Polar lipids from the marine macroalga Palmaria palmata inhibit lipopolysaccharide-induced nitric oxide production in RAW264.7 macrophage cells

Abstract

The EtOAc soluble fraction of a MeOH/CHCl3 extract of Palmaria palmata showed strong nitric oxide (NO) inhibitory activity against lipopolysaccharide (LPS)-induced NO production in murine RAW264.7 cells. NO inhibition-guided isolation led to identification of three new polar lipids including a sulfoquinovosyl diacylglycerol (SQDG) (2S)-1-O-eicosapentaenoyl-2-O-myristoyl-3-O-(6-sulfo-α-d-quinovopyranosyl)-glycerol (1) and two phosphatidylglycerols, 1-O-eicosapentaenoyl-2-O-trans-3-hexadecenoyl-3-phospho-(1′-glycerol)-glycerol (3) and 1-O-eicosapentaenoyl-2-O-palmitoyl-3-phospho-(1′-glycerol)-glycerol (4) from the EtOAc fraction. Seven known lipids were also isolated including a SQDG (2), a phospholipid (5) and five galactolipids (6–10). Structures of the isolated lipids were elucidated by spectral analyses. The isolated SQDGs, phosphatidylglycerols and phospholipid possessed strong and dose-dependent NO inhibitory activity compared to NG-methyl-l-arginine acetate salt (l-NMMA), a well-known NO inhibitor used as a positive control. Further study suggested that these polar lipids suppressed NO production through down-regulation of inducible nitric oxide synthase (iNOS).