Skip to main content

Abstract

The purpose of this article is to review the chemistry of the limonoids isolated from plants of the natural order Meliaceae; limonoids from the Rutaceae and Cneoraceae are not included. The chemistry of the limonoids was last reviewed in this series by Dreyer (84); a more recent review is by Connolly, Overton and Polonsky (73). Taxonomic aspects have been reviewed recently by the present author (199), and chemistry and phyto-chemistry have been discussed at a recent meeting (81). The present article sets out to review advances in limonoid chemistry since the last review in this series (84); the tables however are intended to be comprehensive.

This is a preview of subscription content, log in via an institution to check access.

Access this chapter

Chapter
USD 29.95
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
eBook
USD 39.99
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
Softcover Book
USD 54.99
Price excludes VAT (USA)
  • Compact, lightweight edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info

Tax calculation will be finalised at checkout

Purchases are for personal use only

Institutional subscriptions

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. Adeoye, S. A., and D. A. Bekoe: The Molecular Structure of Cedrela odorata Substance B. J. Chem. Soc. Chem. Commun. 1965, 301.

    Google Scholar 

  2. Adesida, G. A., E. K. Adesogan, D. A. Okorie, B. T. Styles, and D. A. H. Taylor:The Limonoid Chemistry of the Genus Khaya (Meliaceae). Phytochemistry 10, 1845 (1971).

    Article  CAS  Google Scholar 

  3. Adesida, G. A., E. K. Adesogan, and D. A. H. Taylor: Extractives from Khaya senegalensis A. Juss. J. Chem. Soc. Chem. Commun. 1967, 790.

    Google Scholar 

  4. Adesida, G. A., and D. A. Okorie: Heudebolin, a New Limonoid from Trichilia heudelotii. Phytochemistry 12, 3007 (1973).

    Article  CAS  Google Scholar 

  5. Adesida, G. A., and D. A. H. Taylor: The Chemistry of the Genus Entandrophragma. Phytochemistry 6, 1429 (1967).

    Article  CAS  Google Scholar 

  6. — —: Extractives from Soymida febrifuga. Phytochemistry 11, 1520 (1972).

    Article  CAS  Google Scholar 

  7. — —: Isolation of Obacunol from Lovoa trichiliodes. Phytochemistry 11, 2644 (1972).

    Google Scholar 

  8. Adesogan, E. K., C. W. L. Bevan, J. W. Powell, and D. A. H. Taylor: West African timbers. Part XVIII. Some Reactions of Cedrela odorata Substance B and Khayasin. J. Chem. Soc. (C) 1966, 2127.

    Google Scholar 

  9. Adesogan, E. K., D. A. Okorie, and D. A. H. Taylor: Limonoids from Khaya anthotheca (Welw) C. DC. J. Chem. Soc. (C) 1970, 205.

    Google Scholar 

  10. Adesogan, E. K., J. W. Powell, and D. A. H. Taylor: Extractives from the Seed of Khaya senegalensis. J. Chem. Soc. (C) 1967, 554.

    Google Scholar 

  11. Adesogan, E. K., and D. A. H. Taylor: Grandifoliolin, a New Limonoid from Khaya grandifoliola C.DC. J. Chem. Soc. Chem. Commun. 1967, 225.

    Google Scholar 

  12. — —: Extractives from the Seed of Khaya anthotheca (Welw). C. DC. J. Chem. Soc. Chem. Commun. 1967. 379.

    Google Scholar 

  13. — —: Extractives from Khaya senegalensis (Desr.) A. Juss. J. Chem. Soc. (C) 1968, 1974.

    Google Scholar 

  14. — —: Methyl Ivorensate, an A-seco-Limonoid from Khaya ivorensis. J. Chem. Soc. Chem. Commun. 1969, 889.

    Google Scholar 

  15. — —: Limonoid Extractives from Khaya ivorensis. J. Chem. Soc. (C) 1970, 1710.

    Google Scholar 

  16. Ahmed, F. R., A. S. Ng, and A. G. Fallis: 7oc-Acetoxydihydronomilin: Isolation, Spectra. and Crystal Structure. Can. J. Chem. 56, 1020 (1978). 77.

    Google Scholar 

  17. Akinniyi, J. A., J. D. Connolly, D. S. Rycroft, B. L. Sondengam, and N. P. Ifeadike: Tetranortriterpenoids and Related Compounds. Part 25. Two 3,4-Secotirucallane Derivatives and 2/-Hydroxyrohitukin from the Bark of Guarea cedrata (Meliaceae). Can. J. Chem. 58, 1865 (1980).

    Article  CAS  Google Scholar 

  18. Akinniyi, J. A., J. D. Connolly, D. S. Rycroft, and D. A. H. Taylor: Unpubl. work.

    Google Scholar 

  19. Akisanya, A., C. W. L. Bevan, J. Hirst, T. G. Halsall, and D. A. H. Taylor: West African Timbers. Part III. Petroleum Extractives from the Genus Entandrophragma. J. Chem. Soc. 1960, 3827.

    Google Scholar 

  20. Akisanya, A., C. W. L. Bevan, T. G. Halsall, J. W. Powell, and D. A. H. Taylor: West African Timbers. Part IV. Some Reactions of Gedunin. J. Chem. Soc. 1961, 3705.

    Google Scholar 

  21. Arene, E. O., C. W. L. Bevan, J. W. Powell, and D. A. H. Taylor: West African Timbers. Part XI. The Structure of Carapin, an Extractive from Carapa procera. J. Chem. Soc. Chem. Commun. 1965, 302.

    Google Scholar 

  22. Arndt, R. R., and W. H. Baarschers: The Structure of Phragmalin, a Meliacin with a Norbornane Part Skeleton. Tetrahedron 28, 2333 (1972).

    Article  CAS  Google Scholar 

  23. Arigoni, D., D. H. R. Barton, L. Caglioti, E. J. Corey, S. Dev, P. G. Ferrini, E. R. Glazier, O. Jeger, A. Melera, S. K. Pradham, F. Schaffner, S. Sternhell, J. F. Templeton, and S. Tobinaga: The Constitution of Limonin. Experientia 16, 41 (1960).

    Article  CAS  Google Scholar 

  24. Barton, D. H. R., S. K. Pradhan, S. Sternhell, and J. F. Templeton: Triterpenoids. Part XXV. The Constitutions of Limonin and Related Bitter Principles. J. Chem. Soc. 1961, 255.

