73 クワ産生のDiels-Alder付加化合物

概要

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Phytoalexins are antimicrobial compounds produced newly by plants in response to microbial infection, and their production, coupled with the presence of antimicrobial principles in healthy plants, is believed to be an importance disease resistance mechanism in higher plants. We already reported on many antifungal metabolites produced by cortex and phloem tissues and xylem tissues of diseased mulberry and contained in epidermis tissues of healthy mulberry. We describe herein the structure elucidation of three related antifungal compounds, designated as chalcomoracin and albanins F and G. Chalcomoracin (1), mp 185℃ (dec), and [α]_D +194°, was isolated from leaves infected with Fusarium solani f. sp. mori., and qualified as a phytoalexin, and had a molecular formula of C_<39>H_<36>O_9. Albanins F (2) and G (3), each amorphous and [α]_D-458° and -404°, were isolated from healthy epidermis tissues and had molecular formulas of C_<40>H_<36>O_<11> and C_<45>H_<44>O_<11>, respectively. The structures of these metabolites were determined as shown in the formulas on the basis of the spectral and chemical data, especially of the synthesis of model compounds (21 and 22). It is to be noted that these metabolites possess structures (planar structure and relative configuration) regarded biogenetically as Diels-Alder adducts of two "natural" components.
天然有機化合物討論会の論文
1980-09-10