A new cytotoxic fatty acid (5Z,9Z)-22-methyl-5,9-tetracosadienoic acid and the sterols from the far eastern sponge Geodinella robusta

Lipids. 2002 Jan;37(1):75-80. doi: 10.1007/s11745-002-0866-6.

Abstract

A new fatty acid, (5Z,9Z)-22-methyl-5,9-tetracosadienoic acid (1a), and a rare fatty acid, (5Z,9Z)-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 (5Z,9Z)-22- and (5Z,9Z)-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.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Carcinoma, Ehrlich Tumor / drug therapy
  • Chromatography, High Pressure Liquid
  • Cytotoxins / isolation & purification*
  • Cytotoxins / pharmacology*
  • Erythrocytes / drug effects
  • Fatty Acids, Unsaturated / isolation & purification*
  • Fatty Acids, Unsaturated / pharmacology*
  • Gas Chromatography-Mass Spectrometry
  • Hemolysis / drug effects
  • In Vitro Techniques
  • Magnetic Resonance Spectroscopy
  • Mice
  • Porifera / chemistry*
  • Sterols / chemistry*

Substances

  • 22-methyl-5,9-tetracosadienoic acid
  • Cytotoxins
  • Fatty Acids, Unsaturated
  • Sterols
  • 23-methyl-5,9-tetracosadienoic acid