5-O-β-D-glucopyranosyl cirsimaritin | 1346158-90-4

• 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: 5-O-β-D-glucopyranosyl cirsimaritin
• 英文别名: 2-(4-hydroxyphenyl)-6,7-dimethoxy-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-4-one
• CAS: 1346158-90-4
• 化学式: C₂₃H₂₄O₁₁
• 分子量: 476.437
• InChiKey: PQOYCGMXCHXMET-GBHDBEGYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  34
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  164
• 氢给体数：
  5
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  5-O-β-D-glucopyranosyl cirsimaritin 在 盐酸 、 水 作用下， 反应 2.0h， 生成 蓟黄素
  参考文献：
  名称：

  Flavonoid glycosides from Microtea debilis and their cytotoxic and anti-inflammatory effects

  摘要：

  Two new 5-O-glucosylflavones, 5-O-beta-D-glucopyranosyl cirsimaritin (1) and 5, 4'-O-beta-D-diglucopyranosyl cirsimaritin (2), four known flavonoids, cirsimarin (3), cirsimaritin (4), salvigenin (5), 4', 5-dihydroxy-7-methoxyflavone (6), and a norisoprenoid, vomifoliol (7), have been isolated from the aerial parts of Microtea debilis. All isolates were tested for cytotoxicity in human cancer cell lines (Hep G2, COLO 205, and HL-60) and anti-inflammatory activities in LPS-treated RAW264.7 macrophages. Compound 6 was found to be a potent inhibitor to nitrite production in macrophages. Compounds 2, 4, 6, and 7 showed moderate anti-proliferative activity against COLO-205 cells with IC50 values of 7.1, 13.1, 6.1, and 6.8 mu M, respectively. (C) 2010 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.fitote.2010.08.014

文献信息

• Flavonoid glycosides from Microtea debilis and their cytotoxic and anti-inflammatory effects
  作者：Naisheng Bai、Kan He、Marc Roller、Ching-Shu Lai、Xi Shao、Min-Hsiung Pan、Antoine Bily、Chi-Tang Ho

  DOI：10.1016/j.fitote.2010.08.014

  日期：2011.3

  Two new 5-O-glucosylflavones, 5-O-beta-D-glucopyranosyl cirsimaritin (1) and 5, 4'-O-beta-D-diglucopyranosyl cirsimaritin (2), four known flavonoids, cirsimarin (3), cirsimaritin (4), salvigenin (5), 4', 5-dihydroxy-7-methoxyflavone (6), and a norisoprenoid, vomifoliol (7), have been isolated from the aerial parts of Microtea debilis. All isolates were tested for cytotoxicity in human cancer cell lines (Hep G2, COLO 205, and HL-60) and anti-inflammatory activities in LPS-treated RAW264.7 macrophages. Compound 6 was found to be a potent inhibitor to nitrite production in macrophages. Compounds 2, 4, 6, and 7 showed moderate anti-proliferative activity against COLO-205 cells with IC50 values of 7.1, 13.1, 6.1, and 6.8 mu M, respectively. (C) 2010 Elsevier B.V. All rights reserved.