14β-hydroxy-19β-oxobufa-4,20,22-trienolide-3β-O-{α-L-rhamnopyranosyl-[(1→4)-β-D-glucopyranosyl]-(1→3)-α-L-rhamnopyranoside} | 1432501-17-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: 14β-hydroxy-19β-oxobufa-4,20,22-trienolide-3β-O-{α-L-rhamnopyranosyl-[(1→4)-β-D-glucopyranosyl]-(1→3)-α-L-rhamnopyranoside}
• 英文别名: urginin C；(3S,8R,9S,10S,13R,14S,17R)-14-hydroxy-3-[(2R,3R,4S,5S,6S)-3-hydroxy-6-methyl-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-13-methyl-17-(6-oxopyran-3-yl)-1,2,3,6,7,8,9,11,12,15,16,17-dodecahydrocyclopenta[a]phenanthrene-10-carbaldehyde
• CAS: 1432501-17-1
• 化学式: C₄₂H₆₀O₁₈
• 分子量: 852.928
• InChiKey: YLZRFBHMEILVSF-RESWNAECSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.2
• 重原子数：
  60
• 可旋转键数：
  9
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  281
• 氢给体数：
  9
• 氢受体数：
  18

反应信息

• 作为反应物：
  描述：

  14β-hydroxy-19β-oxobufa-4,20,22-trienolide-3β-O-{α-L-rhamnopyranosyl-[(1→4)-β-D-glucopyranosyl]-(1→3)-α-L-rhamnopyranoside} 在 盐酸 、 水 作用下， 反应 4.0h， 以1.4 mg的产率得到3beta,14-二羟基-19-氧代蟾蜍-4,20,22-三烯内酯
  参考文献：
  名称：

  Antiproliferative Homoisoflavonoids and Bufatrienolides from Urginea depressa

  摘要：

  Investigation of the South African plant Urginea depressa Baker (Asparagaceae Juss.) for antiproliferative activity against the A2780 ovarian cancer cell line led to the isolation of the six new homoisoflavonoids urgineanins A-F (1-6), the two known bufatrienolides 7 and 9, and the new bufatrienolides urginins B and C (8 and 10). Structures were elucidated based on analysis of their ID and 2D NMR spectra, electronic circular dichroism, and mass spectrometric data. Five of the six new homoisoflavonoids had good antiproliferative activity against the A2780 ovarian cancer, A2058 melanoma, and H522-T1 human non-small-cell lung cancer cells, and urgineanin A (1) had submicromolar activity against all three cell lines. The four bufatrienolides 7-10 had strong antiproliferative activity against the same cell line, with IC50 values of 24.1, 11.2, 111, and 40.6 nM, respectively.

  DOI：

  10.1021/np300900a

文献信息

• Antiproliferative Homoisoflavonoids and Bufatrienolides from <i>Urginea depressa</i>
  作者：Yumin Dai、Liva Harinantenaina、Peggy J. Brodie、Michael Goetz、Yongchun Shen、Karen TenDyke、David G. I. Kingston

  DOI：10.1021/np300900a

  日期：2013.5.24

  Investigation of the South African plant Urginea depressa Baker (Asparagaceae Juss.) for antiproliferative activity against the A2780 ovarian cancer cell line led to the isolation of the six new homoisoflavonoids urgineanins A-F (1-6), the two known bufatrienolides 7 and 9, and the new bufatrienolides urginins B and C (8 and 10). Structures were elucidated based on analysis of their ID and 2D NMR spectra, electronic circular dichroism, and mass spectrometric data. Five of the six new homoisoflavonoids had good antiproliferative activity against the A2780 ovarian cancer, A2058 melanoma, and H522-T1 human non-small-cell lung cancer cells, and urgineanin A (1) had submicromolar activity against all three cell lines. The four bufatrienolides 7-10 had strong antiproliferative activity against the same cell line, with IC50 values of 24.1, 11.2, 111, and 40.6 nM, respectively.