Monogalactosyldiacylglycerols, potent nitric oxide inhibitors from the marine microalga Tetraselmis chui

Alternative titleMonogalactosyldiacylglycerols, potent nitric oxide inhibitors from a marine microalga Tetraselmis
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DOIResolve DOI: http://doi.org/10.1080/14786419.2012.717285
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TypeArticle
Journal titleNatural Product Research
ISSN1478-6419
1478-6427
Volume27
Issue12
Pages10841090; # of pages: 7
Subjectmonogalactosyldiacylglycerol; nitric oxide; Tetraselmis chui; iNOS; microalgae; galactolipid; glycolipid
AbstractMethanolic extracts of some marine and freshwater microalgae were tested for their nitric oxide (NO) inhibitory activity on lipopolysaccharide-induced NO production in RAW264.7 macrophage cells. Among the tested extracts, Tetraselmis chui extract showed the strongest NO inhibitory activity, thus selected for further study. NO inhibitory activity guided isolation led to identification of two monogalactosyldiacylglycerols (MGDGs) (2S)-1-O-(6Z,9Z,12Z,15Z-octadecatetranoyl)-2-O-(4Z,7Z,10Z,13Z-hexadecatetranoyl)-3-O-β-D-galactopyranosylglycerol (1) and (2S)-1-O-(9Z,12Z,15Z-octadecatrinoyl)-2-O-(4Z,7Z,10Z,13Z-hexadecatetranoyl)-3-O-β-D-galactopyranosylglycerol (2) from the MeOH extract of T. chui. The stereo-chemistry of 1 was elucidated by classical degradation method. MGDGs 1 and 2 showed strong NO inhibitory activity compared to NG-methyl-L-arginine acetate salt, a well known NO inhibitor used as a positive control. Isolated MGDGs suppressed NO production through down-regulation of inducible NO synthase protein. A structure activity relationship study suggested that the polyunsaturated fatty acids of the MGDGs are responsible for NO inhibition. Moreover, increasing unsaturation on the fatty acid side chains enhanced the NO inhibitory potency of the MGDGs.
Publication date
PublisherTaylor & Francis Group
LanguageEnglish
AffiliationNational Research Council Canada; Aquatic and Crop Resource Development
Peer reviewedYes
NRC number54077
NPARC number21268614
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Record identifiere8d1d05b-874f-4d8e-a224-3b13f3a074e5
Record created2013-10-28
Record modified2016-11-09
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