This is a self-archived version of an original article. This version may differ from the original in pagination and typographic details.

Two phytotoxins capable o f inducing scab-like lesions o n immature potato tubers were isolated from field grown and aseptically cultured potato tubers that had been infected b y Streptomyces scabies; the compounds were characterized by spectral methods and partial syntheses as unique 2,5-dioxopiperazines.

No abstract

Extensive chromatography of Streptomyces scabies infected potato tissue yielded five compounds which on aseptically cultured minitubers individually reproduced symptoms typical of the common scab disease. Spectroscopic examination of the minor components elicited sufficient information to identify them as related analogues of the major constituents thaxtomin A and thaxtomin B, which had been previously characterized as unique 4-nitroindol-3-yl-containing 2,5-dioxopiperazines. Subsequently, a number of synthetic variants were prepared to further understanding of the structural requirements for phytoactivity in this class of compounds. * Agriculture Canada.

No abstract