (1981).

    CAS  Google Scholar 

  513. Carmely, S., Y. Kashman, Y. Loya, and Y. Benayahu: New Prostaglandin (PGF) Derivatives from the Soft Coral Lobophyton depressum. Tetrahedron Lett. 21, 875 (1980).

    CAS  Google Scholar 

  514. Corey, E.J., P.T. Lansbury, Jr., and Y. Yamada: Identification of a New Eicosanoid from in Vitro Biosynthetic Experiments with Clavularia viridis. Implications for the Biosynthesis of Clavulones. Tetrahedron Lett. 26, 4171 (1985).

    CAS  Google Scholar 

  515. Kobayashi, M., T. Yasuzawa, M. Yoshihara, H. Akutsu, Y. Kyogoku, and I. Kitagawa: Four New Prostanoids: Claviridenone-A, -B, -C, and -D from the Okinawan Soft Coral Clavularia viridis. Tetrahedron Lett. 23, 5331 (1982).

    CAS  Google Scholar 

  516. Kobayashi, M., T. Yasuzawa, M. Yoshihara, B.W. Son, Y. Kyogoku, and I. Kitagawa: Absolute Stereostructures of Claviridenone-A, -B, -C, and -D, Four Prostanoids from the Okinawan Soft Coral Clavularia viridis. Chem. Pharm. Bull. (Japan) 31, 1440 (1983).

    CAS  Google Scholar 

  517. Kitagawa, I., M. Kobayashi, T. Yasuzawa, B.W. Son, M. Yoshihara, and Y. Kyogoku: New Prostanoids from Soft Coral. Tetrahedron 41, 995 (1985).

    CAS  Google Scholar 

  518. Kikuchi, H., Y. Tsukitani, K. Iguchi, and Y. Yamada: Clavulones, New Type of Prostanoids from the Stolonifer Clavularia viridis Quoy and Gaimard. Tetrahedron Lett. 23, 5171 (1982).

    CAS  Google Scholar 

  519. Absolute Stereochemistry of New Prostanoids Clavulone I, II and III, from Clavularia viridis Quoy and Gaimard. Tetrahedron Lett. 24, 1549 (1983).

    Google Scholar 

  520. Iguchi, K., Y. Yamada, H. Kikuchi, and Y. Tsukitani: Novel C-20-Oxygenated Prostanoids, 20-Acetoxyclavulones, from the Stolonifer Clavularia viridis Quoy and Gaimard. Tetrahedron Lett. 24, 4433 (1983).

    CAS  Google Scholar 

  521. Baker, B.J., R.K. Okuda, P.T.K. Yu, and P.J. Scheuer: Punaglandins: Halogenated Antitumor Eicosanoids from the Octocoral Telesto riisei. J. Am. Chem. Soc. 107, 2976 (1985).

    CAS  Google Scholar 

  522. Iguchi, K., S. Kaneta, K. Mori, Y. Yamada, A. Honda, and Y. Mori: Chlorovulones, New Halogenated Marine Prostanoids with an Antitumor Activity from the Stolonifer Clavularia viridis Quoy and Gaimard. Tetrahedron Lett. 26, 5787 (1985).

    CAS  Google Scholar 

  523. Corey, E.J., and M.M. Mehrotra: Total Synthesis of (±)-Clavulones. J. Am. Chem. Soc. 106, 3384 (1984).

    CAS  Google Scholar 

  524. Nagaoka, H., T. Miyakoshi, and Y. Yamada: Total Synthesis of Marine Prostan­oids Clavulones. Tetrahedron Lett. 25, 3621 (1984).

    CAS  Google Scholar 

  525. Hashimoto, S., Y. Arai, and N. Hamanaka: Synthesis of Clavulones (Claviriden- ones). Tetrahedron Lett. 26, 2679 (1985).

    CAS  Google Scholar 

  526. Kikuchi, H., Y. Tsukitani, H. Nakanishi, I. Shimizu, S. Saitoh, K. Iguchi, and Y. Yamada: New Butenolides from the Gorgonian Euplexaura flava (Nutting). Chem. Lett. 1982, 233.

    Google Scholar 

  527. Kikuchi, H., Y. Tsukitani, H. Nakanishi, I. Shimizu, S. Saitoh, K. Iguchi, and Y. Yamada: Studies on Marine Natural Products. VIII. New Butenolides from the Gorgonian Euplexaura flava (Nutting). Chem. Pharm. Bull. (Japan) 31, 1172 (1983).

    CAS  Google Scholar 

  528. Endo, M., M. Nakagawa, Y. Hamamoto, and T. Nakanishi: Clavularins, a New Class of Cytotoxic Compounds Isolated from the Soft Coral, Clavularia koellikeri. J. Chem. Soc., Chem. Commun. 1983, 322. Erratum: J. Chem. Soc., Chem. Commun. 1983, 980.

    Google Scholar 

  529. Chantrapromma, K., J.S. McManis, and B. Ganem: Synthesis of Cytotoxic Spermidine Metabolites from the Soft Coral Sinularia brongersmai. Tetrahedron Lett. 21, 2605 (1980).

    CAS  Google Scholar 

  530. Kazlauskas, R., J.F. Mar wood, and R.J. Wells: 2-Phenylethylamides of a Novel Lipid Acid; Atrial Stimulants from the Soft Coral Sinularia flexibilis. Aust. J. Chem. 33, 1799 (1980).

    CAS  Google Scholar 

  531. Bowden, B.F., P.S. Clezy, J.C. Coll, B.N. Ravi, and D.M. Tapiólas: Studies of Australian Soft Corals. XXXIV. A New Substituted Pyrrole from a Soft Coral- Sponge Association. Aust. J. Chem. 37, 227 (1984).

    CAS  Google Scholar 

  532. Muramatsu, I., M. Fujiwara, S. Ikushima, and K. Ashida: Effects of Goniopora Toxin on Guinea-Pig Blood Vessels. Naunyn-Schmiedeberg’s Arch. Pharmacol. 312, 193 (1980).

    CAS  Google Scholar 

  533. Fujiwara, M., S.-C. Hong, and I. Muramatsu: Effects of Goniopora Toxin on Non-Adrenergic, Non-Cholinergic Response and Purine Nucleotide Release in Guinea-Pig Taenia Coli. J. Physiol. 326, 515 (1982).

    CAS  Google Scholar 

  534. Ikushima, S., I. Muramatsu, and M. Fujiwara: Nicotine-Induced Response in Guinea-Pig Aorta Enhanced by Goniopora Toxin. J. Pharmacol, exp. Ther. 223, 790 (1982).

    CAS  Google Scholar 

  535. Lesniak, A.P., and E.H. Liu: Characterization of a Hemagglutinin from Leptogorgia virgulata. Comp. Biochem. Physiol. 71B, 305 (1982).

    Google Scholar 

  536. Carlé, J.S., and C. Christophersen: Dogger Bank Itch. The Allergen Is (2-Hydroxy- ethyl)dimethylsulfonium Ion. J. Am. Chem. Soc. 102, 5107 (1980).

    Google Scholar 

  537. Carlé, J.S., and C. Christophersen: Dogger Bank Itch. 2. An Allergic Contact Dermatitis. Bull. Soc. Chim. Belg. 89, 1087 (1980).

    Google Scholar 

  538. Carlé, J.S., and C. Christophersen: Dogger Bank Itch. 4. An Eczema-Causing Sulfoxonium Ion from the Marine Animal, Alcyonidium gelatinosum (Bryozoa). Toxicon 20, 307 (1982).

    Google Scholar 

  539. Carlé, J.S., and C. Christophersen: Marine Alkaloids. 2. Bromo Alkaloids from the Marine Bryozoan Flustra foliacea. Isolation and Structure Elucidation. J. Org. Chem. 45, 1586 (1980).

    Google Scholar 

  540. Carlé, J.S., and C. Christophersen: Marine Alkaloids. 3. Biomo-Substituted Alkaloids from the Marine Bryozoan Flustra foliacea, Flustramine C and Flustraminol A and B. J. Org. Chem. 46, 3440 (1981).

    Google Scholar 

  541. Wright, J.L.C.: A New Antibiotic from the Marine Bryozoan Flustra foliaceae. J. Nat. Prod. 47, 893 (1984).

    CAS  Google Scholar 

  542. Wulff, P., J.S. Carlé, and C. Christophersen: Marine Alkaloids. Part 4. A Form- amide, Flustrabromine, from the Marine Bryozoan Flustra foliacea. J. Chem. Soc., Perkin Trans. I 1981, 2895.

    Google Scholar 

  543. Wulff, P., J.S. Carlé, and C. Christophersen: Marine Alkaloids. 6. The First Naturally Occurring Bromo-Substituted Quino-line from Flustra foliacea. Comp. Biochem. Physiol. 71B, 525 (1982).

    Google Scholar 

  544. Sato, A., and W. Fenical: Gramine-Derived Bromo-Alkaloids from the Marine Bryozoan Zoobotryon verticillatum. Tetrahedron Lett. 24, 481 (1983).

    CAS  Google Scholar 

  545. Ayer, S.W., R.J. Andersen, H. Cun-heng, and J. Clardy: Phidolopin, a New Purine Derivative from the Bryozoan Phidolopora pacifica. J. Org. Chem. 49, 3869 (1984).

    CAS  Google Scholar 

  546. Hirota, K., K. Kubo, Y Kitade, and Y. Maki: Synthesis of Phidolopin, 7-(4-Hy- droxy-3-nitrobenzyl)-l,3-dimethylxanthine from the Bryozoan Phidolopora pacifica. Tetrahedron Lett. 26, 2355 (1985).

    CAS  Google Scholar 

  547. Pettit, G.R., C.L. Herald, D.L. Doubek, D.L. Herald, E. Arnold, and J. Clardy: Isolation and Structure of Bryostatin 1. J. Am. Chem. Soc. 104, 6846 (1982).

    CAS  Google Scholar 

  548. Pettit, G.R., C.L. Herald, Y. Kamano, D. Gust, and R. Aoyagi: The Structure of Bryostatin 2 from the Marine Bryozoan Bugula neritina. J. Nat. Prod. 46, 528 (1983).

    CAS  Google Scholar 

  549. Pettit, G.R., C.L. Herald, and Y. Kamano: Structure of the Bugula neritina (Marine Bryozoa) Antineoplastic Component Bryostatin 3. J. Org. Chem. 48, 5354 (1983).

    CAS  Google Scholar 

  550. Pettit, G.R., Y. Kamano, C.L. Herald, and M. Tozawa: Structure of Bryostatin 4. An Important Antineoplastic Constituent of Geographically Diverse Bugula neritina (Bryozoa). J. Am. Chem. Soc. 106, 6768 (1984).