    Google Scholar 

  25. Banerji, R., and S. K. Nigam: Studies on the Heartwood of Melia birmanica. Fitoterapia 52, 3 (1981).

    CAS  Google Scholar 

  26. Bevan, C. W. L., D. E. U. Ekong, T. G. Halsall, and P. Toft: West African Timbers. Part XIV. The Structure of Turreanthin, a Triterpene Monoacetate from Turreanthus africanus. J. Chem. Soc. Chem. Commun. 1965, 636.

    Google Scholar 

  27. Bevan, C. W. L., D. E. U. Ekong, T. G. Halsall, and P. Toft: West African Timbers. Part XX. The Structure of Turreanthin, an Oxygenated Tetracyclic Triterpene Monoacetate. J. Chem. Soc. (C). 1967, 820.

    Google Scholar 

  28. Bevan, C. W. L., D. E. U. Ekong, and D. A. H. Taylor: Extractives from West African Members of the Family Meliaceae. Nature 206, 1323 (1965).

    Article  CAS  Google Scholar 

  29. Bevan, C. W. L., T. G. Halsall, M. N. Nwaji, and D. A. H. Taylor: West African Timbers. Part V. The Structure of Khivorin, a Constituent of Khaya ivorensis. J. Chem. Soc. 1962, 768.

    Google Scholar 

  30. Bevan, C. W. L., J. W. Powell, and D. A. H. Taylor: West African Timbers Part VI. Petroleum Extracts from Species of the Genera Khaya, Guarea, Carapa and Cedrela. J. Chem. Soc. 1963, 980.

    Google Scholar 

  31. Birch, A. J., D. J. Collins, S. Muhammed, and J. P. Turnbull: The Structure of Flindissol. Some Remarks on the Elemi Acids. J. Chem. Soc. 1963, 2762.

    Google Scholar 

  32. Bredell, L. D.: An Investigation into Extractives from the Meliaceae. M. Sc. Thesis. Durban, 1977.

    Google Scholar 

  33. Breen, G. J. W., E. Ritchie, W. T. L. Sidwell, and W. C. Taylor: The Chemical Constituents of Australian Flindersia species XIX. Triterpenoids from the Leaves of F. bourjotiana F. Muell. Australian J. Chem. 19, 455 (1966).

    Article  CAS  Google Scholar 

  34. Brown, D. A., and D. A. H. Taylor: 13C Nuclear Magnetic Resonance Spectra of Some Limonoids. Part IV. Extractives from Chukrasia tabularis. A. Juss. J. Chem. Res. (S) 20, (M) 0301 (1978).

    Google Scholar 

  35. — —Limonoid Extractives from Aphanamixis polystacha. Phytochemistry 17, 1995 (1978).

    Article  CAS  Google Scholar 

  36. Buchanan, J. G. St. C., and T. G. Halsall: The Synthesis of Possible Intermediates in the Biogenesis of Tetranortriterpenes by the Conversion of the Sidechain of Turreanthin into a ß-Substituted Furan. J. Chem. Soc. Chem. Commun. 1969, 48.

    Google Scholar 

  37. — —The Synthesis of the Simplest Meliacins (Limonoids) from Tetranortirucallane Triterpenoids Containing a ß-Substituted Furyl Sidechain. J. Chem. Soc. Chem. Commun. 1969, 242.

    Google Scholar 

  38. — —Conversion of a Simple Meliacin (7α-Acetoxy meliaca-14,20,22-trien-3-one) into Azadirone and of Khayanthone into Khivorin. J. Chem. Soc. Chem. Commun. 1969, 1493.

    Google Scholar 

  39. — —The Conversion of Turreanthin and Turreanthin A into Simple Meliacins by a Route Involving an Oxidative Rearrangement of Probable Biogenetic Importance. J. Chem. Soc. (C). 1970, 2280.

    Google Scholar 

  40. Burke, B. A., W. R. Chan, K. E. Magnus, and D. R. Taylor: Extractives of Cedrela odorata II. The Structure of Photogedunin. Tetrahedron 25, 5007 (1969).

    Article  CAS  Google Scholar 

  41. Cameron, A. F., J. D. Connolly, A. Maltz, and D. A. H. Taylor: Tetranor- triterpenoids and Related Compounds. Part 21. The Crystal and Molecular Structure of a Rearranged Tetranortriterpenoid Spiro-lactone from the Bark of Carapa procera (Meliaceae). Tetrahedron Letters 1979, 967.

    Google Scholar 

  42. Cason, S. C., and K. S. Brown: Biogenetically Significant Triterpenes in a Species of Meliaceae, Cabralea polytricha. Tetrahedron 28, 315 (1972).

    Article  CAS  Google Scholar 

  43. Chakraborty, D. P., K. C. Das, and C. F. Hammer: Chemical Taxonomy X. Mahoganin. Tetrahedron Letters 1968, 5015.

    Article  Google Scholar 

  44. Chan, W. R., J.A. Gibbs, and D. R. Taylor: The Limonoids of Trichilia havanensis Jacq.: an Epoxide Rearrangement. J. Chem. Soc. Chem. Commun. 1967, 720.

    Google Scholar 

  45. Chan, W. R., K. E. Magnus, and B. S. Mootoo: Extractives from Cedrela odorata L. The Structure of Methyl Angolensate. J. Chem. Soc. (C) 1967, 171.

    Google Scholar 

  46. Chan, W. R., N. L. Holder, D. R. Taylor, G. Snatzke, and H. W. Fehlhaber: Extractives of Cedrela odorata L. Part II. The Structures of the Cedrela Tetracyclic Triterpenes, Odoratol, Iso-odoratol and Odoratone. J. Chem. Soc. (C) 1968, 2485.

    Google Scholar 

  47. Chan, W. R., and D. R. Taylor: Hirtin and Deacetylhirtin: New “Limonoids” from Trichilia hirta. J. Chem. Soc. Chem. Commun. 1966, 206.

    Google Scholar 

  48. Chan, W. R., D. R. Taylor, and T. Yee: Triterpenoids from Entandrophragma cylindricum Sprague. Part I. Structures of Sapelins A and B. J. Chem. Soc. (C) 1970, 311.

