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Use of a Mammalian Cell Culture Benzo(a)pyrene Metabolism Assay for the Detection of Potential Anticarcinogens from Natural Products: Inhibition of Metabolism by Biochanin A, an Isoflavone from Trifolium pratense L¹

Department of Medicinal Chemistry, School of Pharmacy and Pharmacal Sciences, Purdue University, West Lafayette, Indiana 47907

Based on the epidemiological evidence for a relationship between consumption of certain foods and decreased cancer incidence in humans, an assay was developed to screen and fractionate plant extracts for chemopreventive potential. This assay measures effects on the metabolism of [³H]benzo(a)pyrene [B(a)P] in hamster embryo cell cultures. Screening of several plant extracts has generated a number of activity leads. The 95% ethyl alcohol extract of one of these actives, Trifolium pratense L. Leguminosae, red clover, significantly inhibited the metabolism of B(a)P and decreased the level of binding of B(a)P to DNA by 30 to 40%. Using activity-directed fractionation by solvent partitioning and then silica gel chromatography, a major active compound was isolated and identified as the isoflavone, biochanin A. The pure compound decreased the metabolism of B(a)P by 54% in comparison to control cultures and decreased B(a)P-DNA binding by 37 to 50% at a dose of 25 µg/ml. These studies demonstrate that the hydrocarbon metabolism assay can detect and guide the fractionation of potential anticarcinogens from plants. The ability of the isoflavone biochanin A to inhibit carcinogen activation in cells in culture suggests that in vivo studies of this compound as a potential chemopreventive agent are warranted.

¹ Supported by USPHS Grant CA 38151, National Cancer Institute, Department of Health and Human Services. Presented in part at the 1987 Annual Meeting of the American Association for Cancer Research.

² To whom requests for reprints should be addressed, at the College of Pharmacy, The Ohio State University, 500 W. 12th Avenue, Columbus, OH 43210.

Received 3/30/87. Revised 4/ 6/88. Revised 6/20/88. Accepted 7/ 6/88.

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