Lipase-catalyzed regioselective protection/deprotection of hydroxyl groups of the isoflavone irilone isolated from Iris germanica

Abstract

The regioselective acylation of irilone, isolated from Iris germanica, with vinylacetate and propenylacetate and deacylation of irilone diacetate with n-butanol were studied using lipases from Aspergillus niger, Mucor miehei, Pseudomonas cepacia, Candida cylindracea, porcine pancreas and Candida antarctica. Significant conversion of irilone to 4′-O-acetylirilone was achieved using P. cepacia lipase, while irilone diacetate was converted to 5-O-acetylirilone by the enzymatic action of lipases from M. miechei, P. cepacia and porcine pancreas under different experimental conditions. This preferential protection/deprotection furnishes an opportunity to modify the structure of irilone by selective derivatization that may help to change its biological activities by modifying its amphiphilic/lipophilic balance.