Biosynthetic studies of marine lipids. 20. Sequence of double-bond introduction in the sponge sterol 24β-methylcholesta-5,7,22,25-tetraen-3β-ol

Varghese John, Ivan L. Stoilov, Carl Djerassi*, Peter Karuso, Anthony Poiner, Paul J. Scheuer

*Corresponding author for this work

Research output: Contribution to journalArticle

21 Citations (Scopus)

Abstract

The biosynthesis of Δ5,7-sterols in Ciocalypta sp. was studied with radiolabeled Δ5-sterol precursors. Of particular interest was the role of the tetraene, 24β-methylcholesta-5,7,22,25-tetraen-3β-ol, in the biosynthetic sequence. By examining C-24 epimeric pairs, stereospecific conversion of codisterol (but not epicodisterol) into the tetraene and ergosterol was demonstrated, which served also to establish the stereochemistry at C-24 of the natural sponge sterol. These biosynthetic steps are attributed to the sponge because of the absence of symbionts such as fungi and algae as shown by electron microscopy.

Original languageEnglish
Pages (from-to)1642-1647
Number of pages6
JournalJournal of Organic Chemistry
Volume54
Issue number7
Publication statusPublished - 1989
Externally publishedYes

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