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Mar. Drugs 2012, 10(4), 918-931; doi:10.3390/md10040918
Article

Structural Characterization and Anti-HSV-1 and HSV-2 Activity of Glycolipids from the Marine Algae Osmundaria obtusiloba Isolated from Southeastern Brazilian Coast

1
,
1
,
2
 and
3,*
1 Department of Biochemistry and Molecular Biology, Federal University of Paraná, Curitiba 81531-990, PR, Brazil 2 Department of Virology , Institute of Microbiology, Federal University of Rio de Janeiro, Rio de Janeiro 21941-902, RJ, Brazil 3 Department of General Microbiology, Federal University of Rio de Janeiro, Rio de Janeiro 21941-902, RJ, Brazil
* Author to whom correspondence should be addressed.
Received: 5 March 2012 / Revised: 11 April 2012 / Accepted: 17 April 2012 / Published: 23 April 2012
(This article belongs to the Special Issue Marine Anti-infective Agents)
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Abstract

Glycolipids were extracted from the red alga Osmundaria obtusiloba from Southeastern Brazilian coast. The acetone insoluble material was extracted with chloroform/methanol and the lipids, enriched in glycolipids, were fractionated on a silica gel column eluted with chloroform, acetone and then methanol. Three major orcinol-positive bands were found in the acetone and methanol fractions, being detected by thin layer chromatography. The structures of the corresponding glycolipids were elucidated by ESI-MS and 1H/13C NMR analysis, on the basis of their tandem-MS behavior and HSQC, TOCSY fingerprints. For the first time, the structure of sulfoquinovosyldiacylglycerol from the red alga Osmundaria obtusiloba was characterized. This molecule exhibited potent antiviral activity against HSV-1 and HSV-2 with EC50 values of 42 µg/mL to HSV-1 and 12 µg/mL to HSV-2, respectively. Two other glycolipids, mono- and digalactosyldiacylglycerol, were also found in the alga, being characterized by ESI-MS/MS. The structural elucidation of algae glycolipids is a first step for a better understanding of the relation between these structures and their biological activities.
Keywords: Osmundaria obtusiloba; red alga; glycolipids; sulfoquinovosyldiacylglycerol; anti-herpes simplex activity Osmundaria obtusiloba; red alga; glycolipids; sulfoquinovosyldiacylglycerol; anti-herpes simplex activity
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).
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de Souza, L.M.; Sassaki, G.L.; Romanos, M.T.V.; Barreto-Bergter, E. Structural Characterization and Anti-HSV-1 and HSV-2 Activity of Glycolipids from the Marine Algae Osmundaria obtusiloba Isolated from Southeastern Brazilian Coast. Mar. Drugs 2012, 10, 918-931.

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