Mono- and digalactosyldiacylglycerols : potent nitric oxide inhibitors from the marine microalga Nannochloropsis granulata

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DOIResolve DOI: http://doi.org/10.1007/s10811-012-9869-2
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TypeArticle
Journal titleJournal of Applied Phycology
Volume25
Issue2
Pages349357; # of pages: 9
SubjectNannochloropsis granulata; Monogalactosyldiacylglycerol; Digalactosyldiacylglycerol; Nitric oxide; Inducible nitric oxide synthase
AbstractChemical investigation of a marine microalga, Nannochloropsis granulata, led to the isolation of four digalactosyldiacylglycerols namely, (2S)-1-O-eicosapentaenoyl-2-O-palmitoyl-3-O-(β-D-galactopyranosyl-6-1α-D-galactopyranosyl)-glycerol (1), (2S)-1-O-eicosapentaenoyl-2-O-palmitoleoyl-3-O-(β-D-galactopyranosyl-6-1α-D-galactopyranosyl)- glycerol (2), (2S)-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 poss e s s ed s t rong n i t r i c oxide (NO) inhibi tory a c t ivi ty 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.
Publication date
LanguageEnglish
AffiliationNational Research Council Canada; Aquatic and Crop Resource Development
Peer reviewedYes
NRC number50497
NPARC number21268157
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Record identifier6e7f8ad5-2c88-44cf-a189-5c5469f0fcf8
Record created2013-05-10
Record modified2016-11-09
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