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New 17‐Methyl‐13‐Octadecenoic and 3,16‐Docosadienoic Acids from the Sponge Polymastia penicillus
Author(s) -
Denis Claire,
WielgoszCollin Gaëtane,
Bretéché Anne,
Ruiz Nicolas,
Rabesaotra Vony,
BouryEsnault Nicole,
Kornprobst JeanMichel,
Barnathan Gilles
Publication year - 2009
Publication title -
lipids
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.601
H-Index - 120
eISSN - 1558-9307
pISSN - 0024-4201
DOI - 10.1007/s11745-009-3291-9
Subject(s) - sponge , chemistry , palmitic acid , mass spectrometry , vaccenic acid , phospholipid , gas chromatography , double bond , fatty acid , stereochemistry , gas chromatography–mass spectrometry , long chain , chromatography , organic chemistry , biochemistry , biology , botany , conjugated linoleic acid , membrane , linoleic acid , polymer science
The phospholipid fatty acid composition of the North‐East Atlantic sponge Polymastia penicillus (South Brittany, France) was investigated. Sixty fatty acids (FA) were identified as methyl esters (FAME) and N ‐acyl pyrrolidides (NAP) by gas chromatography–mass spectrometry (GC/MS), including eight Δ5,9 unsaturated FA and three long‐chain 2‐hydroxylated FA. The major phospholipid FA were palmitic (14.3% of the total FA mixture), vaccenic (12.7%), 15( Z )‐docosenoic (13.4%) and 5( Z ),9( Z )‐hexacosadienoic (13.3%) acids. In addition to the iso ‐ and anteiso ‐branched saturated FA, several unusual short‐chain branched saturated FA were identified. In addition to the known Δ5,9 FA, and interestingly regarding their identification by GC–MS as N ‐acyl pyrrolidides, was the co‐occurrence of unusual FA possessing a Δ3, Δ4 and Δ5 double bond such as iso ‐4‐pentadecenoic, iso ‐5‐heptadecenoic, anteiso ‐5‐heptadecenoic and two new compounds, not hitherto found in nature, namely 17‐methyl‐13‐octadecenoic (0.8%) and 3,16‐docosadienoic (1.1%) acids.