isoquercitrin

• 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: isoquercitrin
• 英文别名: 3-[(2R,3S,4S,5S)-5-[(1R)-1,2-dihydroxyethyl]-3,4-dihydroxyoxolan-2-yl]oxy-2-(3,4-dihydroxyphenyl)-5,7-dihydroxychromen-4-one
• 化学式: C₂₁H₂₀O₁₂
• 分子量: 464.383
• InChiKey: OPJZLUXFQFQYAI-YAURUVCPSA-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：
  5
• 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：

  sucrose 、 槲皮素 、 尿苷-5’-二磷酸 在 recombinant glycine max sucrose synthase 、 recombinant glycosyltransferase from Arabidopsis 、 uridine-5'-diphosphoglucose 作用下， 以 aq. phosphate buffer 、 二甲基亚砜 为溶剂， 反应 0.5h， 生成 isoquercitrin
  参考文献：
  名称：

  Synergistic Catalysis of Glycosyltransferase and Sucrose Synthase to Produce Isoquercitrin Through Glycosylation of Quercetin

  摘要：

  异槲皮素具有多种生物特性，其水溶性高于槲皮素。在这项研究中，拟南芥中对槲皮素具有高活性的糖基转移酶（AtUGT78D2）与耐受槲皮素的甘氨酸蔗糖合成酶（GmSUS）相结合，通过从UDP再生UDP-葡萄糖来合成异槲皮素。确定了最佳协同催化的重要因素。通过采用进料批次操作，异槲皮素的最终滴度增加到 3830 毫克/升，相应的摩尔转化率为 94.3%，UDP-葡萄糖再生循环的最大次数（RCmax）为 33 次。

  DOI：

  10.1007/s10600-019-02712-9

文献信息

• [EN] USE OF QUERCETIN-3-O-GLUCOSIDE FOR THE TREATMENT OF FLAVIVIRUS INFECTIONS<br/>[FR] UTILISATION DE QUERCÉTINE-3-O-GLUCOSIDE POUR LE TRAITEMENT D'INFECTIONS À FLAVIVIRUS
  申请人：INST NAT SANTE RECH MED

  公开号：WO2019185579A1

  公开（公告）日：2019-10-03

  Flaviviruses are largely pathogenic to humans and other mammals and mostly are transmitted by mosquitoes. To combat flavivirus infections, it is urgent to propose safe and effective anti-viral compounds not only to impair the virus spread but also to mitigate the associated morbidities. Despite the development of antiviral agents from synthetic sources, a novel antiviral approach (economical, simple and environmentally friendly) is to use natural sources such as nutraceutical as preventive treatments against viral infections. The inventors demonstrated that flavonoid isoquercitrin exerts antiviral activity against African historical and Asian epidemic strains of ZIKV in human hepatoma, epithelial and neuroblastoma cell lines. They showed that isoquercitrin acts on ZIKV entry by preventing the internalization of virus particles into the host cell. Next the inventors demonstrated that Q3G exert antiviral activity against Yellow Fever Virus (YFV). These results suggest that Q3G represents a potential prophylactic agent targeting the entry of two medically relevant flavivirus and could thus be used to prevent flavivirus infection. Accordingly, the the present invention relates to use of quercetin-3 -O-glucoside for the treatment of flavivirus infections.