    Google Scholar 

  49. — —Triterpenoids from Entandrophragma cylindricum Sprague. Part II. The Structures of Sapelins C, D, E and F. J. Chem. Soc. (C) 1971, 2662.

    Google Scholar 

  50. Chakrabortty, T., J. D. Connolly, R. McCrindle, K. H. Overton, and J. C. D. Schwarz: Tetranortriterpenoids — VI. [Bicyclononanolides IV] Swietenolide — the Functional Groups. Tetrahedron 24, 1503 (1968).

    Article  Google Scholar 

  51. Chang, F. C., and C. Chiang: Kulinone, a Euphane-type Triterpenoid from Melia azedarach. J. Chem. Soc. Chem. Commun. 1968, 1156.

    Google Scholar 

  52. Kulinone, a Euphane-type Triterpenoid from Melia azedarach. J. Chem. Soc. Chem. Commun. 1968, 1156.

    Google Scholar 

  53. Tetracyclic triterpenes from Melia azedarach II. Trans-2-oxabicyclo[3.3.0]octa-nones. Tetrahedron Letters 1969, 891.

    Google Scholar 

  54. Chatterjee, A., T. Chakrabortty, and S. Chandrasekharan: Chemical Investigation of Cedrela toona. Phytochemistry 10, 2533 (1971).

    Article  CAS  Google Scholar 

  55. Chatterjee, A., and A. B. Kundu: Isolation, Structure and Stereochemistry of Aphanamixin, a New Triterpene from Aphanamixis polystacha. Tetrahedron Letters 1967, 1471.

    Google Scholar 

  56. Chiang, C., and F. C. Chang: Tetracyclic Triterpenoids from Melia azedarach (III). Tetrahedron 29, 1911 (1973).

    Article  CAS  Google Scholar 

  57. Connolly, J. D.: Personal communication.

    Google Scholar 

  58. Connolly, J. D., K. L. Handa, and R. McCrindle: Further Constituents of Nim Oil: the Constitution of Meldenin. Tetrahedron Letters 1968, 437.

    Google Scholar 

  59. Connolly, J. D., K. L. Handa, R. McCrindle, and K. H. Overton: Grandifolione: a Novel Tetranortriterpenoid. J. Chem. Soc. Chem. Commun. 1966, 867.

    Google Scholar 

  60. Tetranortriterpenoids and related substances. Part XI. Odoratol and its Congeners from Cedrela glaziovii. J. Chem. Soc. (C) 1968, 2230.

    Google Scholar 

  61. Connolly, J. D., R. Henderson, R. McCrindle, K. H. Overton, and N. S. Bhacca: Tetranortriterpenoids. Parti. [Bicyclononanolides. Parti.] The Constitution of Swietenine. J. Chem. Soc. 1965, 6935.

    Google Scholar 

  62. Connolly, J. D., C. Labbe, and D. S. Rycroft: Tetranortriterpenoids and Related Substances. Part 20. New Tetranortriterpenoids from the Seed of Chukrasia tabularis (Meliaceae). Simple Esters of Phragmalin and 12a-Acetoxyphragmalin. J. Chem. Soc. Perkin Trans. I, 1978, 285.

    Article  Google Scholar 

  63. Connolly, J. D., C. Labbe, D. S. Rycroft, D. A. Okorie, and D. A. H. Taylor: Tetranortriterpenoids and Related Compounds. Part 23. Complex Tetranortriterpenoids from Trichilia prieuriana and Guarea thompsonii (Meliaceae) and the Hydrolysis Products of Dregeanin, Prieurianin and Related Compounds. J. Chem. Res. (S) 256, (M) 2858 (1979).

    Google Scholar 

  64. Connolly, J. D., C. Labbe, D. S. Rycroft, and D. A. H. Taylor: Tetranortriterpenoids and Related Compounds. Part 22. New Apo-tirucallol Derivatives and Tetranortriterpenoids from the Wood and Seed of Chisocheton paniculatus (Meliaceae). J.Chem. Soc. Perkin Trans. I, 1979, 2959.

    Article  Google Scholar 

  65. Connolly, J. D., and C. Labbe: Tetranortriterpenoids and Related Compounds. Part 24. The Interrelation of Swietenine and Swietenolide, the Major Tetranortriter- penoids from the Seeds of Swietenia macrophylla (Meliaceae). J. Chem. Soc. Perkin Trans. I, 1980, 529.

    Article  Google Scholar 

  66. Connolly, J. D., and R. McCrindle: The Constitution of Grandifoliolenone, a Novel Triterpenöid from Khaya grandifolia. J. Chem. Soc. Chem. Commun. 1967, 1193.

    Google Scholar 

  67. Tetranortriterpenoids and related substances. Part XIII. The Constitution of Grandifoliolenone, an apo-Tirucallol Derivative from Khaya grandifoliola (Meliaceae). J. Chem. Soc. (C) 1971, 1715.

    Google Scholar 

  68. Connolly, J. D., R. McCrindle, and K. H. Overton: Tetranortriterpenoids IV. Bicyclononalides 11’. Constitution and Stereochemistry of Mexicanolide. Tetrahedron 24, 1489 (1968).

    Article  CAS  Google Scholar 

  69. Tetranortriterpenoids VII [Bicyclononanolides III]. The P. M. R. spectrum of Mexicanolide. Tetrahedron 24, 1497 (1968).

    Article  CAS  Google Scholar 

  70. Connolly, J. D., R. McCrindle, K. H. Overton, and J. Feeney: Tetranortriterpenoids. Part II. Heartwood Constituents of Carapa guyanensis Aubl. Tetrahedron 22, 811 (1966).

    Article  Google Scholar 

  71. Connolly, J. D., R. McCrindle, K. H. Overton, and W. D. C. Warnock: Tetranortriterpenoids VII [Bicyclononanolides V]. The Constitution and Stereochemistry of Swietenolide. Tetrahedron 24, 1507 (1968).

    Article  CAS  Google Scholar 

  72. Connolly, J. D., M. MacLellan, D. A. Okorie, and D. A. H. Taylor: Limonoids from Xylocarpus moluccensis (Lam) M. Roem. J. Chem. Soc. Perkin Trans. 1,1976,1993.

    Google Scholar 

  73. Connolly, J. D., K. H. Overton, and J. Polonsky: The Chemistry and Biochemistry of the Limonoids and Quassinoids. Progress in Phytochemistry 2, 385 (1970).

