4 ^<13>C化合物による生合成の研究

概要

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The use of ^<13>C-labeled substrates together with ^<13>C nmr spectroscopy simplifies biosynthetic studies of natural products since the ^<13>C isotopic excess incorporated at different sites can be located and identified by characteristic chemical shifts and an increased signal intensity over the natural abundance peaks. We report the application of the ^<13>C nmr method to the elucidation of the biosynthetic pathway of the microbial metabolite radicinin, which is produced by Stenphylium radicina. The ^<13>C nmr spectrum (Fig.1A) clearly indicates that six carbons of radicinin obtained from sodium acetate-2-^<13>C as precursor are derived from the methyl group of acetate, since only six peaks are evident and no peaks from carbon atoms at natural abundance are discernible. Spectrum (Fig.1B) also conclusively shows that the other six carbons of the labeled radicinin obatined from the sodium acetate-1-^<13>C are enriched at C_2, C_4, C_6, C_8, C_<10> and C_<13>, and must come from the carboxyl of acetate as indicated by the six peaks very evident from this ^<13>C enriched material. Our results confirm and fully support the polyacetate origin of radicinin with the expected alternating labeling of carbon atoms from either the methyl or carboxyl group of acetate. The polyacetate origin of fungal metabolites, sclerotiorin and citrinin was also confirmed with ^<13>C labeled precursors.
天然有機化合物討論会の論文
1970-10-01