Facile and Efficient Acylation of Bioflavonoids Using Whole-Cell Biocatalysts in Organic Solvents

Abstract

Bioflavonoids have many biological and pharmacological activities, but many of them display low bioavailability after oral administration owing to poor lipophilicity of glycoside forms. To improve their lipophilicity, as well as their bioactivity, a new efficient approach was developed for fatty acyl-modification of four vitamin P-like bioflavonoids (troxerutin, rutin, hesperidin, and naringin) using whole-cell biocatalysts in binary solvent systems. Using troxerutin as a typical important bioflavonoid, the acylation activities of 15 strains of different sources were evaluated and Pseudomonas aeruginosa GIM 1.46 showed the highest acylation activity in nonaqueous mediums. 13C NMR, ESI-MS, and FT-IR analysis confirmed that P. aeruginosa catalyzed acylation of troxerutin to produce troxerutin monopropionate (dominant product) and troxerutin dipropionate. In a binary system of n-heptane and pyridine, the cells showed much higher catalytic activity and operational stability than in other solvents, attributing...