1 レモンユーカリ中の新他感作用物質の同定および構造活性相関について

概要

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In connection with the integral utilization of Eucalyptus plants as a renewable biomass, we are concerned with the exploration of biologically active compounds such as plant growth regulator. We report on the isolation, identification, synthesis and structure-activity relationships of allelopathic substances, which are designated as C inhibitors, from E. citriodora Hook. Fractionation of acetone extract of fresh leaves was guided by toxicity to germinating seeds and seedlings of lettuce and some other weeds. Column chromatography of an active fraction gave C_1 and C_2 inhibitors, so called (±)-p-menthane-3,8-cis-diol and (±)-p-menthane-3,8-trans-diol, respectively. The absolute configuration was confirmed by comparisons with physical data of synthetic chiral compounds and chemical transformation to known natural product. Interestingly, the C inhibitors occur in the plant as racemate, and are absent in ontogenetically juvenile tissue of E. citriodora. The biological activity of cis isomers was much higher than that of trans isomers. Furthermore, (+)synthetic C_1 inhibitor had higher activity rather than the optical antipode. The fact indicates that a receptor site concerning germination of lettuce seeds is also chiral.
天然有機化合物討論会の論文
1981-09-10