Activity-Guided Isolation of Constituents of Tephrosia purpurea with the Potential to Induce the Phase II Enzyme, Quinone Reductase

• Published in: Journal of natural products (Washington, D.C.) D.C.), 1997-09, Vol.60 (9), p.869-873
• Main Authors: Chang, Leng Chee, Gerhäuser, Clarissa, Song, Lynda, Farnsworth, Norman R, Pezzuto, John M, Kinghorn, A. Douglas
• Format: Article
• Language: English
• Subjects: (+)-PURPURIN; (+)-TEPHROPURPURIN; (-)-3-HYDROXY-4-METHOXY-8,9-METHYLENE-DIOXYPTEROCARPAN; (-)-MAACKIAIN; (-)-MEDICARPIN; 3'-METHOXYDAIDZEIN; 3,9-DIHYDROXY-8-METHOXYCOUMESTAN; 7,4'-DIHYDROXY-3,5'-DIMETHOXYISOFLAVONE; ACTIVADOR ENZIMATICO; ACTIVATEUR D'ENZYME; ACTIVIDAD ENZIMATICA; ACTIVITE ENZYMATIQUE; Animals; BENZOQUINONE; Biological and medical sciences; CALCONA; CHALCONE; CHALCONES; CHEMICAL COMPOSITION; CHEMICAL STRUCTURE; COMPOSICION QUIMICA; COMPOSITION CHIMIQUE; CYTOTOXIC COMPOUNDS; DEXMOXYHYLLIN B; ENZYME ACTIVATORS; Enzyme Induction - drug effects; ENZYME INHIBITORS; ENZYMIC ACTIVITY; ESPECTROMETRIA; ESTRUCTURA QUIMICA; FLAVONOIDE; FLAVONOIDES; FLAVONOIDS; General pharmacology; HEPATOMA; INDE; INDIA; INHIBIDORES DE ENZIMAS; INHIBITEUR D'ENZYME; ISOFLAVONES; Isothiocyanates; LANCEOLATIN B; Liver Neoplasms, Experimental - metabolism; Magnetic Resonance Spectroscopy; Medical sciences; Mice; NAD(P)H Dehydrogenase (Quinone) - biosynthesis; NEOPLASMAS; NEOPLASME; NEOPLASMS; OXIDOREDUCTASES; OXIDORREDUCTASAS; OXYDOREDUCTASE; Pharmacognosy. Homeopathy. Health food; Pharmacology. Drug treatments; Plant Extracts - pharmacology; Plants, Medicinal - chemistry; PONGAMOL; QUINONAS; QUINONE; QUINONES; SPECTRAL ANALYSIS; SPECTROMETRIE; SPECTROMETRY; Spectrophotometry, Ultraviolet; STRUCTURE CHIMIQUE; SUBSTANCE TOXIQUE; SUSTANCIAS TOXICAS; TEPHROSIA; Thiocyanates - pharmacology; TOXIC SUBSTANCES; Tumor Cells, Cultured
• ISSN: 0163-3864; 1520-6025
• DOI: 10.1021/np970236p

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-methylenedioxypterocarpan (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.