Identification of Novel Alpha-methoxylated Phospholipid Fatty Acids in the Caribbean Sponge Erylus Goffrilleri

Overview

Journal Lipids

Specialty Biochemistry

Date 2007 Aug 22

PMID 17710462

Citations 6

Authors

Nestor M Carballeira

Delise Oyola

Jan Vicente

Abimael D Rodriguez

Affiliations

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Abstract

The phospholipid fatty acid composition of the Caribbean sponge Erylus goffrilleri is described for the first time. A total of 70 fatty acids with chain lengths between 13 and 29 carbons were identified in the sponge. Methyl-branched fatty acids predominated in E. goffrilleri suggesting the presence of a considerable number of bacterial symbionts. The novel fatty acids (5Z,9Z)-2-methoxy-5,9-hexadecadienoic acid, (5Z,9Z)-2-methoxy-5,9-octadecadienoic acid, (5Z,9Z)-2-methoxy-5,9-nonadecadienoic acid, and (5Z,9Z)-2-methoxy-5,9-eicosadienoic acid are described for the first time in the literature. In addition, the iso-methyl-branched fatty acids (9Z)-2-methoxy-15-methyl-9-hexadecenoic acid and (5Z,9Z)-2-methoxy-15-methyl-5,9-hexadecadienoic acid, also identified in E. goffrilleri, were identified for the first time in nature. Based on the identified metabolites it is proposed that the unprecedented biosynthetic sequence: i-17:1Delta9 --> 2-OMe-i-17:1Delta9 --> 2-OMe-i-17:2Delta5,9 might be responsible for the biosynthesis of the novel iso-alpha-methoxylated fatty acids in E. goffrilleri.

Citing Articles

2-Methoxylated FA Display Unusual Antibacterial Activity Towards Clinical Isolates of Methicillin-Resistant Staphylococcus aureus (CIMRSA) and Escherichia coli.

Carballeira N, Montano N, Morales C, Mooney J, Torres X, Diaz D Lipids. 2017; 52(6):535-548.

PMID: 28523480 PMC: 5513723. DOI: 10.1007/s11745-017-4262-1.

Erylusamides: Novel Atypical Glycolipids from Erylus cf. deficiens.

Gaspar H, Cutignano A, Grauso L, Neng N, Cachatra V, Fontana A Mar Drugs. 2016; 14(10).

PMID: 27727161 PMC: 5082327. DOI: 10.3390/md14100179.

Novel Very Long-Chain α-Methoxylated Δ5,9 Fatty Acids from the Sponge Asteropus niger Are Effective Inhibitors of Topoisomerases IB.

Carballeira N, Montano N, Amador L, Rodriguez A, Golovko M, Golovko S Lipids. 2015; 51(2):245-56.

PMID: 26694606 PMC: 4809140. DOI: 10.1007/s11745-015-4114-9.

Fatty acid synthase as a factor required for exercise-induced cognitive enhancement and dentate gyrus cellular proliferation.

Chorna N, Santos-Soto I, Carballeira N, Morales J, de la Nuez J, Catala-Valentin A PLoS One. 2013; 8(11):e77845.

PMID: 24223732 PMC: 3818398. DOI: 10.1371/journal.pone.0077845.

Synthesis of marine α-methoxylated fatty acid analogs that effectively inhibit the topoisomerase IB from Leishmania donovani with a mechanism different from that of camptothecin.

Carballeira N, Montano N, Alvarez-Velilla R, Prada C, Reguera R, Balana-Fouce R Mar Drugs. 2013; 11(10):3661-75.

PMID: 24084785 PMC: 3826128. DOI: 10.3390/md11103661.

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