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.
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