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Whole-Cell-Catalyzed Synthesis of Phenolic Glycoside Esters, and Their Antioxidant and Antimelanogenic Properties
Industrial & Engineering Chemistry Research ( IF 3.8 ) Pub Date : 2020-08-28 , DOI: 10.1021/acs.iecr.0c02940 Haixia Xu 1 , Xiaofeng Li 1 , Xuan Xin 1 , Kun Yuan 1 , Hui Wu 1 , Guanglei Zhao 2
Industrial & Engineering Chemistry Research ( IF 3.8 ) Pub Date : 2020-08-28 , DOI: 10.1021/acs.iecr.0c02940 Haixia Xu 1 , Xiaofeng Li 1 , Xuan Xin 1 , Kun Yuan 1 , Hui Wu 1 , Guanglei Zhao 2
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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.
中文翻译：
酚醛糖苷酯的全细胞催化合成及其抗氧化和抑脂作用
酚类糖苷是植物的主要次生代谢产物，具有多种吸引人的生物学和药理活性。在这项研究中，我们开发了一种通过使用全细胞生物催化剂对苯酚糖苷进行酰基修饰的高效方法，旨在改善其脂溶性和生物活性。使用白藜芦醇，红景天苷，哌替啶和phlorizin作为底物，准假丝酵母的底物识别特征进行了研究，红景天苷显示出最高的转化率（99.5％），但区域选择性较低。随后，揭示了反应时间和有机溶剂对转化率和单酯比的影响的机理。在绿色溶剂（γ-戊内酯）中获得的比塞肽转化率比在THF中更高（95.8对94.6％）。与它们的母体化合物相比，所有单酯产品都具有更高的脂溶性和抗氧化活性。此外，红景天苷和phlorizin的单酯显示出比其父母明显更高的酪氨酸酶抑制和脱色素活性。
更新日期：2020-09-23
中文翻译：
酚醛糖苷酯的全细胞催化合成及其抗氧化和抑脂作用
酚类糖苷是植物的主要次生代谢产物，具有多种吸引人的生物学和药理活性。在这项研究中，我们开发了一种通过使用全细胞生物催化剂对苯酚糖苷进行酰基修饰的高效方法，旨在改善其脂溶性和生物活性。使用白藜芦醇，红景天苷，哌替啶和phlorizin作为底物，准假丝酵母的底物识别特征进行了研究，红景天苷显示出最高的转化率（99.5％），但区域选择性较低。随后，揭示了反应时间和有机溶剂对转化率和单酯比的影响的机理。在绿色溶剂（γ-戊内酯）中获得的比塞肽转化率比在THF中更高（95.8对94.6％）。与它们的母体化合物相比，所有单酯产品都具有更高的脂溶性和抗氧化活性。此外，红景天苷和phlorizin的单酯显示出比其父母明显更高的酪氨酸酶抑制和脱色素活性。
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