Structural characterization and anti-HSV-1 and HSV-2 activity of glycolipids from the marine algae Osmundaria obtusiloba isolated from Southeastern Brazilian coast.
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 (1)H/(13)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 Osmundaria obtusiloba was characterized. This molecule exhibited potent antiviral activity against HSV-1 and HSV-2 with EC(50) 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.
Department of Biochemistry and Molecular Biology, Federal University of Paraná, Curitiba 81531-990, PR, Brazil.
Lauro M
LM
De Souza
Department of Biochemistry and Molecular Biology, Federal University of Paraná, Curitiba 81531-990, PR, Brazil.
Guilherme L
GL
Sassaki
Department of Virology , Institute of Microbiology, Federal University of Rio de Janeiro, Rio de Janeiro 21941-902, RJ, Brazil.
Maria Teresa Villela
MTV
Romanos
Department of General Microbiology, Federal University of Rio de Janeiro, Rio de Janeiro 21941-902, RJ, Brazil.
Eliana
E
Barreto-Bergter
D000818:Animals; D000998:Antiviral Agents / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology*; D001938:Brazil; D038983:Galactolipids / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D006017:Glycolipids / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology*; D018259:Herpesvirus 1, Human / Q000187:drug effects*; D018258:Herpesvirus 2, Human / Q000187:drug effects*; D008055:Lipids / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D009682:Magnetic Resonance Spectroscopy / Q000379:methods; D013058:Mass Spectrometry / Q000379:methods; D000461:Rhodophyta / Q000737:chemistry*; D014709:Vero Cells
D000998:Antiviral Agents; D038983:Galactolipids; D006017:Glycolipids; D008055:Lipids; C007388:digalactosyldiacylglycerol; C015518:sulfolipids; C496611:sulfoquinovosylacylglycerol