Anti-inflammatory and Quinone Reductase Inducing Compounds from Fermented Noni (Morinda citrifolia) Juice Exudates

J Nat Prod. 2016 Jun 24;79(6):1508-13. doi: 10.1021/acs.jnatprod.5b00970. Epub 2016 May 19.

Abstract

A new fatty acid ester disaccharide, 2-O-(β-d-glucopyranosyl)-1-O-(2E,4Z,7Z)-deca-2,4,7-trienoyl-β-d-glucopyranose (1), a new ascorbic acid derivative, 2-caffeoyl-3-ketohexulofuranosonic acid γ-lactone (2), and a new iridoid glycoside, 10-dimethoxyfermiloside (3), were isolated along with 13 known compounds (4-16) from fermented noni fruit juice (Morinda citrifolia). The structures of the new compounds, together with 4 and 5, were determined by 1D and 2D NMR experiments, as well as comparison with published values. Compounds 2 and 7 showed moderate inhibitory activities in a TNF-α-induced NF-κB assay, and compounds 4 and 6 exhibited considerable quinone reductase-1 (QR1) inducing effects.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Anti-Inflammatory Agents / analysis
  • Anti-Inflammatory Agents / chemistry
  • Anti-Inflammatory Agents / isolation & purification*
  • Anti-Inflammatory Agents / pharmacology*
  • Disaccharidases / chemistry
  • Disaccharidases / isolation & purification*
  • Disaccharidases / pharmacology*
  • Fatty Acids / chemistry
  • Fermentation
  • Fruit / chemistry
  • Iridoids / analysis
  • Iridoids / chemistry
  • Iridoids / isolation & purification
  • Iridoids / pharmacology
  • Molecular Structure
  • Morinda / chemistry*
  • NAD(P)H Dehydrogenase (Quinone) / drug effects*
  • NAD(P)H Dehydrogenase (Quinone) / metabolism
  • NF-kappa B / metabolism
  • Tumor Necrosis Factor-alpha / analysis

Substances

  • 2-O-(beta-D-glucopyranosyl)-1-O-(2E,4Z,7Z)-deca-2,4,7-trienoyl-beta-D-glucopyranose
  • Anti-Inflammatory Agents
  • Fatty Acids
  • Iridoids
  • NF-kappa B
  • Tumor Necrosis Factor-alpha
  • NAD(P)H Dehydrogenase (Quinone)
  • NQO1 protein, human
  • Disaccharidases