Antitumor agents, 138. Rotenoids and isoflavones as cytotoxic constitutents from Amorpha fruticosa.
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.
Li
L
L
Natural Products Laboratory, School of Pharmacy, University of North Carolina, Chapel Hill 27599.
Wang
H K
HK
Chang
J J
JJ
McPhail
A T
AT
McPhail
D R
DR
Terada
H
H
Konoshima
T
T
Kokumai
M
M
Kozuka
M
M
Estes
J R
JR
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
C000602523:7-hydroxy-6,4'-dimethoxyisoflavone; D000972:Antineoplastic Agents, Phytogenic; D007529:Isoflavones; D012402:Rotenone