title: Antitumor agents, 138. Rotenoids and isoflavones as cytotoxic constitutents from Amorpha fruticosa.
abstract: Eight cytotoxic compounds have been isolated from the CHCl3 extract of Amorpha fruticosa. One compound, 6'-O-D-beta-glucopyranosyldalpanol [10], is a new cytotoxic rotenoid. Another known rotenoid, 12 alpha beta-hydroxyamorphigenin [6], was first shown to exhibit extremely potent cytotoxicity (ED50 < 0.001 microgram/ml) in six neoplastic cell lines. In addition to these compounds, three isoflavones (afrormosin [1], 7,2',4', 5'-tetramethoxyisoflavone [2], 8-methylretusin [3]) and five rotenoids (amorphispironone [4], amorphigenin [5], dalpanol [7], 12a beta-hydroxydalpanol [8], and tephrosin [9]) were isolated. Compound 8 was isolated for the first time as a natural product from this plant. The structures of these compounds were established on the basis of spectral data; some were further confirmed by X-ray crystallographic analysis.
authors.affiliation: Natural Products Laboratory, School of Pharmacy, University of North Carolina, Chapel Hill 27599.
authors.forename: L
authors.initials: L
authors.lastname: Li
authors.forename: H K
authors.initials: HK
authors.lastname: Wang
authors.forename: J J
authors.initials: JJ
authors.lastname: Chang
authors.forename: A T
authors.initials: AT
authors.lastname: McPhail
authors.forename: D R
authors.initials: DR
authors.lastname: McPhail
authors.forename: H
authors.initials: H
authors.lastname: Terada
authors.forename: T
authors.initials: T
authors.lastname: Konoshima
authors.forename: M
authors.initials: M
authors.lastname: Kokumai
authors.forename: M
authors.initials: M
authors.lastname: Kozuka
authors.forename: J R
authors.initials: JR
authors.lastname: Estes
mesh_terms: D000972:Antineoplastic Agents, Phytogenic / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D002294:Carcinoma, Squamous Cell / Q000188:drug therapy; D004354:Drug Screening Assays, Antitumor; D006801:Humans; D007529:Isoflavones / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D007822:Laryngeal Neoplasms / Q000188:drug therapy; D010946:Plants, Medicinal / Q000737:chemistry*; D012402:Rotenone / Q000031:analogs & derivatives* / Q000737:chemistry / Q000494:pharmacology*; D014407:Tumor Cells, Cultured
chemical_list: C000602523:7-hydroxy-6,4'-dimethoxyisoflavone; D000972:Antineoplastic Agents, Phytogenic; D007529:Isoflavones; D012402:Rotenone