    CAS  Google Scholar 

  551. Pettit, G.R., Y. Kamano, R. Aoyagi, C.L. Herald, D.L. Doubek, J.M. Schmidt, and J.J. Rudloe: Antineoplastic Agents 100. The Marine Bryozoan Amathia convoluta. Tetrahedron 41, 985 (1985).

    CAS  Google Scholar 

  552. Cimino, G., S. de Stefano, S. de Rosa, G. Sodano, and G. Villani: Novel Metabo­lites from Some Predator-Prey Pairs. Bull. Soc. Chim. Belg. 89, 1069 (1980).

    CAS  Google Scholar 

  553. Fuhrman, F.A., G.J. Fuhrman, Y.H. Kim, L.A. Pavelka, and H.S. Mosher: Doridosine: A New Hypotensive N-Methylpurine Riboside from the Nudibranch Anisodoris nobilis. Science 207, 193 (1980).

    CAS  Google Scholar 

  554. Kim, Y.H., R.J. Nachman, L. Pavelka, H.S. Mosher, F.A. Fuhrman, and G.J. Fuhrman: Doridosine, 1-Methylisoguanosine, from Anisodoris nobilis; Structure, Pharmacological Properties, and Synthesis. J. Nat. Prod. 44, 206 (1981).

    CAS  Google Scholar 

  555. Fuhrman, F.A., G.J. Fuhrman, R.J. Nachman, and H.S. Mosher: Isoguanosine: Isolation from an Animal. Science 212, 557 (1981).

    CAS  Google Scholar 

  556. Thompson, J.E., R.P. Walker, S.J. Wratten, and D.J. Faulkner: A Chemical Defense Mechanism for the Nudibranch Cadlina luteomarginata. Tetrahedron 38, 1865 (1982).

    CAS  Google Scholar 

  557. Hellou, J., R.J. Andersen, and J.E. Thompson: Terpenoids from the Dorid Nudi­branch Cadlina luteomarginata. Tetrahedron 38, 1875 (1982).

    CAS  Google Scholar 

  558. Cimino, G., S. de Rosa, S. de Stefano, and G. Sodano: The Chemical Defense of Four Mediterranean Nudibranchs. Comp. Biochem. Physiol. 73B, 471 (1982).

    Google Scholar 

  559. De Silva, E.D., and P.J. Scheuer: Furanoditerpenoids from the Dorid Nudibranch Casella atromarginata. Heterocycles 17, 167 (1982).

    Google Scholar 

  560. Cimino, G., S. de Rosa, S. de Stefano, R. Morrone, and G. Sodano: The Chemical Defense of Nudibranch Molluscs. Structure, Biosynthetic Origin, and Defensive Properties of Terpenoids from the Dorid Nudibranch Dendrodoris grandiflora. Tetrahedron 41, 1093 (1985).

    CAS  Google Scholar 

  561. Schulte, G.R., and P.J. Scheuer: Defense Allomones of Some Marine Mollusks. Tetrahedron 38, 1857 (1982).

    CAS  Google Scholar 

  562. Ayer, S.W., and R.J. Andersen: Steroidal Antifeedants from the Dorid Nudibranch Aldisa sanguinea cooperi. Tetrahedron Lett. 23, 1039 (1982).

    CAS  Google Scholar 

  563. Ayer, S.W., and R.J. Andersen: Degraded Monoterpenes from the Opisthobranch Mollusc Melibe leonina. Experientia 39, 255 (1983).

    CAS  Google Scholar 

  564. Andersen, R.J., and F.W. Sum: Farnesic Acid Glycerides from the Nudibranch Archidoris odhneri: Tetrahedron Lett. 21, 797 (1980).

    CAS  Google Scholar 

  565. Gustafson, K., and R.J. Andersen: Chemical Studies of British Columbia Nudi- branchs. Tetrahedron 41, 1101 (1985).

    CAS  Google Scholar 

  566. Hochlowski, J.E., and D.J. Faulkner: Chemical Constituents of the Nudibranch Chromodoris marislae. Tetrahedron Lett. 22, 271 (1981).

    CAS  Google Scholar 

  567. Cimino, G., S. de Rosa, S. de Stefano, and G. Sodano: Novel Sesquiterpenoid Esters from the Nudibranch Dendrodoris limbata. Tetrahedron Lett. 22, 1271 (1981).

    CAS  Google Scholar 

  568. D’Ischia, M., G. Prota, and G. Sodano: Reaction of Polygodial with Primary Amines: An Alternative Explanation to the Antifeedant Activity. Tetrahedron Lett. 23, 3295 (1982).

    Google Scholar 

  569. Cimino, G., S. de Rosa, S. de Stefano, G. Sodano, and G. Villani: Dorid Nudi­branch Elaborates Its Own Chemical Defense. Science 219, 1237 (1983).

    CAS  Google Scholar 

  570. Okuda, R.K., P.J. Scheuer, J.E. Hochlowski, R.P. Walker, and D.J. Faulkner: Sesquiterpenoid Constituents of Eight Porostome Nudibranchs. J. Org. Chem. 48, 1866 (1983).

    CAS  Google Scholar 

  571. Ayer, S.W., J. Hellou, M. Tischler, and R.J. Andersen: Nanaimoal, a Sesquiterpenoid Aldehyde from the Dorid Nudibranch Acanthodoris nanaimoensis. Tetrahedron Lett. 25, 141 (1984).

    CAS  Google Scholar 

  572. Ayer, S.W., R.J. Andersen, H. Cun-heng, and J. Clardy: Acanthodoral and Isoa- canthodoral, Two Sesquiterpenoids with New Carbon Skeletons from the Dorid Nudibranch Acanthodoris nanaimoensis. J. Org. Chem. 49, 2653 (1984).

    CAS  Google Scholar 

  573. Gustafson, K., R.J. Andersen, M.H.M. Chen, J. Clardy, and J.E. Hochlowski: Terpenoic Acid Glycerides from the Dorid Nudibranch Archidoris montereyensis. Tetrahedron Lett. 25, 11 (1984).

    CAS  Google Scholar 

  574. Rickets, E.F., and J. Calvin: Between Pacific Tides (Fourth Edition), p. 118, Stanford University Press, Stanford, Calif. (1968).

    Google Scholar 

  575. Gustafson, K., R.J. Andersen, H. Cunheng, and J. Clardy: Marginatafuran, a Furanoditerpene with a New Carbon Skeleton from the Dorid Nudibranch Cadlina luteomarginata. Tetrahedron Lett. 26, 2521 (1985).

    CAS  Google Scholar 

  576. Hellou, J., R.J. Andersen, S. Rafii, E. Arnold, and J. Clardy: Luteone, a Twenty Three Carbon Terpenoid from the Dorid Nudibranch Cadlina luteomarginata. Tetrahedron Lett. 22, 4173 (1981).

    CAS  Google Scholar 

  577. Hochlowski, J.E., D.J. Faulkner, L.S. Bass, and J. Clardy: Metabolites of the Dorid Nudibranch Chromodoris sedna. J. Org. Chem. 48, 1738 (1983).

    CAS  Google Scholar 

  578. Walker, R.P., and D.J. Faulkner: Chlorinated Acetylenes from the Nudibranch Diaulula sandiegensis. J. Org. Chem. 46, 1475 (1981).

    CAS  Google Scholar 

  579. Carte, B., and D.J. Faulkner: Defensive Metabolites from Three Nembrothid Nudibranchs. J. Org. Chem. 48, 2314 (1983).

    CAS  Google Scholar 

  580. Gustafson, K., and R.J. Andersen: Triophamine, a Unique Diacylguanidine from the Dorid Nudibranch Triopha catalinae (Cooper). J. Org. Chem. 47, 2167 (1982).

    CAS  Google Scholar 

  581. Piers, E., J.M. Chong, K. Gustafson, and R.J. Andersen: A Total Synthesis of (±)-Triophamine. Can. J. Chem. 62, 1 (1984).

    CAS  Google Scholar 

  582. Yamamura, S., and Y. Hirata: Structures of Aplysin and Aplysinol, Naturally Occurring Bromo-Compounds. Tetrahedron 19, 1485 (1963).

    CAS  Google Scholar 

  583. Hoye, T.R., A.J. Caruso, J.F. Dellaria, Jr., and M. J. Kurth: Two Syntheses of dl-Aplysistatin. J. Am. Chem. Soc. 104, 6704 (1982).

    CAS  Google Scholar 

  584. Schmitz, F.J., Y. Gopichand, D.P. Michaud, R.S. Prasad, S. Remaley, M.B. Hossain, A. Rahman, P.K. Sengupta, and D. van der Helm: Recent Developments in Research on Metabolites from Caribbean Marine Invertebrates. Pure and Appl. Chem. 51, 853 (1981).

    Google Scholar 

  585. Schmitz, F.J., D.P. Michaud, and K.H. Hollenbeak: Marine Natural Products: Dihydroxydeodactol Monoacetate, a Halogenated Sesquiterpene Ether from the Sea Hare Aplysia dactylomela. J. Org. Chem. 45, 1525 (1980).

    CAS  Google Scholar 

  586. Gopichand, Y., F.J. Schmitz, J. Shelly, A. Rahman, and D. van der Helm: Marine Natural Products: Halogenated Acetylenic Ethers from the Sea Hare Aplysia dactylomela. J. Org. Chem. 46, 5192 (1981).

    CAS  Google Scholar 

  587. González, A.G., J.D. Martin, M. Norte, R. Pérez, V. Weyler, A. Perales, and J. Fayos: New Halogenated Constituents of the Digestive gland of the Sea Hare Aplysia dactylomela. Tetrahedron Lett. 24, 847 (1983).

    Google Scholar 

  588. Schmitz, F.J., D.P. Michaud, and P.G. Schmidt: Marine Natural Products: Parguerol, Deoxyparguerol, and Isoparguerol. New Brominated Diterpenes with Modified Pimarane Skeletons from the Sea Hare Aplysia dactylomela. J. Am. Chem. Soc. 104, 6415 (1982). Erratum: J. Am. Chem. Soc. 106, 3385 (1984).

    Google Scholar 

  589. González, A.G., J.D. Martin, M. Norte, R. Pérez, V. Weyler, S. Rafii, and J. Clardy: A New Diterpene from Aplysia dactylomela. Tetrahedron Lett. 24, 1075 (1983).

    Google Scholar 

  590. Pettit, G.R., C.L. Herald, R.H. Ode, P. Brown, D.J. Gust, and C. Michel: The Isolation of Loliolide from an Indian Ocean Opisthobranch Mollusc. J. Nat. Prod. 43, 752 (1980).

    CAS  Google Scholar 

  591. Midland, S.L., R.M. Wing, and J.J. Sims: New Crenulides from the Sea Hare Aplysia vaccaria. J. Org. Chem. 48, 1906 (1983).

