3-β-[(O-β-D-glucopyranosyl-(1->3)-4,6-dideoxy-2-O-methyl-β-D-gulopyranosyl)]-5β,14β-dihydroxy-19-oxocard-20(22)enolide | 1155205-73-4

• 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: 3-β-[(O-β-D-glucopyranosyl-(1->3)-4,6-dideoxy-2-O-methyl-β-D-gulopyranosyl)]-5β,14β-dihydroxy-19-oxocard-20(22)enolide
• 英文别名: (3S,5S,8R,9S,10S,13R,14S,17R)-5,14-dihydroxy-3-[(2S,3R,4R,6R)-3-methoxy-6-methyl-4-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-13-methyl-17-(5-oxo-2H-furan-3-yl)-2,3,4,6,7,8,9,11,12,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene-10-carbaldehyde
• CAS: 1155205-73-4
• 化学式: C₃₆H₅₄O₁₄
• 分子量: 710.816
• InChiKey: VTQWFYXLYNJGCR-OJSOPAHASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.8
• 重原子数：
  50
• 可旋转键数：
  8
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  211
• 氢给体数：
  6
• 氢受体数：
  14

反应信息

• 作为反应物：
  描述：

  3-β-[(O-β-D-glucopyranosyl-(1->3)-4,6-dideoxy-2-O-methyl-β-D-gulopyranosyl)]-5β,14β-dihydroxy-19-oxocard-20(22)enolide 在 β-D-glucosidase from Caldocellum saccharolyticum 作用下， 生成 可得然胶 、 4,6-dideoxy-β-D-allopyranoside
  参考文献：
  名称：

  Cytotoxic and HIF-1α Inhibitory Compounds from Crossosoma bigelovii

  摘要：

  Cytotoxicity-guided fractionation of an organic solvent extract of the plant Crossosoma bigelovii led to the discovery of a new strophanthidin glycoside (1) and two new 2-methylchromone glycosides (2 and 3). Also isolated were the known chromones eugenin and noreugenin, the indole alkaloid ajmalicine, the dibenzylbutane lignan secoisolariciresinol, the dibenzylbutyrolactone lignan matairesinol, and the furanone 5-tetradec-5-enyldihydrofuran-2-one. Further investigation into the biological properties of strophanthidin glycosides revealed a connection between inhibition of HIF-1 activation and the glycosylation of the genin. This work is the first published study of the bioactive phytochemicals of the family Crossosomataceae.

  DOI：

  10.1021/np8006342

文献信息

• Cytotoxic and HIF-1α Inhibitory Compounds from <i>Crossosoma bigelovii</i>
  作者：Paul Klausmeyer、Qin Zhou、Dominic A. Scudiero、Badarch Uranchimeg、Giovanni Melillo、John H. Cardellina、Robert H. Shoemaker、Ching-jer Chang、Thomas G. McCloud

  DOI：10.1021/np8006342

  日期：2009.5.22

  Cytotoxicity-guided fractionation of an organic solvent extract of the plant Crossosoma bigelovii led to the discovery of a new strophanthidin glycoside (1) and two new 2-methylchromone glycosides (2 and 3). Also isolated were the known chromones eugenin and noreugenin, the indole alkaloid ajmalicine, the dibenzylbutane lignan secoisolariciresinol, the dibenzylbutyrolactone lignan matairesinol, and the furanone 5-tetradec-5-enyldihydrofuran-2-one. Further investigation into the biological properties of strophanthidin glycosides revealed a connection between inhibition of HIF-1 activation and the glycosylation of the genin. This work is the first published study of the bioactive phytochemicals of the family Crossosomataceae.