3-O-β-D-glucopyranosyl-(1→4)-6-deoxy-3-O-methyl-β-D-allopyranosyl-(1→4)-β-D-oleandropyranosyl-17β-tenacigenin B

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-O-β-D-glucopyranosyl-(1→4)-6-deoxy-3-O-methyl-β-D-allopyranosyl-(1→4)-β-D-oleandropyranosyl-17β-tenacigenin B
• 英文别名: tenacissimoside G；1-[(1S,3R,6S,7S,8S,9S,10S,11S,14S,16S)-8,9-dihydroxy-14-[(2R,4R,5R,6R)-5-[(2S,3R,4S,5R,6R)-3-hydroxy-4-methoxy-6-methyl-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-4-methoxy-6-methyloxan-2-yl]oxy-7,11-dimethyl-2-oxapentacyclo[8.8.0.01,3.03,7.011,16]octadecan-6-yl]ethanone
• 化学式: C₄₁H₆₆O₁₇
• 分子量: 830.965
• InChiKey: YJEXOKKVHFUILN-QTHQHZGVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.9
• 重原子数：
  58
• 可旋转键数：
  10
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.98
• 拓扑面积：
  245
• 氢给体数：
  7
• 氢受体数：
  17

反应信息

• 作为反应物：
  描述：

  3-O-β-D-glucopyranosyl-(1→4)-6-deoxy-3-O-methyl-β-D-allopyranosyl-(1→4)-β-D-oleandropyranosyl-17β-tenacigenin B 在 β-cellulase 作用下， 以 aq. acetate buffer 为溶剂， 反应 168.0h， 生成 可得然胶 、 tenacigenoside A
  参考文献：
  名称：

  Polyoxypregnane Steroids from the Stems of Marsdenia tenacissima

  摘要：

  A new polyoxypregnane aglycone, tenacigenin D (1), and seven new C21 steroid glycosides, tenacissimosides D-J (2-8), were isolated from the stems of Marsdenia tenacissima. Their structures were determined by interpretation of their 1D and 2D NMR and other spectroscopic data, as well as by comparison with published values for related known compounds. Compound 1 was found to circumvent P-glycoprotein (P-gp)-mediated multidrug resistance through an inhibitory effect on P-gp with a similar potency to verapamil. In addition, compound 1 potentiated the activity of erlotinib and gefitinib in epidermal growth factor receptor tyrosine kinase inhibitor (EGFR TKI)-resistant non-small-cell lung cancer cells.

  DOI：

  10.1021/np500385b

文献信息

• Polyoxypregnane Steroids from the Stems of <i>Marsdenia tenacissima</i>
  作者：Sheng Yao、Kenneth Kin-Wah To、Ya-Zhou Wang、Chun Yin、Chunping Tang、Stella Chai、Chang-Qiang Ke、Ge Lin、Yang Ye

  DOI：10.1021/np500385b

  日期：2014.9.26

  A new polyoxypregnane aglycone, tenacigenin D (1), and seven new C21 steroid glycosides, tenacissimosides D-J (2-8), were isolated from the stems of Marsdenia tenacissima. Their structures were determined by interpretation of their 1D and 2D NMR and other spectroscopic data, as well as by comparison with published values for related known compounds. Compound 1 was found to circumvent P-glycoprotein (P-gp)-mediated multidrug resistance through an inhibitory effect on P-gp with a similar potency to verapamil. In addition, compound 1 potentiated the activity of erlotinib and gefitinib in epidermal growth factor receptor tyrosine kinase inhibitor (EGFR TKI)-resistant non-small-cell lung cancer cells.