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Glycoside carbamates from benzoxazolin-2(3H)-one detoxification in extracts and exudates of corn roots by Dieter Sicker; Bernd Schneider; Lothar Hennig; Mona Knop; Margot Schulz is a Biochemistry, Genetics and Molecular Biology article available to read on EtoBox.

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Zea mays was incubated with the natural phytotoxin benzoxazolin-2(3H)-one (BOA) to investigate the detoxification process. A hitherto unknown detoxification product, 1-(2-hydroxyphenylamino)-1-deoxy-b-gentiobioside 1,2-carbamate (3), was isolated and identified. A reinvestigation of known BOA detoxification products by NMR methods led to the finding that the structure of benzoxazolin-2(3H)-one-N-b-glucoside (1) first reported from Avena sativa has to be revised. In fact, the correct structure is that of the isomeric 1-(2hydroxyphenylamino)-1-deoxy-b-glucoside 1,2-carbamate 2, which is structurally related to 3. It was now shown with a synthetic mixture of 1 and 2 that 1 underwent spontaneous isomerization to form 2 in solution. Thus, N-glucosylation of BOA in the plant led finally to the carbamate 2. In contrast to BOA-6-O-glucosylation, BOA-induced N-glucosylation appears first after 6-8 h of incubation. As soon as Nglucosylation is possible, BOA-6-O-glucoside is not further accumulated, whereas the amount of glucoside carbamate increases continuously during the next 40 h. Synthesis of gentiobioside carbamate seems to be a late event in BOA detoxification. All detoxification produ

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Author

Dieter Sicker; Bernd Schneider; Lothar Hennig; Mona Knop; Margot Schulz

Publisher

Elsevier Science; Elsevier ; Elsevier BV (ISSN 0031-9422)

Published

2001

Language

EN

Field

Biochemistry, Genetics and Molecular Biology (Life Sciences)