14 Coronatineの構造研究

概要

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Coronatine (1), produced by Ps. coronafacience var. atropurpurea, is chlorosis-inducing toxin on the leaf of italian rye grass and also has an activity to expand potato cells in the concentration of 1×10^<-7>mole/1. Coronatine consists of two parts, coronamic acid (4) and coronafacic acid (16a), which are bonded each other by an amide linkage. The former, confirmed by the synthesis, is an unique amino acid having cyclopropane ring (NH_2/CH_2CH_3, trans). The latter exists as two stereoisomers, (16a) and/or (16b) depending on the conditions of crystallization. The erroneous structure (15, R=H) assumed firstly for coronafacic acid was proved to be incorrect by the synthesis, and another possible structure for coronafacic acid was deduced from the spectroscopic data of the derivatives, and conclusive structure was obtained by X-ray crystallographic analysis of (16b), which has not been encountered in nature. Coronatine, resulted by partial synthesis from natural (16a) and synthetic (4), shows the same phsiological activity as natural specimen.
天然有機化合物討論会の論文
1976-09-20