Abstract Following fungal-inoculation, P. vulgaris was found to produce small amounts of 7,4′-dihydroxyisoflavone (daidzein), 7,2′,4′-trihydroxyisoflavone, 7,2′,4′-trihydroxyisoflavanone, (6aR, 11aR)-3,9-dihydroxypterocarpan, and (3R)-7,2′,4′-trihydroxyisoflavan. The structures of the latter four compounds were confirmed by synthesis. The principal pterocarpans isolated were phaseollidin and phaseollin and ORD spectra indicate that these compounds have the same (6aR, 11aR)-configuration as 3,9-dihydroxypterocarpan. A pathway leading to phaseollidin and phaseollin is proposed involving 2′-hydroxylation of daidzein, reduction to the isoflavanone, further reduction, dehydration and cyclization to the pterocarpan, and prenylation to give phaseollidin and then cyclization and dehydrogenation to give phaseollin. No evidence of prenylation at the isoflavone or isoflavanone stage was obtained. The phaseollin metabolite, (6aS, 11aS)-6a-hydroxyphaseollin, was also detected.

中文翻译：

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菜豆中菜豆蛋白的形成和代谢

摘要 接种真菌后，发现 P. vulgaris 产生少量 7,4'-二羟基异黄酮（黄豆苷原）、7,2',4'-三羟基异黄酮、7,2',4'-三羟基异黄酮（6aR、11aR )-3,9-二羟基紫檀木和 (3R)-7,2',4'-三羟基异黄烷。后四种化合物的结构经合成证实。分离出的主要紫檀木是菜豆素和菜豆素，ORD 光谱表明这些化合物具有与 3,9-二羟基紫檀木相同的 (6aR, 11aR) 构型。提出了一种导致菜豆素和菜豆素的途径，包括黄豆苷​​元的 2'-羟基化，还原为异黄酮，进一步还原、脱水和环化为紫檀木，异戊二烯化得到菜豆素，然后环化和脱氢得到菜豆素。没有获得异黄酮或异黄酮阶段异戊二烯化的证据。还检测到菜豆蛋白代谢物 (6aS, 11aS)-6a-羟基菜豆蛋白。