4',4''',5,5'',7,7''-hexahydroxy-3,3''-O-β-D-glucosyl-3',3'''-bisflavonoyl ether | 1326303-84-7

• 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: 4',4''',5,5'',7,7''-hexahydroxy-3,3''-O-β-D-glucosyl-3',3'''-bisflavonoyl ether
• 英文别名: zizyflavoside B；2-[3-[5-[5,7-dihydroxy-4-oxo-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-2-yl]-2-hydroxyphenoxy]-4-hydroxyphenyl]-5,7-dihydroxy-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-4-one
• CAS: 1326303-84-7
• 化学式: C₄₂H₃₈O₂₃
• 分子量: 910.75
• InChiKey: JFQUUIKNBKIVPQ-GHYNRDFMSA-N

物化性质

• 熔点：
  205-206 °C
• 沸点：
  1234.7±65.0 °C(Predicted)
• 密度：
  1.95±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  65
• 可旋转键数：
  10
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  382
• 氢给体数：
  14
• 氢受体数：
  23

反应信息

• 作为反应物：
  描述：

  4',4''',5,5'',7,7''-hexahydroxy-3,3''-O-β-D-glucosyl-3',3'''-bisflavonoyl ether 、 苯甲酰氯 在 盐酸 、 水 、 吡啶 作用下， 反应 2.0h， 生成 1,2,4,6-tetra-O-benzoyl-β-D-glucopyranose
  参考文献：
  名称：

  UNIQUE PHENYL ETHER TYPE BIFLAVONOIDS, ZIZYFLAVOSIDES A AND B WITH BIOMIMETIC SYNTHESIS FOR ZIZYFLAVOSIDE A

  摘要：

  During our investigation of Zizyphus spina-christi (L.) Willd. leaves for anti-inflammatory activity, eight compounds were characterized. Two are new phenyl ether type biflavonoids, which were assigned as zizyflavosides A (1) and B (2). The structures of 1 and 2 were determined by spectroscopic analyses including ID, 2D NMR and MS spectroscopic and chemical data. The other isolated compounds were known flavonoids kaempferol-3-O-rutinoside (5), quercetin-3-O-rutinoside (6), 3`,5`-di-C-beta-D-glucosylphloretine (7), quercetin-3-O-[beta-D-xylosyl-(1 -> 2)-alpha-L-rhamnoside]-4`-O-alpha-L-rhamnoside (8), epiafzelechin (9) and quercetin-3-O-[beta-D-xylosyl-(1 -> 2)-alpha-L-rhamnoside] (10). Zizyflavoside A was synthesized from quercetin-3-O-rutinoside and kaempferol-3-O-rutinoside using laccase as an enzyme and this biomimetic synthesis could be indication to its biosynthetic pathway.

  DOI：

  10.3987/com-10-12002

文献信息

• UNIQUE PHENYL ETHER TYPE BIFLAVONOIDS, ZIZYFLAVOSIDES A AND B WITH BIOMIMETIC SYNTHESIS FOR ZIZYFLAVOSIDE A
  作者：Mahmoud Mostafa、Tomihisa Ohta、Fumihide Takano

  DOI：10.3987/com-10-12002

  日期：——

  During our investigation of Zizyphus spina-christi (L.) Willd. leaves for anti-inflammatory activity, eight compounds were characterized. Two are new phenyl ether type biflavonoids, which were assigned as zizyflavosides A (1) and B (2). The structures of 1 and 2 were determined by spectroscopic analyses including ID, 2D NMR and MS spectroscopic and chemical data. The other isolated compounds were known flavonoids kaempferol-3-O-rutinoside (5), quercetin-3-O-rutinoside (6), 3`,5`-di-C-beta-D-glucosylphloretine (7), quercetin-3-O-[beta-D-xylosyl-(1 -> 2)-alpha-L-rhamnoside]-4`-O-alpha-L-rhamnoside (8), epiafzelechin (9) and quercetin-3-O-[beta-D-xylosyl-(1 -> 2)-alpha-L-rhamnoside] (10). Zizyflavoside A was synthesized from quercetin-3-O-rutinoside and kaempferol-3-O-rutinoside using laccase as an enzyme and this biomimetic synthesis could be indication to its biosynthetic pathway.