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

Research output: Contribution to journalArticleResearchpeer-review

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.

LanguageEnglish
Pages1642-1647
Number of pages6
JournalJournal of Organic Chemistry
Volume54
Issue number7
Publication statusPublished - 1989
Externally publishedYes

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Sterols
Lipids
Ergosterol
Stereochemistry
Biosynthesis
Algae
Fungi
Electron microscopy

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John, Varghese ; Stoilov, Ivan L. ; Djerassi, Carl ; Karuso, Peter ; Poiner, Anthony ; Scheuer, Paul J. / Biosynthetic studies of marine lipids. 20. Sequence of double-bond introduction in the sponge sterol 24β-methylcholesta-5,7,22,25-tetraen-3β-ol. In: Journal of Organic Chemistry. 1989 ; Vol. 54, No. 7. pp. 1642-1647.
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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.",
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Biosynthetic studies of marine lipids. 20. Sequence of double-bond introduction in the sponge sterol 24β-methylcholesta-5,7,22,25-tetraen-3β-ol. / John, Varghese; Stoilov, Ivan L.; Djerassi, Carl; Karuso, Peter; Poiner, Anthony; Scheuer, Paul J.

In: Journal of Organic Chemistry, Vol. 54, No. 7, 1989, p. 1642-1647.

Research output: Contribution to journalArticleResearchpeer-review

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AU - Scheuer, Paul J.

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