Biosynthesis of Chaetochromin A, a Bis(naphtho-γ-pyrone), in Chaetomium spp.

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The biosynthesis of chaetochromin A, a metabolite of Chaetomium gracile, has been studied using [^<13>CH_3]methionine, sodium [1-^<13>C]acetate, sodium [1,2-^<13>C_2]acetate, sodium [1-^<13>C, 2,2,2-^2H_3]acetate, and sodium [1-^<13>C, 1,1-^<18>O_2]acetate as precursors. The folding pattern of the polyketide chain in chaetochromin A, biosynthesized from sodium [1,2-^<13>C_2]acetate as the precursor, was determined to be the same as that of rubrofusarin by carbon-13 nuclear magnetic resonance (^<13>C-NMR) analysis. By using [^<13>CH_3]methionine as a precursor, the source of 2-CH_3 was determined. When sodium [1-^<13>C, 2,2,2-^2H_3]acetate was fed, a β-isotope-shifted peak was observed only for carbon 2. In the ^<13>C-NMR spectra of chaetochromin A and of its hexamethyl ether derived from sodium [1-^<13>C, 1,1-^<18>O_2]acetate, isotope-shifted peaks were observed for carbons 4,5,6,8 and 10a, but not for carbon 2. These results showed that oxygen 1 originated from the same unit of acetate as carbon 10a.
社団法人日本薬学会の論文
1989-08-25