Regio-selective prenylation of flavonoids by plant cell suspension cultures of Cudrania tricuspidata and Morus alba

The cell suspension cultures of Cudrania tricuspidata could regio-selectively prenylate chrysin (1) at C-8, while the cell suspension cultures of Morus alba could regio-selectively prenylate genistein (2), sophoricoside (3) and diosmetin (4) at C-6. Eight products (5–12) were isolated, and five of them (8–12) were new compounds. Additionally, the bioconversion of 1–4 using microsomes of the cell cultures was performed, and the results showed that the bioconversion patterns were identical to those using cell cultures. These investigations would provide an approach to the selective prenylation and structural diversification of flavonoids.

Graphical abstractFigure optionsDownload full-size imageDownload as PowerPoint slideHighlights► Cell suspension cultures of Cudrania tricuspidata could regio-selectively prenylate chrysin at C-8. ► Cell suspension cultures of Morus alba could regio-selectively prenylate genistein, sophoricoside and diosmetin at C-6. ► Eight products were identified, and five of them were new compounds. ► The bioconversion patterns provided by microsomes from the cultured cells were identical to those in cell cultures.