Anti-inflammatory and potential cancer chemopreventive constituents of the fruits of Morinda citrifolia (Noni)

J Nat Prod. 2007 May;70(5):754-7. doi: 10.1021/np068065o. Epub 2007 May 5.

Abstract

A new anthraquinone, 1,5,15-tri-O-methylmorindol (1), and two new saccharide fatty acid esters, 2-O-(beta-D-glucopyranosyl)-1-O-hexanoyl-beta-D-gluropyranose (4) and 2-O-(beta-D-glucopyranosyl)-1-O-octanoyl-beta-D-gluropyranose (5), have been isolated from a methanol extract of the fruits of Morinda citrifolia (noni) along with 10 known compounds, namely, two anthraquinones (2, 3), six saccharide fatty acid esters (6-11), an iridoid glycoside (12), and a flavanol glycoside (13). Upon evaluation of six compounds (5-7, 9, 10, and 13) for inhibitory activity against 12-O-tetradecanoylphorbol-13-acetate (TPA)-induced inflammation (1 microg/ear) in mice, four saccharide fatty acid esters, 5-7 and 9, exhibited potent anti-inflammatory activity, with ID50 values of 0.46-0.79 mg per ear. In addition, when compounds 1-13 were evaluated against the Epstein-Barr virus early antigen (EBV-EA) activation induced by TPA, all of the compounds exhibited moderate inhibitory effects (IC50 values of 386-578 mol ratio/32 pmol TPA).

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Anthraquinones / chemistry
  • Anthraquinones / isolation & purification
  • Anthraquinones / pharmacology*
  • Anti-Inflammatory Agents / chemistry
  • Anti-Inflammatory Agents / isolation & purification
  • Anti-Inflammatory Agents / pharmacology*
  • Anticarcinogenic Agents / chemistry
  • Anticarcinogenic Agents / isolation & purification
  • Anticarcinogenic Agents / pharmacology*
  • Antigens, Viral / drug effects
  • Caproates / chemistry
  • Caproates / isolation & purification
  • Caproates / pharmacology*
  • Caprylates / chemistry
  • Caprylates / isolation & purification
  • Caprylates / pharmacology*
  • Ear
  • Edema / chemically induced
  • Fruit / chemistry
  • Glucosides / chemistry
  • Glucosides / isolation & purification
  • Glucosides / pharmacology*
  • Japan
  • Mice
  • Molecular Structure
  • Morinda / chemistry*
  • Plants, Medicinal / chemistry*
  • Tetradecanoylphorbol Acetate / pharmacology

Substances

  • 1,5,15-tri-O-methylmorindol-(6-hydroxy-1,5-dimethoxy-2-(methoxymethyl)anthraquinone)
  • 2-O-(beta-D-glucopyranosyl)-1-O-hexanoyl-beta-D-gluropyranose
  • 2-O-(beta-D-glucopyranosyl)-1-O-octanoyl-beta-D-gluropyranose
  • Anthraquinones
  • Anti-Inflammatory Agents
  • Anticarcinogenic Agents
  • Antigens, Viral
  • Caproates
  • Caprylates
  • Epstein-Barr virus early antigen
  • Glucosides
  • Tetradecanoylphorbol Acetate