    CAS  Google Scholar 

  74. Connolly, J. D., I. M. S. Thornton, and D. A. H. Taylor: Partial Synthesis of Methyl Angolensate from 7-Oxo-7-acetoxykhivorin. J. Chem. Soc. Chem. Commun. 1970,1205.

    Google Scholar 

  75. Partial Syntheses of Mexicanolide from 7-Oxo-7-deacetoxykhivorin. J. Chem. Soc. Chem. Comm. 1971, 17.

    Google Scholar 

  76. Tetranortriterpenoids. Part XVI. Partial Syntheses of Andirobin, Methyl Angolensate, Mexicanolide and 1-Deoxymexicanolide. J. Chem. Soc. Perkin Trans. I, 1973, 2407.

    Article  Google Scholar 

  77. Connolly, J. D., D. A. Okorie, and D. A. H. Taylor: Limonoid Extractives from Species of Guarea. An Unusual Shielding Effect on an Acetyl group. J. Chem. Soc. Perkin Trans. I, 1972, 1145.

    Google Scholar 

  78. Connolly, J. D., D. A. Okorie, L. D. de Wit, and D. A. H. Taylor: Structure of Dregeanin and Rohitukin, Limonoids from the Subfamily Melioideae of the Family Meliaceae. An Unusually High Absorption Frequency for a Six-membered Lactone Ring. J. Chem. Soc. Chem. Commun. 1976, 909.

    Google Scholar 

  79. Connolly, J. D., W. R. Phillips, D. A. Mulholland, and D. A. H. Taylor: Spicatin, a Protolimonoid from Entandrophragma spicatum. Phytochemistry 20, 2596(1981).

    Google Scholar 

  80. Connolly, J. D., and D. A. H. Taylor: Tetranortriterpenoids. Part XIV. The Structure of Nyasin, a Limonoid from Khaya nyasica; sl Correction. J. Chem. Soc. Perkin Trans. I, 1973, 686.

    Article  Google Scholar 

  81. Connolly, J. D., M. F. Grundon, and D. A. H. Taylor: Phytochemical Society Symposium. Glasgow 1982.

    Google Scholar 

  82. Cotterrlll, G. P., T. G. Halsall, and M. J. Wriglesworth: A Chemical Model for a Possible Oxidative Rearrangement in the Biosynthesis of Tetranortriterpenes. The Preparation of Methyl 3a-Acetoxy-7-oxo-apo-tirucalla-14,24-dien-21-oate. J. Chem. Soc. Chem. Commun. 1967, 1121.

    Google Scholar 

  83. — — — A Chemical Model for a Possible Oxidative Rearrangement in the Biosynthesis of Triterpenes. The Rearrangement of 7a,#a- and 8,9-Epoxytirucallanes. J. Chem. Soc. (C) 1970, 1503.

    Google Scholar 

  84. Dreyer, D. L.: Limonoid Bitter Principles. Fortschritte der Chemie organischer Naturstoffe 26, 190 (1968).

    Article  CAS  Google Scholar 

  85. Ekong, D. E. U.: Chemistry of the Meliacins (Limonoids). The Structure of Nimbolide, a New Meliacin from Azadirachta indica. J. Chem. Soc. Chem. Commun. 1967, 808.

    Google Scholar 

  86. Ekong, D. E. U., C. O. Fakunle, A. K. Fasina, and J. I. Okogun: The Meliacins (limonoids). Nimbolin A and B, two new Meliacin Cinnamates from Azadirachta indica L. and Melia azedarach L. J. Chem. Soc. Chem. Commun. 1969, 1166.

    Google Scholar 

  87. Ekong, D. E. U., S. A. Ibiyemi, and E. O. Olagbemi: The Meliacins (limonoids). Biosynthesis of Nimbolide in the Leaves of Azadirachta indica. J. Chem. Soc. Chem. Commun. 1971, 1117.

    Google Scholar 

  88. Ekong, D. E. U., J. I. Okogun, and B. L. Sondengam: The Meliacins (Limonoids): Minor Constituents of Khaya anthotheca. Reduction of the Meliacins with Zinc-Copper Couple. J. Chem. Soc. Perkin Trans. I, 1975, 2118.

    Google Scholar 

  89. Ekong, D. E. U., and E. O. Olagbemi: Novel Meliacins (Limonoids) from the Wood of Pseudocedrela kotschyii. Tetrahedron Letters 1967, 3525.

    Google Scholar 

  90. Epe, B., and A. Mondon: Zur Kenntnis der Bitterstoffe aus Cneoraceen. XII. Tetrahedron Letters 1979, 2015.

    Google Scholar 

  91. Eshiett, I. T. U., A. Akisanya, and D. A. H. Taylor: Diterpenes from Annona senegalensis. Phytochemistry 10, 3294 (1971).

    Article  Google Scholar 

  92. Ferguson, G., P. A. Gunn, W. C. Marsh, R. McCrindle, R. Restiyo, J. D. Connolly, J. W. B. Fulke, and M. S. Henderson: Tetranortriterpenoids and Related Substances. Part XVII. A New Skeletal Class of Triterpenoids from Guarea glabra (Meliaceae). J. Chem. Soc. Perkin Trans. I, 1975, 491.

    Article  Google Scholar 

  93. Gopinath, K. W., T. R. Goyindachari, P. C. Parthasarathy, N. Viswanathan, D. Arigoni, and W. C. Wildman: The Structure of Cedrelone. Proc. Chem. Soc. 1961,446.

    Google Scholar 

  94. Grant, 1. G., J. A. Hamilton, T. A. Hamor, R. Hodges, S. G. McGeachin, R.A. Raphael, J. Monteath Robertson, and G. A. Sim: The Structure of Cedrelone. Proc. Chem. Soc. 1961, 444.

    Google Scholar 

  95. Grijpma, P.: Personal communication.

    Google Scholar 

  96. Gullo, V. P., I. Mn ra, K. Nakanishi, A. F. Cameron, J. D. Connolly, F. D. Duncanson, A. E. Harding, R. McCrindle, and D. A. H. Taylor: Structure of Prieurianin, a Complex Tetranortriterpenoid; Nuclear Magnetic Resonance Analysis at Non-ambient Temperatures and X-Ray Structure Determination. J. Chem. Soc. Chem. Commun. 1975, 345.

