Identification of novel alpha-methoxylated phospholipid fatty acids in the Caribbean sponge Erylus goffrilleri.
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.
Carballeira
Néstor M
NM
Department of Chemistry, University of Puerto Rico, Rio Piedras Campus, PO Box 23346, San Juan, PR, USA. nmcarballeira@uprrp.edu
Oyola
Delise
D
Vicente
Jan
J
Rodriguez
Abimael D
AD
D000818:Animals; D001419:Bacteria / Q000737:chemistry; D004951:Esterification; D005227:Fatty Acids / Q000032:analysis* / Q000096:biosynthesis / Q000737:chemistry; D008401:Gas Chromatography-Mass Spectrometry; D008745:Methylation; D010743:Phospholipids / Q000032:analysis*; D011161:Porifera / Q000737:chemistry*; D013559:Symbiosis
D005227:Fatty Acids; D010743:Phospholipids
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