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Diverse Odd‐Chain Monoenoic Fatty Acids and Novel Non‐Methylene‐Interrupted Heptadecadienoic Acids in Ovaries of the Limpet Cellana toreuma
Author(s) -
Kawashima Hideki
Publication year - 2018
Publication title -
lipids
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.601
H-Index - 120
eISSN - 1558-9307
pISSN - 0024-4201
DOI - 10.1002/lipd.12089
Subject(s) - limpet , chemistry , methylene , double bond , fatty acid , gas chromatography , mass spectrometry , stereochemistry , chromatography , biology , biochemistry , organic chemistry , ecology , gastropoda
Highly diverse dienoic fatty acids (FA), especially non‐methylene‐interrupted (NMI) FA, have been recognized in triacylglycerols (TAG) and polar lipids of ovaries of the limpet Cellana toreuma. To gain additional insights into the structural diversity of FA in ovaries, this study aimed to clarify previously undescribed minor monoenoic FA isomers and unidentified minor NMI FA by combined argentation thin‐layer chromatography (TLC) and gas chromatography–mass spectrometry (GC‐MS) of their 3‐pyridylcarbinol derivatives. A total 66 monoenoic FA from C14 to C22, including 12 branched‐chain FA, were identified. A surprising finding was a series of 13 heptadecenoic acids with double bonds at either Δ5, Δ6, Δ7, Δ8, Δ9, Δ10, Δ11, Δ12, Δ13, Δ15, or Δ16 positions. Besides previously identified NMI FA, 7,18‐nonadecadienoic (19:2Δ7,18), 9,18‐nonadecadienoic (19:2Δ9,18), 11,18‐nonadecadienoic (19:2Δ11,18), 7,20‐heneicosadienoic (21:2Δ7,20), and 11,20‐heneicosadienoic (21:2Δ11,20) acids, two novel related NMI FA, 5,16‐heptadecadienoic (17:2Δ5,16) and 7,16‐heptadecadienoic (17:2Δ7,16) acids, were found in TAG. These findings could provide new insights into clarifying the biological characteristics of marine NMI FA.