3-O-β-D-oleandropyranosyl-14,16:15,20:18,20-triepoxy-14,15-secopregn-4,6,8(14)triene

• 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-O-β-D-oleandropyranosyl-14,16:15,20:18,20-triepoxy-14,15-secopregn-4,6,8(14)triene
• 英文别名: stauntosaponin A；Stauntosaponin A；(2R,3R,4R,6R)-6-[[(1R,4R,5R,8S,16S,19S,22R)-5,19-dimethyl-15,18,20-trioxahexacyclo[14.5.1.01,14.04,13.05,10.019,22]docosa-9,11,13-trien-8-yl]oxy]-4-methoxy-2-methyloxan-3-ol
• 化学式: C₂₈H₃₈O₇
• 分子量: 486.606
• InChiKey: KNFHQIUXHMJLPI-IXHFUHRASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  35
• 可旋转键数：
  3
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  75.6
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  3-O-β-D-oleandropyranosyl-14,16:15,20:18,20-triepoxy-14,15-secopregn-4,6,8(14)triene 在 盐酸 作用下， 以 甲醇 为溶剂， 反应 2.0h， 生成 D-oleandrose
  参考文献：
  名称：

  Two secopregnane-type steroidal glycosides from Cynanchum stauntonii (Decne.) Schltr.ex Levl.

  摘要：

  Two new steroid glycosides, stauntosaponins A (1) and B (2), were isolated from Cynanchum stauntonii (Decne.) Schltr.ex Levl. (Asclepiadaceae) together with five known compounds, anhydrohirundigenin monothevetoside, glaucogenin C mono-D-thevetoside, hirundoside A, cynatratoside A, and glaucogenin C. Stauntosaponins A and B were formulated as 3-O-beta-D-oleandropyranosyl-14, 16: 15, 20: 18, 20-triepoxy-14, 15-secopregn-4, 6, 8(14)-triene (1) and 3-O-beta-D-thevetopyranosyl-14, 16: 15, 20: 18, 20-triepoxy-14, 15-secopregn-4, 6, 8(14)-triene (2). Compounds 1 and 2 showed moderate inhibitory activities against Na+/K+-ATPase with IC50 values of 21 and 29 mu M, respectively, whereas ouabain as a positive control displayed an IC50 value of 3.5 mu M. (C) 2012 Phytochemical Society of Europe. Published by Elsevier B. V. All rights reserved.

  DOI：

  10.1016/j.phytol.2012.02.007

文献信息

• Two secopregnane-type steroidal glycosides from Cynanchum stauntonii (Decne.) Schltr.ex Levl.
  作者：Makio Shibano、Ayaka Misaka、Kayoko Sugiyama、Masahiko Taniguchi、Kimiye Baba

  DOI：10.1016/j.phytol.2012.02.007

  日期：2012.6

  Two new steroid glycosides, stauntosaponins A (1) and B (2), were isolated from Cynanchum stauntonii (Decne.) Schltr.ex Levl. (Asclepiadaceae) together with five known compounds, anhydrohirundigenin monothevetoside, glaucogenin C mono-D-thevetoside, hirundoside A, cynatratoside A, and glaucogenin C. Stauntosaponins A and B were formulated as 3-O-beta-D-oleandropyranosyl-14, 16: 15, 20: 18, 20-triepoxy-14, 15-secopregn-4, 6, 8(14)-triene (1) and 3-O-beta-D-thevetopyranosyl-14, 16: 15, 20: 18, 20-triepoxy-14, 15-secopregn-4, 6, 8(14)-triene (2). Compounds 1 and 2 showed moderate inhibitory activities against Na+/K+-ATPase with IC50 values of 21 and 29 mu M, respectively, whereas ouabain as a positive control displayed an IC50 value of 3.5 mu M. (C) 2012 Phytochemical Society of Europe. Published by Elsevier B. V. All rights reserved.