60 新抗生物質Vertisporinの構造
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In a continuing search for fungal metabolites having cytotoxic activity, we found that fungus Verticimonosporium diffractum, strains TM-2098 and TM-2492, produced a new cytotoxic antibiotic, vertisporin (Ia) [C_<29>H_<36>O_<10>]. This antibiotic showed limited antifungal activity and inhibited only the growth of Trichophyton asteroides at the concentration of 10 mcg/cm^3. The cytotoxicity effect (ED_<50>) against Hela cells was 0.001 mcg/cm^3. On hydrolysis with KHCO_3 in MeOH, (Ia) gave a diol (IIa) and a dicarboxylic acid (IIIa). Diol (IIa) and its diacetate (IIb) proved to be identical with verrucarol and its acetate, respectively, upon comparison of their IR and ^1H NMR spectra. Therefore, vertisporin was classified as a new cytotoxic compound belonging to the roridin group, and it was assumed by IR, UV, and ^1H NMR spectral studies of (Ia), (Ib), and (IX) to be represented by formula (C). Examinations of ^<13>C NMR spectra of (Ib) and (IIb) lead to a conclusion that seven atoms of the unknown portion in vertisporin, -(C_7H_<11>O_4)-, consist of -O-CH-O-, 2×-CH-O-, -CH_2-O-, C-O-, and 2×-CH_2-. Moreover, vertisporin was indicated to have partial structures (E), (F), and (G) by spin-decoupling and INDOR experiments on the ^1H NMR spectrum of (Ib) and by oxidation of (VIII) giving a five-membered ring lactone (X). On the bases of the above results and the consideration of a biosynthetic route similar to that of roridins, formula (Ia) was derived for the plane structure of vertisporin. The stereochemistry of vertisporin was further elucidated to be (Ia) by studies of the CD spectrum of (VIII) and the NMR spectrum of (IX).
- 天然有機化合物討論会の論文
- 1975-10-01
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