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Glycobiology Advance Access published online on June 24, 2006
Glycobiology, doi:10.1093/glycob/cwl018
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© The Author 2006. Published by Oxford University Press. All rights reserved. For permissions, please e-mail:journals.permissions@oxfordjournals.org
Received November 22, 2005
Revised June 12, 2006
Accepted June 12, 2006

Article

Glycolipids from the red alga Chondria armata (Kütz.) Okamura

Ammar Al-Fadhli 1, Solimabi Wahidulla 1 *, and Lisette D’Souza 1

1 National Institute of Oceanography, Dona Paula, Goa, 403 004 India

* To whom correspondence should be addressed.
Solimabi Wahidulla, E-mail: solima{at}nio.org


  Abstract

Three distinct fractions containing polar glycolipids (PF1-3) were isolated from the chloroform soluble fraction of crude methanolic extract of red alga Chondria armata (Kütz.) Okamura on gel chromatography over Sephadex LH20. Their structure was elucidated by multidimentional nuclear magnetic resonance (NMR) techniques like 1H, 1H correlation spectroscopy (COSY), 1H, 1H total correlation spectroscopy (TOCSY), 1H, 13C heteronuclear multiple quantum coherence (HMQC) and 1H, 13C heteronuclear multiple bond correlation (HMBC) complemented by electrospray ionization mass spectrometry (ESI-MS) in the positive ion mode. The coupling constant of the anomeric proton in 1H NMR spectrum and sign of rotation indicated an exclusive configuration of the sugar molecules in the glycerolipids. Major glycolipids were identified as (2R)-2-O-(5,8,11,14-eicosatetranoyl)-3-O-{alpha}-D-galactopyranosyl-sn-glycerol (GL2), its pentacetate (GL1) and (2R)-1-O-(palmitoyl)-2-O-(5,8,11,14,17-eicosapentanoyl)-3-O-{beta}-D-galactopyranosyl-sn-glycerol (GL3). Each was methanolysed to give the same galactosylglycerol which on ESI-MS provided a pseudomolecular ion at m/z 309 representing deacylated glycolipid with the sodiated sugar moiety. Additionally, six minor glycolipids were also identified on the basis of ESI-MS. These include, a 1,2-di-O-acyl-3-O-(acyl-6’-galactosyl)-glycerol (GL1a), sulfonoglycolipids 2-O-palmitoyl-3-O-(6’-sulfoquinovopyranosyl)-glycerol (GL2a) and its ethyl ether derivative (GL2b), 1-oleoyl-2-palmitoyl-3-O-galactosyl glycerol (GL3a) and 1,2-diacyl phosphatidyl glycerol (GL3b). GL1, GL1a and GL2b are new to the literature. The novelty of the remaining identified compounds lies in the diversity of their fatty acid composition.

Keywords: Antimicrobial/Chondriaarmata/ESI-MS/Glycolipids/NMR.
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