    CAS  Google Scholar 

  592. Sun, H.H., F.J. McEnroe, and W. Fenical: Acetoxycrenulide, a New Bicyclic Cyclopropane-Containing Diterpenoid from the Brown Seaweed Dictyota crenulata. J. Org. Chem. 48, 1903 (1983).

    CAS  Google Scholar 

  593. Schulte, G.R., M.C.H. Chung, and P.J. Scheuer: Two Bicyclic C15 Enynes from the Sea Hare Aplysia oculifera. J. Org. Chem. 46, 3870 (1981).

    CAS  Google Scholar 

  594. Gopichand, Y., and F.J. Schmitz: Bursatellin: A New Diol Dinitrile from the Sea Hare Bursatella leachiipleii. J. Org. Chem. 45, 5383 (1980).

    CAS  Google Scholar 

  595. Pettit, G.R., Y. Ramano, Y. Fujii, C.L. Herald, M. Inoue, P. Brown, D. Gust, K. Kitahara, J.M. Schmidt, D.L. Doubek, and C. Michel: Marine Animal Biosynthetic Constituents for Cancer Chemotherapy. J. Nat. Prod. 44, 482 (1981).

    CAS  Google Scholar 

  596. Pettit, G.R., Y. Kamano, P. Brown, D. Gust, M. Inoue, and C.L. Herald: Structure of the Cyclic Peptide Dolastatin 3 from Dolabella auricularia. J. Am. Chem. Soc. 104, 905 (1982).

    CAS  Google Scholar 

  597. Hamada, Y., K. Kohda, and T. Shioiri: Proposed Structure of the Cyclic Peptide Dolastatin 3, a Powerful Cell Growth Inhibitor, Should be Revised! Tetrahedron Lett. 25, 5303 (1984).

    CAS  Google Scholar 

  598. Schmidt, U., and R. Utz: Synthesestudien zur Ermittlung von Struktur und Konfi- guration des Dolastatins 3. Angew. Chem. 96, 723 (1984).

    CAS  Google Scholar 

  599. Yoshiba, S., and S. Sakurai: Comparative Studies on the Toxicities of Venoms of Five Species of Conus and the Effect of Ligation as a Treatment for Conus-stings. Jpn. J. med. Sci. Biol. 35, 139 (1982).

    Google Scholar 

  600. Kobayashi, J., H. Nakamura, Y. Hirata, and Y. Ohizumi: Effect of Venoms from Conidae on Skeletal, Cardiac, and Smooth Muscles. Toxicon 20, 823 (1982).

    CAS  Google Scholar 

  601. Gray, W.R., A. Luque, B.M. Olivera, J. Barrett, and L.J. Cruz: Peptide Toxins from Conus geographus Venom. J. Biol. Chem. 256, 4734 (1981).

    CAS  Google Scholar 

  602. Nishiuchi, Y., and S. Sakakibara: Primary and Secondary Structure of Conotoxin GI, a Neurotoxic Tridecapeptide from a Marine Snail. Febs Lett. 148, 260 (1982).

    CAS  Google Scholar 

  603. Stone, B.L., and W.R. Gray: Occurrence of Hydroxyproline in a Toxin from the Marine Snail Conus geographus. Arch. Biochem. Biophys. 216, 765 (1982).

    CAS  Google Scholar 

  604. Nakamura, H., J. Kobayashi, Y. Ohizumi, and Y. Hirata: Isolation and Amino Acid Compositions of Geographutoxin I and II from the Marine Snail Conus geogra­phus Linné. Experientia 39, 590 (1983).

    CAS  Google Scholar 

  605. Sato, S., H. Nakamura, Y. Ohizumi, J. Kobayashi, and Y. Hirata: The Amino Acid Sequences of Homologous Hydroxyproline-Containing Myotoxins from the Marine Snail Conus geographus Venom. Febs Lett. 155, 277 (1983).

    CAS  Google Scholar 

  606. Clark, C., B.M. Olivera, and L.J. Cruz: A Toxin from the Venom of the Marine Snail Conus geographus which Acts on the Vertebrate Central Nervous System. Toxicon 19, 691 (1981).

    CAS  Google Scholar 

  607. McIntosh, M., L.J. Cruz, M.W. Hunkapiller, W.R. Gray, and B.M. Olivera: Isolation and Structure of a Peptide Toxin from the Marine Snail Conus magus. Arch. Biochem. Biophys. 218, 329 (1982).

    CAS  Google Scholar 

  608. Kobayashi, J., H. Nakamura, and Y. Ohizumi: Excitatory and Inhibitory Effects of a Myotoxin from Conus magus Venom on the Mouse Diaphragm, the Guinea-pig Atria, Taenia Caeci, Ileum and Vas Deferens. Eur. J. Pharmacol. 86, 283 (1983).

    Google Scholar 

  609. Strichartz, G.R., G.K. Wang, J. Schmidt, R. Hahin, and B.I. Shapiro: Modifica­tion of Ionic Currents in Frog Nerve by Crude Venom and Isolated Peptides of the Mollusc Conus striatus. Fed. Proc. 39, 2065 (1980).

    Google Scholar 

  610. Kobayashi, J., H. Nakamura, and Y. Ohizumi: Biphasic Mechanical Responses of the Guinea-pig Isolated Ileum to the Venom of the Marine Snail Conus striatus. Br. J. Pharmac. 73, 583 (1981).

    CAS  Google Scholar 

  611. Kobayashi, J., H. Nakamura, Y. Hirata, and Y. Ohizumi: Isolation of a Cardiotonic Glycoprotein, Striatoxin, from the Venom of the Marine Snail Conus striatus. Biochem. Biophys. Res. Commun. 105, 1389 (1982).

    CAS  Google Scholar 

  612. Jimenez, E.C., B.M. Olivera, and L.J. Cruz: Localization of Enzymes and Possible Toxin Precursors in Granules from Conus striatus Venom. Toxicon Suppl. 3, 199 (1983).

    Google Scholar 

  613. Kobayashi, J., Y. Ohizumi, H. Nakamura, and Y. Hirata: Pharmacological Study on the Venom of the Marine Snail Conus textile. Toxicon 19, 757 (1981).

    CAS  Google Scholar 

  614. Nakamura, H., J. Kobayashi, Y. Ohizumi, and Y. Hirata: The Occurrence of Arachidonic Acid in the Venom Duct of the Marine Snail Conus textile. Experientia 38, 897 (1982).

    CAS  Google Scholar 

  615. Kobayashi, J., H. Nakamura, Y. Hirata, and Y. Ohizumi: Tessulatoxin, the Vasoactive Protein from the Venom of the Marine Snail Conus tessulatus. Comp. Biochem. Physiol. 74B, 381 (1983).

    CAS  Google Scholar 

  616. Kobayashi, J., H. Nakamura, Y. Hirata, and Y. Ohizumi: Isolation of Eburnetoxin, a Vasoactive Substance from the Conus ebur- neus Venom. Life Sciences 31, 1085 (1982).

    CAS  Google Scholar 

  617. Yoshiba, S., and S. Sakurai: Analysis on the Toxicity of the Venom of a Cone Shell Bekko-Imogai Chelyconus fulmen (Reeve, 1843). Japan. J. Med. Sci. Biol. 33, 38 (1980).

    Google Scholar 

  618. Olivera, B.M., J.M. McIntosh, C. Clark, D. Middlemas, W.R. Gray, and L.J. Cruz: A Sleep-Inducing Peptide from Conus geographus Venom. Toxicon 23, 277 (1985).

    CAS  Google Scholar 

  619. Tymiak, A.A., and K.L. Rinehart, Jr.: Structures of Kelletinins I and II, Antibacterial Metabolites of the Marine Mollusk Kelletia kelletii. J. Am. Chem. Soc. 105, 7396 (1983).

    CAS  Google Scholar 

  620. Kosuge, T., K. Tsuji, K. Hirai, K. Yamaguchi, T. Okamoto, and Y. Iitaka: Isolation and Structure Determination of a New Marine Toxin, Neosurugatoxin, from the Japanese Ivory Shell, Babylonia japónica. Tetrahedron Lett. 22, 3417 (1981).

    CAS  Google Scholar 

  621. Kosuge, T., K. Tsuji, and K. Hirai: Isolation of Neosurugatoxin from the Japanese Ivory Shell, Babylonia japónica. Chem. Pharm. Bull. (Japan) 30, 3255 (1982).

    CAS  Google Scholar 

  622. Kosuge, T., K. Tsuji, K. Hirai, K. Yamaguchi, T. Okamoto, and Y. Iitaka: Isolation and Structural Determination of a New Marine Toxin, Neosurugatoxin, from the Japanese Ivory Shell Babylonia japónica. Tennen Yuki Kagobutsu Toronkai Koen Yoshishu, 24th 1981, 127.

    Google Scholar 

  623. Noguchi, T., J. Maruyama, Y. Ueda, K. Hashimoto, and T. Harada: Occurrence of Tetrodotoxin in the Japanese Ivory Shell Babylonia japónica. Bull. Japan. Soc. Sci. Fish. 47, 909 (1981).

    CAS  Google Scholar 

  624. Yasumoto, T., Y. Oshima, M. Hosaka, and S. Miyakoshi: Occurrence of Tetrodotoxin in the Ivory Shell Babylonia japónica from Wakasa Bay. Bull. Japan. Soc. Sci. Fish. 47, 929 (1981).

    CAS  Google Scholar 

  625. Narita, H., T. Noguchi, J. Maruyama, Y. Ueda, K. Hashimoto, Y. Watanabe, and K. Hida: Occurrence of Tetrodotoxin in a Trumpet Shell, “Boshubora” Charonia sauliae. Bull. Japan. Soc. Sci. Fish. 47, 935 (1981).

    CAS  Google Scholar 

  626. Noguchi, T., J. Maruyama, H. Narita, and K. Hashimoto: Occurrence of Tetrodo­toxin in the Gastropod Mollusk Tutufa lissostoma (Frog Shell). Toxicon 22, 219 (1984).

    CAS  Google Scholar 

  627. Hochlowski, J.E., and D.J. Faulkner: Antibiotics from the Marine Pulmonate Siphonaria diemenensis. Tetrahedron Lett. 24, 1917 (1983).

    CAS  Google Scholar 

  628. Biskupiak, J.E., and C.M. Ireland: Pectinatone, a New Antibiotic from the Mollusc Siphonaria pectinata. Tetrahedron Lett. 24, 3055 (1983).

    CAS  Google Scholar 

  629. Hochlowski, J.E., D.J. Faulkner, G.K. Matsumoto, and J. Clardy: The Denticu- latins, Two Polypropionate Metabolites from the Pulmonate Siphonaria denticulata. J. Am. Chem. Soc. 105, 7413 (1983).

    CAS  Google Scholar 

  630. Capon, R.J., and D.J. Faulkner: Metabolites of the Pulmonate Siphonaria lessoni. J. Org. Chem. 49, 2506 (1984).

    CAS  Google Scholar 

  631. Hochlowski, J.E., and D.J. Faulkner: Metabolites of the Marine Pulmonate Si­phonaria australis. J. Org. Chem. 49, 3838 (1984).

