Characterization of a New Trioxilin and a Sulfoquinovosyl Diacylglycerol with Anti-Inflammatory Properties from the Dinoflagellate Oxyrrhis marina

Mar Drugs. 2017 Feb 27;15(3):57. doi: 10.3390/md15030057.

Abstract

Two new compounds-a trioxilin and a sulfoquinovosyl diacylglycerol (SQDG)-were isolated from the methanolic extract of the heterotrophic dinoflagellate Oxyrrhis marina cultivated by feeding on dried yeasts. The trioxilin was identified as (4Z,8E,13Z,16Z,19Z) -7(S),10(S),11(S)-trihydroxydocosapentaenoic acid (1), and the SQDG was identified as (2S)-1-O-hexadecanosy-2-O-docosahexaenoyl-3-O-(6-sulfo-α-d-quinovopyranosyl)-glycerol (2) by a combination of nuclear magnetic resonance (NMR) spectra, mass analyses, and chemical reactions. The two compounds were associated with docosahexaenoic acid, which is a major component of O. marina. The two isolated compounds showed significant nitric oxide inhibitory activity on lipopolysaccharide-induced RAW264.7 cells. Compound 2 showed no cytotoxicity against hepatocarcinoma (HepG2), neuroblastoma (Neuro-2a), and colon cancer (HCT-116) cells, while weak cytotoxicity was observed for compound 1 against Neuro-2a cells.

Keywords: Oxyrrhis marina; docosahexaenoic acid; nitric oxide inhibition; sulfoquinovosyl diacylglycerols; trioxilin.

MeSH terms

  • Animals
  • Anti-Inflammatory Agents / pharmacology*
  • Carcinoma, Hepatocellular / drug therapy
  • Cell Line
  • Colonic Neoplasms / drug therapy
  • Diglycerides / pharmacology*
  • Dinoflagellida / chemistry*
  • HCT116 Cells
  • Hep G2 Cells
  • Humans
  • Lipopolysaccharides / pharmacology
  • Mice
  • Neuroblastoma / drug therapy

Substances

  • Anti-Inflammatory Agents
  • Diglycerides
  • Lipopolysaccharides
  • sulphoquinovosyl-diacylglycerol