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Cyano glucoside biosynthesis in white clover trifolium repens



Cyano glucoside biosynthesis in white clover trifolium repens



Phytochemistry 15(5): 697-701



L-valine-(U[uniformly labeled]-14C), isobutyraldoxime-(U-14C) and 2-hydroxyisobutyraldoxime-(1,3-14C) were fed to white clover shoots which contained or lacked cyanoglucoside. Plants which were unable to synthesize linamarin from these precursors lacked the ability to glucosylate 2-hydroxyisobutyronitrile. When L-valine-(U-14C) was fed to cyanoglucoside-producing plants in the presence of cold isobutyraldoxime, radioactivity could be trapped in this compound. No radioactivity was trapped in isobutyraldoxime fed to non-cyanoglucoside-producing shoots demonstrating that this phenotype also lacks the ability to convert valine into the aldoxime. The non-cyanoglucoside-producing plants apparently have at least 2 steps in the biosynthesis of linamarin missing. Differences between the linamarin biosynthetic enzymes of white clover and flax were demonstrated using the inhibitor O-methylthreonine and by the failure of cyanoglucoside-producing white clover shoots to synthesize linamarin when fed 2-hydroxyisobutyraldoxime.

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Accession: 005077158

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