    CAS  Google Scholar 

  632. Hochlowski, J.E., J.C. Coll, D.J. Faulkner, J.E. Biskupiak, C.M. Ireland, Z. Qi-tai, H. Cun-heng, and J. Clardy: Novel Metabolites of Four Siphonaria Species. J. Am. Chem. Soc. 106, 6748 (1984).

    Google Scholar 

  633. Ireland, C., and J. Faulkner: The Metabolites of the Marine Molluscs Tridachiella diomedea and Tridachia crispata. Tetrahedron 37, Supplement No. 1, 233 (1981).

    Google Scholar 

  634. Cimino, G., G. Sodano, A. Spinella, and E. Trivellone: Aglajne-1, a Polypro­pionate Metabolite from the Opisthobranch Mollusk Aglaja depicta. Determination of Carbon-Carbon Connectivity Via Long-Range 1H-13C Couplings. Tetrahedron Lett. 26, 3389 (1985).

    CAS  Google Scholar 

  635. Ireland, C.M., J.E. Biskupiak, G.J. Hite, M. Rapposch, P.J. Scheuer, and J.R. Ruble: Ilikonapyrone Esters, Likely Defense Allomones from the Mollusc Onchidium verruculatum. J. Org. Chem. 49, 559 (1984).

    CAS  Google Scholar 

  636. Biskupiak, J.E., and C.M. Ireland: Cytotoxic Metabolites from the Mollusc Peronia peronii. Tetrahedron Lett. 26, 4307 (1985).

    CAS  Google Scholar 

  637. Sanduja, R., A.J. Weinheimer, K.L. Euler, and M. Alam: Unusual Occurrence of Fulvoplumierin, an Antibacterial Pigment, in the Marine Mollusk Nerita albicilla. J. Nat. Prod. 48, 335 (1985).

    CAS  Google Scholar 

  638. Sleeper, H.L., V.J. Paul, and W. Fenical: Alarm Pheromones from the Marine Opisthobranch Navanax inermis. J. Chem. Ecol. 6, 57 (1980).

    CAS  Google Scholar 

  639. Coval, S.J., and P.J. Scheuer: An Intriguing C16-Alkadienone-Substituted 2-Pyri- dine from a Marine Mollusc. J. Org. Chem. 50, 3024 (1985).

    CAS  Google Scholar 

  640. Albizati, K.F., J.R. Pawlik, and D.J. Faulkner: Limatulone, a Potent Defensive Metabolite of the Intertidal Limpet Collisella limatula. J. Org. Chem. 50, 3428 (1985).

    CAS  Google Scholar 

  641. Andersen, R.J., D.J. Faulkner, H. Cun-heng, G.D. van Duyne, and J. Clardy: Metabolites of the Marine Prosobranch Mollusc Lamellaria sp. J. Am. Chem. Soc. 107, 5492 (1985).

    CAS  Google Scholar 

  642. Khalil, M.W., D.R. Idler, and G.W. Patterson: Sterols of Scallop. III. Characterization of Some C-24 Epimeric Sterols by High Resolution (220 MHz) Nuclear Magnetic Resonance Spectroscopy. Lipids 15, 69 (1980).

    CAS  Google Scholar 

  643. Swift, M.L., D. White, and M.B. Ghassemieh: Distribution of Neutral Lipids in the Tissues of the Oyster Crassostrea virginica. Lipids 15, 129 (1980).

    CAS  Google Scholar 

  644. Teshima, S., G.W. Patterson, and S.R. Dutky: Sterols of the Oyster, Crassostrea virginica. Lipids 15, 1004 (1980).

    CAS  Google Scholar 

  645. Teshima, S., and G.W. Patterson: Identification of 4a-Methylsterols in the Oyster Crassostrea virginica. Comp. Biochem. Physiol. 69B, 175 (1981).

    Google Scholar 

  646. Berenberg, C.J., and G.W. Patterson: The Relationship between Dietary Phyto-sterols and the Sterols of Wild and Cultivated Oysters. Lipids 16, 276 (1981).

    CAS  Google Scholar 

  647. Boutry, J.L., and M. Barbier: New Results About the C26 Sterols Also Concerning Their Possible Origin. Bull. Soc. Chim. Belg. 89, 1075 (1980).

    CAS  Google Scholar 

  648. Romero, M.S., and A.M. Seldes: Sterol Composition of the Mollusk Aulacomya ater. J. Nat. Prod. 46, 588 (1983).

    CAS  Google Scholar 

  649. Sterols of the Clam Chlamys tehuelcha. Experientia 39, 258 (1983).

    Google Scholar 

  650. Matsuno, T., and S. Sakaguchi: A Novel Marine Carotenoid, Mactraxanthin from the Japanese Edible Surf Clam. Tetrahedron Lett. 24, 911 (1983).

    CAS  Google Scholar 

  651. Matsuno, T., and T. Maoka: Carotenoids of Shellfishes. I. Isolation of a New Carotenoid, 3,4,3’,-Trihydroxy-7’,8’-didehydro-p-carotene from Sea Mussels. Nippon Suisan Gakkaishi 47, 377 (1981).

    CAS  Google Scholar 

  652. Matsuno, T., and T. Maoka: Carotenoids of Shellfish. III. Isolation of Diatoxanthin, Pectenoxanthin, Pec- tenolone, and a New Carotenoid 3,4,3’-Trihydroxy-7’,8’-didehydro-β-carotene from Arkshell and Related Three Species of Bivalves. Nippon Suisan Gakkaishi 47, 495 (1981).

    CAS  Google Scholar 

  653. Leung, M., and G.B. Stefano: Isolation of Molluscan Opioid Peptides. Life Sciences 33, Sup. I, 77 (1983).

    Google Scholar 

  654. Isolation and Identification of Enkephalins in Pedal Ganglia of Mytilus edulis (Mollusca). Proc. Natl. Acad. Sci. U.S.A. 81, 955 (1984).

    Google Scholar 

  655. Sheumack, D.D., M.E.H. Howden, and I. Spence: Occurrence of a Tetrodotoxin- Like Compound in the Eggs of the Venomous Blue-ringed Octopus (Hapalochlaena maculosa). Toxicon 22, 811 (1984).

    CAS  Google Scholar 

  656. Burnell, D.J., and J.W. ApSimon: Echinoderm Saponins. In: Marine Natural Prod­ucts. Chemical and Biological Perspectives (P.J. Scheuer, ed.), vol. V, p. 287. New York-San Francisco-London: Academic Press. 1983.

    Google Scholar 

  657. Anisimov, M.M., N.G. Prokofieva, L.Y. Korotkikh, I.I. Kapustina, and V.A. Stonik: Comparative Study of Cytotoxic Activity of Triterpene Glycosides from Marine Organisms. Toxicon 18, 221 (1980).

    CAS  Google Scholar 

  658. Minale, L., C. Pizza, R. Riccio, and F. Zollo: Steroidal Glycosides from Star­fishes. Pure & Appi. Chem. 54, 1935 (1982).

    CAS  Google Scholar 

  659. Okano, K., and S. Ikegami: Separation of Ovarian Asterosaponins in the Starfish Asterias amurensis. Agric. Biol. Chem. 45, 801 (1981).

    CAS  Google Scholar 

  660. Okano, K., T. Nakamura, Y. Kamiya, and S. Ikegami: Structure of Ovarian Astero- saponin-1 in the Starfish Asterias amurensis. Agric. Biol. Chem. 45, 805 (1981).

    CAS  Google Scholar 

  661. De Simone, F., A. Dini, E. Finamore, L. Minale, C. Pizza, R. Riccio, and F. Zollo: Starfish Saponins. Part 5. Structure of Sepositoside A, a Novel Steroidal Cyclic Glycoside from the Starfish Echinaster sepositus. J. Chem. Soc., Perkin Trans. I 1981, 1855.

    Google Scholar 

  662. Riccio, R., E. de Simone, A. Dini, L. Minale, C. Pizza, F. Senatore, and F. Zollo: Starfish Saponins VI - Unique 22,23-Epoxysteroidal Cyclic Glycosides, Minor Constituents from Echinaster sepositus. Tetrahedron Lett. 22, 1557 (1981). Erra­tum: Tetrahedron Lett. 22, 2242 (1981).

    Google Scholar 

  663. Riccio, R., A. Dini, L. Minale, C. Pizza, F. Zollo, and T. Sevenet: Starfish Saponins VII. Structure of Luzonicoside, a Further Steroidal Cyclic Glycoside from the Pacific Starfish Echinaster luzonicus. Experientia 38, 68 (1982).

    CAS  Google Scholar 

  664. Riccio, R., L. Minale, C. Pizza, F. Zollo, and J. Pusset: Starfish Saponins. Part 8. Structure of Nodososide, a Novel Type of Steroidal Glycoside from the Starfish Protoreaster nodosus. Tetrahedron Lett. 23, 2899 (1982).

    CAS  Google Scholar 

  665. Minale, L., C. Pizza, R. Riccio, and F. Zollo: Starfish Saponins. Part 9. A Novel 24-O-Glycosidated Steroid from the Starfish Hacelia attenuata. Experientia 39, 567 (1983).

    CAS  Google Scholar 

  666. Minale, L., C. Pizza, R. Riccio, and F. Zollo: Starfish Saponins. Part 10. Further 24-O-Glycosidated Steroids from the Starfish Hacelia attenuata. Experientia 39, 569 (1983).

    CAS  Google Scholar 

  667. Minale, L., C. Pizza, F. Zollo, and R. Riccio: Trace Polyhydroxylated Steroids from Starfish Hacelia attenuata. J. Nat. Prod. 46, 736 (1983).

    CAS  Google Scholar 

  668. Minale, L., C. Pizza, R. Riccio, F. Zollo, J. Pusset, and P. Laboute: Starfish Saponins, XIII. Occurrence of Nodososide in the Starfish Acanthaster planci and Linckia laevigata. J. Nat. Prod. 47, 558 (1984).

    CAS  Google Scholar 

  669. Komori, T., J. Matsuo, Y. Itakura, K. Sakamoto, Y. Ito, S. Taguchi, and T. Kawasaki: Biologically Active Glycosides from Asteroidea, II. Steroid Oligoglyco- sides from the Starfish Acanthaster planci L., 1. Isolation and Structure of the Oligo- glycoside Sulfates. Liebigs Ann. Chem. 1983, 24.

    Google Scholar 

  670. Komori, T., H. Nanri, Y. Itakura, K. Sakamoto, S. Taguchi, R. Higuchi, T. Kawasaki, and T. Higuchi: Biologically Active Glycosides from Asteroidea, III. Steroid Oligoglycosides from the Starfish Acanthaster planci L., 2. Structure of Two Newly Characterized Genuine Sapogenins and an Oligoglycoside Sulfate. Liebigs Ann. Chem. 1983, 37.

