title: Biocatalytic synthesis, structural elucidation, antioxidant capacity and tyrosinase inhibition activity of long chain fatty acid acylated derivatives of phloridzin and isoquercitrin.
abstract: Our present investigation describes the regioselective enzymatic acylation of two series of acylated derivatives of phloridzin and isoquercitrin with six different long chain saturated, mono- and poly-unsaturated fatty acids. The biocatalytic synthesis was optimized to achieve 81-98% yields, using immobilized lipase B, from Candida antarctica (Novozym 435), in acetone at 45°C. The synthesized esters have been analyzed by (1)H NMR, (13)C NMR spectroscopy and evaluated for their antioxidant capacity and tyrosinase inhibition, using in vitro assays. Among all the phloridzin and isoquercitrin derivatives, the greatest potential for inhibition of tyrosinase activity (p ≤ 0.05) was exhibited by the α-linolenic acid ester of isoquercitrin.
authors.affiliation: Department of Environmental Sciences, Faculty of Agriculture, Dalhousie University, Truro, Nova Scotia, Canada B2N 5E3.
authors.lastname: Ziaullah
authors.forename: Khushwant S
authors.initials: KS
authors.lastname: Bhullar
authors.forename: Sumudu N
authors.initials: SN
authors.lastname: Warnakulasuriya
authors.forename: H P Vasantha
authors.initials: HP
authors.lastname: Rupasinghe
mesh_terms: D000975:Antioxidants / Q000737:chemistry / Q000378:metabolism / Q000494:pharmacology*; D055162:Biocatalysis; D004305:Dose-Response Relationship, Drug; D004791:Enzyme Inhibitors / Q000737:chemistry / Q000378:metabolism / Q000494:pharmacology*; D005227:Fatty Acids / Q000737:chemistry* / Q000378:metabolism; D015394:Molecular Structure; D014442:Monophenol Monooxygenase / Q000037:antagonists & inhibitors* / Q000378:metabolism; D010695:Phlorhizin / Q000096:biosynthesis / Q000737:chemistry / Q000494:pharmacology*; D011794:Quercetin / Q000031:analogs & derivatives* / Q000096:biosynthesis / Q000737:chemistry / Q000494:pharmacology; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
chemical_list: D000975:Antioxidants; D004791:Enzyme Inhibitors; D005227:Fatty Acids; C016527:isoquercitrin; D011794:Quercetin; D010695:Phlorhizin; D014442:Monophenol Monooxygenase