Novel Epoxy Steroids from the Indian Ocean Soft Coral Sarcophyton crassocaule

• Published in: Journal of natural products (Washington, D.C.) Vol. 63; no. 1; pp. 112 - 118
• Main Authors: Anjaneyulu, Ammanamanchi S. R, Krishna Murthy, Moturu V. R, Gowri, Ponnapalli M
• Format: Journal Article
• Language: English
• Published: Washington, DC American Chemical Society 01-01-2000; Glendale, AZ American Society of Pharmacognosy
• Subjects: Analytical, structural and metabolic biochemistry; Animals; Biological and medical sciences; chemical composition; chemical structure; Cnidaria - chemistry; corals; Fundamental and applied biological sciences. Psychology; Molecular Structure; Other biological molecules; secondary metabolites; spectral analysis; Spectrum Analysis; steroids; Steroids - chemistry; Steroids - isolation & purification; Terpenes, steroids. Hormones; Andaman and Nicobar Islands; Indian Ocean; Marine environment; Steroid; Coelenterata; Cnidaria; Epoxide; Animal origin; Isolation; Invertebrata; Secondary alcohol; Acylate; Structural analysis
• ISSN: 0163-3864; 1520-6025
• DOI: 10.1021/np990205p

A detailed further examination of the Indian Ocean soft coral Sarcophyton crassocaule resulted in the isolation of altogether 17 compounds of which two (1 and 2) are novel 17β,20β-epoxy steroids and one is a new dihydroxygorgost-5-en (3). The other compounds include the four hippurin steroids (4−7) reported earlier, and some known derivatives such as methyl arachidonate, batyl alcohol, a mixture of monohydroxy sterols, 3β-hydroxypregn-5-en-20-one, two prostaglandin derivatives (PGB2 acid and its methyl ester), and 9-oxo-9,11-secogorgost-5-ene-3β,11-diol (8). The structure of new dihydroxygorgostene derivative was established as gorgost-5-ene-3β,11α-diol (3), while the structures of the novel epoxy steroids were established as 17β,20β-epoxy-23,24-dimethylcholest-5-ene-3β,22-diol (2) and its 3β,22-diacetate (1), respectively.