Whole-Cell-Catalyzed Synthesis of Phenolic Glycoside Esters, and Their Antioxidant and Antimelanogenic Properties
Whole-Cell-Catalyzed Synthesis of Phenolic Glycoside Esters, and Their Antioxidant and Antimelanogenic Properties
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全细胞催化合成酚苷酯及其抗氧化和抗黑色素生成特性
DOI：
10.1021/acs.iecr.0c02940
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发表时间：
2020
期刊：
影响因子：
--
通讯作者：
Guanglei Zhao
中科院分区：
文献类型：
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作者：
Haixia Xu;Xiaofeng Li;Xuan Xin;Kun Yuan;Hui Wu;Guanglei Zhao
酚苷类化合物是植物体内主要的次生代谢产物，具有多种生物活性和药理活性。本研究采用全细胞生物催化剂对酚苷类化合物进行酰基化修饰，以提高其脂溶性和生物活性。以白藜芦醇、红景天苷、云杉苷和根皮苷为底物，研究了近茎假丝酵母的底物识别特性，其中红景天苷的转化率最高（99.5%），但区域选择性较低。随后，反应时间和有机溶剂对转化率和单酯比的影响的机制被揭示。在绿色溶剂（γ-戊内酯）中白藜芦醇苷的转化率（95.8%）高于在THF中的转化率（94.6%）。与其母体化合物相比，所有单酯产物均表现出更高的脂溶性和抗氧化活性。此外，红景天苷和根皮苷单酯的酪氨酸酶抑制活性和脱色活性显著高于其亲本。
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 ofCandida parapsilosiswere 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.