49 バイケイソウアルカロイドの生合成

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It has been already shown that acetate-1-^<14>C, cholesterol-4-^<14>C-3-phosphate and cholesterol-26-^<14>C were incorporated into solanidanine, jerveratrum and ceveratrum alkaloids in Veratrum grandiflorum LOESEN. fil. It was found that the radioactive solanidinyl glycoside was accumulated under the etiolated condition with acetate-1-^<14>C. The transportation of the radioactivity of solanidine to jerveratrum alkaloids was started by irradiation on etiolated Veratrum plant and the biosynthesis of jerveratrum alkaloids from solanidine was proved under these condition. This report deals with the structural elucidation, synthesis and the biosynthetic role of the compound (XIV) from the neutral fraction of Veratrum grandiflorum, as a possible precursor of solanidine (II), yamogenin (XIII) and other C-27 steroids. XIV was concluded to be (25S)-Δ^5-cholestene-3β,26-diol-22-one by spectroscopic data and the biogenetic relation. The formation of hemiketal (XV) from XIV was confirmed by TLC, NMR and ORD. The mixture of XIV and XIVa was synthesized by a 8-step procedure as shown in chart 6 and the conformation of c-25 was proved by the dehalogenation of XXVb as shown in chart 7. Labelled compound of XIV was also synthesized using XXIV-methyl-^<14>C and XVII. (25S)-Δ^5-Cholestene-3β,26-diol-22-one-27-^<14>C (specific activity; 1.0 X 10^6dpm/m mol) was fed to the etiolated V. grandiflorum. The isolated solanidine had the specific activity of 2.9 X 10^4dpm/m mol. From these results, the biosynthetic routes of Veratrum alkaloids and the biogenesis of natural occurring C-27 steroids were proposed as chart 8.
天然有機化合物討論会の論文
1970-10-01

49 バイケイソウアルカロイドの生合成

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