Skip Navigation

This Article
Right arrow Full Text Freely available
Right arrow FREE Full Text (PDF) Freely available
Right arrow Alert me when this article is cited
Right arrow Alert me if a correction is posted
Services
Right arrow Email this article to a friend
Right arrow Similar articles in this journal
Right arrow Similar articles in ISI Web of Science
Right arrow Similar articles in PubMed
Right arrow Alert me to new issues of the journal
Right arrow Add to My Personal Archive
Right arrow Download to citation manager
Right arrow Search for citing articles in:
ISI Web of Science (5)
Right arrowRequest Permissions
Right arrow Disclaimer
Google Scholar
Right arrow Articles by Sassaki, G. L.
Right arrow Articles by Iacomini, M.
Right arrow Search for Related Content
PubMed
Right arrow PubMed Citation
Right arrow Articles by Sassaki, G. L.
Right arrow Articles by Iacomini, M.
Social Bookmarking
Add to CiteULike   Add to Connotea   Add to Del.icio.us  
What's this?

Glycobiology, 2001, Vol. 11, No. 4 345-351
© 2001 Oxford University Press

Sulfonoglycolipids from the lichenized basidiomycete Dictyonema glabratum: isolation, NMR, and ESI-MS approaches

Guilherme L. Sassaki, Philip A.J. Gorin, Cesar A. Tischer and Marcello Iacomini1

Departamento de Bioquímica, Universidade Federal do Paraná, Curitiba-PR, Cx.P. 19046, 81.531-990, Brazil

Two distinct sulfonoglycolipid fractions were isolated from the basidiolichen Dictyonema glabratum by chromatography on Diethylaminoethyl (DEAE)-Sepharose, which resulted in rapid elution, followed by partition between aqueous sulfuric acid and an ethyl acetate-methanol-chloroform mixture and the content of the organic layer chromatographed of a column of silicic acid. The products were examined by nuclear magnetic resonance spectroscopy in their native rather than their acetylated forms, as in previous investigations. Each was methanolyzed to give the same methyl glycoside, Me-G. On electrospray ionization mass spectrometry (ESI-MS), it provided a pseudomolecular ion at m/z 303 in the positive-ion mode and a molecular ion at m/z 257 with a daughter ion at m/z 146 in the negative-ion mode, showing the presence of a sulfonate group S-linked to a hexosyl ring. An exclusively {alpha}-glucopyranosyl configuration was indicated by 1H, 1H correlation spectroscopy (COSY) and 1H, 1H total correlation spectroscopy (TOCSY). S-substitution occurred at CH2-6, because a high-field 13C signal at {delta} 52.6 gave an inverted distortionless enhancement by polarization transfer (DEPT) signal and 1H, 3C heteronuclear multiple quantum coherence (HMQC) showed correlation with two H-6 signals. This 6-sulfono-{alpha}-quinovopyranoside group was present in the glycolipid fractions, O-{alpha}-D-Quip-6-sulfono-(1'{leftrightarrow}1)-2,3-diacyl-D-glycerol (polar fraction 1a; PF1a) and O-{alpha}-D-Quip-6-sulfono-(1'{leftrightarrow}1)-2- or -3-monoacyl-D-glycerol (polar fraction 1b; PF1b), the monoacyl derivatives not having been previously completely characterized in other systems. All components are typical of plant glycolipids. The most abundant fatty acid ester in PF1a and PF1b was C16:0. Other esters present in PF1a were C14:0, C17:0, C18:0, C18:1 (oleic), C20:0, C21:0, and C24:0, in contrast with C14:0, C17:0, C18:0, and C20:0 in PF1b. HMQC and TOCSY data can be used as fingerprints for detection of glycosylacylglycerides and sulfonoglycolipids and the positive ESI-MS ions at m/z 329 and 271 for identification of the latter.

1 To whom correspondence should be addressed


Add to CiteULike CiteULike   Add to Connotea Connotea   Add to Del.icio.us Del.icio.us    What's this?


This article has been cited by other articles:


Home page
 GlycobiologyHome page
A. Al-Fadhli, S. Wahidulla, and L. D'Souza
Glycolipids from the red alga Chondria armata (Kutz.) Okamura
Glycobiology, October 1, 2006; 16(10): 902 - 915.
[Abstract] [Full Text] [PDF]


Disclaimer:
Please note that abstracts for content published before 1996 were created through digital scanning and may therefore not exactly replicate the text of the original print issues. All efforts have been made to ensure accuracy, but the Publisher will not be held responsible for any remaining inaccuracies. If you require any further clarification, please contact our Customer Services Department.