quercetin-3'-α-D-glucopyranoside

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 英文名称: quercetin-3'-α-D-glucopyranoside
• 英文别名: quercetin 3’-α-D-glucoside；3'-O-α-D-glucopyranosyl quercetin；3,5,7-trihydroxy-2-[4-hydroxy-3-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]chromen-4-one
• 化学式: C₂₁H₂₀O₁₂
• 分子量: 464.383
• InChiKey: YLWQTYZKYGNKPI-WNZLTNKYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  33
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  207
• 氢给体数：
  8
• 氢受体数：
  12

反应信息

• 作为产物：
  描述：

  槲皮素 、 蔗糖 在 蔗糖磷酸钠 作用下， 以 aq. buffer 为溶剂， 反应 24.0h， 生成 quercetin-3'-α-D-glucopyranoside 、 4'-O-α-D-glucopyranosyl quercetin
  参考文献：
  名称：

  为大型受体创造空间：用于水系统中白藜芦醇糖基化的合理生物催化剂设计

  摘要：

  多酚具有许多有趣的特性，但它们的低溶解度限制了其实际应用。在这方面，糖基化提供了一种解决方案，蔗糖磷酸化酶已被提议作为一种具有成本效益的生物催化剂。但是，对于合成目的，其在其他受体底物上的活性太低，通常需要添加有机（共）溶剂。在这里，我们描述了来自解热嗜热厌氧杆菌的酶的工程化，以使白藜芦醇的糖基化成为测试用例。根据对接和建模研究，预计活动位点环会阻碍结合。实际上，未修饰的环变体R134A对白藜芦醇显示出有用的亲和力（K m = 185 m M），可用于在水性体系中定量生产白藜芦醇3-α-葡萄糖苷。对于其他受体也显示出改善的活性，将变体R134A引入作为有希望的新的生物催化剂，用于在庞大的酚类受体上进行糖基化反应。

  DOI：

  10.1002/anie.201503605

文献信息

• Creating Space for Large Acceptors: Rational Biocatalyst Design for Resveratrol Glycosylation in an Aqueous System
  作者：Mareike E. Dirks-Hofmeister、Tom Verhaeghe、Karel De Winter、Tom Desmet

  DOI：10.1002/anie.201503605

  日期：2015.8.3

  unbolted loop variant R134A showed useful affinity for resveratrol (Km=185 mM) and could be used for the quantitative production of resveratrol 3‐α‐glucoside in an aqueous system. Improved activity was also shown for other acceptors, introducing variant R134A as promising new biocatalyst for glycosylation reactions on bulky phenolic acceptors.

  多酚具有许多有趣的特性，但它们的低溶解度限制了其实际应用。在这方面，糖基化提供了一种解决方案，蔗糖磷酸化酶已被提议作为一种具有成本效益的生物催化剂。但是，对于合成目的，其在其他受体底物上的活性太低，通常需要添加有机（共）溶剂。在这里，我们描述了来自解热嗜热厌氧杆菌的酶的工程化，以使白藜芦醇的糖基化成为测试用例。根据对接和建模研究，预计活动位点环会阻碍结合。实际上，未修饰的环变体R134A对白藜芦醇显示出有用的亲和力（K m = 185 m M），可用于在水性体系中定量生产白藜芦醇3-α-葡萄糖苷。对于其他受体也显示出改善的活性，将变体R134A引入作为有希望的新的生物催化剂，用于在庞大的酚类受体上进行糖基化反应。
• Leuconostoc mesenteroides glucansucrase synthesis of flavonoid glucosides by acceptor reactions in aqueous-organic solvents
  作者：Anne Bertrand、Sandrine Morel、François Lefoulon、Yves Rolland、Pierre Monsan、Magali Remaud-Simeon

  DOI：10.1016/j.carres.2006.02.008

  日期：2006.5

  attempted using two glucansucrases: the dextransucrase from Leuconostoc mesenteroides NRRL B-512F and the alternansucrase from L. mesenteroides NRRL B-23192. Reactions were carried out in aqueous-organic solvents to improve luteolin solubility. A molar conversion of 44% was achieved after 24h of reaction catalysed by dextransucrase from L. mesenteroides NRRL B-512F in a mixture of acetate buffer (70%)/bis(2-methoxyethyl)

  木犀草素的酶促葡萄糖基化尝试使用两种葡聚糖蔗糖：来自肠膜间叶隐球菌NRRL B-512F的右旋糖核酸酶和来自肠系膜劳森氏菌NRRL B-23192的交替糖蔗糖酶。反应在水性有机溶剂中进行以提高木犀草素的溶解度。在葡聚糖乙酸酯缓冲液（70％）/双（2-甲氧基乙基）醚（30％）的混合物中，由葡聚糖转化酶催化的肠膜肠球菌NRRL B-512F催化反应24小时后，摩尔转化率为44％。通过核磁共振（NMR）光谱表征了两种产物：木犀草素-3'-O-α-d-吡喃葡萄糖苷和木犀草素-4'-O-α-d-吡喃葡萄糖苷。在来自肠膜曼森特罗氏菌NRRL B-23192的交替糖蔗糖酶的存在下，获得了三种另外的产物，其木犀草素转化率为8％。
• Water soluble phenolics derivatives with dermocosmetic and therapeutic applications
  申请人：Libragen

