5,8-Epidioxysterols and related derivatives from a Chinese Soft Coral Sinularia flexibilis

Steroids

Volumn 71, Issue 11-12, 2006, Pages 955-959

  Yu, Shanjiang ^a   Deng, Zhiwei ^b   van Ofwegen, Leen ^c   Proksch, Peter ^d   Lin, Wenhan ^a  

^a PEKING UNIVERSITY   (China)

^b BEIJING NORMAL UNIVERSITY   (China)

^c NATURALIS BIODIVERSITY CENTER   (Netherlands)

^d HEINRICH HEINE UNIVERSITY   (Germany)

Author keywords

Sinularia flexibilis; Soft coral; Sterols; Structure identification

Indexed keywords

22ALPHA,28 EPIDIOXYCHOLESTA 5,23(E) DIEN 3BETA OL; 22BETA,28 EPIDIOXYCHOLESTA 5,23(E) DIEN 3BETA OL; 5ALPHA,8ALPHA EPIDIOXYGORGOSTA 6 EN 3BETA OL; 5ALPHA,8ALPHA EPIDIOXYGORGOSTA 6,9(11) DIEN 3BETA OL; METHANOL; STEROL; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHROMATOGRAPHY; CORAL; DRUG ISOLATION; DRUG STRUCTURE; EPIMER; INFRARED SPECTROSCOPY; MASS SPECTROMETRY; NUCLEAR OVERHAUSER EFFECT; PROTON NUCLEAR MAGNETIC RESONANCE; SEPARATION TECHNIQUE; SINULARIA FLEXIBILIS; SPECTROSCOPY;

ANIMALS; ANTHOZOA; CHINA; MOLECULAR STRUCTURE; OXYGEN; STEROLS;

ALCYONACEA; SINULARIA FLEXIBILIS;

EID: 33750014500     PISSN: 0039128X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.steroids.2006.07.002     Document Type: Article

References (28)

