3α-hydroxyglycyrrhetic acid | 90365-60-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 3α-hydroxyglycyrrhetic acid
• 英文别名: 3alpha-Hydroxyglycyrrhetinic acid；(2S,4aS,6aR,6aS,6bR,8aR,10R,12aS,14bR)-10-hydroxy-2,4a,6a,6b,9,9,12a-heptamethyl-13-oxo-3,4,5,6,6a,7,8,8a,10,11,12,14b-dodecahydro-1H-picene-2-carboxylic acid
• CAS: 90365-60-9
• 化学式: C₃₀H₄₆O₄
• 分子量: 470.693
• InChiKey: MPDGHEJMBKOTSU-GBWCSKBLSA-N

物化性质

• 熔点：
  308-310 °C(Solv: methanol (67-56-1))
• 沸点：
  588.3±50.0 °C(Predicted)
• 密度：
  1.14±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  34
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  74.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3α-hydroxyglycyrrhetic acid 、 二苯基重氮甲烷 以 甲醇 、 乙醚 为溶剂， 以85%的产率得到(3α,18β,20β)-3-hydroxy-11-oxoolean-12-en-29-oic acid diphenylmethyl ester
  参考文献：
  名称：

  Synthesis of glycyrrhetinic acid derivatives for the treatment of metabolic diseases

  摘要：

  The effect of glycyrrhetinic acid (GA) and GA-derivatives towards 11 beta-hydroxysteroid dehydrogenase (11 beta-HSD) was investigated. Novel compounds with modi. cations at positions C-3, C-11 and C-29 of the GA skeleton were prepared. Single crystal X-ray diffraction data of selected substances are reported and discussed. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.10.036
• 作为产物：
  描述：

  (3beta,20beta)-3-羟基-11-氧代-齐墩果-12-烯-29-酸甲酯 在 偶氮二异丁腈 、 氢溴酸 、 三正丁基氢锡 、 三乙胺 、 间氯过氧苯甲酸 、 lithium iodide 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 苯 为溶剂， 反应 9.17h， 生成 3α-hydroxyglycyrrhetic acid
  参考文献：
  名称：

  Glycyrrhetinic acid derivatives as potent inhibitors of Na+, K+-ATPase. Synthesis and structure-activity relationships

  摘要：

  A series of ring A-modified GA derivatives (26 compounds) has been systematically synthesized and the structure-activity relationship investigated for inhibition of canine kidney Na+, K+-ATPase in vitro. The most potent inhibitory activity was found with a group of the 3-deoxygenated derivatives including 5, 6, 9, 10 and 11. The high inhibition may be closely related to the hydrophobic character of the A-ring of these compounds. This finding suggests that the ATP-binding site at the active center of the enzyme is located in a hydrophobic environment.

  DOI：

  10.1016/0223-5234(92)90147-s

文献信息

• Simultaneous Determination of Glycyrrhizin Metabolites Formed by the Incubation of Glycyrrhizin with Rat Feces by Semi-micro High-Performance Liquid Chromatography
  作者：Nobuyuki Okamura、Hidetoshi Miyauchi、Tominari Choshi、Takashi Ishizu、Akira Yagi

  DOI：10.1248/bpb.26.658

  日期：——

  A method for semi-micro high-performance liquid chromatography (HPLC) has been established for the simultaneous determination of 3α-hydroxyglycyrrhetic acid and 3-dehydroglycyrrhetic acid together with glycyrrhizin, glycyrrhetic acid and glycyrrhetic acid mono-glucuronide formed by incubation of glycyrrhizin with rat feces. The analysis was accomplished within 25 min with a TSKgel ODS-80TsQA (150×2.0 mm i.d.) column by linear gradient elution using a mobile phase containing aqueous phosphoric acid and acetonitrile at a flow rate of 0.2 ml·min−1, a thermostatic oven at 25 °C, and detection at 254 nm. The detection limits of these compounds were 0.2 pmol per injection (5 μl). The metabolites of glycyrrhizin, by anaerobic or aerobic incubation with rat fecal suspension over 48 h, were determined. Glycyrrhizin was almost completely converted to metabolite glycyrrhetic acid, and metabolites 3α-hydroxyglycyrrhetic acid and 3-dehydroglycyrrhetic acid in negligible amounts in anaerobic conditions. However, the metabolic time courses of 3-dehydroglycyrrhetic acid when incubated in aerobic conditions revealed that it apparently continued increasing during the whole incubation period.