    Google Scholar 

  97. Harris, M., R. Henderson, R. McCrindle, K. H. Overton, and D. W. Turner: Tetranortriterpenoids VIII. The Constitution and Stereochemistry of Nimbin. Tetrahedron 24, 1517 (1968).

    Article  CAS  Google Scholar 

  98. Halsall, T. G., and J. A. Troke: The Structure of Three New Meliacins Isolated from Khaya anthotheca heartwood. J. Chem. Soc. Perkin Trans. I, 1975, 1758.

    Article  Google Scholar 

  99. Halsall, T. G., K. Wragg, J. D. Connolly, M. A. MacLellan, L. D. Bredell, and D. A. H. Taylor: 13C Nuclear Magnetic Resonance Spectra of Some Limonoids. Part III. The Spectra of Some Derivatives of Entandrophragmin and a Revised Structure for Candollein. J. Chem. Res. (S) 154, (M) 1727 (1977).

    Google Scholar 

  100. Hanni, R., and Ch. Tamm: Structure of the Tetranortriterpene Bussein, J. Chem. Soc. Chem. Commun. 1972, 1253.

    Google Scholar 

  101. Hanni, R., Ch. Tamm, V. P. Gullo, and K. Nakanishi: Modification of the Structure of Bussein. J. Chem. Soc. Chem. Commun. 1975, 563.

    Google Scholar 

  102. Harrison, H. R., O. J. R. Hodder, C. W. L. Bevan, D. A. H. Taylor, and T. G. Halsall: Crystallographic Structure Determination of Utilin, C41H52O17, a Complex Meliacin with a 1,29 Cycloswietenan Skeleton. J. Chem. Soc. Chem. Commun. 1970, 1388.

    Google Scholar 

  103. Henderson, R., R. McCrindle, A. Melera, and K. H. Overton: Tetranortriterpenoids IX. The Constitution and Stereochemistry of Salannin. Tetrahedron 24, 1525 (1968).

    Article  CAS  Google Scholar 

  104. Housely, J. R., F. E. King, T. J. King, and P. R. Taylor: The Chemistry of Hardwood Extractives. Part XXXIV. Constituents of Guarea species. J. Chem. Soc. 1962, 5095.

    Google Scholar 

  105. Jibodu, K. O., N. S. Ohochuku, and D. A. H. Taylor: Chemical Shifts of the Tertiary Methyl Groups in the Nuclear Magnetic Resonance Spectra of Some Limonoids. Part II. J. Chem. Soc. (C) 1970, 2396.

    Google Scholar 

  106. Jolad, S. D., J. J. Hoffmann, J. R. Cole, M. S. Tempesta, and R. B. Bates: Constituents of Trichilia hispida (Meliaceae) 2. A New Triterpene, Hispidone, and Bourjotinolone A. J. Org. Chem. 45, 3132 (1980).

    CAS  Google Scholar 

  107. Jolad, S. D., J. J. Hoffmann, K. H. Schräm, J. R. Cole, M. S. Tempesta, and R. B. Bates: Constituents of Trichilia hispida (Meliaceae) 3. Structures of the Cytotoxic Limonoids, Hispidins A, B and C. J. Org. Chem. 46, 641 (1981).

    Article  CAS  Google Scholar 

  108. Jolad, S. D., R. M. Wiedhopf, and J. R. Cole: Cytotoxic Agents from Bursera klugii (Burseraceae) I. Isolation of Sapelins A and B. J. Pharm. Sci. 66, 889 (1977). Chemical Abstracts 87, 78324z (1977).

    Article  CAS  Google Scholar 

  109. King, T. J., and D. A. H. Taylor: Limonoid Extractives from Aphanamixis polystacha Part II. Phytochemistry 22, 307 (1983).

    Article  CAS  Google Scholar 

  110. Kraus, W., and M. Bokel: Neue Tetranortriterpenoide aus Melia azedarach Linn. (Meliaceae). Chem. Ber. 114, 267 (1981).

    Article  CAS  Google Scholar 

  111. Kraus, W., and R. Cramer: 17-Epi-Azadiradione und 17-ß-Hydroxy-azadiradione; zwei neue Inhaltsstoffe aus Azadirachta indica A. Juss. Tetrahedron Letters 1978, 2395.

    Google Scholar 

  112. — —Neue Tetranortriterpenoide mit insektenfraßhemmender Wirkung aus Neem-Öl. Liebigs Ann. Chem. 1981, 187.

    Google Scholar 

  113. — — Pentanortriterpenoide aus Azadirachta indica A. Juss (Meliaceae). Chem. Ber. 114, 2375 (1981).

    Article  CAS  Google Scholar 

  114. Kraus, W., R. Cramer, and G. Sawitzka: Tetranortriterpenoids from the Seeds of Azadirachta indica. Phytochemistry 20, 117 (1981).

    Article  CAS  Google Scholar 

  115. Kraus, W., and K. Kypke: Surenone and Surenin, two Novel Tetranortriterpenoids from Toona sureni [Blume] Merrill. Tetrahedron Letters 1979, 2715.

    Google Scholar 

  116. Kraus, W., K. Kypke, M. Bokel, W. Grimminger, G. Sawitzki, and G. Schwinger: Surenolactone, ein neues Tetranortriterpenoid-A/B-dilacton aus Toona sureni [Blume] Merrill (Meliaceae). Liebigs Ann. Chem. 1982, 87.

    Google Scholar 

  117. Kraus, W., and W. Grimminger: 23-(R,S)-hydroxytoonacilid und 21-(R,S)-Hydroxy- toonacilid, zwei neue B-seco-Tetranortriterpenoide mit insektenfraßhemmender Wirkung aus Toona ciliata M. J. Roem var. Australis (Meliaceae). Nouveau Journal de Chimie 4, 651 (1980).

    CAS  Google Scholar 

  118. Kraus, W., and W. Grimminger: Toonafolin, ein neues Tetranortriterpenoid-B-lacton aus Toona ciliata var australis (Meliaceae). Liebigs Ann. Chem. 1981, 1838.

    Google Scholar 

  119. Kraus, W., W. Grimminger, and G. Sawitzki: Toonacilin and 6-Acetoxytoonacilin, Two Novel B-Seco-tetranortriterpenoids with Antifeeding Activity. Angewandte Chemie International Edition 17, 452 (1978).