1. Paul V.J., Puglisi M.P., and Ritson-Williams R. Marine chemical ecology. Nat Prod Rep 23 (2006) 153-180
2. Fleury B.G., Coll J.C., Sammarco P.W., Tentori E., and Duquesne S. Complementary (secondary) metabolites in an octocoral competing with a scleractinian coral: effects of varying nutrient regimes. J Exp Mar Biol Ecol 303 (2004) 115-131
3. Lages B.G., Fleury B.G., Ferreira C.E.L., and Pereira R.C. Chemical defense of an exotic coral as invasion strategy. J Exp Mar Biol Ecol 328 (2006) 127-135
4. Van A.K., Wylie C.R., Paul V.J., and Meyer K. Anti-predator defenses in tropical Pacific soft corals (Coelenterata: Alcyonacea). The relative importance of chemical and structural defenses in three species of Sinularia. J Exp Mar Biol Ecol 178 (1994) 17-34
5. La Barre S.C., Coll J.C., and Sammarco P.W. Competitive strategies of soft corals (Coelenterata: Octocorallia). III. Spacing and aggressive interactions between alcyonaceans. Mar Ecol Prog Ser 28 (1986) 147-156
6. Ramesh P., and Venkateswarlu Y. Novel steroid constituents of the soft coral Sinularia dissecta. Steroids 64 (1999) 785-789
7. Ahmed A.F., Dai C.F., Kuo Y.H., and Sheu J.H. 1α,3β,5β-trihydroxy-24-methylenecholestan-6-one: a novel steroid from a soft coral Sinularia gibberosa. Steroids 68 (2003) 377-381
8. Jin P., Deng Z., Pei Y., Fu H., Li J., Ofwegen L., et al. Polyhydroxylated steroids from the soft coral Sinularia dissecta. Steroids 70 (2005) 487-493
9. Faulkner D.J. Marine natural products. Nat Prod Rep 14 (1997) 259-302 [and literature cited in the previous reviews]
10. Anjaneyulu A.S.R., and Rao G.V. The chemical constituents of the soft coral species of Sinularia genus: a review. J Sci Ind Res 54 (1995) 637-649
11. Hsieh P.W., Chang F.R., McPhail A.T., Lee K.H., and Wu Y.C. New cembranolide analogues from the formosan soft coral Sinularia flexibilis and their cytotoxicity. Nat Prod Res 17 (2003) 409-418
12. Duh C.Y., Wang S.K., Tseng H.K., and Sheu J.H. A novel cytotoxic biscembranoid from the Formosan soft coral Sinularia flexibilis. Tetrahydron Lett 39 (1998) 7121-7122
13. Duh C.Y., Wang S.K., Tseng H.K., Sheu J.H., and Chiang M.Y. Novel cytotoxic cembranoids from the soft coral Sinularia flexibilis. J Nat Prod 61 (1998) 844-847
14. Gunatilaka A.A.L., Gopichand Y., Schmitz F.J., and Djerassi C. Minor and trace sterols in marine invertebrates. 26. Isolation and structure elucidation of nine new 5,8-epidoxy sterols from four marine organisms. J Org Chem 46 (1981) 3860-3866
15. Wang J.F., Huang Y.J., Fang M.J., Xie W.L., Su W.J., and Zhao Y.F. 5α,7α-Epidioxyergosta-6,22-dien-3β-ol (ergosterol peroxide) methanol solvate. Acta Crystallogr (E) 60 (2004) 764-765
16. Sheu J.H., Chang K.C., and Duh C.Y. A cytotoxic 5α,8α-epidioxysterol from a soft coral Sinularia species. J Nat Prod 63 (2000) 149-151
17. Yasunori Y., Keiko A., Hiroyuki O., Katsuyuki F., Akihiro M., Toshihiko M., et al. Sterol constituents from five edible mushrooms. Chem Pharm Bull 46 (1998) 944-950
18. Zhang G.W., Ma X.Q., Zeng L.M., and Su J.Y. Studies on the chemical constituents of the soft coral Cladiella sp. Yingyong Huaxue 20 (2003) 1021-1024
19. Venkateswarlu Y., Sridevi K.V., and Rao M.R. New furanocembranoid diterpenes from the soft coral Sinularia maxima. J Nat Prod 62 (1999) 756-758
20. Luo X., Wu S., Ma Y., and Wu D. Chemical constituent of Amoora yunnanensis. Zhiwu Xuebao 43 (2001) 426-430
21. Tanaka J., Trianto A., Musman M., Issa H.H., Ohtani I.I., Ichiba T., et al. New polyoxygenated sterols exhibiting reversal of multidrug resistance from the gorgonian Isis hippuris. Tetrahedron 58 (2002) 6259-6266
22. Subrabmanyam C., Rao C.V., and Kulatheeswaran R. A new sterol peroxide from a Lobophytum species soft coral. Indian J Chem B 34 (1995) 1114-1115
23. Anjaneyulu A.S.R., and Sagar K.S. Two new 5α,8α-epidioxy sterols from the Indian ocean soft coral Sinularia maxima. J Chem Res (1995) 142-143
24. Bocking T., Barrow K.D., Netting A.G., Chilcott T.C., Coster H.L.C., and Hofer M. Effects of singlet oxygen on membrane sterols in the yeast Saccharomyces cerevisiae. Eur J Biochem 267 (2000) 1607-1618
25. Jimenz C., Quinoa E., and Riguera R. The dietary origin of epidioxysteroids in Actinia equina: a carbon-14 incorporation experiment. J Nat Prod 52 (1989) 619-622
26. Wilson S., Burns K., and Codi S. Identifying sources of organic matter in sediments from detritivorous coral reef fish territory. Org Geochem 32 (2001) 1257-1269
27. Volkman J.K., Rijpstra W.I.C., Leeuw J.W., Mansour M.P., Jackson A.E., and Blackburn S.I. Sterols of four dinoflagellates from the genus Prorocentrum. Phytochemistry 52 (1999) 659-668
28. Elenkov I., Milkova T., Andreev S., and Popov S. Sterol composition and biosynthesis in the Black Sea sponge Dysidea fragilis. Comp Biochem Physiol B 107 (1994) 547-551