Synthesis of the glucuronic acid conjugate of methylazoxymethanol.
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.
D000818:Animals; D001391:Azo Compounds / Q000031:analogs & derivatives; D055598:Chemical Phenomena; D002621:Chemistry; D005260:Female; D005965:Glucuronates / Q000138:chemical synthesis; D005966:Glucuronidase / Q000494:pharmacology; D008297:Male; D008746:Methylazoxymethanol Acetate / Q000031:analogs & derivatives / Q000138:chemical synthesis / Q000633:toxicity; D009153:Mutagens; D051381:Rats
D001391:Azo Compounds; D005965:Glucuronates; D009153:Mutagens; D008746:Methylazoxymethanol Acetate; D005966:Glucuronidase