7,3'-di-O-methylquercetin 4'-O-β-D-glucopyranosyl-3-O-[6'-(3-hydroxy-3-methylglutaroyl)]-α-D-glucopyranoside | 1426344-17-3

• 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: 7,3'-di-O-methylquercetin 4'-O-β-D-glucopyranosyl-3-O-[6'-(3-hydroxy-3-methylglutaroyl)]-α-D-glucopyranoside
• 英文别名: 3-hydroxy-3-methyl-5-oxo-5-[[(2R,3S,4S,5R,6R)-3,4,5-trihydroxy-6-[5-hydroxy-7-methoxy-2-[3-methoxy-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]-4-oxochromen-3-yl]oxyoxan-2-yl]methoxy]pentanoic acid
• CAS: 1426344-17-3
• 化学式: C₃₅H₄₂O₂₁
• 分子量: 798.706
• InChiKey: QZQKAOPSDLKNDI-CEKALKGBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.8
• 重原子数：
  56
• 可旋转键数：
  15
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.51
• 拓扑面积：
  327
• 氢给体数：
  10
• 氢受体数：
  21

反应信息

• 作为反应物：
  描述：

  7,3'-di-O-methylquercetin 4'-O-β-D-glucopyranosyl-3-O-[6'-(3-hydroxy-3-methylglutaroyl)]-α-D-glucopyranoside 在 盐酸 、 水 作用下， 反应 3.0h， 生成 葡萄糖
  参考文献：
  名称：

  Diarylheptanoids and Flavonoids from Viscum album Inhibit LPS-Stimulated Production of Pro-inflammatory Cytokines in Bone Marrow-Derived Dendritic Cells

  摘要：

  Three new diarylheptanoids, (3S,5R)-3-hydroxy-5-methoxy-1,7-bis(4-hydroxyphenyl)-6E-heptene (1), (3S,5S)-3-hydroxy-5-methoxy-1,7-bis(4-hydroxypheny1)-6E-heptene (2), and (3S)-3-hydroxy-1,7-bis(4-hydroxypheny1)-6E-hepten-5-one (3), four new flavonoid glycosides, 3,7,3'-tri-O-methylquercetin-4'-O-beta-D-apiofuranosyl-(1 -> 2)-O-beta-D-glucopyranoside (4), 7,3'-di-O-methylquercetin-4'-O-beta-D-glucopyranosy1-3-O-[6'''-(3-hydroxy-3-methylglutaroyl)]-alpha-D-glucopyranoside (5), 7,3'-di-O-methylquercetin-4'-O-beta-D-glucopyranosyl-3-O-[(6''''-45'''')-O-1''''-(sinap-4-yl)-beta-D-glucopyranosyl-6'''-(3-hydroxy-3-methylglutaroyl)]-alpha-D-glucopyranoside (6), and (2S)-5-hydroxy-7,3'-dimethoxyflavanone-4'-O-beta-D-apiofuranosyl-(1 -> 5)-O-beta-D-apiofuranosyl-(1 -> 2)-O-beta-D-glucopyranoside (9), and 17 known compounds were isolated from the leaves and twigs of Viscum album. Compounds 1, 4, and 19 significantly inhibited LPS-stimulated production of TNF-alpha, IL 6, and IL-12p40 with IC50 values ranging from 0.09 +/- 0.01 to 8.96 +/- 0.45 mu M. (+)-Medioresinol (13) showed inhibitory effects on LPS-stimulated production of IL-12p40 with an IC50 value of 2.00 +/- 0.15 mu M.

  DOI：

  10.1021/np300490v

文献信息

• Diarylheptanoids and Flavonoids from <i>Viscum album</i> Inhibit LPS-Stimulated Production of Pro-inflammatory Cytokines in Bone Marrow-Derived Dendritic Cells
  作者：Nguyen X. Nhiem、Phan V. Kiem、Chau V. Minh、Nanyoung Kim、SeonJu Park、Hwa Young Lee、Eun Sil Kim、Young Ho Kim、Sohyun Kim、Young-Sang Koh、Seung Hyun Kim

  DOI：10.1021/np300490v

  日期：2013.4.26

  Three new diarylheptanoids, (3S,5R)-3-hydroxy-5-methoxy-1,7-bis(4-hydroxyphenyl)-6E-heptene (1), (3S,5S)-3-hydroxy-5-methoxy-1,7-bis(4-hydroxypheny1)-6E-heptene (2), and (3S)-3-hydroxy-1,7-bis(4-hydroxypheny1)-6E-hepten-5-one (3), four new flavonoid glycosides, 3,7,3'-tri-O-methylquercetin-4'-O-beta-D-apiofuranosyl-(1 -> 2)-O-beta-D-glucopyranoside (4), 7,3'-di-O-methylquercetin-4'-O-beta-D-glucopyranosy1-3-O-[6'''-(3-hydroxy-3-methylglutaroyl)]-alpha-D-glucopyranoside (5), 7,3'-di-O-methylquercetin-4'-O-beta-D-glucopyranosyl-3-O-[(6''''-45'''')-O-1''''-(sinap-4-yl)-beta-D-glucopyranosyl-6'''-(3-hydroxy-3-methylglutaroyl)]-alpha-D-glucopyranoside (6), and (2S)-5-hydroxy-7,3'-dimethoxyflavanone-4'-O-beta-D-apiofuranosyl-(1 -> 5)-O-beta-D-apiofuranosyl-(1 -> 2)-O-beta-D-glucopyranoside (9), and 17 known compounds were isolated from the leaves and twigs of Viscum album. Compounds 1, 4, and 19 significantly inhibited LPS-stimulated production of TNF-alpha, IL 6, and IL-12p40 with IC50 values ranging from 0.09 +/- 0.01 to 8.96 +/- 0.45 mu M. (+)-Medioresinol (13) showed inhibitory effects on LPS-stimulated production of IL-12p40 with an IC50 value of 2.00 +/- 0.15 mu M.