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- Title
Mono- and digalactosyldiacylglycerols: potent nitric oxide inhibitors from the marine microalga Nannochloropsis granulata.
- Authors
Banskota, Arjun; Stefanova, Roumiana; Gallant, Pamela; McGinn, Patrick
- Abstract
Chemical investigation of a marine microalga, Nannochloropsis granulata, led to the isolation of four digalactosyldiacylglycerols namely, (2 S)-1- O-eicosapentaenoyl-2- O-palmitoyl-3- O-( β- d-galactopyranosyl-6-1 α- d-galactopyranosyl)-glycerol ( 1), (2 S)-1- O-eicosapentaenoyl-2- O-palmitoleoyl-3- O-( β- d-galactopyranosyl-6-1α- d-galactopyranosyl)-glycerol ( 2), (2 S)-1- O-eicosapentaenoyl-2- O-myristoyl-3- O-( β- d-galactopyranosyl-6-1α- d-galactopyranosyl)-glycerol ( 3), and (2S)-1,2-bis- O-eicosapentaenoyl-3- O-( β- d-galactopyranosyl-6-1α- d-galactopyranosyl)-glycerol ( 4), together with their monogalactosyl analogs ( 5- 8). Among the isolated galactolipids 2 and 3 were new natural products. Complete stereochemistry of 1, 4, 5, 7, and 8 was determined for the first time by both spectroscopic techniques and classical degradation methods. Both mono- and digalactosyldiacylglycerols isolated from N. granulata possessed strong nitric oxide (NO) inhibitory activity against lipopolysaccharide-induced NO production in RAW264.7 macrophage cells through downregulation of inducible nitric oxide synthase expression indicating the possible use as anti-inflammatory agents.
- Subjects
NITRIC oxide; MICROALGAE; NITRIC-oxide synthases; MONOGALACTOSYLDIACYLGLYCEROL synthase; STEREOCHEMISTRY; ANTI-inflammatory agents
- Publication
Journal of Applied Phycology, 2013, Vol 25, Issue 2, p349
- ISSN
0921-8971
- Publication type
Article
- DOI
10.1007/s10811-012-9869-2