Bioprospecting Prenyl Flavanones from Dalea boliviana: Structural Insights and Antifungal Properties Against Azole-Resistant Candida albicans

Abstract

Prenyl flavonoids are natural compounds with a relatively narrow distribution in plants with particular structural and pharmacological properties. A prenylated flavanone from the Dalea genus was reported as having potent antifungal action. As part of an extensive study on the chemistry and pharmacology of prenylated flavonoids from the Dalea genus, we report here on a new chromene flavanone isolated from the roots of Dalea boliviana Britton, Fabaceae. The results obtained from spectroscopic and spectrophotometric methodologies allowed us to elucidate the structure of compound 1 as (‒)-(2S)-5,2′-dihydroxy-6″,6″-dimethylchromene-(7,8:2″,3″)-flavanone, and provided new valuable data for the use of MS-MS as a tool for the elucidation and identification of prenylated flavonoids from the Dalea genus. In addition, the antifungal properties of 1 and other prenyl flavanones obtained from D. boliviana were investigated on multidrug-resistant Candida albicans.