FORMATION OF SULFATOGLUCOSIDES FROM EXOGENOUS ALDOXIMES IN PLANT-CELL CULTURES AND ORGANS

Feeding of 2-nitrobenzaldoxime to Brassica species led to the accumulation of the artificial 2-nitrophenylglucosinolate as well as several unknown sulfated side products. Isolation, proton nuclear magnetic resonance spectroscopy and hydrolysis by sulfatase and β-glucosidase led to the identification of these compounds as E- and Z-2-nitrobenzaldoxime-β-d-(6-sulfato)-gycopyranoside and 2-nitrobenzyl alcohol-β-d-sulfatoglucopyranoside. The alcohol conjugate arose via hydrolysis of the aldoxime and subsequent reduction of the aldehyde. A variety of aryl and aliphatic aldoximes were converted to sulfatoglucosides. Screening of a number of unrelated crop plants showed that the ability to form sulfatoglucosides of exogenous aldoximes occurs widely. Among the plants that tested positive were Brassica spp, Arabidopsis, nasturtium, flax, sorghum, carrot, bromegrass, soybean and sunflower. © 1990.