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

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Abstract

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.

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DATA AVAILABILITY

The data that support the findings of this study are available from the corresponding author upon reasonable request.

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ACKNOWLEDGMENTS

The work was performed using the equipment of the Collective Facilities Center “The Far Eastern Center for Structural Molecular Research (NMR/MS) of G.B. Elyakov Pacific Institute of Bioorganic Chemistry of the Far Eastern Branch of Russian Academy of Sciences” (NMR spectroscopy and mass spectrometry).

The authors thank O.P. Moiseenko, Ph.D. L.P. Ponomarenko, and E.G. Lyakhova for their assistance in the GC-MS analysis and the isolation of the FA ethyl esters, academician V.A. Stonik for discussion of some issues of this work, Ph.D. V.A. Denisenko and V.V. Isakov and operators N.V. Zvyagintsev and D.V. Denisenko for recording the NMR spectra.

Funding

The work was supported by the Russia Foundation for Basic Research (grant no. 20-03-00014).

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  1. G.B. Elyakov Pacific Institute of Bioorganic Chemistry, Far-Eastern Branch of Russian Academy of Sciences, 690022, Vladivostok, Russia

    Е. А. Santalova & S. А. Kolesnikova

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Abbreviations: FA, fatty acids; ECL, equivalent chain length; 1Н, 1Н-COSY, proton-proton correlation spectroscopy; НМВС, heteronuclear multiple bond correlation; HSQC, heteronuclear single-quantum coherence.

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Santalova, Е.А., Kolesnikova, S.А. 9-Chloro-5,9-dienoic and Other Fatty Acids from Marine Sponge Penares sp.. Russ J Bioorg Chem 50, 418–431 (2024). https://doi.org/10.1134/S1068162024020249

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