Indigofera endecaphylla

Glucose esters of 3-N. (endecaphyllins) are responsible for the toxicity of Indigofera endecaphylla for grazing animals. 3-N. functions as suicide substrate of succinate dehydrogenase where the formed 3-nitro-acrylic acid adds to the active thiol group of the enzyme. The compound is formed biosynthetically in Penicillium atrovenetum from L-aspartic acid which is oxidized to the a-nitrosuccinate and then decarboxy-lated to furnish the aci-nitro form of 3-N.. Malonate and N-hydroxymalonamate appear to be intermediates in Indigofera spicata. 

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