24 バイケイソウにおけるSolanidanine Alkaloid並びにJerveratrum Alkaloidの生合成

概要

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It was found that the etiolated Veratrum grandiflorum Losen. fil. accumulated solanidine glycoside in the leaf and subsequently, when the etiolated plant was illuminated, the accumulated solanidine glycoside was converted gradually to jerveratrum alkaloid. It seems reasonable to accept that, at the budding period and in the early stage of etiolation, the veratrum plant probably accumulates important precursors which are converted rapidly to solanidine under etiolated condition. On the other hand, when the etiolated plant is illuminated, it seems to remain some intermediates of the reaction of C-nor-D-homo rearrangement from solanidanine alkaloid to jerveratrum alkaloid. At the first point, etioline (22, 26-iminocholesta-5, 22(N)-diene-3β, 16α-diol) was isolated as major alkaloid from the budding veratrum plant and its structure was determined by its physical and cheimical properties. It appears that etioline is located on the rout of solanidine biosynthesis from cholestene derivatives. The hydroxylated solanidine was isolated from the leaf and rhizome of veratrum plant which was illuminated during the relatively short times after etiolated culture. Its structure was determined as 12β-hydroxy-rubijervine (epirubijervine) by molecular rotation. This alkaloid was named illuminine and it was assumed to be the inducing substance in the reaction of C-nor-D-homo rearrangment in veratrum plant.
天然有機化合物討論会の論文
1971-10-01