Abstract
Abstract Feeding experiments with 14C- and 13C-labelled precursors have demonstrated that the phloroglucinol ring of the 3-ethylchromone phytoalexin lathodoratin from cupric sulphate-induced pods of sweet pea (Lathyrus odoratus) has a polyketide origin. The remaining five carbon ‘isoprene unit’ is derived from the amino acid isoleucine which provides the starter unit, probably 2-methylbutanoate, for acetate-malonate chain extension. The pterocarpan phytoalexin pisatin is produced along with lathodoratin, and precursors were incorporated in agreement with earlier studies. Two minor 3-ethylchromones were also synthesized on cupric sulphate treatment of the pods. These were the previously reported 7-O-methyl ether of lathodoratin (methyl-lathodoratin) and a new compound, the 5,7-di-O-methyl ether (dimethyl-lathodoratin). Dimethyl-lathodoratin is the most fungitoxic of the 3-ethylchromone phytoalexins.
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