Identification and Total Synthesis of Novel Fatty Acids from the Caribbean Sponge Calyx podatypa

Abstract

The phospholipid fatty acid composition of the Caribbean sponge Calyx podatypa was studied, and 85 different fatty acids were identified, in particular the 11-methylpentadecanoic acid and 10-tricosenoic acid, which have no literature precedence. Structural characterization was accomplished by means of gas chromatography-mass spectrometry on their corresponding methyl esters and dimethyl disulfide derivatives. The structure of 11-methylpentadecanoic acid was further confirmed by total synthesis (17% overall yield) starting from commercially available 10-hydroxydecanoic acid.

Unusual Fatty Acids in the Fat Body of the Early Nesting Bumblebee, Bombus pratorum

“…Monounsaturated 9-26:1 and 9-24:1 were detected in B. pratorum at trace levels, but they are more common in nature than 9,19-26:2. Several papers reported their presence in both marine [19][20][21][22][23][24][25][26] and freshwater [27,28] sponges. Their abundances are also low, at percent or subpercent levels.…”

Marine natural products

“…Several new fatty acids have been isolated from sponges, including 2-methoxyhexadecanoic acid 175 from Amphimedon compressa, 151 and both 11-methylpentadecanoic acid 176 and 10-tricosenoic acid 177 from Calyx podatypa. 152 (5Z)-2-Methoxyhexadec-5-enoic acid 178 and (6Z)-2-methoxyhexadec-6-enoic acid 179, both of which were found in several Caribbean sponges, 151,153 have been synthesized. 154 The ceramide 180, which inhibits fouling by macroalgae, was isolated from Haliclona koremella collected in Palau.…”

Multibranched Polyunsaturated and Very-Long-Chain Fatty Acids of Freshwater Israeli Sponges

“…30 Both branched and polyunsaturated fatty acids are widespread in nature, but few sources, including sponges, 3 contain branched polyunsaturated fatty acids. These were found in different marine species 31,32 (e.g., 24-methyl-5,9-pentacosadienoic acid or (6Z)-2-methoxy-13-methyl-6-tetradecenoic acid); polyunsaturated isoprenoid fatty acids were found in a freshwater sponge. 13 An interesting correlation was discovered between the geographical occurrence and the chirality of compounds 1-5.…”