Highly regioselective synthesis of novel aromatic esters of arbutin catalyzed by immobilized lipase from Penicillium expansum

Ester derivatives of phenolic glycosides have attracted more attention in food, cosmetic and pharmaceutical industries, due to their potent biological activities. In the present study, a group of novel aromatic esters of arbutin were successfully synthesized by using immobilized lipase from Penicillium expansum with excellent 6′-regioselectivities (>99%) and moderate to excellent isolated yields (68–93%), except for 6′-O-vanilloyl-arbutin and 6′-O-(p-hydroxycinnamoyl)-arbutin with 28% and 34% yields, respectively. Among all the acyl donors tested, the lipase was most active towards vinyl 3-phenylpropionate, while remarkable decrease in the activity was recorded when the phenyl of acyl donors carried the hydroxyl and/or methoxyl.

Research highlights▶ We synthesized a group of novel aromatic esters of arbutin with highly potent interests. ▶ Immobilized lipase from Penicillium expansum displayed excellent 6′- regioselectivity (99%). ▶ Some interesting information of the interactions between the enzyme and acyl groups was obtained.