Biosynthesis of the necic acids of the pyrrolizidine alkaloids. Further investigations of the formation of senecic and isatinecic acids in Senecio species

Abstract
Five-carbon intermediates of the pathway of isoleucine metabolism, 2-methylbutanoic acid, angelic acid (5), and 2-methyl-3-oxobutanoic acid, were not specifically incorporated into senecic acid (1), the necic acid component of senecionine (2) in Senecio magnificus. The mechanism of the coupling of isoleucine-derived units during necic acid biosynthesis was investigated through incorporation experiments with [6-3H]- and [4-3H2]-isoleucine (3) in S. magnificus and S. isatideus. 2-Amino-3-[3H2]methylenepentanoic acid (β-[3H2]methylenenorvaline)(13) was incorporated specifically into senecic acid (1).

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