Sponge fatty acids. 3. Occurrence of series of n−7 monoenoic andiso‐5,9 dienoic long‐chain fatty acids in the phospholipids of the marine spongeCinachyrella aff.schulzei keller

Abstract

The fatty acid composition of phospholipids from the New Caledonian spongeCinachyrella aff.schulzei Keller was studied. More than 60 fatty acids were identified as methyl esters andN‐acyl pyrrolidides by gas chromatography and gas chromatography/mass spectrometry. Two isoprenoid fatty acids also were shown to be present, namely 4,8,12‐trimethyltridecanoic and 5,9,13‐trimethyltetradecanoic acids. The unusual 6‐tetradecenoic, 6‐pentadecenoic, 12‐nonadecenoic and 26‐methylheptacosanoic (iso‐28∶0) acids were found for the first time in sponge phospholipids. A series of six n−7 monoenoic long‐chain fatty acids (C23 to C28) were identified, including the rare 16‐tricosenoic, 18‐pentacosenoic and 21‐octacosenoic acids. Fifteen fatty acids possessing the typical 5,9 dienoic moiety accounted for 30% of the total fatty acid mixture. Two new fatty acids were identified, namely 5(Z)‐octacosenoic and 27‐methyl‐5(Z),9(Z)‐octacosadienoic (iso‐5,9‐29∶2). Based on gas chromatography/Fourier transform infrared experiments, the double bonds were assigned the (Z) configuration.

Acides gras inhabituels des organismes marins : une illustration de la biodiversité moléculaire marine

“…(Li et al, 1995), Cinachyrella aff. schulzei (Barnathan et al, 1994), Cinachyrella alloclada . L'acide 6-bromo-5,9,13-docosatriènoïque a été identifié chez l'anémone de mer Stoichanthus helianthus (Carballeira et Medina, 1994b) et les acides 6-bromo-heptacosa-5E,9Z,24E-triènoïque et 6-bromo-octacosa-5E,9Z,24Z-triènoïque d'épon-ges Xestospongia sp.…”

Fatty acids from the Okhotsk sea sponge Forcepia uschakowi

“…Polyunsaturated acids represented of 64.1% of the total FA of F. uschakowi. Of these, the principal ones were non-methylene-separated acids 26:2(5,9) and 26:3(5,9,19), which are typical of sponges, and bromo-acid 9).The search for new fatty acids, the elucidation of their structures and biosynthetic pathways, and the study of their properties and roles in organisms are currently of great biochemical interest. From this viewpoint, some of the most interesting subjects are representatives of the phylum Porifera.…”

“…Of these, the main ones were nonmethylene-separated acids 26:2 (5,9) and 26:3 (5,9,19), which are typical of sponges, and bromo-acid 6-Br-26:2 (5,9) (Table 1). Furthermore, 24:2, 25:2, and 27:2, which contain the 5,9-diene structure, were observed in total lipids of this sponge in smaller quantities.…”

“…Polyunsaturated acids represented of 64.1% of the total FA of F. uschakowi. Of these, the principal ones were non-methylene-separated acids 26:2(5,9) and 26:3(5,9,19), which are typical of sponges, and bromo-acid 9).…”

“…24:2 24:3 (5,9,20) 25:2 (5,9) 25:3 (5,9,18) 26:1(15) 26:2 (5,9) 26:3 (5,9,19) 27:2 (5,9) 27:3 (5,9,20) 28:3 (5,9,19) 28:3 (5,9,21) 6-Br-26:2(5,9) Polyunsaturated FA (PUFA) made up 64.1% of the total FA from F. uschakowi. Of these, the main ones were nonmethylene-separated acids 26:2 (5,9) and 26:3 (5,9,19), which are typical of sponges, and bromo-acid 6-Br-26:2 (5,9) (Table 1).…”