甲基偶氮甲醇葡萄糖醛酸共轭物的合成。

Synthesis of the glucuronic acid conjugate of methylazoxymethanol.

作者信息

Matsumoto H, Takata R H, Komeiji D Y

出版信息

Cancer Res. 1979 Aug;39(8):3070-3.

Abstract

The glucuronic acid conjugate of methylazoxymethanol was synthesized by oxidizing the primary alcohol of the glucose moiety of cycasin (methylazoxymethanol-beta-D-glycopyranoside) to a carboxylic acid. The oxidation was carried out by bubbling oxygen gas through a cycasin solution in the presence of a platinum-on-carbon catalyst. A band at 1715 cm-1, not present in the cycasin infrared spectrum, appeared in the spectrum of the oxidized cycasin product, establishing the presence of a carboxylic acid group. The oxidation product is methylazoxymethanol-beta-D-glucosiduronic acid because, when hydrolyzed with Escherichia coli beta-glucuronidase, it produced methylazoxymethanol and glucuronic acid and also indicated retention of the beta-linkage of cycasin. Varying quantities of the synthesized methylazoxymethanol-glucosiduronic acid, injected into Wistar rats of both sexes and of varying weights, were not acutely toxic. The compound was mutagenic to Salmonella typhimurium when preincubated with E. coli beta-glucuronidase, but not when preincubated with bovine liver glucuronidase.

摘要

通过将苏铁素（甲基偶氮甲醇-β-D-吡喃葡萄糖苷）葡萄糖部分的伯醇氧化为羧酸，合成了甲基偶氮甲醇的葡萄糖醛酸共轭物。氧化反应是在铂-炭催化剂存在下，向苏铁素溶液中通入氧气进行的。氧化后的苏铁素产物光谱中出现了一个1715 cm-1的吸收带，而苏铁素红外光谱中不存在该吸收带，这表明存在羧酸基团。该氧化产物是甲基偶氮甲醇-β-D-葡萄糖醛酸，因为在用大肠杆菌β-葡萄糖醛酸酶水解时，它产生了甲基偶氮甲醇和葡萄糖醛酸，并且还表明保留了苏铁素的β-连接。将不同量合成的甲基偶氮甲醇-葡萄糖醛酸注射到不同体重的雌雄Wistar大鼠体内，均未产生急性毒性。该化合物与大肠杆菌β-葡萄糖醛酸酶预孵育时对鼠伤寒沙门氏菌具有致突变性，但与牛肝葡萄糖醛酸酶预孵育时则无致突变性。