Minor and Trace Sterols in Marine Invertebrates. 26.1 Isolation and Structure Elucidation of Nine New 5α,8α-Epidioxy Sterols from Four Marine Organisms

A. A. Leslie Gunatilaka, Yalamanchili Gopichand, Francis J. Schmitz, Carl Djerassi

Research output: Contribution to journalArticle

164 Scopus citations

Abstract

Sixteen 5α,8α-epidioxy ∆6 and ∆6,9(11) sterols, of which nine are new, have been isolated from the marine organisms Ascidia nigra, Dendrogyra cylindrus, Thalysias juniperina, and Aplysia dactyLornela by reverse-phase highperformance liquid chromatography and characterized by high-resolution mass spectrometry and 360-MHz proton NMR spectroscopy. Attention is drawn to some unusual concentration-dependent NMR shifts of methyl signals. The probable biological significance of these epidioxy sterols is discussed with special reference to sterol biosynthesis.

Original languageEnglish (US)
Pages (from-to)3860-3866
Number of pages7
JournalJournal of Organic Chemistry
Volume46
Issue number19
DOIs
StatePublished - Sep 1981
Externally publishedYes

ASJC Scopus subject areas

  • Organic Chemistry

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