    Google Scholar 

  671. Itakura, Y., T. Komori, and T. Kawasaki: Biologically Active Gylcosides from Asteroidea, IV. Steroid Oligoglycosides from the Starfish Astropecten latespinosus Meissner. Liebigs Ann. Chem. 1983, 56.

    Google Scholar 

  672. Itakura, Y., T. Komori, and T. Kawasaki: Biologically Active Glycosides from Asteroidea, V. Steroid Oligoglycosides from the Starfish Asterias amurensis (cf.). versicolor Sladen, 1. Structural Elucidation of a New Oligoglycoside Sulfate. Liebigs Ann. Chem. 1983, 2079.

    Google Scholar 

  673. Komori, T., H.C. Krebs, Y. Itakura, R. Higuchi, K. Sakamoto, S. Taguchi, and T. Kawasaki: Biologisch aktive Glycoside aus Asteroidea, VI. Steroid-Oligogly- coside aus dem Seestern Luidia maculata Müller et Troschel, 1. Die Strukturen eines neuen Aglyconsulfats und von zwei neuen Oligoglycosidsulfaten. Liebigs Ann. Chem. 1983, 2092.

    Google Scholar 

  674. Krebs, H.C., T. Komori, and T. Kawasaki: Biologisch aktive Glycoside aus Asteroidea, VII. Steroid-Oligoglycoside aus dem Seestern Luidia maculata Müller et Troschel, 2. Die Strukturen von zwei neuen Oligoglycosidsulfaten. Liebigs Ann. Chem. 1984, 296.

    Google Scholar 

  675. Neira, C., M. Hoeneisen, M. Silva, and P.G. Sammes: Marine Organic Chemistry, III. Isolation of 3β,6α,Dihydroxy-5α-cholest-9(11)-en-23-one from the Starfish Stichaster striatus. J. Nat. Prod. 47, 182 (1984).

    CAS  Google Scholar 

  676. Findlay, J.A., and V.K. Agarwal: Aglycones from the Saponin of the Starfish Asterias vulgaris. J. Nat. Prod. 46, 876 (1983).

    CAS  Google Scholar 

  677. Findlay, J.A., V.K. Agarwal, and Y.E. Moharir: On the Saponins of the Starfish Asterias vulgaris. J. Nat. Prod. 47, 113 (1984).

    CAS  Google Scholar 

  678. Dini, A., F.A. Mellon, L. Minale, C. Pizza, R. Riccio, R. Self, and F. Zollo: Starfish Saponins - XI. Isolation and Partial Characterization of the Saponins from the Starfish Marthasterias glacialis. Comp. Biochem. Physiol. 76B, 839 (1983).

    Google Scholar 

  679. Bruno, I., L. Minale, C. Pizza, F. Zollo, R. Riccio, and F.M. Mellon: Starfish Saponins. Part 14. Structures of the Steroidal Glycoside Sulphates from the Starfish Marthasterias glacialis. J. Chem. Soc., Perkin Trans. I 1984, 1875.

    Google Scholar 

  680. Minale, L., R. Riccio, O. Squillace-Greco, J. Pusset, and J.L. Menou: Starfish Saponins - XVI. Composition of the Steroidal Glycoside Sulphates from the Starfish Luidia maculata. Comp. Biochem. Physiol. 80B, 113 (1985).

    Google Scholar 

  681. Riccio, R., C. Pizza, O. Squillace-Greco, and L. Minale: Starfish Saponins. Part 17. Steroidal Glycoside Sulphates from the Starfish Ophidiaster ophidianus (Lamarck) and Hacelia attenuata (Gray). J. Chem. Soc., Perkin Trans. 1 1985, 655.

    Google Scholar 

  682. Riccio, R., O. Squillace-Greco, L. Minale, J. Pusset, and J.L. Menou: Starfish Saponins, Part 18. Steroidal Glycoside Sulfates from the Starfish Linckia laevigata. J. Nat. Prod. 48, 97 (1985).

    CAS  Google Scholar 

  683. Riccio, R., F. Zollo, E. Finamore, L. Minale, D. Laurent, G. Bargibant, and J. Pusset: Starfish Saponins, 19. A Novel Steroidal Glycoside Sulfate from the Star­fishes Protoreaster nodosus and Pentaceraster alveolatus. J. Nat. Prod. 48, 266 (1985).

    CAS  Google Scholar 

  684. Fusetani, N., Y. Kato, K. Hashimoto, T. Komori, Y. Itakura, and T. Kawasaki: Biological Activities of Asterosaponins with Special Reference to Structure-Activity Relationships. J. Nat. Prod. 47, 997 (1984).

    CAS  Google Scholar 

  685. Kicha, A.A., A.I. Kalinovsky, E.V. Levina, V.A. Stonik, and G.B. Elyakov: Asterosaponin Pi from the Starfish Patina pectinifera. Tetrahedron Lett. 24, 3893 (1983).

    CAS  Google Scholar 

  686. Voogt, P.A., and J.W.A. van Rheenen: Carbohydrate Content and Composition of Asterosaponins from Different Organs of the Sea Star Asterias rubens: Relation to Their Haemolytic Activity and Implications for Their Biosynthesis. Comp. Biochem. Physiol. 72B, 683 (1982).

    Google Scholar 

  687. Burnell, D.J., J.W. ApSimon, and M.W. Gilgan: Variations in the Levels of Asterone and Asterogenol, Two Steroids from the Saponins of the Starfish, Asterias vulgaris (Verrill). Steroids 44, 67 (1984).

    CAS  Google Scholar 

  688. De Simone, F., A. Dini, L. Minale, R. Riccio, and F. Zollo: The Sterols of the Asteroid Echinaster sepositus. Comp. Biochem. Physiol. 66B, 351 (1980).

    Google Scholar 

  689. Sato, S., N. Ikekawa, A. Kanazawa, and T. Ando: Identification of 23-Demethyl- acanthasterol in an Asteroid, Acanthaster planci and Its Synthesis. Steroids 36, 65 (1980).

    CAS  Google Scholar 

  690. Burnell, D.J., J.W. ApSimon, and M.W. Gilgan: Seasonal and Geographic Variations of the Sterols from the Starfish Asterias vulgaris (Verrill). Steroids 39, 357 (1982).

    CAS  Google Scholar 

  691. Seldes, A.M., and E.G. Gros: Main Sterols from the Starfish Comasterias lurida. Comp. Biochem. Physiol. 80B, 337 (1985).

    Google Scholar 

  692. Minale, L., C. Pizza, R. Riccio, C. Sorrentino, F. Zollo, J. Pusset, and G. Bargibant: Minor Polyhydroxylated Sterols from the Starfish Protoreaster nodosus. J. Nat. Prod. 47, 790 (1984).

    CAS  Google Scholar 

  693. Riccio, R., L. Minale, S. Pagonis, C. Pizza, F. Zollo, and J. Pusset: A Novel Group of Highly Hydroxylated Steroids from the Starfish Protoreaster nodosus. Tetrahedron 38, 3615 (1982).

    CAS  Google Scholar 

  694. Minale, L., C. Pizza, F. Zollo, and R. Riccio: 5a-Cholestane-3β,6β,15α,16 β,26- pentol: a Polyhydroxylated Sterol from the Starfish Hacelia attenuata. Tetrahedron Lett. 23, 1841 (1982).

    CAS  Google Scholar 

  695. Minale, L., C. Pizza, R. Riccio, O. Squillace Greco, F. Zollo, J. Pusset, and J.L. Menou: New Polyhydroxylated Sterols from the Starfish Luidia maculata. J. Nat. Prod. 47, 784 (1984).

    CAS  Google Scholar 

  696. D’Auria, M.V., E. Finamore, L. Minale, C. Pizza, R. Riccio, F. Zollo, M. Pusset, and P. Tirard: Steroids from the Starfish Euretaster insignis: a Novel Group of Sulphated 3β,21-Dihydroxysteroids. J. Chem. Soc., Perkin Trans. I 1984, 2277.

    Google Scholar 

  697. Komori, T., Y. Sanechika, Y. Ito, J. Matsuo, T. Nohara, T. Kawasaki, and H.-R. Schulten: Biologisch aktive Glycoside aus Asteroidea, I. Strukturen eines neuen Cerebrosidgemischs und von Nucleosiden aus dem Seestern Acanthaster planci. Liebigs Ann. Chem. 1980, 653.

    Google Scholar 

  698. Nakamura, H., J. Kobayashi, and Y. Hirata: Isolation and Structure of a 330 nm UV-absorbing Substance, Asterina-330 from the Starfish Asterina pectinifera. Chem. Lett. 1981, 1413.

    Google Scholar 

  699. Noguchi, T., H. Narita, J. Maruyama, and K. Hashimoto: Tetrodotoxin in the Starfish Astropecten polyacanthus, in Association with Toxification of a Trumpet Shell, “Boshubora” Charonia sauliae. Bull. Japan. Soc. Sei. Fish. 48, 1173 (1982).

    Google Scholar 

  700. Maruyama, J., T. Noguchi, J.K. Jeon, T. Harada, and K. Hashimoto: Occurrence of Tetrodotoxin in the Starfish Astropecten latespinosus. Experientia 40, 1395 (1984).

    CAS  Google Scholar 

  701. Kuznetsova, T.A., M.M. Anisimov, A.M. Popov, S.I. Baranova, S.S. Afiyatullov, I.I. Kapustina, A.S. Antonov, and G.B. Elyakov: A Comparative Study in vitro of Physiological Activity of Triterpene Glycosides of Marine Invertebrates of Echinoderm Type. Comp. Biochem. Physiol. 73C, 41 (1982).

    CAS  Google Scholar 

  702. Kitagawa, I., T. Nishino, M. Kobayashi, and Y. Kyogoku: Marine Natural Products. VIII. Bioactive Triterpene-Oligoglycosides from the Sea Cucumber Holothuria leucospilota Brandt (2). Structure of Holothurin A. Chem. Pharm. Bull. (Japan) 29, 1951 (1981).

    CAS  Google Scholar 

  703. Kitagawa, I., T. Nishino, M. Kobayashi, T. Matsuno, H. Akutsu, and Y. Kyogoku: Marine Natural Products. VII. Bioactive Triterpene Oligoglycosides from the Sea Cucumber Holothuria leucospilota Brandt (1). Structure of Holothurin B. Chem. Pharm. Bull. (Japan) 29, 1942 (1981).

    CAS  Google Scholar 

  704. Ivanova, N.S., O.F. Smetanina, and T.A. Kuznetsova: Glycosides of Marine Invertebrates. XXVI. Holothurin A from the Pacific Ocean Holothurian Holothuria squamifera. Isolation of the Native Aglycone. Khim. Prir. Soedin. 1984, 448.

