Acylation of natural flavonoids using lipase of candida antarctica as biocatalyst

Several flavonoids (quercetin, hesperidin, rutin and esculin) were acylated with fatty acids using an immobilised lipase from Candida antarctica in 2-methyl-2-butanol at 60degreesC. It appears that esculin with primary OH on the sugar part is the most reactive substrate. With palmitic acid as acyl donor, the conversion yields were of about 80, 71 and 38%, respectively, for esculin, rutin and hesperidin. No reaction was observed with aglycon flavonoid (quercetin). For a given flavonoid (rutin), the conversion yield increased from 42 to 76% when the carbon number of the fatty acids rose from C6 to C12. For fatty acids with higher carbon-chain length, both conversion yield and initial rate dropped slightly. Furthermore, compared to the saturated fatty acid (C 18: 0), the unsaturated one (C 18: 1) exhibited a lower reactivity. For all molecules studied H-1 nuclear magnetic resonance (NMR) and C-13 NMR analyses indicated that only flavonoid monoester was produced. (C) 2004 Elsevier B.V. All rights reserved.