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Isolation of brominated long‐chain fatty acids from the phospholipids of the tropical marine sponge Amphimedon terpenensis
Author(s) -
Garson Mary J.,
Zimmermann Mary P.,
Hoberg Max,
Larsen Rundi M.,
Battershill Christopher N.,
Murphy Peter T.
Publication year - 1993
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/bf02537123
Subject(s) - chemistry , sponge , fatty acid , bromine , substituent , mass spectrometry , organic chemistry , stereochemistry , chromatography , biology , botany
Preliminary investigation of the phospholipid fatty acid composition of the tropical marine sponge Amphimedon terpenensis by gas chromatography/mass spectrometry revealed the presence of some novel brominated fatty acids. Two new brominated fatty acids, (5 E , 9 Z )‐6‐bromo‐5,9‐tetracosadienoic acid (2a) and (5 E , 9 Z )‐6‐bromo‐5,9‐pentacosadienoic acid (3a) were subsequently isolated from a chloroform/methanol (3∶1, vol/vol) extract of the sponge and characterized as their methyl esters 2b and 3b. The known brominated fatty acid (5 E , 9 Z )‐6‐bromo‐5,9‐hexacosadienoic acid (4a) was also isolated. The new fatty acid methyl esters were confirmed as brominated δ5,9 acid derivatives by chemical ionization mass spectrometry. The position of the bromine substituent was determined to be C‐6 by nuclear magnetic resonance techniques while the stereochemistry of the two double bonds was deduced by nuclear Overhauser enhancement difference spectroscopy. The biosynthetic implications of the co‐occurrence of the three brominated acids are discussed.