    Article  Google Scholar 

  120. Kubo, I., and J. A. Klocke: Les Mediateurs Chimiques. INRA Colloque 7, 117 (1981).

    Google Scholar 

  121. Lavie, D., and M. K. Jain: Tetranortriterpenoids from Melia azadirachta L. J. Chem. Soc. Chem. Commun. 1967, 278.

    Google Scholar 

  122. Lavie, D., M. K. Jain, and I. Kirson: Terpenoids. Part VI. The Complete Structure of Melianone. J. Chem. Soc. (C) 1967, 1347.

    Google Scholar 

  123. Lavie, D., M. K. Jain, and S. R. Shpan-Gabrielith: A Locust Phagorepellent from Two Melia Species. J. Chem. Soc. Chem. Commun. 1967, 910.

    Google Scholar 

  124. Lavie, D., and E. C. Levy: Studies on Epoxides IV. Rearrangements in Triterpenoids. Tetrahedron Letters 1968, 2097.

    Google Scholar 

  125. — — Compounds Linking Meliones with Melianes. Tetrahedron Letters 1969, 3525.

    Google Scholar 

  126. — — Oxidative Reactions of Biogenetic Interest. Tetrahedron Letters 1970, 1315.

    Google Scholar 

  127. — — Meliane-Meliacin Relation. Tetrahedron 27, 3941 (1971).

    Article  CAS  Google Scholar 

  128. Lavie, D., E. C. Levy, and M. K. Jain: Limonoids of Biogenetic Interest from Melia azadirachta. Tetrahedron 27, 3927 (1971).

    Article  CAS  Google Scholar 

  129. Lavie, D., E. C. Levy, and R. Zelnik: Constituents of Carapa guianensis and their Biogenetic Relationship. Bioorganic Chemistry 2, 59 (1972). Chemical Abstracts 78, 58635n (1973).

    Article  CAS  Google Scholar 

  130. Lavie, D., E. C. Levy, C. Rosito, and R. Zelnik: Studies on Tetranortriterpenoids from Cedrela angustifolia Sessee and Moc. Tetrahedron 26, 219 (1970).

    Article  CAS  Google Scholar 

  131. Lukacova, V., J. Polonsky, C. Moretti, G. R. Pettit, and J. M. Schmidt: Isolation and Structure of 14ß,15ß-Epoxyprieurianin from the South American Tree Guarea guidona. J. Natural Products 45, 288 (1982). Chemical Abstracts 97, 69260e (1982).

    Article  CAS  Google Scholar 

  132. MacLachlan, L. K., and D. A. H. Taylor: Limonoids from Nymania capensis. Phytochemistry 21, 1701 (1982).

    CAS  Google Scholar 

  133. — — A Revision of the Structures of Three Limonoids. Phytochemistry 21, 2426 (1982).

    Article  CAS  Google Scholar 

  134. Mitra, C. R., H. S. Gary, and G. H. Pandey: Constituents of Azadirachta indica III. Phytochemistry 10, 857 (1971).

    Article  CAS  Google Scholar 

  135. Mulholland, D. A., and D. A. H. Taylor: A New Limonoid from Aphanamixis polystacha. J. Chem. Res. (S) 291, (M) 3101 (1979).

    Google Scholar 

  136. — — Limonoids from the Seed of the Natal Mahogany, Trichilia dregeana. Phytochemistry 19, 2421 (1980).

    Article  CAS  Google Scholar 

  137. Nakanishi, K.: Personal communication.

    Google Scholar 

  138. Nakatani, M., J. C. James, K. Nakanishi: Isolation and Structures of Trichilins, Antifeedants against the Southern Army Worm. J. Amer. Chem. Soc. 103, 1228 (1981).

    Article  CAS  Google Scholar 

  139. Narayanan, C. R., R. V. Pachapurkar, S. K. Pradhan, V. R., Shah, and N. S. Narasimhan: Structure of Nimbin. Chemistry and Industry 1964, 322. Chemical Abstracts 60, 12063d (1964).

    Google Scholar 

  140. Narayanan, C. R., and K. N. Iyer: Isolation and Characterisation of Deacetylnimbin. Indian J. Chem. 5, 460 (1967). Chemical Abstracts 68, 27509h (1968).

    CAS  Google Scholar 

  141. Narayanan, C. R., R. V. Pachapurkar, B. M. Sawant, and M. S. Waida: Vepinin, a New Constituent of Neem Oil. Indian J. Chem. 7, 187 (1969). Chemical Abstracts 71, 50267d (1969).

    CAS  Google Scholar 

  142. Ng, A. S., and A. G. Fallis: Comment: 7a-Acetoxydihydronomilin and Mexicanolide: Limonoids from Xylocarpus granatum (Koenig). Canadian J. Chem. 57, 3088 (1979).

    Article  CAS  Google Scholar 

  143. Obasi, M. E., J. I. Okogun, and D. E. U. Ekong: The Meliacins (Limonoids). Partial Synthesis of Mexicanolide. J. Chem. Soc. Chem. Commun. 1971, 727.

    Google Scholar 

  144. — — — The meliacins (Limonoids). Some Transformations and Interconversions of the Meliacins. J. Chem. Soc. Perkin Trans. I, 1972, 1943.

    Article  Google Scholar 

  145. Ochi, M., H. Kotsuki, K. Hirotsu, and T. Tokoroyama: Sendanin, a New Limonoid from Melia azedarach L. var. japonica Makino. Tetrahedron Letters 1976, 2877.

    Google Scholar 

  146. Ochi, M., H. Kotsuki, M. Ido, H. Nakai, M. Shiro, and T. Tokoroyama: Limonoids from Melia azedarach L. var.japonica Makino V. The Structures of Ohchinolide A and B. Chemistry Letters 1979, 1137. Chemical Abstracts 91, 189780x (1979).

    Google Scholar 

  147. Ochi, M., H. Kotsuki, H. Ishida, and T. Tokoroyama: Limonoids from Melia azedarach. L. var. japonica Makino. The Natural Hydroxyl Precursor of Sendanin. Chemistry Letters 1978, 99. Chemical Abstracts 88, 136807t (1978).

    Google Scholar 

  148. Ochi, M., H. Kotsuki, T. Kataoka, T. Tada, and T. Tokoroyama: Limonoids from Melia azedarach L. var.japonica Makino III. The Structures of Ohchinal and Ohchinin Acetate. Chemistry Letters 1978, 331. Chemical Abstracts 89, 43845j (1978).

