digipurpurogenin II | 4644-99-9

• 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: digipurpurogenin II
• 英文别名: isoramanone；3β,12β,14-trihydroxy-14β-pregn-5-en-20-one；3β,12β,14-Trihydroxy-14β-pregn-5-en-20-on；3β, 12β, 14-Trihydroxy-14β-pregn-5-en-20-one；1-[(3S,8R,9S,10R,12R,13S,14S,17S)-3,12,14-trihydroxy-10,13-dimethyl-1,2,3,4,7,8,9,11,12,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl]ethanone
• CAS: 4644-99-9
• 化学式: C₂₁H₃₂O₄
• 分子量: 348.483
• InChiKey: NWFNMRFBJUONKD-TWHJCCPZSA-N

物化性质

• 熔点：
  222-232 °C(Solv: acetone (67-64-1))
• 沸点：
  516.9±50.0 °C(Predicted)
• 密度：
  1.22±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  25
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  77.8
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  12-O-β-tigloyl-3β,14β-dihydroxy-pregn-5-en-20-one 在 氢氧化钾 作用下， 以 甲醇 为溶剂， 反应 3.0h， 以12 mg的产率得到digipurpurogenin II
  参考文献：
  名称：

  An appetite suppressant from Hoodia species

  摘要：

  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.

  DOI：

  10.1016/j.phytochem.2007.05.022

文献信息

• Pharmaceutical compositions having appetite suppressant activity
  申请人：CSIR

  公开号：US20020168427A1

  公开（公告）日：2002-11-14

  A pharmaceutical composition contains an extract obtainable from a plant of the genus Trichocaulon or Hoodia containing an appetite suppressant agent having the formula (1). A process for obtaining the extract and a process for synthesizing compound (1) and its analogues and derivatives is also provided. The invention also extends to the use of such extracts and compound (1) and its analogues for the manufacture of medicaments having appetite suppressant activity. The invention further provides novel intermediates for the synthesis of compound (1).

  一种药物组合物包含可从Trichocaulon或Hoodia属植物中获得的提取物，其中包含具有式（1）的食欲抑制剂。还提供了获得该提取物的过程以及合成化合物（1）及其类似物和衍生物的过程。该发明还扩展到利用这些提取物和化合物（1）及其类似物制造具有食欲抑制活性的药物。该发明还提供了合成化合物（1）的新型中间体。
• Use of extracts from Hoodia gordonii and Hoodia lugardii for the preparation of a medicament for use in the suppression of appetite
  申请人：CSIR

  公开号：EP1438965A1

  公开（公告）日：2004-07-21

  Extracts obtainable from Hoodia gordonii or lugardii containing an appetite suppressant agent having the formula (1) are disclosed for the manufacture of medicaments having appetite suppressant activity.

  公开了从 Hoodia gordonii 或 lugardii 中提取的含有式（1）食欲抑制剂的提取物，用于制造具有食欲抑制活性的药物。
• Method of suppressing appetite
  申请人：CSIR

  公开号：EP1598054A2

  公开（公告）日：2005-11-23

  A non-therapeutic method of suppressing appetite in a human or animal comprises administering to the said human or animal a composition, for example a foodstuff or beverage, comprising an extract from a plant of the genus Trichocaulon or the genus Hoodia, which extract contains an effective amount of an appetite-suppressant steroidal glycoside from said plant, wherein the steroidal glycoside has the formula

  一种抑制人或动物食欲的非治疗方法，包括向所述人或动物施用一种组合物，例如一种食品或饮料，该组合物包含来自毛果芸香属或茄属植物的提取物，该提取物包含有效量的来自所述植物的抑制食欲的甾体苷，其中所述甾体苷的式为
• Pregnane glycosides from Hoodia gordonii
  作者：Yatin J. Shukla、Rahul S. Pawar、Yuanqing Ding、Xing-Cong Li、Daneel Ferreira、Ikhlas A. Khan

  DOI：10.1016/j.phytochem.2009.02.006

  日期：2009.3

  Hoodia gordonii is a 'weight loss' herb, which has gained popularity in the western countries as an appetite suppressant dietary supplement. Phytochemical study of its aerial parts led to isolation of seven pregnane glycosides (hoodigosides W-Z, hoodistanalosides A-B). Their structures were elucidated by chemical degradation studies and spectroscopic methods, including 1D and 2D NMR and CD spectroscopic methods. (C) 2009 Elsevier Ltd. All rights reserved.
• Compounds and pharmaceutical compositions having appetite suppressant activity
  申请人：CSIR

  公开号：EP1213020B1

  公开（公告）日：2009-02-11