    Google Scholar 

  705. Ivanova, N.S., and T.A. Kuznetsova: Holothurin A - The Main Triterpene Glycoside of the Cuvierian Organs of the Holothurian Bohadschia graeffei. The Structures of the Native Aglycone and of Progenins. Khim. Prir. Soedin. 1985, 123.

    Google Scholar 

  706. Oleinikova, G.K., T.A. Kuznetsova, N.S. Ivanova, A.I. Kalinovskii, N.V. Rovnykh, and G.B. Elyakov: Glycosides of Marine Invertebrates. XV. A New Triter­pene Glycoside - Holothurin A1 - from Caribbean Holothurians of the Family Holothuriidae. Khim. Prir. Soedin. 1982, 464.

    Google Scholar 

  707. Kitagawa, I., T. Inamoto, M. Fuchida, S. Okada, M. Kobayashi, T. Nishino, and Y. Kyogoku: Structures of Echinoside A and B, Two Antifungal Oligoglyco­sides from the Sea Cucumber Actinopyga echinites (Jaeger). Chem. Pharm. Bull. (Japan) 23, 1651 (1980).

    Google Scholar 

  708. Kalinin, V.I., and V.A. Stonik: Glycosides of Marine Invertebrates. Structure of Holothurin A2 from the Holothurian Holothuria edulis. Khim. Prir. Soedin. 1982, 215.

    Google Scholar 

  709. Kalinin, V.I., and V.A. Stonik: Glycosides of the Holothurian Bohadschia graeffei. Khim. Prir. Soedin. 1982, 789.

    Google Scholar 

  710. Oleinikova, G.K., T.A. Kuznetsova, N.V. Rovnykh, A.I. Kalinovskii, and G.B. Elyakov: Glycosides of Marine Invertebrates. XVIII. Holothurin A2 from the Ca­ribbean Holothurian Holothuria floridana. Khim. Prir. Soedin. 1982, 527.

    Google Scholar 

  711. Elyakov, G.B., N.I. Kalinovskaya, A.I. Kalinovskii, V.A. Stonik, and T.A. Kuznetsova: Glycosides of Marine Invertebrates. XIII. New Holothurinogenins of Holothurin B1 from Holothuria floridana. Khim. Prir. Soedin. 1982, 323.

    Google Scholar 

  712. Kuznetsova, T.A., N.I. Kalinovskaya, A.I. Kalinovskii, G.K. Oleinikova, N.V. Rovnykh, and G.B. Elyakov: Glycosides of Marine Invertebrates. XIV. Structure of Holothurin Bt from the Holothurian Holothuria floridana. Khim. Prir. Soedin. 1982, 482.

    Google Scholar 

  713. Oleinikova, G.K., and T.A. Kuznetsova: Two-Stage Smith Degradation of Ho­lothurin Bx from the Holothurian Holothuria floridana. Khim. Prir. Soedin. 1983, 534.

    Google Scholar 

  714. Kitagawa, I., M. Kobayashi, and Y. Kyogoku: Marine Natural Products. IX. Structural Elucidation of Triterpenoidal Oligoglycosides from the Bahamean Sea Cucumber Actinopyga agassizi Selenka. Chem. Pharm. Bull. (Japan) 30, 2045 (1982).

    CAS  Google Scholar 

  715. Kitagawa, I., M. Kobayashi, M. Hori, and Y. Kyogoku: Structures of Four New Triterpenoidal Oligoglycosides, Bivittoside A, B, C, and D, from the Sea Cucumber Bohadschia bivittata Mitsukuri. Chem. Pharm. Bull. (Japan) 29, 282 (1981).

    CAS  Google Scholar 

  716. Habermehl, G.G., and J.H. Kirsch: Synthesis of Bivittoside C Genine. Tetrahedron Lett. 24, 2981 (1983).

    CAS  Google Scholar 

  717. Habermehl, G., and G. Volkwein: Aglycones of the Toxins from the Cuvierian Organs of Holothuria forskali and a New Nomenclature for the Aglycones from Holothurioideae. Toxicon 9, 319 (1971).

    CAS  Google Scholar 

  718. Stonik, V.A., V.F. Sharypov, T.A. Kuznetsova, and A.I. Kalinovskii: Native Aglycones of Triterpene Glycosides of the Holothurian Bohadschia argus. Khim. Prir. Soedin. 1982, 790.

    Google Scholar 

  719. Kitagawa, I., M. Kobayashi, T. Inamoto, T. Yasuzawa, Y. Kyogoku, and M. Kido: Stichlorogenol and Dehydrostichlorogenol, Genuine Aglycones of Stichloro-sides A1, B1, C1, and A2, B2, C2, from the Sea Cucumber Stichopus chloronotus (Brandt). Chem. Pharm. Bull. (Japan) 29, 1189 (1981).

    CAS  Google Scholar 

  720. Kitagawa, I., M. Kobayashi, T. Inamoto, T. Yasuzawa, and Y. Kyogoku: The Structures of Six Antifungal Oligoglycosides, Stichlorosides Al, A2, Bl, B2, C1, and C2, from the Sea Cucumber Stichopus chloronotus (Brandt). Chem. Pharm. Bull. (Japan) 29, 2387 (1981).

    CAS  Google Scholar 

  721. Elyakov, G.B., V.A. Stonik, S.S. Afiyatullov, A.I. Kalinovskii, V.F. Sharypov, and L.Y. Korotkikh: Native Genins from Glycosides of Holothurians. Dokl. Akad. Nauk SSSR 259, 1367 (1981).

    CAS  Google Scholar 

  722. Sharypov, V.F., A.D. Chumak, V.A. Stonik, and G.B. Elyakov: Glycosides of Marine Invertebrates. X. The Structure of Stichoposides A and B from the Holothurian Stichopus chloronotus. Khim. Prir. Soedin. 1981, 181.

    Google Scholar 

  723. Stonik, V.A., I.I. Mal’tsev, A.I. Kalinovskii, C. Conde, and G.B. Elyakov: Glycosides of Marine Invertebrates. XI. Two New Triterpene Glycosides from Holothu­rians of the Family Stichopodidae. Khim. Prir. Soedin. 1982, 194.

    Google Scholar 

  724. Stonik, V.A., I.I. Mal’tsev, A.I. Kalinovskii, and G.B. Elyakov: Glycosides of Marine Invertebrates. XII. Structure of a New Triterpene Oligoglycoside from Holo­thurians of the Family Stichopodidae. Khim. Prir. Soedin. 1982, 200.

    Google Scholar 

  725. Mal’tsev, 1.1., V.A. Stonik, and A.I. Kalinovskii: Stichoposide E - A New Triterpene Glycoside from Holothurians of the Family Stichopodidae. Khim. Prir. Soedin. 1983, 308.

    Google Scholar 

  726. Kelecom, A., B. Tursch, and M. Vanhaelen: Chemical Studies of Marine Inverte­brates XIX. Glycosidic Chain Structure of Thelothurins A and B, Two New Saponins from the Indo-Pacific Sea Cucumber Thelenota ananas Jaeger (Echinodermata). Bull. Soc. Chim. Belg. 85, 277 (1976).

    CAS  Google Scholar 

  727. Stonik, V.A., I.I. Mal’tsev, and G.B. Elyakov: The Structure of Thelenotosides A and B from the Holothurian Thelenota ananas. Khim. Prir. Soedin. 1982, 624.

    Google Scholar 

  728. Afiyatullov, S.S., V.A. Stonik, and G.B. Elyakov: Glycosides of Marine Inverte­brates. Cucumarioside Gt from the Holothurian Cucumaria fraudatrix. Khim. Prir. Soedin. 1983, 654.

    Google Scholar 

  729. Avilov, S.A., L.Y. Tishchenko, and V.A. Stonik: Structure of Cucumarioside A2 - 2 - A Triterpene Glycoside from the Holothurian Cucumaria japonica. Khim. Prir. Soedin. 1984, 799.

    Google Scholar 

  730. Afiyatullov, S.S., V.A. Stonik, A.I. Kalinovskii, and G.B. Elyakov: Glycosides of Marine Invertebrates. XVI. Cucumariogenin from Glycosides of the Holothurian Cucumaria fraudatrix. Khim. Prir. Soedin. 1983, 59.

    Google Scholar 

  731. Findlay, J.A., and A. Daljeet: Frondogenin, a New Aglycone from the Sea Cucum­ber Cucumaria frondosa. J. Nat. Prod. 47, 320 (1984).

    CAS  Google Scholar 

  732. Smetanina, O.F., A.I. Kalinovskii, T.A. Kuznetsova, V.A. Stonik, and G.B. Elyakov: Glycosides of Marine Invertebrates. XVII. New Genins of Glycosides from the Caribbean Holothurian Parathyona sp. ( Holothurioidae, Cucumariidae). Khim. Prir. Soedin. 1983, 64.

    Google Scholar 

  733. Garneau, F.-X., J.-L. Simard, O. Harvey, J.W. ApSimon, and M. Girard: The Structure of Psoluthurin A, the Major Triterpene Glycoside of the Sea Cucumber Psolus fabricii. Can. J. Chem. 61, 1465 (1983).

    CAS  Google Scholar 

  734. Kalinin, V.I., V.R. Stepanov, and V.A. Stonik: Psolusoside A - A New Triterpene Glycoside from the Holothurian Psolus fabricii. Khim. Prir. Soedin. 1983, 789.

    Google Scholar 

  735. Kalinovskii, A.I., S.A. Avilov, V.R. Stepanov, and V.A. Stonik: Glycosides of Marine Invertebrates. XXIII. Kurilogenin - A New Genin from the Glycosides of the Holothurian Duasmodactyla kurilensis. Khim. Prir. Soedin. 1983, 724.

    Google Scholar 

  736. Gorshkov, B.A., I.A. Gorshokova, V.A. Stonik, and G.B. Elyakov: Effect of Marine Glycosides on Adenosinetriphosphatase Activity. Toxicon 20, 655 (1982).

    CAS  Google Scholar 

  737. Kalinovskaya, N.I., T.A. Kuznetsova, and G.B. Elyakov: Sterol Composition of Pacific Holothurian Stichopus japonicus selenka. Comp. Biochem. Physiol. 74B, 597 (1983).

    Google Scholar 

  738. Elyakov, G.B., N.I. Kalinovskaya, V.A. Stonik, and T.A. Kuznetsova: Glyco­sides of Marine Invertebrates VI. Steroid Glycosides from Holothurian Stichopus japonicus. Comp. Biochem. Physiol. 65B, 309 (1980).

    Google Scholar 

  739. Smetanina, O.F., E. Nait, T.A. Kuznetsova, and G.B. Elyakov: Sulfated Deriv­atives from Marine Organisms. II. Sulfated Steroyl Alcohols from the Holo­thurian Parathyona sp. ( Holothurioidea, Cucumariidae). Khim. Prir. Soedin. 1981, 585.

