55 スギバゴケに含まれる植物生長阻害物質,(-)-Isobicyclogermacrenal,(-)-Lepidozenalおよび(+)-Vitrenalの構造

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Since, during the investigation on terpenoids of the liverworts, we had sometimes observed allelopathy between liverworts and some vascular plants in fields, the work was undertaken to isolate plant growth inhibitors from the liverworts. The present work was carried out on the methanol extract of the leafy liverwort Lepidozia vitrea Steph. because the extract showed a plant growth-inhibitory activity on the biological test using rice seedlings. Three sesquiterpene aldehydes naming (-)-isobicyclogermacrenal, (-)-lepidozenal, and (+)-vitrenal were isolated from the methanol extract by combination of column and preparative TLC together with ent-bicyclogermacrene and ent-aroma-dendrene. The structures including absolute configuration were determined, based on the chemical and spectroscopic examination and the X-ray analysis, to be ent-isobicyclogermacra-1(10)E,4E-dien-14-al (1), ent-lepidoza-1(10)E,4E-dien-14-al (2), and ent-vitr-4-en-14-al (3). These compounds inhibit almost perfectly the growth of leaves and roots of rice seedlings in concentrations of 50, 250, and 25ppm, respectively.
天然有機化合物討論会の論文
1980-09-10