Constituents of the bark and twigs of Artocarpus dadah with cyclooxygenase inhibitory activity.
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.
Su
Bao-Ning
BN
Department of Medicinal Chemistry and Pharmacognosy, College of Pharmacy, University of Illinois at Chicago, 60612, USA.
Cuendet
Muriel
M
Hawthorne
Michael E
ME
Kardono
Leonardus B S
LB
Riswan
Soedarsono
S
Fong
Harry H S
HH
Mehta
Rajendra G
RG
Pezzuto
John M
JM
Kinghorn
A Douglas
AD
D015127:9,10-Dimethyl-1,2-benzanthracene / Q000494:pharmacology; D000107:Acetylation; D000818:Animals; D001572:Benzofurans / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D001940:Breast; D002392:Catechin; D002471:Cell Transformation, Neoplastic / Q000187:drug effects*; D002851:Chromatography, High Pressure Liquid; D002855:Chromatography, Thin Layer; D051545:Cyclooxygenase 1; D051546:Cyclooxygenase 2; D052246:Cyclooxygenase 2 Inhibitors; D016861:Cyclooxygenase Inhibitors / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D004195:Disease Models, Animal; D007214:Indonesia; D007527:Isoenzymes / Q000037:antagonists & inhibitors; D008565:Membrane Proteins; D008745:Methylation; D051379:Mice; D008807:Mice, Inbred BALB C; D015394:Molecular Structure; D029586:Moraceae / Q000737:chemistry*; D019906:Nuclear Magnetic Resonance, Biomolecular; D009924:Organ Culture Techniques; D024301:Plant Bark / Q000737:chemistry; D010936:Plant Extracts; D018520:Plant Shoots / Q000737:chemistry; D010946:Plants, Medicinal / Q000737:chemistry*; D011451:Prostaglandin-Endoperoxide Synthases; D017550:Spectroscopy, Fourier Transform Infrared; D013237:Stereoisomerism; D013267:Stilbenes / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology
C451301:3-(2,3-dihydroxy-3-methylbutyl)resveratrol; C451303:3-(gamma,gamma-dimethylallyl)resveratrol; C451302:5-(dimethylallyl)oxyresveratrol; D001572:Benzofurans; D052246:Cyclooxygenase 2 Inhibitors; D016861:Cyclooxygenase Inhibitors; D007527:Isoenzymes; D008565:Membrane Proteins; D010936:Plant Extracts; D013267:Stilbenes; C034912:puag-haad; D015127:9,10-Dimethyl-1,2-benzanthracene; D002392:Catechin; D051545:Cyclooxygenase 1; D051546:Cyclooxygenase 2; D011451:Prostaglandin-Endoperoxide Synthases; C496512:Ptgs1 protein, mouse