    Google Scholar 

  740. Batrakov, S.G., V.B. Muratov, O.G. Sakandelidze, O.S. Reshetova, and B.V. Rozynov: Sterol Sulfates from the Far Eastern Holothurian Cucumaria japonica. Khim. Prir. Soedin. 1984, 470.

    Google Scholar 

  741. Findlay, J.A., A. Daljeet, J. Matsoukas, and Y.E. Moharir: Constituents of the Sea Cucumber Cucumaria frondosa. J. Nat. Prod. 47, 560 (1984).

    CAS  Google Scholar 

  742. Elyakov, G.B., S.N. Fedorov, A.D. Chumak, V.V. Isakov, and V.A. Stonik: Sulfated Derivatives from Marine Invertebrates - 1. Sulfated Sterols from Some Species of Echinoderms. Comp. Biochem. Physiol. 71B, 325 (1982).

    Google Scholar 

  743. D’Auria, M.V., R. Riccio, and L. Minale: Ophioxanthin, a New Marine Carot- enoid Sulfate from the Ophiuroid Ophioderma longicaudum. Tetrahedron Lett. 26, 1871 (1985).

    Google Scholar 

  744. Rideout, J.A., N.B. Smith, and M.D. Sutherland: Chemical Defense of Crinoids by Polyketide Sulfates. Experientia 35, 1273 (1979).

    CAS  Google Scholar 

  745. Rideout, J.A., and M.D. Sutherland: Pigments of Marine Animals. XIV. Polyke­tide Sulfates from the Crinoid Comatula pectinata. Aust. J. Chem. 34, 2385 (1981).

    CAS  Google Scholar 

  746. Rideout, J.A., and M.D. Sutherland: Pigments of Marine Animals. XV. Bianthrones and Realated Polyketides from Lamprometra palmata gyges and Other Species of Crinoids. Aust. J. Chem. 38, 793 (1985).

    CAS  Google Scholar 

  747. Kimura, A., and H. Nakagawa: Action of an Extract from the Sea Urchin Toxopneustes pileolus on Isolated Smooth Muscle. Toxicon 18, 689 (1980).

    CAS  Google Scholar 

  748. Nakagawa, H., A. Kimura, M. Takei, and K. Endo: Histamine Release from Rat Mast Cells Induced by an Extract from the Sea Urchin Toxopneustes pileolus. Toxicon 20, 1095 (1982).

    CAS  Google Scholar 

  749. Nakagawa, H., and A. Kimura: Partial Purification and Characterization of a Toxic Substance from Pedicellariae of the Sea Urchin Toxopneustes pileolus. Japan. J. Pharmacol. 32, 966 (1982).

    CAS  Google Scholar 

  750. Kimura, A., H. Nakagawa, H. Hayashi, and K. Endo: Seasonal Changes in Contractile Activity of a Toxic Substance from the Pedicellaria of the Sea Urchin Toxopneustes pileolus. Toxicon 22, 353 (1984).

    CAS  Google Scholar 

  751. Mebs, D.: A Toxin from the Sea Urchin Tripneustes gratilla. Toxicon 22, 306 (1984).

    CAS  Google Scholar 

  752. Pettit, G.R., J.A. Rideout, J.A. Hasler, D.L. Doubek, and P.R. Reucroft: Isolation and Characterization of Lytechinastatin. J. Nat. Prod. 44, 713 (1981).

    CAS  Google Scholar 

  753. Pettit, G.R., J.A. Hasler, K.D. Paull, and C.L. Herald: Antineoplastic Agents. 76. The Sea Urchin Strongylocentrotus droebachiensis. J. Nat. Prod. 44, 701 (1981).

    CAS  Google Scholar 

  754. Kamerling, J.P., R. Schauer, J.F.G. Vliegenthart, and K. Hotta: Identification of the Sialic Acids from the Egg Jelly Coat of the Sea Urchin Pseudocentrotus depressus (Okayama). Hoppe-Seyler’s Z. Physiol. Chem. 361, 1511 (1980).

    CAS  Google Scholar 

  755. Palumbo, A., M. D’Ischia, G. Misuraca, and G. Prota: Isolation and Structure of a New Sulphur-Containing Aminoacid from Sea Urchin Eggs. Tetrahedron Lett. 23, 3207 (1982).

    CAS  Google Scholar 

  756. Ireland, C., and P.J. Scheuer: Ulicyclamide and Ulithiacyclamide, Two New Small Peptides from a Marine Tunicate. J. Am. Chem. 102, 5688 (1980).

    CAS  Google Scholar 

  757. Wasylyk, J.M., J.E. Biskupiak, C.E. Costello, and C.M. Ireland: Cyclic Peptide Structures from the Tunicate Lissoclinum patella by FAB Mass Spectrometry. J. Org. Chem. 48, 4445 (1983).

    CAS  Google Scholar 

  758. Biskupiak, J.E., and C.M. Ireland: Absolute Configuration of Thiazole Amino Acids in Peptides. J. Org. Chem. 48, 2302 (1983).

    CAS  Google Scholar 

  759. a. Schmidt, U., and P. Gleich: Totalsynthese von Ulicyclamid. Angew. Chem. 97, 606 (1985).

    CAS  Google Scholar 

  760. Ireland, C.M., A.R. Durso, Jr., R.A. Newman, and M.P. Hacker: Antineoplastic Cyclic Peptides from the Marine Tunicate Lissoclinum patella. J. Org. Chem. 47, 1807 (1982).

    CAS  Google Scholar 

  761. Hamada, Y., M. Shibata, and T. Shioiri: New Methods and Reagents in Organic Synthesis. 55. Total Syntheses of Patellamides B and C, Cytotoxic Cyclic Peptides from a Tunicate. 1. Their Proposed Structures Should be Corrected. Tetrahedron Lett. 26, 5155 (1985).

    CAS  Google Scholar 

  762. Hamada, Y., M. Shibata, and T. Shioiri: New Methods and Reagents in Organic Synthesis. 56. Total Syntheses of Patellamides B and C, Cytotoxic Cyclic Peptides from a Tunicate. 2. Their Real Structures have been Determined by Their Syntheses. Tetrahedron Lett. 26, 5159 (1985).

    CAS  Google Scholar 

  763. Hamada, Y., M. Shibata, and T. Shioiri: New Methods and Reagents in Organic Synthesis. 58. A Synthesis of Patellamide A, a Cytotoxic Cyclic Peptide from a Tunicate. Revision of Its Proposed Structure. Tetrahedron Lett. 26, 6501 (1985).

    CAS  Google Scholar 

  764. Rinehart, Jr., K.L., J.B. Gloer, R.G. Hughes, Jr., H.E. Renis, J.P. McGovren, E.B. Swynenberg, D.A. Stringfellow, S.L. Kuentzel, and L.H. Lr. Didemnins: Antiviral and Antitumor Depsipeptides from a Caribbean Tunicate. Science 212, 933 (1981).

    CAS  Google Scholar 

  765. Rinehart, Jr, K.L., J.B. Gloer, G.R. Wilson, R.G. Hughes, Jr., L.H. Li, H.E. Renis, and J.P. McGovren: Antiviral and Antitumor Compounds from Tunicates. Fed. Proc. 42, 87 (1983).

    CAS  Google Scholar 

  766. Rinehart, Jr., K.L., J.B. Gloer, J.C. Cook, Jr., S.A. Mizsak, and T.A. Scahill: Structures of the Didemnins, Antiviral and Cytotoxic Depsipeptides from a Caribbean Tunicate. J. Am. Chem. Soc. 103, 1857 (1981).

    CAS  Google Scholar 

  767. Rinehart, Jr., K.L.: Fast Atom Bombardment Mass Spectrometry. Science 218, 254 (1982).

    CAS  Google Scholar 

  768. Hamamoto, Y., M. Endo, M. Nakagawa, T. Nakanishi, and K. Mizukawa: A New Cyclic Peptide, Ascidiacyclamide, Isolated from Ascidian. J. Chem. Soc., Chem. Commun. 1983, 323.

    Google Scholar 

  769. Bruening, R.C., E.M. Oltz, J. Furukawa, K. Nakanishi, and K. Kustin: Isola­tion and Structure of Tunichrome B-l, a Reducing Blood Pigment from the Tunicate Ascidia nigra L. J. Am. Chem. Soc. 107, 5298 (1985).

    CAS  Google Scholar 

  770. Ireland, C.M., A.R. Durso, Jr., and P. J. Scheuer: N,N’-Diphenethylurea, a Metab­olite from the Marine Ascidian Didemnum ternatanum. J. Nat. Prod. 44, 360 (1981).

    CAS  Google Scholar 

  771. Sesin, D.F., and C.M. Ireland: Iodinated Phenethylamine Products from a Didemnid Tunicate. Tetrahedron Lett. 25, 403 (1984).

    CAS  Google Scholar 

  772. Heitz, S., M. Durgeat, M. Guyot, C. Brassy, and B. Bachet: Nouveau Dérivé Indolique du Thiadiazole-1,2,4, Isolé D’Un Tunicier (Dendrodoa grossularia). Tetra­hedron Lett. 21, 1457 (1980).

    CAS  Google Scholar 

  773. Hogan, I.T., and M. Sainsbury: The Synthesis of Dendrodoine, 5-[3-(N,N-Dimethylamino)-l,2,4-thiadiazolyl]-3-indolylmethanone, a Metabolite of the Marine Tunicate Dendroda grossular. Tetrahedron 40, 681 (1984).

    CAS  Google Scholar 

  774. Roll, D.M., and C.M. Ireland: Citorellamine, a New Bromoindole Derivative from Polycitorella mariae. Tetrahedron Lett. 26, 4303 (1985).

    CAS  Google Scholar 

  775. Moquin, C., and M. Guyot: Grossularine, a Novel Indole Derivative from the Marine Tunicate, Dendrodoa grossularia. Tetrahedron Lett. 25, 5047 (1984).

    CAS  Google Scholar 

  776. Rinehart, Jr., K.L., J. Kobayashi, G.C. Harbour, R.G. Hughes, Jr., S.A. Mizsak, and T.A. Scahill: Eudistomins C, E, K, and L, Potent Antiviral Compounds Con­taining a Novel Oxathiazepine Ring from the Caribbean Tunicate Eudistoma olivaceum. J. Am. Chem. Soc. 106, 1524 (1984).

    CAS  Google Scholar 

  777. Kobayashi, J., G.C. Harbour, J. Gilmore, and K.L. Rinehart, Jr.: Eudistomins A, D, G, H, I, J, M, N, O, P, and Q, Bromo-, Hydroxy-, Pyrrolyl-, and 1-Pyrrolinyl-β- carbolines from the Antiviral Caribbean Tunicate Eudistoma olivaceum. J. Am. Chem. Soc. 106, 1526 (1984).

