This Article Full Text (PDF) Alert me when this article is cited Alert me if a correction is posted Services Email this article to a friend Similar articles in this journal Similar articles in PubMed Alert me to new issues of the journal Download to citation manager Citing Articles Citing Articles via Google Scholar Google Scholar Articles by Matsumoto, H. Articles by Komeiji, D. Y. Search for Related Content PubMed PubMed Citation Articles by Matsumoto, H. Articles by Komeiji, D. Y.

Synthesis of the Glucuronic Acid Conjugate of Methylazoxymethanol¹

Department of Agricultural Biochemistry, University of Hawaii, Honolulu, Hawaii 96822

The glucuronic acid conjugate of methylazoxymethanol was synthesized by oxidizing the primary alcohol of the glucose moiety of cycasin (methylazoxymethanol-ß-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-ß-D-glucosiduronic acid because, when hydrolyzed with Escherichia coli ß-glucuronidase, it produced methylazoxymethanol and glucuronic acid and also indicated retention of the ß-linkage of cycasin.

Varying quantities of the synthesized methylazoxymethanolglucosiduronic 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 ß-glucuronidase, but not when preincubated with bovine liver glucuronidase.

¹ This investigation was supported in part by Grant CA 18631, awarded by the National Cancer Institute, Department of Health, Education, and Welfare. Published as Journal Paper 2330, Hawaii Agricultural Experiment Station.

² To whom requests for reprints should be addressed, at Department of Agricultural Biochemistry, University of Hawaii, 1800 East-West Road, Honolulu, Hawaii 96822.

³ Present address: Pathology Associates, Medical Laboratories, 4400 Kalanianaole Highway, Honolulu, Hawaii 96821.

Received 11/ 6/78. Accepted 5/ 8/79.