12-O-β-tigloyl-3β,14β-dihydroxy-pregn-5-en-20-one

• 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: 12-O-β-tigloyl-3β,14β-dihydroxy-pregn-5-en-20-one
• 英文别名: gordonoside A；3β-hydroxy-12β-tigloyl-14β-hydroxy-pregn-5-en-20-one；12-O-tigloyldigipurpurogenin II；Hoodigogenin A；12β-O-tigloyloxy-3β,14β-dihydroxypregn-5-en-20-one；12-O-β-tigloyl-3β,14β-dihydroxy-pregn-5-ene-20-one；14β-hydroxypreg-5-ene-12β-tigloyl-20-one；[(3S,8R,9S,10R,12R,13S,14S,17S)-17-acetyl-3,14-dihydroxy-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
• 化学式: C₂₆H₃₈O₅
• 分子量: 430.585
• InChiKey: ATLKEQLPGRQWQA-SXXOWLQRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  31
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  83.8
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  12-O-β-tigloyl-3β,14β-dihydroxy-pregn-5-en-20-one 在 trifluoromethanesulfonyloxy(triphenylphosphine)gold(I) 、 sodium carbonate 作用下， 以 甲醇 、 二氯甲烷 、 甲苯 为溶剂， 反应 13.0h， 生成 14β-hydroxypregn-5-ene-12β-tigloyl-20-one-3β-O-(2,4-di-O-acetyl-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 、 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 、 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 28.0h， 生成 12-O-β-tigloyl-3β,14β-dihydroxy-pregn-5-en-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

• 孕甾皂苷P57及其衍生物的中间体、制备方法和用途、及孕甾皂苷P57衍生物
  申请人：中国科学院上海有机化学研究所

  公开号：CN114075261A

  公开（公告）日：2022-02-22

  本发明涉及式I所示的用于孕甾皂苷P57及其衍生物的中间体、制备方法和用途、及孕甾皂苷P57衍生物。该方法采用汇聚式合成策略实现了P57及其衍生物的合成，合成路线短，收率高，适合工业化生产。式I中的各取代基的定义与权利要求书中的定义相同。
• Synthesis of Hoodigogenin A, aglycone of natural appetite suppressant glycosteroids extracted from Hoodia gordonii
  作者：Philippe Geoffroy、Blandine Ressault、Eric Marchioni、Michel Miesch

  DOI：10.1016/j.steroids.2011.03.014

  日期：2011.6

  14 beta-hydroxy pregnane glycosides extracted from Hoodia gordonii, a succulent plant isolated from Apocynaceae are suggested to have appetite suppressant properties in animals and humans. However, limited reports on biological studies concerning the appetite suppressant properties are available in the open literature. One reason for that is the poor availability of these glycosteroids because H. gordonii is a protected plant and the yield of extraction lies between 0.003% and 0.02%. Starting from 3 alpha,12 alpha-diacetoxy-pregnanone 1, we disclose in this report the synthesis of Hoodigogenin A. the aglycone of the natural 14 beta-hydroxy pregnane glycosides extracted from H. Gordonii. (C) 2011 Elsevier Inc. All rights reserved.
• 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.
• 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.
• New oxypregnane glycosides from appetite suppressant herbal supplement Hoodia gordonii
  作者：Rahul S. Pawar、Yatin J. Shukla、Shabana I. Khan、Bharathi Avula、Ikhlas A. Khan

  DOI：10.1016/j.steroids.2007.03.003

  日期：2007.6

  Hoodigosides A-K (1-11), eleven new oxypregnane glycosides and a previously reported oxypregnane glycoside P57AS3 were isolated from the aerial parts of Hoodia gordonii. The structures of these 12-O-beta-tigloyl isoramanone glycosides were determined on the basis of chemical evidence and extensive spectroscopic methods that include one-dimensional and two-dimensional NMR. Cytotoxicity and antioxidant activities of these compounds were tested in cell based assays where they were found to be inactive. (c) 2007 Elsevier Inc. All rights reserved.