Effect of acyl donor chain length on isoquercitrin acylation and biological activities of corresponding esters

• Published in: Process Biochemistry
• Main Authors: Hadj Salem, J., Humeau, C., Chevalot, I., Harscoat, C., Vanderesse, R., Blanchard, Fabian, Fick, M.
• Other Authors: Laboratoire des Sciences du Génie Chimique (LSGC), Institut National Polytechnique de Lorraine (INPL)-Centre National de la Recherche Scientifique (CNRS), Laboratoire d'Ingénierie des Biomolécules (LIBio), Université de Lorraine (UL), Laboratoire de Chimie Physique Macromoléculaire (LCPM), Institut de Chimie - CNRS Chimie (INC-CNRS)-Université de Lorraine (UL)-Centre National de la Recherche Scientifique (CNRS)
• Format: Article in Journal/Newspaper
• Language: English
• Published: HAL CCSD 2010
• Subjects: Isoquercitrin; Enzymatic acylation; Candida antarctica lipase B; Flavonoid esters; Antioxidant activity; Antiproliferative activity; [SPI.GPROC]Engineering Sciences [physics]/Chemical and Process Engineering; Antarc*; Antarctica
• Online Access: https://hal.science/hal-00507937; https://doi.org/10.1016/j.procbio.2009.10.012

International audience The enzymatic acylation of isoquercitrin with fatty acid esters of various carbon chain lengths was carried out in 2-methyl-2-butanol using Novozym 435®. The conversion yield and the initial rate decreased from 66% to 38% and from 17.7 to 10.1 μmol/h respectively, as the carbon chain of the acyl donor increased from C4 to C18. Isoquercitrin acylated derivatives showed higher xanthine oxidase inhibition activities than isoquercitrin. This property increased with the lipophilicity of the derivative esters. The scavenging activity of isoquercitrin esters against ABTS and DPPH radicals decreased with the acyl chain length. Conversely, for esters from C6 to C18, a linear growing relationship can be established between the chain length and the superoxide radical scavenging activity. Furthermore, an improved antiproliferative effect on Caco2 cancer cells was induced by addition of isoquercitrin esters comparing with isoquercitrin.