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

Lauro M. de Souza²  Guilherme L. Sassaki²  Maria Teresa Villela Romanos¹ 

[1] Department of Virology , Institute of Microbiology, Federal University of Rio de Janeiro, Rio de Janeiro 21941-902, RJ, Brazil;Department of Biochemistry and Molecular Biology, Federal University of Paraná, Curitiba 81531-990, PR, Brazil;

关键词: Osmundaria obtusiloba;    red alga;    glycolipids;    sulfoquinovosyldiacylglycerol;    anti-herpes simplex activity;   

DOI  :  10.3390/md10040918

来源: mdpi

【 摘 要 】

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.

【 授权许可】

CC BY   
© 2012 by the authors; licensee MDPI, Basel, Switzerland.