Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2012, Issue 27, Pages 5171-5176Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201200676
Keywords
Natural products; Biosynthesis; Terpenoids; Glycolipids; Hopanoids
Categories
Funding
- European Commission [229893, 311848]
- Italian Ministero dell'Universita e della Ricerca (MIUR)
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Plakohopanoid (3a), a new type of hopanoid derivative composed of a C32 hopanoid acid ester linked to a mannosyl-myo-inositol, was isolated from the sponge Plakortis cf. lita as its peracetyl derivative 3b. The structure of 3b was determined by a combination of spectroscopic analysis and micro-scale chemical degradation. Even though plakohopanoid was isolated from a sponge, its component parts are clearly of bacterial origin, and its bacterial biosynthesis is very likely. Until now, C32 hopanoic acids have been considered to be geohopanoids, i.e., diagenetic products that are formed through abiotic degradation of the biohopanoids present in bacteria. The presence of 3a in a marine living organism shows that there is a biosynthetic pathway to C32 hopanoic acids, and these substances should therefore no longer with certainty be considered to be geohopanoids.
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