caudatin

• 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: caudatin
• 英文别名: [(3S,8S,9R,10R,12R,13S,14R,17S)-17-acetyl-3,8,14,17-tetrahydroxy-10,13-dimethyl-1,2,3,4,7,9,11,12,15,16-decahydrocyclopenta[a]phenanthren-12-yl] 3,4-dimethylpent-2-enoate
• 化学式: C₂₈H₄₂O₇
• 分子量: 490.637
• InChiKey: VWLXIXALPNYWFH-ZCARJHNXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.98
• 重原子数：
  35.0
• 可旋转键数：
  4.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  124.29
• 氢给体数：
  4.0
• 氢受体数：
  7.0

反应信息

• 作为产物：
  描述：

  otophylloside L 在 盐酸 作用下， 以 甲醇 为溶剂， 反应 0.25h， 生成 caudatin
  参考文献：
  名称：

  New pregnane glycosides from the roots of Cynanchum otophyllum

  摘要：

  Six new pregnane glycosides with an acyl at C-12 and a straight sugar chain at C-3, namely otophyllosides H-M (1-6), were isolated from the roots of Cynanchum otophyllum (Asclepiadaceae) collected from Eryuan County in Yunnan province of China. Their structures were characterized to be qingyangshengenin 3-0-beta-D-glucopyranosyl-(1 -> 4)-beta -D-glucopyranosyl-(1 -> 4)-beta-D-cymaropyranosyl-(1 -> 4)-beta-D-cymaropyranosyl-(l -> 4)-beta-D-digitoxopyranoside (1), qingyangshengenin 3-0-beta-D-glucopyranosyl-(1 -> 4)-beta-D-cymaropyranosyl-(1 - 4)-0-D-cymaropyranosyI-(1 - 4)-p-D-digitoxopyranoside (2), qingyangshengenin 3-0-beta-D-glucopyranosyl-(1 -> 4)-beta-D-cymaropyranosyl-(1 -> 4)- beta-D-oleandropyranosyl-(1 -> 4)-beta-D-cymaropyranosyl-(1 -> 4)-beta-D-digitoxopyranoside (3), qingyangshengenin 3-0-beta-D-glucopyranosyl-(1 -> 4)-beta-D-thevetopyranosyl-(1 -> 4)-beta-D-cymaropyranosyl(1 -> 4)-beta-D-digitoxopyranoside (4), caudatin 3-0-beta-D-glucopyranosyl-(1 -> 4)-beta-D-glucopyranosyl-(1 -> 4 )-beta-D-cymaropyranosyl-(1 -> 4)-beta-D-oleandropyranosyl-(1 -> 4)-beta-D-cymaropyranoside (5), caudatin 3-0-beta-D-glucopyranosyl-(1 -> 4)-beta-D-cymaropyranosyl-(1 -> 4)-beta-D-oleandropyranosyl-(1 -> 4)-beta-D-cymaropyranosyl-(1 -> 4)-beta-D-cymaropyranoside (6), respectively, on the basis of detailed spectroscopic analysis and chemical method. (c) 2007 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2007.06.001

文献信息

• Cytotoxicity of pregnane glycosides of Cynanchum otophyllum
  作者：Mi Zhang、Xiang Li、Cheng Xiang、Yi Qin、Jing He、Bao-Cai Li、Peng Li

  DOI：10.1016/j.steroids.2015.08.010

  日期：2015.12

  Fourteen new pregnane glycosides, including nine caudatin glycosides (1-9), three qinyangshengenin glycosides (10-12), one kidjoranin glycosides (13) and one gagaminin glycosides (14), along with twelve known analogs (15-26) were isolated from roots of Cynanchum otophyllum Schneid. Their structures were deduced by detailed analysis of 1D and 2D NMR spectra, as well as HRESIMS. In this study, all pregnane glycosides obtained (1-26) were evaluated for their cytotoxic activities using three cancer cell lines (HepG2, Hela, U251). As results, except 6 and 10, other twenty-four pregnane glycosides showed cytotoxicities at different degrees against three cell lines. (C) 2015 Elsevier Inc. All rights reserved.
• New pregnane glycosides from the roots of Cynanchum otophyllum
  作者：Xiao-Xia Ma、Fang-Ting Jiang、Qing-Xiong Yang、Xiu-Hua Liu、Ying-Jun Zhang、Chong-Ren Yang

  DOI：10.1016/j.steroids.2007.06.001

  日期：2007.10

  Six new pregnane glycosides with an acyl at C-12 and a straight sugar chain at C-3, namely otophyllosides H-M (1-6), were isolated from the roots of Cynanchum otophyllum (Asclepiadaceae) collected from Eryuan County in Yunnan province of China. Their structures were characterized to be qingyangshengenin 3-0-beta-D-glucopyranosyl-(1 -> 4)-beta -D-glucopyranosyl-(1 -> 4)-beta-D-cymaropyranosyl-(1 -> 4)-beta-D-cymaropyranosyl-(l -> 4)-beta-D-digitoxopyranoside (1), qingyangshengenin 3-0-beta-D-glucopyranosyl-(1 -> 4)-beta-D-cymaropyranosyl-(1 - 4)-0-D-cymaropyranosyI-(1 - 4)-p-D-digitoxopyranoside (2), qingyangshengenin 3-0-beta-D-glucopyranosyl-(1 -> 4)-beta-D-cymaropyranosyl-(1 -> 4)- beta-D-oleandropyranosyl-(1 -> 4)-beta-D-cymaropyranosyl-(1 -> 4)-beta-D-digitoxopyranoside (3), qingyangshengenin 3-0-beta-D-glucopyranosyl-(1 -> 4)-beta-D-thevetopyranosyl-(1 -> 4)-beta-D-cymaropyranosyl(1 -> 4)-beta-D-digitoxopyranoside (4), caudatin 3-0-beta-D-glucopyranosyl-(1 -> 4)-beta-D-glucopyranosyl-(1 -> 4 )-beta-D-cymaropyranosyl-(1 -> 4)-beta-D-oleandropyranosyl-(1 -> 4)-beta-D-cymaropyranoside (5), caudatin 3-0-beta-D-glucopyranosyl-(1 -> 4)-beta-D-cymaropyranosyl-(1 -> 4)-beta-D-oleandropyranosyl-(1 -> 4)-beta-D-cymaropyranosyl-(1 -> 4)-beta-D-cymaropyranoside (6), respectively, on the basis of detailed spectroscopic analysis and chemical method. (c) 2007 Elsevier Inc. All rights reserved.