52 Chaetomium globosumの代謝する細胞毒性物貭Chaetoglobosin A-Fの構造

概要

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In the course of mycotoxin screening, the strains of Chaetomium globosum were moticed by their characteristic cytotoxicity to cultured HeLa cells, inhibiting cytoplasmic cleavage to form multinucleated cells. The causative agents named chaetoglobosins A-F were isolated from the mold and their physical properties are shown in Table I and II. The precise PMR examinations revealed the partial formulae shown in Chart 1 for chaetoglobosin A and, along with other evidences such as the formation of B and D from A by acid-treatment (Chart 3), the structures (1), (2), and (3) (without stereochemistry) were proposed for chaetoglobosins A, B, and D. The stereochemistry including the absolute configuration of chaetoglobosin A was then established by the X-ray analysis as (1). Thus the structures of B and D were shown by the formulae (2) and (3). Since chaetoglobosin A isomerizes into C by base-treatment and such reactions were observed for B and D to form iso-B and iso-D, the structure (4) was proposed for C by the comparison of PMR data. The strcuture was later verified by the X-ray analysis by Springer, et al. The structures of F (5) and E (6) were again suggested by PMR data and then confirmed by the reactions shown in Chart 3. Cytotoxic effects of chaetoglobosins, in which the phenyl group in cytochalasins so far reported is replaced by an indol-3-yl group, are shown in Table III.
天然有機化合物討論会の論文
1976-09-20