Koizumi M, Akao T, Kadota S, Kikuchi T, Okuda T, Kobashi K
Faculty of Pharmaceutical Sciences, Toyama Medical and Pharmaceutical University, Japan.
Chem Pharm Bull (Tokyo). 1991 Oct;39(10):2638-43. doi: 10.1248/cpb.39.2638.
This report discusses a novel type of arylsulfotransferase (AST) which was derived from human intestinal bacterium sulfated polyphenolic compounds when p-nitrophenyl sulfate (PNS) was taken as a donor substrate. (+)-Catechin, (+/-)-catechin, (-)-epicatechin and (-)-epicatechin gallate were better substrates than tyramine. (-)-Epigallocatechin and (-)-epigallocatechin gallate were slightly worse substrates than tyramine. Although gallic acid was a bad substrate, alkyl gallate esters were better substrates than tyramine. The degree of acceptor specificity increased in proportion to the length of the alkyl group up to the carbon number of five. Pedunculagin, geraniin and corilagin were less effective than tyramine. Rosmarinic acid and penta-O-galloyl-beta-D-glucose were similarly well sulfated. Two products, 4'-monosulfate and 4',5-disulfate of (+)-catechin, were detected at a two-fold molar excess of PNS over (+)-catechin. When (+)-catechin-4'-monosulfate as an acceptor was enzymatically sulfated with PNS as a donor, only the 4',5-disulfate was produced. Thus, arylsulfotransferase was useful for the convenient preparation of sulfate esters of polyphenols at their specific hydroxyl groups.
本报告讨论了一种新型芳基硫酸转移酶（AST），当以对硝基苯硫酸酯（PNS）作为供体底物时，该酶来源于人肠道细菌对多酚化合物进行硫酸化。（+）-儿茶素、（+/-）-儿茶素、（-）-表儿茶素和（-）-表儿茶素没食子酸酯是比酪胺更好的底物。（-）-表没食子儿茶素和（-）-表没食子儿茶素没食子酸酯是比酪胺稍差的底物。虽然没食子酸是一种不良底物，但没食子酸烷基酯是比酪胺更好的底物。受体特异性程度与烷基长度成正比，直至碳原子数为5。委陵菜素、老鹳草素和柯里拉京的效果比酪胺差。迷迭香酸和五-O-没食子酰-β-D-葡萄糖的硫酸化效果相似。当PNS相对于（+）-儿茶素的摩尔过量为两倍时，检测到（+）-儿茶素的两种产物，即4'-单硫酸酯和4'，5-二硫酸酯。当以（+）-儿茶素-4'-单硫酸酯作为受体，以PNS作为供体进行酶促硫酸化时，仅产生4'，5-二硫酸酯。因此，芳基硫酸转移酶可用于方便地在多酚的特定羟基处制备硫酸酯。