  公开号：EP1867729A1

  公开（公告）日：2007-12-19

  The invention relates to the preparation of phenolics derivatives by enzymatic condensation of phenolics selected among pyrocatechol or its derivatives including (i) protocatechuic acid and its derivatives, (ii) 3,4-dihydroxycinnamic acid with its transisomer or caffeic acid and its derivatives, especially hydrocaffeic acid, rosmarinic acid, chlorogenic acid and caffeic acid phenethyl ester, and with its cis-isomer and its derivatives, especially esculin, (iii) dihydroxyphenylglycol, and (iv) members of the flavonoid familly such as taxifolin and fustin (dihydroflavonols), fisetin (a flavonol), eriodictyol (a flavanone), , with the glucose moiety of sucrose. The production of said phenolics derivatives is achieved with a glucosyltransferase (EC 2.4.1.5) obtained from a culture of Leuconostoc species, and more particularly from the culture of Leuconostoc mesenteroides NRRL B-512F. These O-glucosides of selected phenolics are new, have a solubility in water higher than that of their parent polyphenol and have useful applications in cosmetic and pharmaceutical compositions, such as antioxidative, antiviral, antibacterial, immune-stimulating, antiallergic, antihypertensive, antiischemic, antiarrhytmic, antithrombotic, hypocholesterolemic, antilipoperoxidant, hepatoprotective, anti-inflammatory, anticarcinogenic antimutagenic, antineoplastic, anti-thrombotic, and vasodilatory formulations, or in any other field of application. All the more, glucosylated phenolics derivatives objects of the invention can be hydrolyzed by the human natural microbiotes, thus releasing the active part of the phenolic compound upon time during their usage or by an α-glucosidase (EC 3.2.1.20).

  本发明涉及用酶缩合法制备酚类衍生物，所选酚类包括焦儿茶酚或其衍生物，包括(i) 原儿茶酸及其衍生物，(ii) 3,4-二羟基肉桂酸与其反式异构体或咖啡酸及其衍生物，特别是氢咖啡酸、(iii) 二羟基苯甘醇，以及 (iv) 黄酮家族成员，如 taxifolin 和 fustin（二氢黄酮醇）、fisetin（一种黄酮醇）、eriodictyol（一种黄酮），以及蔗糖的葡萄糖分子。上述酚类衍生物的生产是通过一种葡糖基转移酶（EC 2.4.1.5）实现的，该酶是从白色念珠菌（Leuconostoc species）的培养物中获得的，尤其是从中肠白色念珠菌（Leuconostoc mesenteroides NRRL B-512F）的培养物中获得的。抗高血压、抗缺血、抗心律失常、抗血栓、降胆固醇、抗脂过氧化、保肝、抗炎、抗癌、抗突变、抗肿瘤、抗血栓和血管扩张配方，或任何其他应用领域。此外，本发明的葡糖基化酚类衍生物可被人体天然微生物水解，从而在使用过程中或通过α-葡萄糖苷酶（EC 3.2.1.20）释放出酚类化合物的活性部分。
• Flavonoids O-A-glucosylated on the B cycle, method for the production thereof and uses
  申请人：Institut National de la Recherche Agronomique

  公开号：US10647739B2

  公开（公告）日：2020-05-12

  The invention relates to a method for producing derivatives of O-α-glucosylated flavonoid, comprising at least one step of incubating a glucansucrase with a flavonoid and at least one sucrose, the flavonoid being a flavonoid which is monohydroxylated or hydroxylated in a non-vicinal manner on the B cycle. The invention also relates to novel O-α-glucosylated flavonoid derivatives, and to the use thereof.

  本发明涉及一种生产O-α-葡糖基化类黄酮衍生物的方法，该方法至少包括一个步骤，即将葡聚糖琥珀酸酶与类黄酮和至少一种蔗糖孵育，类黄酮是一种在B周期上以非乙烯基方式单羟基化或羟基化的类黄酮。本发明还涉及新型 O-α-葡萄糖基化黄酮衍生物及其用途。
• Enzymatic Glycosylation of Phenolic Antioxidants: Phosphorylase-Mediated Synthesis and Characterization
  作者：Karel De Winter、Griet Dewitte、Mareike E. Dirks-Hofmeister、Sylvie De Laet、Helena Pelantová、Vladimír Křen、Tom Desmet

  DOI：10.1021/acs.jafc.5b04380

  日期：2015.11.25

  Although numerous biologically active molecules exist as glycosides in nature, information on the activity, stability, and solubility of glycosylated antioxidants is rather limited to date. In this work, a wide variety of antioxidants were glycosylated using different phosphorylase enzymes. The resulting antioxidant library, containing alpha/beta-glucosides, different regioisomers, cellobiosides, and cellotriosides, was then characterized. Glycosylation was found to significantly increase the solubility and stability of all evaluated compounds. Despite decreased radical-scavenging abilities, most glycosides were identified to be potent antioxidants, outperforming the commonly used 2,6-bis(1,1-dimethylethyl)-4-methylphenol (BHT). Moreover, the point of attachment, the anomeric configuration, and the glycosidic chain length were found to influence the properties of these phenolic glycosides.