70(PA2-10) Curcuma aromaticaのセスキテルペンとGermacrone 4,5-epoxideのトランスアンニュラー反応(ポスター発表の部)

概要

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Twenty-one kinds of sesquiterpenes, K-1 (1) - K-21 (21), were isolated from the chloroform soluble fraction of fresh Rhizomes of Curcuma aromatica (Zingiberaceae). Their structures were elucidated by spectral data, such as ^1H-NMR and ^<13>C-NMR spectra. The absolute structure of K-7 was elucidated by X-ray analysis and chemical derivation from (4S,5S)-germacrone 4,5-epoxide (2). The structures of the other sesquiterpenes were also confirmed by chemical derivation from 2. These sesquiterpenes have biogenetically related structures, so a hypothetical biogenetic pathway was supposed, in which the transannular reaction of 2 plays an inportant role. According to the hypothetical biogenetic pathway, the key-intermediate (2) was transformed by several acidic connditions to give guaiane-type sesquiterpenes or seco-guaiane-type sesquiterpenes. some of which were identified with the natural sesquiterpenes isolated from C. aromatica. (4S,5S)-Germacrone 4,5-epoxide (2) and dehydrocurdione (3) were incubated with callus of C. longa. After 1 week. 2 were metabolized to give diols (7 and 8 ) having guaiane skeltons.
天然有機化合物討論会の論文
1987-07-25