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A new 9,11-secosterol with a 1,4-quinone from a Korean marine sponge Ircinia sp.

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Abstract

An intensive investigation of chemical components for Ircinia sp. led to the isolation of a new 9,11-secosterol. The chemical structure of this compound was elucidated based on the interpretation of NMR and MS spectroscopic data. The isolated compound exhibited antibacterial activities against Staphylococcus epidermidis and Bacillus subtilis with MIC values of 6.3 and 25 μg ml−1, respectively.

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References

  • Adinolfi, R., A. Migliuogo, V. Piccialli, and D. Sica. 1994. Isolation and synthesis of a new 9,11-secosterol from the sponge Spongzia officinalis. Journal of Natural Products 57(9): 1200–1226.

    Article  Google Scholar 

  • Aknin, M., V. Costantino, A. Mangoni, E. Fattorusso, and E.M. Gaydou. 1998. New 9,11-secosterols from gorgonian Subergorgia suberosa of the Indian Ocean. Steroids 63: 575–578.

    Article  CAS  PubMed  Google Scholar 

  • Anta, C., N. González, J. Rodríguez, and C. Jiménez. 2002. A new secosterol from the Indonesian octocoral Pachyclavularia violacea. Journal of Natural Products 65(9): 1357–1359.

    Article  CAS  PubMed  Google Scholar 

  • Bhandari, P., N. Kumar, B. Singh, and V.K. Kaul. 2006. Bacosterol glycoside, a new 13,14-seco-steroid glycoside from Bacopa monnieri. Chemical & Pharmaceutical Bulletin 54(2): 240–241.

    Article  CAS  Google Scholar 

  • Bonini, C., C.B. Cooper, R. Kazlauskas, R.J. Wells, and C. Djerassi. 1983. Minor and trace sterols in marine invertebrates. 41. Structure and stereochemistry of naturally occurring 9,11-seco sterols. Journal of Organic Chemistry 48: 2108–2111.

    Article  CAS  Google Scholar 

  • Capon, R.J., and D.J. Faulkner. 1985. Herbasterol, an ichthyotoxic 9,11-secosterol from the sponge Dysidea herbacea. Journal of Organic Chemistry 58: 4771–4773.

    Article  Google Scholar 

  • Chen, B.-W., S.-M. Chang, C.-Y. Huang, J.-H. Su, Z.-H. Wen, Y.-C. Wu, and J.-H. Sheu. 2011a. Hirsutosterols A–G, polyoxygenated steroids from a Formosan soft coral Cladiella hirsuta. Organic & Biomolecular Chemistry 9: 3272–3278.

  • Cheng, S.-Y., H.-P. Chen, S.-K. Wang, and C.-Y. Duh. 2011b. Three new 9,11-secosterols from the Formosan soft coral Sinularia leptoclados. Bulletin of the Chemical Society Japan 84(6): 648–652.

  • Davis, C.D. 2008. Vitamin D and cancer: current dilemmas and future research needs. The American Journal of Clinical Nutrition 88: 565S–569S.

    CAS  PubMed  Google Scholar 

  • De Rosa, S., A. De Giulio, A. Crisping, C. Iodice, and G. Tommonaro. 1999. New 9,11-secosterol from the Tyrrhenian sponge Fasciospongia cavernosa. Natural Product Letters 13(1): 15–20.

    Article  Google Scholar 

  • Epifanio, R., L. Maia, J. Pawlik, and W. Fenical. 2007. Antipredatory secosterols from the octocoral Pseudopterogorgia americana. Marine Ecology Progress Series 329: 307–310.

    Article  CAS  Google Scholar 

  • Fusetani, N., H. Nagata, H. Hirota, and T. Tsuyuki. 1989. Astrogorgiadiol and astrogorgin, inhibitors of cell division in fertilized starfish eggs, from a gorgonian Astrogorgia sp. Tetrahedron Letters 30(50): 7079–7082.

    Article  CAS  Google Scholar 

  • He, H., P. Kulanthaivel, B.J. Baker, K. Kalter, J. Darges, D. Cofield, L. Wolff, and L. Adams. 1995. New antiproliferative and antiinflammatory 9,11-secosterols from the gorgonian Pseudopterogorgia sp. Tetrahedron 51(1): 51–58.

