67(P37) 蟾酥中の新規アルカロイドBufobutanoic AcidとBufopyramideの構造、ならびにBufarenoginとψ-Bufarenoginのコンホメーション(ポスター発表の部)

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The chinese traditional drug Ch'an Su is the preparation from the skin secretions of the local toads such as Bufo bufo gargarizanz cantor or Bufo melanostrictus Schneider. Although the steroidal bufadienolides with an α-pyrone ring at C-17 position were the major biologically and pharmaceutically active components, the water-soluble basic components such as catecholamines and indolealkylamines were also responsible for the activity. Until now, the twelve indole alkylamines: serotonine, bufotenine, bufotenidine, bufoviridine, bufothionine, O-methylbufotenine, dehydrobufotenin, bufoviridine-N-sulphate, O-methylbufotenine-N-sulphate, 5-hydroxy-N-methyl-tryptamine, 5-methyltrypt-amine and 5-methyl-N-methyltrypt-amine have been isolated from many kinds of toad. However, in Ch'an Su, the presence of bufotenine, bufotenidine, bufothionine and dehydrobufotenine were irregularly reported. A consideration of the above facts and an interest in the water-soluble components of Ch'an Su have led to the present investigation. Here we describe the isolation and structural elucidation of two novel indole alkaloids, bufobutanoic acid 2 and bufopyramide 3, in addition to the isolation of known bufotenine 1 (Figure. 1). Bufobutanoic acid 2 and bufopyramide 3 inhibited for the murine P388 lymphocytic leukemia cells at IC_<50> valuses of 22μg/ml and 7.6μg/mi, respectively. On the other hand, the two known bufadienolides, bufarenogin 4 and ψ-bufarenogin 5 were isolated from the same source by the above chromatography (Figure. 1). In the NMR spectral analysis, the solution state conformations of two toad poison bufadienolides, bufarenogin 4 and ψ-bufarenogin 5, which are the epimers at C-12, were analyzed by using NOE experiments and molecular dynamics simulation study. Interestingly, the C-ring of bufarenogin 4 with 12β-hydroxy function was shown to take a chair form, whereas that of ψ-bufarenogin 5 with 12α-hydroxy function, a boat form. Thus, we have discussed about conformational preference of two bufadienolides, 4 and 5.
天然有機化合物討論会の論文
1998-08-31

67(P37) 蟾酥中の新規アルカロイドBufobutanoic AcidとBufopyramideの構造、ならびにBufarenoginとψ-Bufarenoginのコンホメーション(ポスター発表の部)

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