Norartocarpanone and Disease-Models--Animal

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.

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