New diacylglyceryltrimethylhomoserines from the marine microalga Nannochloropsis granulata and their nitric oxide inhibitory activity

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DOIResolve DOI: http://doi.org/10.1007/s10811-012-9967-1
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TypeArticle
Journal titleJournal of Applied Phycology
ISSN0921-8971
1573-5176
Volume25
Issue5
Pages15131521; # of pages: 9
SubjectBetaine lipid; Diacylglyceryltrimethylhomoserine (DGTS); Inducible nitric oxide synthase; Microalgae; Nannochloropsis granulata; Nitric oxide
AbstractChemical investigation of polar lipids from the marine eustigmatophyte microalga Nannochloropsis granulata led to the isolation of six betaine lipid diacylglyceryltrimethylhomoserine (DGTS), namely, (2S)-1,2-bis-O-eicosapentaenoylglyceryl-3-O-4′-(N,N,N-trimethyl)-homoserine (1), (2S)-1-O-eicosapentaenoyl-2-O-arachidonoylglyceryl-3-O-4′-(N,N,N-trimethyl)-homoserine (2), (2S)-1-O-eicosapentaenoyl-2-O-myristoylglyceryl-3-O-4′-(N,N,N-trimethyl)-homoserine (3), (2S)-1-O-eicosapentaenoyl-2-O-palmitoylglyceryl-3-O-4′-(N,N,N-trimethyl)-homoserine (4), (2S)-1-O-eicosapentaenoyl-2-O-palmitoleoylglyceryl-3-O-4′-(N,N,N-trimethyl)-homoserine (5), and (2S)-1-O-eicosapentaenoyl-2-O-linoleoylglyceryl-3-O-4′-(N,N,N-trimethyl)-homoserine (6). Structures of the isolated DGTSs were elucidated based on both spectroscopic technique and degradation methods. This is the first report of isolation of 1 in pure state, and 2–6 are all new compounds. The isolated betaine lipids showed dose-dependent nitric oxide (NO) inhibitory activity against lipopolysaccharide-induced nitric oxide production in RAW264.7 macrophage cells. Further study suggested that these betaine lipids (1–6) inhibit NO production in RAW264.7 macrophage cells through downregulation of inducible nitric oxide synthase expression, indicating the possible use as an anti-inflammatory agent. This is the first report of DGTS with anti-inflammatory activity.
Publication date
PublisherSpringer
LanguageEnglish
AffiliationNational Research Council Canada; Aquatic and Crop Resource Development
Peer reviewedYes
NRC number55465
NPARC number21268640
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Record identifier5e5e0377-b496-4685-8da3-7a0862bc0485
Record created2013-11-05
Record modified2016-05-09
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