Constituents of the bark and twigs of Artocarpus dadah with cyclooxygenase inhibitory activity

J Nat Prod. 2002 Feb;65(2):163-9. doi: 10.1021/np010451c.

Abstract

Fractionation of an ethyl acetate-soluble extract of the bark of Artocarpus dadah has led to the isolation of three new prenylated stilbenoid derivatives, 3-(gamma,gamma-dimethylallyl)resveratrol (1), 5-(gamma,gamma-dimethylallyl)oxyresveratrol (2), 3-(2,3-dihydroxy-3-methylbutyl)resveratrol (3), and a new benzofuran derivative, 3-(gamma,gamma-dimethylpropenyl)moracin M (4), along with six known compounds, oxyresveratrol, (+)-catechin, afzelechin-3-O-alpha-L-rhamnopyranoside, (-)-epiafzelechin, dihydromorin, and epiafzelechin-(4beta-->8)-epicatechin. From an ethyl acetate-soluble extract of the twigs of the same plant were isolated compound 4 and two new neolignan derivatives, dadahols A (5) and B (6), as well as 10 known compounds, oxyresveratrol, (+)-catechin, afzelechin-3-O-alpha-L-rhamnopyranoside, resveratrol, steppogenin, moracin M, isogemichalcone B, gemichalcone B, norartocarpetin, and engeletin. The structures of compounds 1-6 were determined using spectroscopic and chemical methods. Isolates were evaluated for their inhibitory effects against both cyclooxygenase-1 (COX-1) and -2 (COX-2) and in a mouse mammary organ culture assay.

Publication types

  • Research Support, U.S. Gov't, P.H.S.

MeSH terms

  • 9,10-Dimethyl-1,2-benzanthracene / pharmacology
  • Acetylation
  • Animals
  • Benzofurans / chemistry
  • Benzofurans / isolation & purification
  • Benzofurans / pharmacology
  • Breast
  • Catechin
  • Cell Transformation, Neoplastic / drug effects*
  • Chromatography, High Pressure Liquid
  • Chromatography, Thin Layer
  • Cyclooxygenase 1
  • Cyclooxygenase 2
  • Cyclooxygenase 2 Inhibitors
  • Cyclooxygenase Inhibitors / chemistry
  • Cyclooxygenase Inhibitors / isolation & purification*
  • Cyclooxygenase Inhibitors / pharmacology
  • Disease Models, Animal
  • Indonesia
  • Isoenzymes / antagonists & inhibitors
  • Membrane Proteins
  • Methylation
  • Mice
  • Mice, Inbred BALB C
  • Molecular Structure
  • Moraceae / chemistry*
  • Nuclear Magnetic Resonance, Biomolecular
  • Organ Culture Techniques
  • Plant Bark / chemistry
  • Plant Extracts
  • Plant Shoots / chemistry
  • Plants, Medicinal / chemistry*
  • Prostaglandin-Endoperoxide Synthases
  • Spectroscopy, Fourier Transform Infrared
  • Stereoisomerism
  • Stilbenes / chemistry
  • Stilbenes / isolation & purification*
  • Stilbenes / pharmacology

Substances

  • 3-(2,3-dihydroxy-3-methylbutyl)resveratrol
  • 3-(gamma,gamma-dimethylallyl)resveratrol
  • 5-(dimethylallyl)oxyresveratrol
  • Benzofurans
  • Cyclooxygenase 2 Inhibitors
  • Cyclooxygenase Inhibitors
  • Isoenzymes
  • Membrane Proteins
  • Plant Extracts
  • Stilbenes
  • puag-haad
  • 9,10-Dimethyl-1,2-benzanthracene
  • Catechin
  • Cyclooxygenase 1
  • Cyclooxygenase 2
  • Prostaglandin-Endoperoxide Synthases
  • Ptgs1 protein, mouse