» Articles » PMID: 19266225

New 17-methyl-13-octadecenoic and 3,16-docosadienoic Acids from the Sponge Polymastia Penicillus

Overview
Journal Lipids
Specialty Biochemistry
Date 2009 Mar 7
PMID 19266225
Citations 6
Authors
Affiliations
Soon will be listed here.
Abstract

The phospholipid fatty acid composition of the North-East Atlantic sponge Polymastia penicillus (South Brittany, France) was investigated. Sixty fatty acids (FA) were identified as methyl esters (FAME) and N-acyl pyrrolidides (NAP) by gas chromatography-mass spectrometry (GC/MS), including eight Delta5,9 unsaturated FA and three long-chain 2-hydroxylated FA. The major phospholipid FA were palmitic (14.3% of the total FA mixture), vaccenic (12.7%), 15(Z)-docosenoic (13.4%) and 5(Z),9(Z)-hexacosadienoic (13.3%) acids. In addition to the iso- and anteiso-branched saturated FA, several unusual short-chain branched saturated FA were identified. In addition to the known Delta5,9 FA, and interestingly regarding their identification by GC-MS as N-acyl pyrrolidides, was the co-occurrence of unusual FA possessing a Delta3, Delta4 and Delta5 double bond such as iso-4-pentadecenoic, iso-5-heptadecenoic, anteiso-5-heptadecenoic and two new compounds, not hitherto found in nature, namely 17-methyl-13-octadecenoic (0.8%) and 3,16-docosadienoic (1.1%) acids.

Citing Articles

Essential Oil and Fatty Acid Composition of Endemic Schreb. from Turkey.

Servi H, Eren Keskin B, Celik S, Budak U, Kababiyik B Turk J Pharm Sci. 2020; 16(2):220-226.

PMID: 32454717 PMC: 7227973. DOI: 10.4274/tjps.galenos.2018.49140.


Non-methylene interrupted and hydroxy fatty acids in polar lipids of the alga Grateloupia turuturu over the four seasons.

Kendel M, Barnathan G, Fleurence J, Rabesaotra V, Wielgosz-Collin G Lipids. 2013; 48(5):535-45.

PMID: 23515999 DOI: 10.1007/s11745-013-3783-5.


Atkamine: a new pyrroloiminoquinone scaffold from the cold water Aleutian Islands Latrunculia sponge.

Zou Y, Hamann M Org Lett. 2013; 15(7):1516-9.

PMID: 23472820 PMC: 4137554. DOI: 10.1021/ol400294v.


New 2-methyl-13-icosenoic acid from the temperate calcisponge Leuconia johnstoni.

Quevrain E, Barnathan G, Meziane T, Domart-Coulon I, Rabesaotra V, Bourguet-Kondracki M Lipids. 2011; 47(4):345-53.

PMID: 22120658 DOI: 10.1007/s11745-011-3631-4.


Phospholipid distribution and phospholipid fatty acids of the tropical tunicates Eudistoma sp. and Leptoclinides uniorbis.

Dagorn F, Dumay J, Wielgosz-Collin G, Rabesaotra V, Viau M, Monniot C Lipids. 2010; 45(3):253-61.

PMID: 20213322 DOI: 10.1007/s11745-010-3389-0.


References
1.
Genin E, Wielgosz-Collin G, Njinkoue J, Velosaotsy N, Kornprobst J, Gouygou J . New trends in phospholipid class composition of marine sponges. Comp Biochem Physiol B Biochem Mol Biol. 2008; 150(4):427-31. DOI: 10.1016/j.cbpb.2008.04.012. View

2.
Litchfield C, Greenberg A, Noto G, Morales R . Unusually high levels of C24-C30 fatty acids in sponges of the class Demospongiae. Lipids. 1976; 11(7):567-73. DOI: 10.1007/BF02532903. View

3.
Carballeira N, Shalabi F, Negron V . 2-Hydroxy fatty acids from marine sponges. 2. The phospholipid fatty acids of the Caribbean sponges Verongula gigantea and Aplysina archeri. Lipids. 1989; 24(3):229-32. DOI: 10.1007/BF02535240. View

4.
Kaneda T . Iso- and anteiso-fatty acids in bacteria: biosynthesis, function, and taxonomic significance. Microbiol Rev. 1991; 55(2):288-302. PMC: 372815. DOI: 10.1128/mr.55.2.288-302.1991. View

5.
Haack S, Garchow H, Odelson D, Forney L, Klug M . Accuracy, reproducibility, and interpretation of Fatty Acid methyl ester profiles of model bacterial communities. Appl Environ Microbiol. 1994; 60(7):2483-93. PMC: 201674. DOI: 10.1128/aem.60.7.2483-2493.1994. View