    Google Scholar 

  149. Ochi, M., H. Kotsuki, and T. Tokoroyama: Limonoids from Melia azedarach L. var. japonica Makino. Sendanal, a New Limonoid. Chemistry Letters 1978, 621. Chemical Abstracts 89,12975In (1978).

    Google Scholar 

  150. Ochi, M., H. Kotsuki, T. Tokoroyama, and T. Kubota: The Structure of Sendanolactone; a New Triterpenoid from Melia azedarach L. var. japonica Makino. Bull. Chem. Soc. Japan 50, 2499 (1977).

    Article  CAS  Google Scholar 

  151. Ohochuku, N. S., and D. A. H. Taylor: Chemical Shift of the Tertiary Methyl Groups in the Nuclear Magnetic Resonance Spectra of Some Limonoids. J. Chem. Soc. (C) 1969, 864.

    Google Scholar 

  152. Ohochuku, N. S., and D. A. H. Taylor: 6ß-Hydroxygedunin. J. Chem. Soc. (C) 1970, 421.

    Google Scholar 

  153. Okogun, J. I., C. O. Fakunle, D. E. U. Ekong, and J. D. Connolly: Chemistry of the Meliacins (Limonoids). The Structure of Melianin A, a New Protomeliacin from Melia azedarach. J. Chem. Soc. Perkin Trans I 1975, 1352.

    Article  Google Scholar 

  154. Okorie, D. A., and D. A. H. Taylor: The Structure of Heudelottin, an Extractive from Trichilia heudelottii. J. Chem. Soc. Chem. Commun. 1967, 83.

    Google Scholar 

  155. — — The Mechanism of the Rearrangement of Havanensin. J. Chem. Soc. Chem. Comm. 1968, 737.

    Google Scholar 

  156. — — Limonoids from the Timber of Trichilia heudelottii Planch ex Oliv. J. Chem. Soc. (C), 1968, 1828.

    Google Scholar 

  157. — — Extractives from the Seed of Cedrela odorata L. Phytochemistry 7, 1683 (1968).

    Article  CAS  Google Scholar 

  158. — — Limonoids from Xylocarpus granatum. J. Chem. Soc. (C) 1970, 211.

    Google Scholar 

  159. — — Limonoids from Swietenia humilis. Phytochemistry 10, 469 (1971).

    Article  CAS  Google Scholar 

  160. — — Limonoids from Trichilia heudelottii Part II. J. Chem. Soc. Perkin Trans I, 1972, 1488.

    Article  Google Scholar 

  161. — — Triterpenes from the Seed of Entandrophragma Species. Phytochemistry 16, 2029.

    Google Scholar 

  162. Ollis, W. D., A. D. Ward, H. M. de Oliviera, and R. Zelnik: Andirobin. Tetrahedron 26, 1037 (1970).

    Google Scholar 

  163. Ollis, W. D., A. D. Ward, and R. Zelnik: Andirobin. Tetrahedron Letters 1964,2607.

    Google Scholar 

  164. Pachapurkar, R. V., P. M. Kornule, and C. R. Narayanan: New Hexacyclic Tetranortriterpenoid. Chemistry Letters 1974, 357. Chemical Abstracts 80, 146356 u (1974).

    Google Scholar 

  165. Pegel, K. H.: Personal communication.

    Google Scholar 

  166. Polonsky, J., Z. Varon, B. Arnoux, C. Pascard, G. R. Pettit, J. H. Schmidt, and L. M. Lange: Isolation and Structure of Aphanastatin. J. Amer. Chem. Soc. 100, 2575.(1978)

    Article  CAS  Google Scholar 

  167. Polonsky, J., Z. Varon, B. Arnoux, C. Pascard, G. R. Pettit, and J. H. Schmidt: Isolation and Structure of Amoorastatin. J. Amer. Chem. Soc. 100, 7731 (1978).

    Article  CAS  Google Scholar 

  168. Polonsky, J., Z. Varon, C. Marazano, B. Arnoux, G. R. Pettit, J. H. Schmidt, M. Ochi, and H. Kotsuki: The Structure of Amoorastatone and the Cytotoxic Limonoid 12-Hydroxyamoorastatin. Experientia 35, 987 (1979).

    Article  CAS  Google Scholar 

  169. Purushothaman, K. K., and S. Chandrasekharan: Occurrence of Methyl Angolensate and Deoxyandirobin in Soymida febrifuga. Indian J. Chem. 12, 207 (1974). Chemical Abstracts 81, 101847j (1974).

    CAS  Google Scholar 

  170. Purushothaman, K. K., S. Chandrasekharan, J. D. Connolly, and D. S. Rycroft: Tetranortriterpenoids and Related Substances Part 18. Two New Tetranortriterpenoids with a Modified Furan Ring from the Bark of Soymida febrifuga A. Juss (Meliaceae). J. Chem. Soc. Perkin Trans I. 1977, 1873.

    Article  Google Scholar 

  171. Ragettli, T., and Ch. Tamm: Die Chukrasine A, B, C, D und E, fünf neue Tetranortriterpene aus Chukrasia tabularis A. Juss. Helv. Chim. Acta 61, 1814 (1978).

    Article  CAS  Google Scholar 

  172. Rao, M. M., A. S. Gupta, P. P. Singh, and E. M. Krishna: Structure of Febrinin A, a New Tetranortriterpenoid from the Heartwood of Soymida febrifuga. Indian J. Chem. 17B, 158 (1979). Chemical Abstracts, 92, 22648 u (1980).

    Google Scholar 

  173. Rao, M. M., E. M. Krishna, P. S. Gupta, and P. P. Singh: A New Tetranortriterpenoid Isolated from the Heartwood of Soymida febrifuga. Indian J. Chem. 16B, 823 (1978). Chemical Abstracts 90, 168783q (1979).

    Google Scholar 

  174. Rao, M. M., H. Meshulam, R. Zelnik, and D. Lavie: Cabralea eichleriana DC. (Meliaceae)-1. Structure and Stereochemistry of Wood Extractives. Tetrahedron 31,333 (1975).

    Article  CAS  Google Scholar 

  175. — — Cabralea eichleriana extractives II. Structure and Stereochemistry of Limonoids of Cabralea eichleriana. Phytochemistry 14, 1071 (1975).

