Inhibitors of delta 4-3-ketosteroid (5 alpha) reductase, which had been prepared from rat prostate and converted testosterone to 5 alpha-dihydrotestosterone and 4-androstene-3,17-dione, were isolated from 50% ethanol extract of Populus nigra. They were identified as pinobanksin (I, 3,5,7-trihydroxyflavanone), 3,7-dimethylquercetin (II, 3',4',5-trihydroxy-3,7-dimethoxyflavone) and pinocembrin (III, 5,7-dihydroxyflavanone). Compound III showed the most potent inhibitory activity among them.
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Yasuo Komoda (1989) studied this question.