Whole-Cell-Catalyzed Synthesis of Phenolic Glycoside Esters, and Their Antioxidant and Antimelanogenic Properties

Abstract

Phenolic glycosides are the major secondary metabolites of plants, which exhibit multiple attractive biological and pharmacological activities. In this study, we developed a new and efficient method for acyl modification of phenolic glycosides by using whole-cell biocatalysts, aiming to improve their liposolubility and bioactivities. Using resveratrol, salidroside, piceid, and phlorizin as substrates, the substrate recognition characteristics of Candida parapsilosis were studied and salidroside showed the highest conversion (99.5%) but lower regioselectivity than others. Subsequently, the mechanism underlying the influences of the reaction time and organic solvents on the conversion and monoester ratio was revealed. A higher conversion of piceid was obtained in a green solvent (γ-valerolactone) than that in THF (95.8 vs 94.6%). Compared to their parent compounds, all monoester products exhibit higher liposolubility and antioxidant activity. In addition, the monoesters of salidroside and phlorizin showed significantly higher tyrosinase-inhibiting and depigmentation activities than their parents.

Efficient Enzymatic Synthesis of Lipophilic Phenolic Glycoside Azelaic Acid Esters and Their Depigmenting Activity

“…Cell culture methods are in accordance with the literature. 48 Briefly, B16 mouse melanoma cells were cultured in Dulbecco's modified Eagle's medium (DMEM) supplemented with 1% penicillin/ streptomycin and 10% fetal bovine serum solution in a humidified incubator with 5% CO 2 at 37 °C. After the cells had grown to 85− 90% confluence, they were harvested and seeded at the appropriate number counted with a hemocytometer into wells of cell culture plates for further experiments.…”

“…Cell culture methods are in accordance with the literature . Briefly, B16 mouse melanoma cells were cultured in Dulbecco’s modified Eagle’s medium (DMEM) supplemented with 1% penicillin/streptomycin and 10% fetal bovine serum solution in a humidified incubator with 5% CO 2 at 37 °C.…”

Antityrosinase Mechanism and Antimelanogenic Effect of Arbutin Esters Synthesis Catalyzed by Whole-Cell Biocatalyst

“…Acylation is an effective approach to improve the bioactivity and liposolubility of phenolic glycosides. 17,18 Previous studies showed that arbutin laurate had higher antioxidant activity than arbutin itself against the oxidation of linoleic acid, 19 and acetylated arbutin strongly inhibited B16 mouse melanoma cell migration in a dose-dependent manner, which was not possessed by arbutin itself. 20 These findings further promoted researchers in developing new methods for the preparation of arbutin esters.…”