Synthesis, oxygen radical absorbance capacity, and tyrosinase inhibitory activity of glycosides of resveratrol, pterostilbene, and pinostilbene
Synthesis, oxygen radical absorbance capacity, and tyrosinase inhibitory activity of glycosides of resveratrol, pterostilbene, and pinostilbene
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DOI：
10.1080/09168451.2016.1240606
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发表时间：
2017-02
期刊：
影响因子：
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通讯作者：
Daisuke Uesugi;H. Hamada;K. Shimoda;N. Kubota;S. Ozaki;N. Nagatani
中科院分区：
文献类型：
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作者：
Daisuke Uesugi;H. Hamada;K. Shimoda;N. Kubota;S. Ozaki;N. Nagatani
利用重组大肠杆菌表达的美洲商陆葡萄糖基转移酶对二苯乙烯类化合物白藜芦醇进行糖基化，除生成3-O-β-D-葡萄糖苷外，还生成4′-O-β-D-葡萄糖苷。该酶将紫檀芪转化为4′-O-β-D-葡萄糖苷，并将松芪转化为4′-O-β-D-葡萄糖苷作为主要产物和3-O-β-D-葡萄糖苷作为次要产物。抗氧化能力的分析表明，上述二苯乙烯苷具有较低的氧自由基吸收能力（ORAC）的值比相应的二苯乙烯苷元。其中白藜芦醇的3-O-β-D-葡萄糖苷的ORAC值最高，松芪的ORAC值最高。二苯乙烯苷元的酪氨酸酶抑制活性通过糖基化得到提高，二苯乙烯苷的活性高于二苯乙烯苷元。白藜芦醇3-O-β-D-葡萄糖苷对酪氨酸酶的抑制活性最高。二苯乙烯苷的合成与评价。
The stilbene compound resveratrol was glycosylated to give its 4′-O-β-D-glucoside as the major product in addition to its 3-O-β-D-glucoside by a plant glucosyltransferase from Phytolacca americana expressed in recombinant Escherichia coli. This enzyme transformed pterostilbene to its 4′-O-β-D-glucoside, and converted pinostilbene to its 4′-O-β-D-glucoside as a major product and its 3-O-β-D-glucoside as a minor product. An analysis of antioxidant capacity showed that the above stilbene glycosides had lower oxygen radical absorbance capacity (ORAC) values than those of the corresponding stilbene aglycones. The 3-O-β-D-glucoside of resveratrol showed the highest ORAC value among the stilbene glycosides tested, and pinostilbene had the highest value among the stilbene compounds. The tyrosinase inhibitory activities of the stilbene aglycones were improved by glycosylation; the stilbene glycosides had higher activities than the stilbene aglycones. Resveratrol 3-O-β-D-glucoside had the highest tyrosinase inhibitory activity among the stilbene compounds tested. Graphical abstract Synthesis and evaluation of stilbene glucosides.