3β-O-(β-D-cymaropyranoside)-14β-hydroxy-pregn-5-ene-12β-tigloyl-20-one | 957217-39-9

• 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: 3β-O-(β-D-cymaropyranoside)-14β-hydroxy-pregn-5-ene-12β-tigloyl-20-one
• 英文别名: 3-O-(β-D-cymaropyranosyl)-12-O-tigloyldigipurpurogenin II；[(3S,8R,9S,10R,12R,13S,14S,17S)-17-acetyl-14-hydroxy-3-[(2R,4S,5R,6R)-5-hydroxy-4-methoxy-6-methyloxan-2-yl]oxy-10,13-dimethyl-1,2,3,4,7,8,9,11,12,15,16,17-dodecahydrocyclopenta[a]phenanthren-12-yl] (E)-2-methylbut-2-enoate
• CAS: 957217-39-9
• 化学式: C₃₃H₅₀O₈
• 分子量: 574.755
• InChiKey: QNIUHQWQUIZGCV-RKMFXWKNSA-N

物化性质

• 沸点：
  670.0±55.0 °C(predicted)
• 密度：
  1.20±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  41
• 可旋转键数：
  7
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  112
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  3β-O-(β-D-cymaropyranoside)-14β-hydroxy-pregn-5-ene-12β-tigloyl-20-one 在 trifluoromethanesulfonyloxy(triphenylphosphine)gold(I) 、 potassium hydroxide 作用下， 以 甲醇 、 甲苯 、 苯 为溶剂， 反应 4.5h， 生成 14β-hydroxypregn-5-ene-12β-tigloyl-20-one-3-O-(β-D-thevetopyranosyl)-(1->4)-α-D-cymaropyranosyl-(1->4)-β-D-cymaropyranoside
  参考文献：
  名称：

  Expeditious synthesis of saponin P57, an appetite suppressant from Hoodia plants

  摘要：

  孕烷糖苷P57，一种来自Hoodia的食欲抑制成分，被迅速合成，其特点是从地高辛制备了苷元Hoodigogenin A，并通过糖基O-炔基苯甲酸酯作为供体来组装脱氧三糖。

  DOI：

  10.1039/c2cc34404a
• 作为产物：
  描述：

  地高辛 在 吡啶 、 咪唑 、 lithium aluminium tetrahydride 、 三甲基氯硅烷 、 trifluoromethanesulfonyloxy(triphenylphosphine)gold(I) 、 硫酸 、 2,4,6-三氯苯甲酰氯 、 potassium tert-butylate 、 四丁基氟化铵 、 4-甲基苯磺酸吡啶 、 碳酸氢钠 、 sodium carbonate 、 戴斯-马丁氧化剂 、 对甲苯磺酸 、 臭氧 、 三乙胺 、 原甲酸三乙酯 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 二甲基亚砜 、 N,N-二甲基甲酰胺 、 丙酮 、 甲苯 、 苯 为溶剂， 反应 37.0h， 生成 3β-O-(β-D-cymaropyranoside)-14β-hydroxy-pregn-5-ene-12β-tigloyl-20-one
  参考文献：
  名称：

  Expeditious synthesis of saponin P57, an appetite suppressant from Hoodia plants

  摘要：

  孕烷糖苷P57，一种来自Hoodia的食欲抑制成分，被迅速合成，其特点是从地高辛制备了苷元Hoodigogenin A，并通过糖基O-炔基苯甲酸酯作为供体来组装脱氧三糖。

  DOI：

  10.1039/c2cc34404a

文献信息

• An appetite suppressant from Hoodia species
  作者：Fanie R. van Heerden、R. Marthinus Horak、Vinesh J. Maharaj、Robert Vleggaar、Jeremiah V. Senabe、Philip J. Gunning

  DOI：10.1016/j.phytochem.2007.05.022

  日期：2007.10

  Studies conducted at the Council for Scientific and Industrial Research (CSIR, South Africa) identified extracts from Hoodia species, in particular Hoodia pilifera and Hoodia gordonii, as possessing appetite suppressing properties. Two pregnane glycosides were isolated by fractionation of the dried stems of H. gordonii. Their structures were determined as 3 beta-[beta-D-thevetopyranosyl-(1 -> 4)-beta-D-cymaropyranosyl- (1 -> 4)-beta-D-cymaropyranosyloxy]-12 beta-tigloyloxy-14 beta-hydroxypregn-5-en-20-one (1) and 3 beta-[beta-D-cymaropyranosyl-(1 -> 4)-beta-D-6-thevetopyranosyl- (1 -> 4)-beta-D-cymaropyranosyl-(1 -> 4)-beta-D-cymaropyranosyloxy]-12 beta-tigloyloxy-14 beta-hydroxypregn-5-en-20-one (2) on the basis of spectroscopic studies and conversion to known compounds. Compounds 1 and 2 were also isolated from H. pilifera. Compound 1 was tested for its appetite suppressant properties in rats by oral gavage at 6.25-50 mg/kg and the results showed that all doses resulted in a decrease of food consumption over an eight day period and a body mass decrease when compared to the control sample receiving only the vehicle. In a comparative study against a fenfluramine control sample, compound 1 resulted in a reduction in food intake over the study period, with a concomitant overall decrease in body weight while fenfluramine resulted in a small decrease in food intake, but an increase in body weight (though less than control group) over the same period of time. (C) 2007 Elsevier Ltd. All rights reserved.