Novel naturally occurring α-methoxy acids from the phospholipids of caribbean sponges1

Structural Analysis of Fatty Acids

“…The procedure has been used to identify a variety of monoenoic fatty acids from natural sources [32,86,124,141,151,152,160,174,l82, 205,206,230,231). In addition to more conventional monoenoic fatty acids, branched-chain [41,230,231), 2-methoxy [37,39) and 2-hydroxy [43) monounsaturated fatty acids have been identified in this way. Dimethyl disulphide adducts can be resolved better even than the unchanged esters on GC columns, and this property has been used to separate and quantify petroselinic, oleic and vaccenic acids in seed oils [200).…”

Marine natural products

“…299 Mycalazal 2 and mycalazol 11, pyrrole-containing lipids isolated from Mycale micranthoxea, 300 have been synthesised using a Stille coupling. 301 A synthesis of (2R,5Z,9Z)-2-methoxyhexacosa-5,9-dienoic acid, from Topsentia roquensis, 302 has been accomplished using a novel HgO mediated O-alkylation. 303 A racemic synthesis of plakortone E 206 304 has established the relative stereochemistry, 305 and an asymmetric synthesis of plakortone G 207 306 defined both the relative and absolute stereochemistries.…”

Fatty Acids and Other Lipids of Marine Sponges

“…For example, in the lipid composition of the Mediterranean sponge Agelas oroides , 33 various monomethylinterrupted FAs were revealed (48.9% of FA total content; Table 1) [97]. Acids 3-Ia-15 : 0 and 3-Ia-16 : 0 were isolated from the lipids of the Caribbean sponge Erylus formosus [36]. The 20-Me-26 : 0 acid was revealed in the lipids of the Verongia aerophoba sponge [83].…”

“…Rare 2-metoxy acids, saturated monoenes and polyenes, were revealed in Higginsia tethyoides in trace quantities: 2-metoxy-23 : 0 (0.6%); 2-metoxy-24 : 0 (3.2%); 2-metoxy-24 : 1∆17 (1.9%); 2-metoxy-25 : 1∆18 (0.5%); 2-metoxy-26 : 1∆19 (1.3%); 2-metoxy-26 : 2∆5,9 (2.7%); 2-metoxy-28 : 1∆21 (13.7%); 2-metoxy-28 : 2∆7,21 (2.7%); and 2-metoxy-26 : 3 and 2-metoxy-28 : 3 [8]. The acid 2-metoxy-26 : 2∆5,9 was isolated from the phospholipids of the sponge Tropsentia roquensis [36].…”