8 ベラトラムアルカロイドの生合成研究 : 正常ステロイド骨格からC-ノル-D-ホモ転換機構の解明

概要

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In our detailed experiments on the separation of steroidal alkaloids which accumulate particularly in the illuminated Veratrum plants but not found in the etiolated plants, two new cevanine alkaloids, shinonomenine (1a), (25S)-20-epi-cev-5-enin-3β-ol, which was finally determined by X-ray crystal structure analysis, veraflorizine (2a), (25S)-cev-5-enine-3β,20β-diol, which was synthesized from verticinone, an unique cevanidane alkaloid, procevine (5a), (22R,25S)-cevanid-5-en-3β-ol, which was synthesized from isorubijervine(4a), and a solanidanine alkaloid, isorubijervine (4a) were isolated. The isolation of these alkaloids from the illuminated Veratrum plants suggests the biogenesis of cevanine alkaloid via formation of C-18-N bond from isorubijervine (4a), before C-nor-D-homo rearrangement. In continuation of our works on separation of alkaloids in the illuminated Veratrum plants, hosukinidine (6a), (20R,22R,25S)-veratra-5,12-dien-3β-ol, which was settled by X-ray crystal structure analysis, and epirubijervine (7a), solanid-5-ene-3β,12β-diol, which was synthesized from rubijervine (11), were isolated. The separation of both alkaloids suggests mechanism of C-nor-D-homo rearrangement in the biogenesis of jervanine and veratranine alkaloid.
天然有機化合物討論会の論文
1979-09-20