A new cytotoxic fatty acid (5<Emphasis Type="Italic">Z</Emphasis>,9<Emphasis Type="Italic">Z</Emphasis>)-22-methyl-5,9-tetracosadienoic acid and the sterols from the far Eastern sponge <Emphasis Type="Italic">Geodinella robusta</Emphasis> |
| |
Authors: | Tatyana?N?Makarieva Elena?A?Santalova Irina?A?Gorshkova Andrei?S?Dmitrenok Alla?G?Guzii Vladimir?I?Gorbach Vassilii?I?Svetashev Email author" target="_blank">Valentin?A?StonikEmail author |
| |
Affiliation: | (1) Laboratory of the Marine Natural Products, Pacific Institute of Bioorganic Chemistry of the Russian Academy of Sciences, Pr. 100-letya Vladivostoka 159, 690022 Vladivostok, Russian Federation;(2) Bioorganic Chemistry and Biotechnology Department, Institute of Chemistry and Applied Ecology, Far-Eastern State University, 690600 Vladivostok, Russian Federation;(3) Institute of Marine Biology of the Russian Academy of Sciences, 690022 Vladivostok, Russian Federation |
| |
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. |
| |
Keywords: | |
本文献已被 PubMed SpringerLink 等数据库收录! |
|