J. Cross, P. Herzmark, W. Guilford
Feb 1, 1995
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Journal
Journal of Agricultural and Food Chemistry
Abstract
SC-2053, 1-(4-chlorophenyl)-4-oxo-5-(methoxyethoxy)cinnoline-3-carboxylic acid, is a pollen suppressant (chemical hybridizing agent) in wheat. Metabolism of this compound was studied using [ 14 C]SC-2053 labeled uniformly in the chlorophenyl ring. Wheat plants were treated when the spike was 2-4 cm in length. The floral spike contained about 10% of the label taken up into the plant 4 days after treatment, 15% 14 days after treatment. Unchanged [ 14 C]SC-2053 plus two more polar metabolites were 90-95% of the total 14 C extracted from the plants 14 days after treatment. The more polar metabolite was a glycoside of the other. Treated wheat plants and wheat callus cultures metabolized [ 14 C]SC-2053 by a similar route. The aglycon purified from a callus culture filtrate was identified as 1-(4-chlorophenyl)-4-oxo-5-(2-hydroxyethoxy)cinnoline-3-carboxylic acid. Tits alcohol results from demethylation of the 5-methoxyethoxy group. In plants this metabolite is glycosylated, but in callus cultures only the initial demethylated compound accumulated in the medium. The major metabolite in mature straw was the glycoside