Cultured cells of
Sophora flavescens produce (2
S)-naringenin-derived prenylated flavanone sophoraflavanone G and liquiritigenin-derived trifolirhizin 6′-
O-malonate. The regulation of flavonoid biosynthesis was examined by analyzing the metabolites produced in the cultured cells fed (2
RS)-naringenin. The amount of sophoraflavanone G in cells fed 0.1 or 0.3 mM (2
RS)-naringenin was two-fold that in control cells, although the conversion ratio was only 5 to 10% of the administered (2
S)-naringenin. On the other hand, (2
R)-naringenin, which does not occur naturally, was efficiently converted into its 4′,7-di-
O-β-D-glucoside. (2
S)-Naringenin prenylation activity was higher at the logarithmic growth stage. The cells fed (2
RS)-naringenin at a lower concentration (below 0.1 mM), accumulated sophoraflavanone G as the main prenylated flavanone. In contrast, cells fed 0.3 mM (2
RS)-naringenin accumulated 8-prenylnaringenin and leachianone G, intermediates of sophoraflavanone G in large amounts. Accumulation of trifolirhizin 6′-
O-malonate was suppressed by the addition of naringenin.
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