title: Potential cancer chemopreventive constituents of the leaves of Macaranga triloba.
abstract: Activity-guided fractionation of the leaves of Macaranga triloba, using an in vitro bioassay based on the inhibition of cyclooxygenase-2, resulted in the isolation of a rotenoid, 4,5-dihydro-5'alpha-hydroxy-4'alpha-methoxy-6a,12a-dehydro-alpha-toxicarol (1), as well as 12 known compounds, (+)-clovan-2beta,9alpha-diol, ferulic acid, 3,7,3',4'-tetramethylquercetin, 3,7,3'-trimethylquercetin, 3,7-dimethylquercetin, abscisic acid, 1beta,6alpha-dihydroxy-4(15)-eudesmene, 3beta-hydroxy-24-ethylcholest-5-en-7-one, loliolide, scopoletin, taraxerol, and 3-epi-taraxerol. The structure of compound 1 was determined using spectroscopic methods. All isolates were evaluated for their potential to inhibit cyclooxygenases-1 and -2 by measuring PGE(2) production, and to induce quinone reductase in cultured Hepa 1c1c7 mouse hepatoma cells.
authors.affiliation: Department of Medicinal Chemistry and Pharmacognosy, College of Pharmacy, University of Illinois at Chicago, 833 South Wood Street, Chicago, IL 60612, USA.
authors.forename: Dae Sik
authors.initials: DS
authors.lastname: Jang
authors.forename: Muriel
authors.initials: M
authors.lastname: Cuendet
authors.forename: Alison D
authors.initials: AD
authors.lastname: Pawlus
authors.forename: Leonardus B S
authors.initials: LB
authors.lastname: Kardono
authors.forename: Kazuko
authors.initials: K
authors.lastname: Kawanishi
authors.forename: Norman R
authors.initials: NR
authors.lastname: Farnsworth
authors.forename: Harry H S
authors.initials: HH
authors.lastname: Fong
authors.forename: John M
authors.initials: JM
authors.lastname: Pezzuto
authors.forename: A Douglas
authors.initials: AD
authors.lastname: Kinghorn
mesh_terms: D000438:Alcohols / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D000818:Animals; D016588:Anticarcinogenic Agents / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology*; D045744:Cell Line, Tumor; D051545:Cyclooxygenase 1; D051546:Cyclooxygenase 2; D004790:Enzyme Induction / Q000187:drug effects; D004791:Enzyme Inhibitors / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D019665:Euphorbiaceae / Q000737:chemistry*; D005419:Flavonoids / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D020128:Inhibitory Concentration 50; D007527:Isoenzymes / Q000037:antagonists & inhibitors; D008114:Liver Neoplasms, Experimental; D008565:Membrane Proteins; D051379:Mice; D015394:Molecular Structure; D016660:NAD(P)H Dehydrogenase (Quinone) / Q000096:biosynthesis; D019906:Nuclear Magnetic Resonance, Biomolecular; D018515:Plant Leaves / Q000737:chemistry; D011451:Prostaglandin-Endoperoxide Synthases
chemical_list: D000438:Alcohols; D016588:Anticarcinogenic Agents; D004791:Enzyme Inhibitors; D005419:Flavonoids; D007527:Isoenzymes; D008565:Membrane Proteins; D051545:Cyclooxygenase 1; D051546:Cyclooxygenase 2; D011451:Prostaglandin-Endoperoxide Synthases; C496512:Ptgs1 protein, mouse; D016660:NAD(P)H Dehydrogenase (Quinone)