    Article  CAS  Google Scholar 

  • Huang, C.-Y., J.-H. Su, C.-Y. Duh, B.-W. Chen, Z.-H. Wen, Y.-H. Kuo, and J.-H. Sheu. 2012. A new 9,11-secosterol from the soft coral Sinularia granosa. Bioorganic & Medicinal Chemistry Letters 22(13): 4373–4376.

    Article  CAS  Google Scholar 

  • Ioannou, E., A.F. Abdel-Razik, X. Alexi, C. Vagias, M.N. Alexis, and V. Roussis. 2009. 9,11-secosterols with antiproliferative activity from the gorgonian Eunicella cavolini. Bioorganic & Medicinal Chemistry 17(13): 4537–4541.

    Article  CAS  Google Scholar 

  • Kirson, I., Z. Zaretskii, and E. Glotter. 1976. Withaphysalin C, a naturally occurring 13,14-seco-steroid. Journal of the Chemical Society, Perkin Transactions 1: 1244–1247.

    Article  Google Scholar 

  • Koljak, R., T. Pehk, I. Jarving, M. Liiv, A. Lopp, K. Varvas, A. Vahemets, U. Lille, and N. Samel. 1993. New antiproliferative 9,11-secosterol from soft coral Gersemia fruticosa. Tetrahedron Letters 34(12): 1985–1986.

    Article  CAS  Google Scholar 

  • Kovganko, N., and Y. Chernov. 2001. 13C NMR spectra of 6-hydroximinosteroids of the stigmastane series. Chemistry of Natural Compounds 37(4): 351–355.

    Article  CAS  Google Scholar 

  • Li, H., S. Matsunaga, and N. Fusetani. 1994. A new 9,11-secosterol, stellettasterol from a marine sponge Stelletta sp. Experientia 50: 771–773.

    Article  CAS  Google Scholar 

  • Lopp, A., A. Pihlak, H. Paves, K. Samuel, and R. Koljak. 1994. The effect of 9,11-secosterol, a newly discovered compound from the soft coral Gersemia fruticosa, on the growth and cell cycle progression of various tumor cells in culture. Steroids 59: 274–281.

    Article  CAS  PubMed  Google Scholar 

  • Lu, Q., and D.J. Faulkner. 1997. Two new sesterterpenoids and a new 9,11-secosterol from Spongia matamata. Journal of Natural Products 60: 195–198.

    Article  CAS  PubMed  Google Scholar 

  • Matsumoto, T., T. Takano, H. Saito, and F. Takahashi. 2014. Vitamin D analogs and bone: Preclinical and clinical studies with eldecalcitol. BoneKEy Reports 3: 513.

    Article  PubMed Central  PubMed  Google Scholar 

  • Mattila, P.H., V.I. Piironen, E.J. Uusi-rauva, and P.E. Koivistoinen. 1994. Vitamin D contents in edible mushrooms. Journal of Agriculture and Food Chemistry 42: 2449–2453.

    Article  CAS  Google Scholar 

  • Migliuolo, A., V. Piccialli, and D. Sica. 1991. Structure elucidation and synthesis of 3β,6α-dihydroxy-9-oxo-9,11-seco-5α-cholest-7-en-11-al, a novel 9,11-secosterol from the sponge Spongia officinalis. Tetrahedron 47(37): 7937–7950.

    Article  CAS  Google Scholar 

  • Migliuolo, A., V. Piccialli, and D. Sica. 1992. Two new 9,11-secosterols from the marine sponge Spongia oficinalis. Synthesis of 9,11-seco-3β,6α,11-trihydroxy-5α-cholest-7-en-9-one. Steroids 57: 344–347.

    Article  CAS  PubMed  Google Scholar 

  • Minh, C.V., N.X. Cuong, T.A. Tuan, E.M. Choi, Y.H. Kim, and P.V. Kiem. 2007. A new 9,11-secosterol from the Vietnamese Sea soft coral, Sarcophyton mililatensis, increases the function of osteoblastic MC3T3-E1 cells. Natural Product Communications 2(11): 1095–1100.

