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首页> 外文期刊>RSC Advances >Expanded investigations of the aglycon promiscuity and catalysis characteristic of flavonol 3-O-rhamnosyltransferase AtUGT78D1 from Arabidopsis thaliana
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Expanded investigations of the aglycon promiscuity and catalysis characteristic of flavonol 3-O-rhamnosyltransferase AtUGT78D1 from Arabidopsis thaliana

机译：扩大了来自拟南芥的黄酮3-O-rhamnosyl转移酶Atugt78d1的aglycon滥交和催化特征的研究

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Rhamnosides usually possess better bioavailabilities and improved solubilities compared with their aglycons and are a major source of bioactive natural products. However, biosynthesis of rhamnosides is hindered by the commercially expensive UDP-rhamnose (UDP-Rha) donor and a lack of universal rhamnosyltransferases. In the present study, an efficient UDP-Rha production system via a two-step enzymatic reactions using UDP-glucose (UDP-Glc) as a substrate was constructed. Extensive in vitro enzymatic assays and preparative reactions using the obtained UDP-Rha/UDP-Glc highlighted the robust glycosylation promiscuity of the reported rhamnosyltransferase AtUGT78D1. Based on HPLC-UV and HR-MS analyses, 30 of the tested aromatic compounds belonging to 7 structural types, including flavonoids, flavonoid glycosides, phenylethyl chromones, benzophenones, coumarins, lignanoids, and anthraquinones, were accepted by AtUGT78D1 to conduct the corresponding rhamnosylation and/or glucosylation with one or more glycosyl substitutions at different positions. Further preparative reactions expanded the catalytic characteristic of AtUGT78D1 since it can catalyse the rhamnosylation at the 3-OH position of the flavonols, glucosylation at the 7-OH position of the flavone baicalein, and multiple hydroxyl substitutions for diverse types of aromatics. Interestingly, a unique reversible catalysis activity of AtUGT78D1 was observed, and it has been effectively used in one-pot rhamnosylation of the desired rhamnoside. The enzymatic rhamnosylations of diverse “drug-like” scaffolds as well as bidirectional catalysis for one-pot rhamnosylations by plant rhamnosyltransferase were rarely reported before, which indicated that AtUGT78D1 was expected to be a universal and effective tool for chemo-enzymatic synthesis of diverse bioactive rhamnosylated derivatives for drug discovery.
机译：与其酰胺相比，菌丝苷通常具有更好的生物缺陷和改善的溶解度，并且是生物活性天然产品的主要来源。然而，通过商业上昂贵的UDP-rhamnose（UDP-RHA）供体和缺乏通用鼠瘤转移酶来阻碍rhamnosides的生物合成。在本研究中，构建了使用UDP-葡萄糖（UDP-GLC）作为基材的两步酶促反应的有效UDP-RHA生产系统。使用所得UDP-RHA / UDP-GLC的广泛的体外酶测定和制备反应强调了报告的rhAMnosyl转移酶ATAGT78D1的鲁棒糖基化滥用。基于HPLC-UV和HR-MS分析，由Atugt78D1接受atugt78d1接受了属于7种结构类型的测试芳族化合物，包括黄酮类化合物，类黄酮糖苷，苯基乙酮，植物素，植物酮和蒽醌，进行相应的鼠瘤化和/或葡萄糖化，其具有不同位置的一个或多个糖基取代。进一步的制备反应扩增了Atugt78D1的催化特征，因为它可以催化黄酮醇的3-OH位置的鼠瘤化，黄酮菌黄酮的7-OH位置处的葡萄糖囊化，以及用于多种类型的芳烃的多种羟基取代。有趣的是，观察到ATUGT78D1的独特可逆催化活性，并且已在所需菱形钠的单壶鼠李灭菌化中有效地使用。以前的植物鼠李糖基转移酶的单位“药物状”支架的酶ramnoSylation以及一锅鼠李灭菌酶的双向催化剂，这表明预期Atugt78d1是化学酶促合成各种生物活性的普通有效工具用于药物发现的rhamnosy衍生物。

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