(+)-catechin-4'-O-α-D-glucoside | 1037072-19-7

• 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: (+)-catechin-4'-O-α-D-glucoside
• 英文别名: catechin O-α-D-glucoside；4'-O-α-D-glucopyranosyl-(+)-catechin；(2R,3S)-2-[3-hydroxy-4-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]-3,4-dihydro-2H-chromene-3,5,7-triol
• CAS: 1037072-19-7
• 化学式: C₂₁H₂₄O₁₁
• 分子量: 452.415
• InChiKey: LTDLFQZRSXJVAN-KLIUUODMSA-N

物化性质

• 沸点：
  826.1±65.0 °C(Predicted)
• 密度：
  1.670±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.4
• 重原子数：
  32
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  190
• 氢给体数：
  8
• 氢受体数：
  11

反应信息

• 作为产物：
  描述：

  蔗糖 、 儿茶提取物 在 葡聚糖蔗糖酶 作用下， 以 水 、 二甲基亚砜 为溶剂， 反应 22.0h， 生成 (+)-catechin-4'-O-α-D-glucoside
  参考文献：
  名称：

  Water Soluble and Activable Phenolics Derivatives with Dermocosmetic and Therapeutic Applications and Process for Preparing Said Derivatives

  摘要：

  该发明涉及通过酶催化将选择自间苯二酚或其衍生物的酚类与蔗糖的葡萄糖部分进行缩合来制备酚类衍生物。所述酚类衍生物的生产是通过葡萄糖转移酶（EC 2.4.1.5）实现的。所选酚类的这些O-α-葡糖苷是新的，其在水中的溶解度高于它们的原始多酚，并且在化妆品和药用组合物中具有有用的应用，如抗氧化、抗病毒、抗菌、免疫刺激、抗过敏、降压、抗缺血、抗心律失常、抗血栓形成、降胆固醇、抗脂质过氧化、肝脏保护、抗炎症、抗癌变突变、抗肿瘤、抗血栓形成和扩血管等配方，或者在任何其他应用领域中。

  公开号：

  US20090233876A1

文献信息

• Glucansucrases from lactic acid bacteria as biocatalysts for multi-ring catechol glucosylation
  作者：Johannes Nolte、Alexander Kempa、Matthias Hochgürtel、Ulrich Schörken

  DOI：10.1080/10242422.2020.1784882

  日期：2021.1.2

  Catechins are the major group of bioactive flavanols in green tea and cacao. 17 glucansucrase-active strains were identified from a set of 41 lactic acid bacteria, which were able to glucosylate (+)-catechin in a non-natural acceptor reaction. In total cell free extracts of 12Leuconostocand 5Weissellastrains were active on catechin and also 8 cell fractions exhibited catechin glucosylation activity. Six enzymes were selected for further evaluation and enriched up to 37 fold in yields of at least 40%. Glucansucrase ofL. citreumDSM 5577 was the most efficient biocatalyst for (+)-catechin transformation with conversions of >40% after 24 h. NMR analysis of the major reaction product confirmed the (+)-catechin-4 '-O-alpha-d-glucoside. OnlyL. kimchiB-65337 produced a second catechin monoglucoside. Four out of six glucansucrases glucosylated esculetin and all enzymes were active on haematoxylin. Glucansucrases ofL. citreumDSM 5577,L. kimchiB-65337 andW. beninensisDSM 22752 were the best suited biocatalysts with conversions of >30% for esculetin and >60% for haematoxylin.W. beninensisDSM 22752 glucansucrase produced 89% haematoxylin glucosides without process optimization.L. kimchiB-65337 andW. beninensisDSM 22752 synthesized >40% diglucosides with the bifunctional haematoxylin. NMR analysis of the purified esculetin products confirmed formation of the 6-O-alpha-d- and 7-O-alpha-d-glucosides. Also two haematoxylin monoglucosides were identified as the 9-O-alpha-d- and 3-O-alpha-d-glucosides.