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Biosynthetic studies of marine lipids 18. Biosynthesis of 3β-(hydroxymethyl)-A-nor-5α-cholest-15-ene in the marine sponge phakellia aruensis

✍ Scribed by Sohail Malik; Ivan L. Stoilov; Carl Djerassi


Publisher
Elsevier Science
Year
1988
Tongue
French
Weight
226 KB
Volume
29
Category
Article
ISSN
0040-4039

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✦ Synopsis


Through appropriate labeling experiments, it was shown that the unusual sterol 3B-(hydroxymethyl)-A-nor-Sa-cholest-15-ene ( 1) is generated by ring contraction of dietary cholesterol followed by the introduction of the 15-16 double bond, rather than by ring contraction of 15-dehydrocholesterol (4).


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Biosynthetic studies of marine lipids 15
✍ N. Lucinda Cordeiro; Russell G. Kerr; Carl Djerassi 📂 Article 📅 1988 🏛 Elsevier Science 🌐 French ⚖ 202 KB

Tritium labeled parka01 (z), but not lanosterol (3) or cycloartenol (a), was transformed by the sea cucumber Holothuria arenfcola into 14a-methyl-5a-cholest-9(ll)-en-3R-01 (5). thus implying that squalene-2,3-oxide cyclizes directly to parkeol (2).