9-Chloro-5,9-dienoic and Other Fatty Acids from Marine Sponge Penares sp.

Autor: Santalova, Е. А., Kolesnikova, S. А.
Předmět:
Zdroj: Russian Journal of Bioorganic Chemistry; Apr2024, Vol. 50 Issue 2, p418-431, 14p
Abstrakt: Objective: Structural analysis of the fatty acids and their ethyl esters from the extract of sponge Penares sp. (South China Sea). Methods: Separation by high-performance liquid chromatography. Analysis by gas chromatography-mass spectrometry using pyrrolidine, 4,4-dimethyloxazoline, dimethyl disulfide, and hydrogenated derivatives. Analysis by 1Н and 13С NMR spectroscopy. Results and Discussion: 71 acids with a chain length from C12 to C28 were found, including 12 new compounds, i.e., (5Z,9Z)-9-chloro-24-methy-5,9-pentacosadienoic, (5Z,9Z)-9-chloro-25-methyl-5,9-hexacosadienoic, (5Z,9Z)-9-chloro-24-methyl-5,9-hexacosadienoic, (5Z,9Z)-9-chloro-25-methyl-5,9-heptacosadienoic, 6-chloro-20-methyl-4-heneicosenoic, 6-chloro-19-methyl4-heneicosenoic, 6-chloro-20-methyl-4-docosenoic, cis-17,18-methylene-tetracosanoic, 16,21-dimethyldocosanoic, 18,23-dimethyltetracosanoic, 16,18,22-trimethyltricosanoic, and 18,20,24-trimethylpentacosanoic acids. Conclusions: The characteristic features of the fatty acid mixture from Penares sp. were a high level of constituents with monomethylated chains (over 50%) and the nearly total substitution of common demospongic acids for their previously unknown chloro derivatives, (5Z,9Z)-9-chloro-5,9-dienoic acids, due to, presumably, the activity of sponge-associated microorganisms. [ABSTRACT FROM AUTHOR]
Databáze: Complementary Index