In:
Lipids, Wiley, Vol. 37, No. 1 ( 2002-01), p. 75-80
Abstract:
A new fatty acid, (5 Z ,9 Z )‐22‐methyl‐5,9‐tetracosadienoic acid ( 1a ), and a rare fatty acid, (5 Z ,9 Z )‐23‐methyl‐5,9‐tetracosadienoic acid ( 2a ), the predominant constituents of the free fatty acid fraction from the lipids of the sponge Geodinella robusta , were isolated and partly separated by reversed phase high‐performance liquid chromatography, followed by multifold crystallization from MeOH to give 1a and 2a in 70% and 60% purity, respectively. These fatty acids were identified as (5 Z ,9 Z )‐22‐and (5 Z ,9 Z )‐23‐methyl‐5,9‐tetracosadienoic acids by nuclear magnetic resonance techniques, including distortionless enhancement by polarization transfer, heteronuclear multiple quantum connectivity, and correlation spectroscopy experiments, as well as from mass‐spectrometric data for their methyl esters, the methyl esters of their perhydro derivatives, and their pyrrolidides. Mixtures of 1a and 2a showed cytotoxic activity against mouse Ehrlich carcinoma cells and a hemolytic effect on mouse erythrocytes. The sterol fraction from the same sponge was analyzed by gas liquid chromatography mass spectrometry, and 24‐methylenecholesterol was identified as a main constituent of this fraction. The implications of the co‐occurrence of membranolytic long‐chain fatty acids and 24‐methylenecholesterol as a main membrane sterol are discussed in terms of the phenomenon of biochemical coordination.
Type of Medium:
Online Resource
ISSN:
0024-4201
,
1558-9307
DOI:
10.1007/s11745-002-0866-6
Language:
English
Publisher:
Wiley
Publication Date:
2002
detail.hit.zdb_id:
2030265-4
SSG:
12
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