    CAS  Google Scholar 

  778. Watanabe, K., S. Matsunaga, and S. Konosu: Studies on the Extractive Components of Ascidians II. Halocynine, a Novel Betaine Isolated from the Muscle of Ascidian Halocynthia roretzi. Tetrahedron Lett. 25, 2003 (1984).

    Google Scholar 

  779. Carté, B., and D.J. Faulkner: Revised Structures for the Polyandrocarpidines. Tetrahedron Lett. 23, 3863 (1982).

    Google Scholar 

  780. Kazlauskas, R., J.F. Mar wood, P.T. Murphy, and R.J. Wells: A Blue Pigment from a Compound Ascidian. Aust. J. Chem. 35, 215 (1982).

    CAS  Google Scholar 

  781. Kobayashi, J., H. Nakamura, and Y. Hirata: Isolation and Structure of a UV- Absorbing Substance 337 from the Ascidian Halocynthia roretzi. Tetrahedron Lett. 22, 3001 (1981).

    CAS  Google Scholar 

  782. Watanabe, K., H. Maezawa, H. Nakamura, and S. Konosu: Seasonal Variation of Extractive Nitrogen and Free Amino Acids in the Muscle of the Ascidian Halocynthia roretzi. Bull. Japan. Soc. Sci. Fish. 49, 1755 (1983).

    CAS  Google Scholar 

  783. Targett, N.M., and W.S. Keeran: A Terpenehydroquinone from the Marine Ascid­ian Aplidium constellatum. J. Nat. Prod. 47, 556 (1984).

    CAS  Google Scholar 

  784. Matsuno, T., and M. Ookubo: A New Carotenoid, Halocynthiaxanthin from the Sea Squirt, Halocynthia roretzi. Tetrahedron Lett. 22, 4659 (1981).

    CAS  Google Scholar 

  785. Matsuno, T., and M. Ookubo: A New Marine Carotenoid, Mytiloxanthinone from the Sea Squirt, Halocynthia roretzi. Chem. Lett. 1982, 1605.

    Google Scholar 

  786. Belaud, C., and M. Guyot: Sidnyaxanthin, a New Carotenoid from the Tunicate, Sidnyum argus. Tetrahedron Lett. 25, 3087 (1984).

    CAS  Google Scholar 

  787. Matsuno, T., M. Ookubo, and T. Komori: Carotenoids of Tunicates, III. The Structural Elucidation of Two New Marine Carotenoids, Amarouciaxanthin A and B. J. Nat. Prod. 48, 606 (1985).

    Google Scholar 

  788. Rebachuk, N.M., O.B. Maksimov, L.S. Boguslavskaya, and S.A. Fedoreev: Carotenoids of the Ascidian Halocynthia aurantium. Khim. Prir. Soedin. 1984, 431.

    Google Scholar 

  789. Ha, T.B.T, W.C.M.C. Kokke, and C. Djerassi: Minor Sterols of Marine Inverte­brates 37. Isolation of Novel Coprostanols and 4a-Methyl Sterols from the Tunicate Ascidia nigra. Steroids 40, 433 (1982).

    Google Scholar 

  790. Kljajic, Z., N. Dogovic, and M.J. Gasic: Sterols in Adriatic Sea Ascidians. Comp. Biochem. Physiol. 75B, 519 (1983).

    Google Scholar 

  791. Guyot, M., and M. Durgeat: Occurrence of 9(11)-Unsaturated Sterol Peroxides in Tunicates. Tetrahedron Lett. 22, 1391 (1981).

    CAS  Google Scholar 

  792. Guyot, M., D. Davoust, and C. Belaud: Hydroperoxy-24 Vinyl-24 Cholesterol, Nouvel Hydroperoxide Naturel Isolé De Deux Tuniciers: Phallusia mamillata et Ciona intestinalis. Tetrahedron Lett. 23, 1905 (1982).

    CAS  Google Scholar 

  793. Albano, R.M., and P.A.S. Mouräo: Presence of Sulfated Glycans in Ascidian Tunic and in the Body Wall of a Sea Cucumber. Biochim. Biophys. Acta 760, 192 (1983).

    CAS  Google Scholar 

  794. Dunn, W.C., W.L. Carrier, and J.D. Regan: Effects of an Extract from the Sea Squirt Ecteinascidia turbinata on DNA Synthesis and Excision Repair in Human Fibroblasts. Toxicon 20, 703 (1982).

    CAS  Google Scholar 

  795. Blumenthal, K.M., and W.R. Kem: Structure and Action of Heteronemertine Poly­peptide Toxins. Primary Structure of Cerebratulus lacteus Toxin A-III. J. Biol. Chem. 255, 8266 (1980).

    CAS  Google Scholar 

  796. Blumenthal, K.M.: Structure and Action of Heteronemertine Polypeptide Toxins. Disulfide Bonds of Cerebratulus lacteus Toxin A-III. J. Biol. Chem. 255, 8273 (1980).

    CAS  Google Scholar 

  797. Blumenthal, K.M.: Structure and Action of Heteronemertine Polypeptide Toxins. Membrane Penetra­tion by Cerebratulus lacteus Toxin A-III. Biochem. 21, 4229 (1982).

    CAS  Google Scholar 

  798. Blumenthal, K.M., P.S. Keim, R.L. Heinrikson, and W.R. Kem: Structure and Action of Heteronemertine Polypeptide Toxins. Amino Acid Sequence of Cerebratulus lacteus Toxin B-II and Revised Structure of Toxin B-IV. J. Biol. Chem. 256, 9063 (1981).

    CAS  Google Scholar 

  799. Blumenthal, K.M., and W.R. Kem: Structure and Action of Heteronemertine Poly­peptide Toxins: Inactivation of Cerebratulus lacteus Toxin B-IV by Tyrosine Nitration. Arch. Biochem. Biophys. 203, 816 (1980).

    CAS  Google Scholar 

  800. Blumenthal, K.M.: Structure and Action of Heteronemertine Polypeptide Toxins: Inactivation of Cerebratulus lacteus Toxin B-IV Concomitant with Tryptophan Alkylation. Arch. Biochem. Biophys. 203, 822 (1980).

    CAS  Google Scholar 

  801. Ballantine, J.A., A.F. Psaila, A. Pelter, P. Murray-Rust, V. Ferrito, P. Schembri, and V. Jaccarini: The Structure of Bonellin and its Derivatives. Unique Physiologically Active Chlorins from the Marine Echurian Bonellia viridis. J. Chem. Soc., Perkin Trans. I 1980, 1080.

    Google Scholar 

  802. Higa, T., T. Fujiyama, and P.J. Scheuer: Halogenated Phenol and Indole Constitu­ents of Acorn Worms. Comp. Biochem. Physiol. 65B, 525 (1980).

    Google Scholar 

  803. Hovingh, P., and A. Linker: An Unusual Heparan Sulfate Isolated from Lobsters (.Homarus americanus). J. Biol. Chem. 257, 9840 (1982).

    CAS  Google Scholar 

  804. Cannon, J.R., J.S. Edmonds, K.A. Francesconi, C.L. Raston, J.B. Saunders, B.W. Skelton, and A.H. White: Isolation, Crystal Structure and Synthesis of Arse- nobetain, a Constituent of the Western Rock Lobster, the Dusky Shark, and Some Samples of Human Urine. Aust. J. Chem. 34, 787 (1981).

    CAS  Google Scholar 

  805. Fusetani, N., H. Endo, K. Hashimoto, and K. Takahashi: Occurrence of Potent Toxins in the Horseshoe Crab Carcinoscorpius rotundicauda. Toxicon 20, 662 (1982).

    CAS  Google Scholar 

  806. Fusetani, N., H. Endo, K. Hashimoto, and M. Kodama: Occurrence and Properties of Toxins in the Horseshoe Crab Carcinoscorpius rotundicauda. Toxicon Suppl. 3, 165 (1983).

    Google Scholar 

  807. Endean, R., R. Lewis, P. Gyr, and J. Williamson: Toxic Material from the Crab Atergatisfloridus. Toxicon Suppl. 3, 111 (1983).

    Google Scholar 

  808. De Freitas, J.C., and R.S. Jacobs: Biotoxins in Brachyuran Decapod Crustaceans. Toxicon Suppl. 3, 157 (1983).

    Google Scholar 

  809. Noguchi, T., A. Uzu, K. Daigo (Koyama), Y. Shida, and K. Hashimoto: A Tetro- dotoxin-Like Substance as a Minor Toxin in the Xanthid Crab Atergatis floridus. Toxicon 22, 425 (1984).

    CAS  Google Scholar 

  810. Raj, U., H. Haq, Y. Oshima, and T. Yasumoto: The Occurrence of Paralytic Shell­fish Toxins in Two Species of Xanthid Crab from Suva Barrier Reef, Fiji Islands. Toxicon 21, 547 (1983).

    CAS  Google Scholar 

  811. Fusetani, N., K. Hashimoto, I. Mizukami, H. Kamiya, and S. Yonabaru: Lethality in Mice of the Coconut Crab Birgus latro. Toxicon 18, 694 (1980).

    CAS  Google Scholar 

  812. Bishayee, S., and D.T. Dorai: Isolation and Characterization of a Sialic Acid- Binding Lectin (Carcinoscorpin) from Indian Horseshoe Crab Carcinoscorpius rotunda cauda. Biochim. Biophys. Acta 623, 89 (1980).

    CAS  Google Scholar 

  813. Brandin, E.R., and T.G. Pistole: Polyphemin: A Teichoic Acid-Binding Lectin from the Horseshoe Crab, Limulus polyphemus. Biochem. Biophys. Res. Commun. 113, 611 (1983).

    CAS  Google Scholar 

  814. Watson, R.D., and E. Spaziani: Rapid Isolation of Ecdysteroids from Crustacean Tissues and Culture Media Using Sep-Pak C18 Cartridges. J. Liquid Chromatography 5, 525 (1982).

    CAS  Google Scholar 

  815. Newcomb, R.W.: Peptides in the Sinus Gland of Cardisoma carnifex: Isolation and Amino Acid Analysis. J. Comp. Physiol. 153, 207 (1983).

    CAS  Google Scholar 

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Krebs, H.C. (1986). Recent Developments in the Field of Marine Natural Products with Emphasis on Biologically Active Compounds. In: Herz, W., Grisebach, H., Kirby, G.W., Tamm, C. (eds) Fortschritte der Chemie organischer Naturstoffe / Progress in the Chemistry of Organic Natural Products. Fortschritte der Chemie organischer Naturstoffe / Progress in the Chemistry of Organic Natural Products, vol 49. Springer, Vienna. https://doi.org/10.1007/978-3-7091-8846-0_3

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  • DOI: https://doi.org/10.1007/978-3-7091-8846-0_3

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