Here reports new conversions methods of tomato saponins, esculeoside A (1) and a mixture of esculeosides B-1 (2) and B-2 (3), (the latter two were obtained from tomato cans) into pregnane derivative (5) by an alkal treatment followed by acid treatment. Compound 1 or a mixture of 2 and 3 were each refluxed with 1 N KOH to afford a characteristic pyridine steroidal glycoside (4), which was then treated with 2 N HCl-MeOH to afford a pregnane derivative, 3β-hydroxy-5α-pregn-16-en-20-one (5). The results of the above two reactions indicated that tomato saponins are chemically closely related to pregnane hormones. We assume that the assimilated tomato saponins via the small intestine are metabolized into pregnane derivatives, demonstrating various bioactivities such as anti-cancer, anti-osteoporosis, and anti-menopausal disorder activities.

译文

:这里报道了将番茄皂苷,七叶皂甙A(1)和七叶皂甙B-1(2)和B-2(3)的混合物(后两者是从番茄罐中获得)转化为孕烷衍生物的新方法(5)通过碱处理,然后进行酸处理。将化合物1或2和3的混合物分别与1 N KOH回流以提供特征性的吡啶甾体糖苷(4),然后将其用2 N HCl-MeOH处理以提供孕烷衍生物3β-羟基-5α-孕烯-16-en-20-one(5)。上述两个反应的结果表明,番茄皂苷在化学上与孕激素具有密切的关系。我们假设通过小肠吸收的番茄皂苷被代谢成孕烷衍生物,表现出各种生物活性,例如抗癌,抗骨质疏松和抗更年期疾病活动。

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