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.
Highlights
Glycolipids constitute an important class of membrane lipids that are synthesized by both prokaryotic and eukaryotic organisms
In the present study we evaluated the inhibitory activity of sulfoquinovosyldiacylglycerol from the red marine alga Osmundaria obtusiloba on the herpes simplex virus type 1 (HSV-1) and type 2 (HSV-2)
Osmundaria obtusiloba was treated with acetone and kept overnight at −14 °C
Summary
Glycolipids constitute an important class of membrane lipids that are synthesized by both prokaryotic and eukaryotic organisms Major glycolipids such as monogalactosyldiacylglycerol (MGDG), digalactosyldiacylglycerol (DGDG) and sulfoquinovosyldiacylglycerol (SQDG), along with phospholipids were isolated from red, green and brown algae, such as, for example, Anfeltia tobuchiensis (Rhodophyta), Ulva fenestrate (Chlorophyta), Laminaria japonica (Chlorophyta), Sargassum pallidum (Phaeophyta) [1], Sargassum thunbergii (Phaeophyta) [2], Exophlyllum wentii (Rhodophyta) [3] and Chondria armata (Rhodophyta) [4], as well as in simbiotic organisms having mycroalgae [5,6]. Despite acyclovir is the drug of choice for treating the HSV infections, new antiviral agents exhibiting different mechanisms of action is urgently needed, mainly due to the high number of acyclovir-resistant strains [23]
Sign-in/Register to view highlights & summary Sign-in/Register to access full text options 
Free) 
Talk to us
Join us for a 30 min session where you can share your feedback and ask us any queries you have
Schedule a call
