4',4''',5,5'',7,7''-hexahydroxy-3,3''-O-rutinosyl-3',3'''-bisflavonoyl ether | 1326303-82-5

• 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-rutinosyl-3',3'''-bisflavonoyl ether
• 英文别名: zizyflavoside A；2-[3-[5-[5,7-dihydroxy-4-oxo-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxymethyl]oxan-2-yl]oxychromen-2-yl]-2-hydroxyphenoxy]-4-hydroxyphenyl]-5,7-dihydroxy-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxymethyl]oxan-2-yl]oxychromen-4-one
• CAS: 1326303-82-5
• 化学式: C₅₄H₅₈O₃₁
• 分子量: 1203.04
• InChiKey: PZZDFPGGXPOMIR-ZUUCRDDSSA-N

物化性质

• 密度：
  1.88±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -2.3
• 重原子数：
  85
• 可旋转键数：
  14
• 环数：
  10.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  500
• 氢给体数：
  18
• 氢受体数：
  31

反应信息

• 作为反应物：
  描述：

  4',4''',5,5'',7,7''-hexahydroxy-3,3''-O-rutinosyl-3',3'''-bisflavonoyl ether 、 乙酸酐 在 吡啶 作用下， 反应 4.5h， 以98.7%的产率得到zizyflavoside A octadecaacetate
  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
• 作为产物：
  描述：

  莰菲醇-3-O-芸香糖苷 、 芦丁 在 laccase (EC 1.10.3.2) from Pycnoporus cinnabarinus 作用下， 以 甲醇 、 水 为溶剂， 反应 0.25h， 以8%的产率得到4',4''',5,5'',7,7''-hexahydroxy-3,3''-O-rutinosyl-3',3'''-bisflavonoyl ether
  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.