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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,*
Received: 5 March 2012; in revised form: 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 which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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MDPI and ACS Style

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.

AMA Style

de Souza LM, Sassaki GL, Romanos MTV, 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. Marine Drugs. 2012; 10(4):918-931.

Chicago/Turabian Style

de Souza, Lauro M.; Sassaki, Guilherme L.; Romanos, Maria Teresa Villela; Barreto-Bergter, Eliana. 2012. "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 10, no. 4: 918-931.


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