Identification of novel alpha-methoxylated phospholipid fatty acids in the Caribbean sponge Erylus goffrilleri

Lipids. 2007 Nov;42(11):1047-53. doi: 10.1007/s11745-007-3110-0. Epub 2007 Aug 21.

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.

Publication types

  • Research Support, N.I.H., Extramural

MeSH terms

  • Animals
  • Bacteria / chemistry
  • Esterification
  • Fatty Acids / analysis*
  • Fatty Acids / biosynthesis
  • Fatty Acids / chemistry
  • Gas Chromatography-Mass Spectrometry
  • Methylation
  • Phospholipids / analysis*
  • Porifera / chemistry*
  • Symbiosis

Substances

  • Fatty Acids
  • Phospholipids