Activity-guided isolation of constituents of Tephrosia purpurea with the potential to induce the phase II enzyme, quinone reductase.
An isoflavone, 7,4'-dihydroxy-3',5'-dimethoxyisoflavone (1), and a chalcone, (+)-tephropurpurin (2), both novel compounds, as well as six constituents of known structure, (+)-purpurin (3), pongamol (4), lanceolatin B (5), (-)-maackiain (6), (-)-3-hydroxy-4-methoxy-8,9-methylene-dioxypterocarpan (7), and (-)-medicarpin (8), were obtained as active compounds from Tephrosia purpurea, using a bioassay based on the induction of quinone reductase (QR) activity with cultured Hepa 1c1c7 mouse hepatoma cells. Additionally, three inactive compounds of known structure, 3'-methoxydaidzein, desmoxyphyllin B, and 3,9-dihydroxy-8-methoxycoumestan, were isolated and identified. The structure elucidation of compounds 1 and 2 was carried out by spectral data interpretation.
Chang
L C
LC
Department of Medical Chemistry and Pharmacognosy, College of Pharmacy, University of Illinois at Chicago 60612, USA.
Gerhäuser
C
C
Song
L
L
Farnsworth
N R
NR
Pezzuto
J M
JM
Kinghorn
A D
AD
D000818:Animals; D004790:Enzyme Induction / Q000187:drug effects; D007194:India; D017879:Isothiocyanates; D008114:Liver Neoplasms, Experimental / Q000378:metabolism; D009682:Magnetic Resonance Spectroscopy; D051379:Mice; D016660:NAD(P)H Dehydrogenase (Quinone) / Q000096:biosynthesis*; D010936:Plant Extracts / Q000494:pharmacology; D010946:Plants, Medicinal / Q000737:chemistry*; D013056:Spectrophotometry, Ultraviolet; D013454:Sulfoxides; D013861:Thiocyanates / Q000494:pharmacology; D014407:Tumor Cells, Cultured
D017879:Isothiocyanates; D010936:Plant Extracts; D013454:Sulfoxides; D013861:Thiocyanates; D016660:NAD(P)H Dehydrogenase (Quinone); C016766:sulforaphane