19 タカネハネゴケとマルバハネゴケの新セスキテルペノイド類の構造

概要

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In the course of our investigation on terpene constituents of the liverworts, several kinds of enantiomeric sesquiterpenoids consisted of novel carbon skeletons have been isolated. From methanol extracts of the leafy liverworts, P. semidecurrens and P. ovalifolia, belonging to the genus Plagiochila of the Junger-maniales, six new ent-2,3-seco-alloaromadendrane type sesquiterpenoids were isolated by means of combination of column and preparative thin layer chromatography. The structures and absolute configurations of these compounds were, respectively, determined as (+)-ovalifoliene(4), (+)-acetoxy-ovalifoliene(5), (-)-hanegokedial(6), (+)-ovalifilienalone(7), (+)-ovalifolienal(8) and (+)-hanegoketrial(9) based on the chemical and spectral evidence and X-ray analysis. The Unique metabolites, that is, the enantiomeric sesquiterpenoids may be biosynthesized from ent-alloaromadendrane skeleton via oxidative cleavage of the C_2-C_3 bond and followed by formation of cyclic hemiacetal. The main constituents,2, 4 and 8, inhibited the growth of roots of rice at concentration of 50 ppm and 7 did at 100 ppm.
天然有機化合物討論会の論文
1979-09-20