异硫氰酸苄酯及其半胱氨酸共轭物的代谢
The metabolism of benzyl isothiocyanate and its cysteine conjugate.
作者信息
Brüsewitz G, Cameron B D, Chasseaud L F, Görler K, Hawkins D R, Koch H, Mennicke W H
出版信息
Biochem J. 1977 Jan 15;162(1):99-107. doi: 10.1042/bj1620099.
Abstract
- The corresponding cysteine conjugate was formed when the GSH (reduced glutathione) or cysteinylglycine conjugates of benzyl isothiocyanate were incubated with rat liver or kidney homogenates. When the cysteine conjugate of benzyl isothiocyanate was similarly incubated in the presence of acetyl-CoA, the corresponding N-acetylcysteine conjugate (mercapturic acid) was formed. 2. The non-enzymic reaction of GSH with benzyl isothiocyanate was rapid and was catalysed by rat liver cytosol. 3. The mercapturic acid was excreted in the urine of rats dosed with benzyl isothiocyanate or its GSH, cysteinyl-glycine or cysteine conjugate, and was isolated as the dicyclohexylamine salt. 4. An oral dose of the cysteine conjugate of [14C]benzyl isothiocyanate was rapidly absorbed and excreted by rats and dogs. After 3 days, rats had excreted a mean of 92.4 and 5.6% of the dose in the urine and faeces respectively, and dogs had excreted a mean of 86.3 and 13.2% respectively. 5. After an oral dose of the cystein conjugate of [C]benzyl isothiocyanate, the major 14C-labelled metabolite in rat urine was the corresponding mercapturic acid (62% of the dose), whereas in dog urine it was hippuric acid (40% of the dose). 5. Mercapturic acid biosynthesis may be an important route of metabolism of certain isothiocyanates in some mammalian species.
摘要
- 当异硫氰酸苄酯的谷胱甘肽（还原型谷胱甘肽）或半胱氨酰甘氨酸共轭物与大鼠肝脏或肾脏匀浆一起孵育时，会形成相应的半胱氨酸共轭物。当异硫氰酸苄酯的半胱氨酸共轭物在乙酰辅酶A存在下进行类似孵育时，会形成相应的N - 乙酰半胱氨酸共轭物（硫醚氨酸）。2. 谷胱甘肽与异硫氰酸苄酯的非酶促反应迅速，且由大鼠肝细胞溶胶催化。3. 硫醚氨酸在给大鼠服用异硫氰酸苄酯或其谷胱甘肽、半胱氨酰甘氨酸或半胱氨酸共轭物后经尿液排出，并以二环己胺盐形式分离出来。4. 口服[¹⁴C]异硫氰酸苄酯的半胱氨酸共轭物后，大鼠和狗能迅速吸收并排出。3天后，大鼠分别在尿液和粪便中排出了平均92.4%和5.6%的剂量，狗分别排出了平均86.3%和13.2%。5. 口服[¹⁴C]异硫氰酸苄酯的半胱氨酸共轭物后，大鼠尿液中主要的¹⁴C标记代谢物是相应的硫醚氨酸（占剂量的62%），而在狗尿液中是马尿酸（占剂量的40%）。5. 硫醚氨酸生物合成可能是某些哺乳动物物种中某些异硫氰酸酯代谢的重要途径。
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