Synthesis of lauroyl phenolic glycoside by immobilized lipase in organic solvent and its antioxidative activity

Synthesis of Acyl Arbutin by an Immobilized Lipase and Its Suppressive Ability against Lipid Oxidation in a Bulk System and O/W Emulsion

“…The reaction conditions of the concentration of substrate and temperature were determined according to the results for a similar reaction system in previous reports. 10,13) The conversion for immobilized lipase at 10 and 20 g/l-solvent reached 45% over 2 d, whereas that at 2 g/l-solvent was less than 25%. The gradual decrease at 10 g/l-solvent would indicate the oxidative degradation of arbutin as a substrate and/or of dodecanoyl arbutin as a product during the reaction.…”

“…Tel: +81-82-434-7000; Fax: +81-82-434-7890; E-mail: wysyk@hiro.kindai.ac.jp NMR spectral analysis of the product had revealed that the primary hydroxyl group at position C-6 in the glucose moiety in arbutin was esterified by dodecanoic acid. 10) After the sampling, the headspace was filled with nitrogen gas again. The transient changes in conversion for dodecanoyl arbutin synthesis were measured in duplicate, and mean values were calculated.…”

“…To obtain a new amphiphilic antioxidant, we synthesized dodecanoyl phenolic glycosides through the condensation of phenolic glycosides like arbutin and lauric acid by using an immobilized lipase, and examined their antioxidative properties. 10) A high conversion for the enzymatic synthesis of dodecanoyl arbutin was achieved, but the reaction conditions and potential applications as an amphiphilic antioxidant needed further study. Therefore, in this present study, we examined the effect of the amount of immobilized lipase on the synthesis of dodecanoyl arbutin for industrial use, and the antioxidative effects of various acyl arbutins on methyl linoleate in a bulk system and O/W emulsion.…”

Highly efficient and regioselective acylation of arbutin catalyzed by lipase from Candida sp.

“…For example, the acylated arbutin has been reported to have higher inhibitory effect on tyrosinase [10] and can inhibit the oxidation of low-density lipoproteins more efficiently than arbutin [11]. The acylated derivatives have also been reported to have higher anti-melanogenesis and anti-oxidant activities than its parent compound [12]. Therefore, acylation of arbutin has already attracted much attention in recent years.…”

Significantly Enhanced Synthesis of Aromatic Esters of Arbutin Catalyzed by Immobilized Lipase in Co-solvent Systems

“…Arbutin exhibits several pharmacological effects, such as antioxidant, antimicrobial, antiinflammatory, antihyperglycaemic, antitumor, alpha-amylase inhibitory and tyrosinase inhibitor (Taha et al, 2012;Migas and Krauze-Baranowska, 2015;Jurica et al, 2017;Ahmadian et al, 2019;Zhao et al, 2019). It is reported that arbutin ester derivatives displayed higher biological activity than the precursor compounds (Tokiwa et al, 2007;Chigorimbo-Murefu et al, 2009;Watanabe et al, 2009;Xu et al, 2014). For example, 6 -Ocaffeoylarbutin showed a twice-higher antimelanin activity and twice-lower toxicity than those of arbutin (Xu et al, 2014).…”