    Google Scholar 

  • Morris, L.A., E.M. Christie, M. Jaspars, and L.P. Van Ofwegen. 1998. A bioactive secosterol with an unusual A- and B-ring oxygenation pattern isolated from an Indonesian soft coral Lobophytum sp. Journal of Natural Products 61: 538–541.

    Article  CAS  PubMed  Google Scholar 

  • Norman, P.E., and J.T. Powell. 2014. Vitamin D and cardiovascular disease. Circulation Research 114(2): 379–393.

    Article  CAS  PubMed  Google Scholar 

  • Ochi, M., K. Yamada, H. Kotsuki, and K. Shibata. 1991. Calicoferols A and B, two novel secosterols possessing brine-shrimp lethality from the gorgonian Calicogorgia sp. Chemistry Letters 20(3): 427–430.

    Article  Google Scholar 

  • Qiu, L., F. Zhao, Z.-H. Jiang, L.-X. Chen, Q. Zhao, H.-X. Liu, X.-S. Yao, and F. Qiu. 2008. Steroids and flavonoids from Physalis alkekengi var. franchetii and their inhibitory effects on nitric oxide production. Journal of Natural Products 71: 642–646.

    Article  CAS  PubMed  Google Scholar 

  • Reddy, M.V., M.K. Harper, and D.J. Faulkner. 1997. Luffasterols A–C, 9,11-secosterols from the Palauan sponge Luffariella sp. Journal of Natural Products 60(1): 41–43.

    Article  CAS  PubMed  Google Scholar 

  • Rho, J.-R., H.-S. Lee, Y. Seo, K.W. Cho, and J. Shing. 2000. New bioactive steroids from the gorgonian Acalycigorgia inermis. Bulletin of the Korean Chemical Society 21: 518–520.

    CAS  Google Scholar 

  • Rueda, A., E. Zubia, M.J. Ortega, J.L. Carballo, and J. Salva. 1998. New metabolites from the sponge Spongia agaricina. Journal of Natural Products 61: 258–261.

    Article  CAS  PubMed  Google Scholar 

  • Su, J.-H., Y.-J. Tseng, H.-H. Huang, A.F. Ahmed, C.-K. Lu, Y.-C. Wu, and J.-H. Sheu. 2006. 9,11-Secosterols from the soft corals Sinularia lochmodes and Sinularia leptoclados. Journal of Natural Products 69: 850–852.

    Article  CAS  PubMed  Google Scholar 

  • USDA (U.S. Department of Agriculture), Agricultural Research Service. 2011. USDA National Nutrient Database for Standard Reference, Release 24. Nutrient Data Laboratory home page. http://www.ars.usda.gov/ba/bhnrc/ndl. Accessed 5 Jan 2015.

  • Van Altena, I.A., A.J. Butler, and S.J. Dunne. 1999. A new cyclized 9,11-secosterol enol-ether from the Australian sponge Euryspongia arenaria. Journal of Natural Products 62: 1154–1157.

    Article  PubMed  Google Scholar 

  • Yang, I., H. Choi, D.H. Won, S.-J. Nam, and H. Kang. 2014. An antibacterial 9,11-secosterol from a marine sponge Ircinia sp. Bulletin of the Korean Chemical Society 35(11): 3360–3362.

    Article  CAS  Google Scholar 

  • Yin, K., and D.K. Agrawal. 2014. Vitamin D and inflammatory diseases. Journal of Inflammation Research 2014: 69–87.

    Google Scholar 

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Acknowledgments

This work was supported by Suncheon Research Center for Natural Medicines. I. Yang was in part supported by the BK21 program, Ministry of Education, Korea.

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The authors declare that they have no conflict of interest.

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Correspondence to Sang-Jip Nam or Heonjoong Kang.

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Inho Yang and Hyukjae Choi have contributed equally to this work.

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Yang, I., Choi, H., Nam, SJ. et al. A new 9,11-secosterol with a 1,4-quinone from a Korean marine sponge Ircinia sp.. Arch. Pharm. Res. 38, 1970–1974 (2015). https://doi.org/10.1007/s12272-015-0620-9

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  • DOI: https://doi.org/10.1007/s12272-015-0620-9

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