Increasing Structural Diversity of Prenylated Chalcones by Two Fungal Prenyltransferases

Abstract

Prenylated chalcones are found mainly in plants and exhibit diverse biological and pharmacological activities. Some of these compounds are components of food and dietary supplements with significant health benefits. In plants, they are derived from chalcones by prenylation with membrane-bound prenyltransferases. In this study, we demonstrate prenylations of 10 chalcones by two fungal prenyltransferases (AtaPT/AnaPT) in the presence of dimethylallyl diphosphate. Eleven mono<b>-</b> (<b>1a</b>-<b>10a</b> and <b>9b</b>) and four diprenylated products (<b>8b</b>, <b>9c</b>, <b>10b</b>, and <b>10c</b>) were obtained. Among them, 12 have new structures (<b>1a</b>, <b>2a</b>, <b>4a</b>-<b>6a</b>, <b>8a</b>, <b>8b</b>, <b>9b</b>, <b>9c</b>, <b>10a</b>, <b>10b</b>, and <b>10c</b>). Most of the obtained prenylated chalcones are products of AnaPT and carry prenyl moieties at ring B. Our study provides an excellent example for increasing structural diversity of plant metabolites with microbial enzymes.