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

• Main Authors: Eliana Barreto-Bergter, Maria Teresa Villela Romanos, Guilherme L. Sassaki, Lauro M. de Souza
• Format: Article
• Language: English
• Published: MDPI AG 2012-04-01
• Series: Marine Drugs
• Subjects: <em>Osmundaria</em> <em>obtusiloba</em> red alga; glycolipids; sulfoquinovosyldiacylglycerol; anti-herpes simplex activity
• Online Access: http://www.mdpi.com/1660-3397/10/4/918

Glycolipids were extracted from the red alga <em>Osmundaria obtusiloba </em>from<em> </em>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 <sup>1</sup>H/<sup>13</sup>C 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 <em>Osmundaria obtusiloba</em> was characterized. This molecule exhibited potent antiviral activity against HSV-1 and HSV-2 with EC<sub>50</sub> 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.