    Article  CAS  Google Scholar 

  176. Saikia, B., J. C. S. Kataky, R. K. Mathur, and J. N. Baruah: New Meliacins from the Fruits of Chisocheton paniculatus Hiern. Indian J. Chem. 16B, 1042 (1978). Chemical Abstracts 91, 2507y (1979).

    Google Scholar 

  177. Shiengthong, D., U. Kokpol, P. Karntiang, and R. A. Massey-Westropp: Triterpenoid Constituents of Thai medicinal plants — II. Isomeric Aglaitriols and Aglaiondiol. Tetrahedron 30, 2211 (1974).

    Article  CAS  Google Scholar 

  178. Schulte, K. E., G. Ruecker, and H. U. Matern: Some Constituents of the Fruit and Roots of Melia azedarach L. Planta Medica 35, 76 (1979). Chemical Abstracts 90, 164741b (1979).

    Article  CAS  Google Scholar 

  179. Shu, G., and X. Liang: Correction of the Structure of Chuanliansu. Hua Hsueh Hsueh Pao 38, 196 (1980). Chemical Abstracts 93, 239693k (1982).

    CAS  Google Scholar 

  180. Siddiqui, S., S. Fuchs, J. Lücke, and W. Voelter: Struktur eines neuen Naturstoffes aus Melia azadirachta L. 17-Hydroxyazadiradion. Tetrahedron Letters 1978, 611.

    Google Scholar 

  181. Singh, S., H. S. Garg, and N. M. Khanna: Dysobinin, a New Tetranortriterpene from Dysoxylum binectariferum. Phytochemistry 15, 2001 (1978).

    Article  Google Scholar 

  182. Sondengam, B. L., C. S. Kamga, and J. D. Connolly: Evodulone, a New Tetranortriterpenoid from Carapa procera. Tetrahedron Letters 1979, 1357.

    Google Scholar 

  183. — — — Personal communication.

    Google Scholar 

  184. Sondengam, B. L., C. S. Kamga, S. F. Kimbu, and J. D. Connolly: Proceranone, a New Tetranortriterpenoid from Carapa procera. Phytochemistry 20, 173 (1981).

    Article  CAS  Google Scholar 

  185. Straka, H., F. Albers, and A. Mondon: Die Stellung und Gliederung der Familie Cneoraceae (Rutales). Biologie der Pflanzen 52, 267 (1976).

    Google Scholar 

  186. Taylor, D. A. H.: Extractives from East African Timbers. Part 1. J. Chem. Soc. 1965, 2495.

    Google Scholar 

  187. — — Nyasin, an Extractive from Khaya nyasica Stapf. J. Chem. Soc. Chem. Commun. 1967, 500.

    Google Scholar 

  188. — — 11 ß-Acetoxykhivorin, a New Limonoid. J. Chem. Soc. Chem. Commun. 1968,1172.

    Google Scholar 

  189. — — Extractives from Swietenia mahogani (L) Jacq. J. Chem. Soc. Chem. Commun. 1969, 58.

    Google Scholar 

  190. — — Limonoids from Khaya nyasica Stapf, ex Bäk. J. Chem. Soc. (C). 1969, 2439.

    Google Scholar 

  191. — — Limonoids from Khaya madagascariensis Jumelle et Perrier. J. Chem. Soc. (C) 1970, 336.

    Google Scholar 

  192. — — The Structure of Fissinolide. Tetrahedron Letters 1970, 2797.

    Google Scholar 

  193. Taylor, D. A. H., and F. W. Wehrli: The Structure of Fissinolide and Angustidienolide, Limonoids from Species of Meliaceae. J. Chem. Soc. Perkin Trans 1. 1973, 1599.

    Article  Google Scholar 

  194. Taylor, D. A. H.: 13C Nuclear Magnetic Resonance Spectra of Some Limonoids. Part I. The Structure of Procerin, an Extractive from Carapa procera. J. Chem. Soc. Perkin Trans I 1974, 437.

    Article  Google Scholar 

  195. — — The Structure of an Extractive from Khaya ivorensis. Phytochemistry 16, 1847 (1977).

    Article  CAS  Google Scholar 

  196. — — A Limonoid, Pseudrelone B, from Pseudocedrela kotschyii. Phytochemistry 18, 1574 (1979).

    Article  CAS  Google Scholar 

  197. — — Ekebergin, a Limonoid Extractive from Ekebergia capensis. Phytochemistry 20,2263 (1981).

    Article  CAS  Google Scholar 

  198. — — A New Structural Proposal for the Tetranortriterpenoid Dregeanin. J. Chem. Res. (S) 1982, 55.

    Google Scholar 

  199. — — Flora Neotropica. Monograph Number 28. Meliaceae. Chemotaxonomy 450 (1981).

    Google Scholar 

  200. — — Unpublished work.

    Google Scholar 

  201. Taylor, D. R.: New Limonoids from Trichilia trifolia (Meliaceae). Revista Latinoamericana de Quimica 2, 87 (1971). Chemical Abstracts 75, 129969a (1971).

    CAS  Google Scholar 

  202. Zanno, P. R., I. Miura, K. Nakanishi, and D. L. Elder: Structure of the Insect Phagorepellent Azadirachtin. Application of PRFT/CWD Carbon-13 Nuclear Magnetic Resonance. J. Amer. Chem. Soc. 97, 1975 (1975).

    Article  CAS  Google Scholar 

  203. Zelnik, R.: Tetranortriterpenoids from Cabralea eichleriana. Phytochemistry 11, 1866 (1972).

    Article  CAS  Google Scholar 

  204. Zelnik, R., and C. M. Rosito: Le Fissinolide. Tetrahedron Letters 1966, 6441.

    Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Rights and permissions

Reprints and permissions

Copyright information

© 1984 Springer-Verlag/Wien

About this chapter

Cite this chapter

Taylor, D.A.H. (1984). The Chemistry of the Limonoids from Meliaceae. In: 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 45. Springer, Vienna. https://doi.org/10.1007/978-3-7091-8717-3_1

Download citation

  • DOI: https://doi.org/10.1007/978-3-7091-8717-3_1

  • Publisher Name: Springer, Vienna

  • Print ISBN: 978-3-7091-8719-7

  • Online ISBN: 978-3-7091-8717-3

  • eBook Packages: Springer Book Archive

Publish with us

Policies and ethics