17 ピングイサン型セスキテルペンの構造と生合成(口頭発表の部)

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Pinguisane-type sesquiterpenes are biosynthetically interesting since biogenesis of their structures is difficult to be simply explained with the isoprene rule. In the course of our study on pinguisane-type sesquiterpenes, we examined the liverworts Aneura pinguis and Porella grandiloba. Five new pinguisane-type sesquiterpenes, 6a-hydroxy-3-oxo-pinguis-5(10)-ene-11,6-olide, 6a-methoxy-3-oxo-pinguis-5(10)-ene-11,6-olide, 3-oxo-pinguis-5(10),6-diene-11,6-olide, 5a,6a-epoxy-3-oxo-pinguis-11,6-olide and 3-oxo-ptychanolide together with pinguisone have been isolated from an axenic culture of the liverwort, A.pinguis. Three new pinguisane-type sesquiterpenes, grandilobalide A, B and 6a-hydroxy-pinguis-4,8-dimethoxycarbony1-11,6-olide, and a new rearranged pinguisane-type, grandilobalide C, together with six known sesqui- and diterpenes have been also isolated from the liverwort P.grandiloba grown in the field. Their structures were elucidated on the basis of spectroscopic evidence and chemical correlation. A biosynthetic study on the formation of pinguisane-type sesquiterpenes was also carried out by feeding [2-^<13>C]-acetate and [6,6,6-^2H_3]-mevalonate(MVA)to the cultured gametophytes of A. pinguis. Pinguisone and its derivatives were labeled at an adequate level to determine the labeling positions by ^2H- and ^<13>C-NMR analysis. The labeling pattern indicated two-methyl migration and C-C bond cleavage of the main chain in farnesyl diphosphate in the formation of pinguisone and its derivatives. From these observations, we proposed a biosynthetic pathway of pinguisane-type sesquiterpenes. Further experiments by incorporation of [2,2-^2H_2]- and [4,5-^<13>C_2]-MVAs have been done to confirm the proposed biosynthetic pathway.
天然有機化合物討論会の論文
1996-09-02

17 ピングイサン型セスキテルペンの構造と生合成(口頭発表の部)

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