Novel brominated phospholipid fatty acids from the Caribbean spongeAgelas sp.

Abstract

The very long-chain fatty acids, (5E,9Z)-6-bromo-5,9-tetracosadienoic, (5E,9Z)-6-bromo-23-methyl-5,9-tetracosadienoic, (5E,9Z)-6-bromo-5,9-pentacosadienoic and (5E,9Z)-6-bromo-24-methyl-5,9- pentacosadienoic acids, were identified in the phospholipids (mainly phosphatidylethanolamine) of the sponge Agelas sp. Structure elucidation was accomplished by means of mass spectrometry and chemical transformations, including deuteration with Wilkinson's catalyst. All of the sterols from the sponge had the delta 5,7 nucleus, with 24-methylcholesta-5,7,22-trien-3 beta-ol (ergosterol) and 24-ethyl-cholesta-5,7, 22-trien-3 beta-ol being the most abundant.

Bioactive Secondary Metabolites from the Marine Sponge Genus Agelas

“…Apart from alkaloids, four new brominated phospholipid fatty acids ( 286 – 289 ) ( Figure 29 ) were also detected in the Caribbean Agelas spp. [ 115 ].…”

Structural Analysis of Fatty Acids

“…It was also used to confirm the structures of fatty acids with two bis-methylene-interrupted double bond systems in the alkyl chain from a sponge [111]. Deuterated pyrrolidide derivatives were used in conjunction with GC-MS to characterize novel long-chain bromine-containing dienoic fatty acids from Caribbean sponges [35,40].…”

“…In subsequent work, further components were identified by prefractionation of the mixture by silver ion TLC before analysis by GC-MI-FI'IR [142]. In addition, GC-FI'IR (light-pipe instrument) has been used to determine the presence or absence of trans double bonds in a number of natural fatty acid samples including the unusual fatty acids of sponges [23,24,35,40,41,43], heat-treated borage oil [217] and tissue lipids of rats fed heated oils [44]. GC-MI-FI'IR has been used for the characterization of conjugated fatty acids [229] and to study lipid oxidation products [228].…”

Secondary metabolites from marine sponges of the genus Agelas: a comprehensive update insight on structural diversity and bioactivity

“…178 The identification of four brominated phospholipid fatty acids 340–343 from the Caribbean Agelas sp. 179 and an anti-mycobacterial bisfunctionalized sphingolipid, leucettamol A ( 344 ), detected in another unclassified Indonesian Agelas specimen 180 have been also achieved. The Okinawan A. nakamurai produced three uncommon diterpenoids, nakamurols A–C ( 345–347 ).…”