7-O-[2'-O-feruloyl-β-D-glucuronopyranosyl(1->2)-O-β-D-glucuronopyranoside]chrysoeriol | 380468-53-1

• 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: 7-O-[2'-O-feruloyl-β-D-glucuronopyranosyl(1->2)-O-β-D-glucuronopyranoside]chrysoeriol
• 英文别名: chrysoeriol 7-O-[(2-O-trans-feruloylglucuronopyranosyl) (1→2)]-O-β-D-glucuronopyranoside；5-Hydroxy-2-(4-hydroxy-3-methoxyphenyl)-4-oxo-4H-1-benzopyran-7-yl 2-O-[2-O-[(2E)-3-(4-hydroxy-3-methoxyphenyl)-1-oxo-2-propen-1-yl]-I(2)-D-glucopyranuronosyl]-I(2)-D-glucopyranosiduronic acid；(2S,3S,4S,5R,6S)-5-[(2R,3R,4S,5S,6S)-6-carboxy-4,5-dihydroxy-3-[(E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxyoxan-2-yl]oxy-3,4-dihydroxy-6-[5-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-4-oxochromen-7-yl]oxyoxane-2-carboxylic acid
• CAS: 380468-53-1
• 化学式: C₃₈H₃₆O₂₁
• 分子量: 828.691
• InChiKey: CQSOKHCNRZFEOH-BWRVQHKVSA-N

物化性质

• 沸点：
  1152.4±65.0 °C(Predicted)
• 密度：
  1.74±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  59
• 可旋转键数：
  13
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  324
• 氢给体数：
  9
• 氢受体数：
  21

反应信息

• 作为反应物：
  描述：

  7-O-[2'-O-feruloyl-β-D-glucuronopyranosyl(1->2)-O-β-D-glucuronopyranoside]chrysoeriol 在 水 、 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 1.0h， 生成 chrysoeriol 7-O-[β-D-glucuronopyranosyl-(1->2)]-O-β-D-glucuronopyranoside 、 阿魏酸
  参考文献：
  名称：

  Antioxidative Caffeoylquinic Acids and Flavonoids from Hemerocallis fulva Flowers

  摘要：

  Tumor necrosis factor-alpha (TNF-alpha)-induced reactive oxygen species (ROS) production in HepG2 was used to screen hepatocyte protective compounds from the flowers of Hemerocallis fulva. Three new polyphenols, n-butyl 4-trans-O-caffeoylquinate (1), kaempferol 3-O-{alpha-L-rhamnopyranosyl(1 -> 6)[alpha-L-rhamnopyranosyl(1 -> 2)]}-beta-D-galactopyranoside (2), and chrysoeriol 7-O-[beta-D-glucuronopyranosyl(1 -> 2)(2-O-trans-feruloyl)-beta-D-glucuronopyranoside (3), together with four caffeoylquinic acid derivatives (4-7), eight known flavones (8-15), one naphthalene glycoside, stelladerol (16), one tryptophan derivative (17), adenosine (18), and guanosine (19) were isolated from the bioactive fractions of the aqueous ethanol extract of H. fulva flowers. The structures of isolated compounds were characterized by means of spectroscopic data. Compounds 1-3 were described as first isolated natural products. Among the above-mentioned compounds, the caffeoylquinic acid derivatives are the major components with potent free radical scavenging activity in HepG2 cells and are for the first time isolated from H. fulva flowers. A convenient ultraperformance liquid chromatography (UPLC) method was also developed to simultaneously separate and identify caffeoylquinic acids and flavonoids promptly.

  DOI：

  10.1021/jf201166b

文献信息

• Antioxidative Caffeoylquinic Acids and Flavonoids from Hemerocallis fulva Flowers
  作者：Yun-Lian Lin、Chung-Kuang Lu、Yeh-Jeng Huang、Hong-Jhang Chen

  DOI：10.1021/jf201166b

  日期：2011.8.24

  Tumor necrosis factor-alpha (TNF-alpha)-induced reactive oxygen species (ROS) production in HepG2 was used to screen hepatocyte protective compounds from the flowers of Hemerocallis fulva. Three new polyphenols, n-butyl 4-trans-O-caffeoylquinate (1), kaempferol 3-O-alpha-L-rhamnopyranosyl(1 -> 6)[alpha-L-rhamnopyranosyl(1 -> 2)]}-beta-D-galactopyranoside (2), and chrysoeriol 7-O-[beta-D-glucuronopyranosyl(1 -> 2)(2-O-trans-feruloyl)-beta-D-glucuronopyranoside (3), together with four caffeoylquinic acid derivatives (4-7), eight known flavones (8-15), one naphthalene glycoside, stelladerol (16), one tryptophan derivative (17), adenosine (18), and guanosine (19) were isolated from the bioactive fractions of the aqueous ethanol extract of H. fulva flowers. The structures of isolated compounds were characterized by means of spectroscopic data. Compounds 1-3 were described as first isolated natural products. Among the above-mentioned compounds, the caffeoylquinic acid derivatives are the major components with potent free radical scavenging activity in HepG2 cells and are for the first time isolated from H. fulva flowers. A convenient ultraperformance liquid chromatography (UPLC) method was also developed to simultaneously separate and identify caffeoylquinic acids and flavonoids promptly.