  建立了一种用于半微量高效液相色谱（HPLC）的方法，以同时测定3α-羟基甘草次酸和3-脱氢甘草次酸与甘草酸、甘草次酸和甘草次酸单葡萄糖醛酸苷的形成，这些化合物是在甘草酸与大鼠粪便共培养过程中生成的。通过使用含有磷酸水溶液和乙腈的流动相在0.2 ml·min−1的流速下进行线性梯度洗脱，使用TSKgel ODS-80TsQA（150×2.0 mm内径）柱，在25 °C恒温箱中，并在254 nm处检测，分析在25分钟内完成。这些化合物的检测限为每次注射0.2 pmol（5 μl）。通过在厌氧或需氧条件下与大鼠粪便悬浮液共培养48小时，测定了甘草酸的代谢物。在厌氧条件下，甘草酸几乎完全转化为代谢物甘草次酸，并且代谢物3α-羟基甘草次酸和3-脱氢甘草次酸的含量可以忽略不计。然而，在需氧条件下的共培养过程中，3-脱氢甘草次酸的代谢时间进程显示其在整个共培养期间继续明显增加。
• Synthesis and antitumor activity of ring A modified glycyrrhetinic acid derivatives
  作者：René Csuk、Stefan Schwarz、Bianka Siewert、Ralph Kluge、Dieter Ströhl

  DOI：10.1016/j.ejmech.2011.08.038

  日期：2011.11

  Triterpenoic acids show many pharmacological effects, among them an antiinflammatory or an antitumor activity. One of these, glycyrrhetinic acid (1) is of interest because of its antitumor profile. Glycyrrhetinic acid is not only cytotoxic but also triggers apoptosis in various human tumor cell lines. To improve the cytotoxicity of parent 1 we set out to synthesize new derivatives of it-differing in structure and lipophilicity. These compounds were tested in a sulforhodamine B assay for cytotoxicity, and screened for their ability to induce apoptosis using an acridine orange/ethidium bromide assay and trypan blue staining. The most active compound, 34, a benzyl glycyrrhetinate holding an extra 3-N-(3-aminopropyl)glycyl substituent showed IC50 between 1.96 and 5.14 mu m for five human cancer cell lines and triggers apoptosis in 80% of the cells. (C) 2011 Elsevier Masson SAS. All rights reserved.
• BIOSENSORS, REAGENTS AND DIAGNOSTIC APPLICATIONS OF DIRECTED EVOLUTION
  申请人：Maxygen, Inc.

  公开号：EP1373889A2

  公开（公告）日：2004-01-02
• [EN] BIOSENSORS, REAGENTS AND DIAGNOSTIC APPLICATIONS OF DIRECTED EVOLUTION<br/>[FR] BIOCAPTEURS, REACTIFS ET APPLICATIONS DIAGNOSTIQUES D'EVOLUTION DIRIGEE
  申请人：MAXYGEN INC

  公开号：WO2002010750A2

  公开（公告）日：2002-02-07

  Methods for sensing test stimuli using arrays of biopolymers are provided. Libraries of biopolymers, such nucleic acid variants, and expression products encoded by nucleic acid variants are provided. Reusable library arrays, and methods for their use are provided.
• Synthesis of glycyrrhetinic acid derivatives for the treatment of metabolic diseases
  作者：Igor Beseda、Laszlo Czollner、Priti S. Shah、Rupesh Khunt、Rawindra Gaware、Paul Kosma、Christian Stanetty、Maria Carmen del Ruiz-Ruiz、Hassan Amer、Kurt Mereiter、Thierry Da Cunha、Alex Odermatt、Dirk Claßen-Houben、Ulrich Jordis

  DOI：10.1016/j.bmc.2009.10.036

  日期：2010.1

  The effect of glycyrrhetinic acid (GA) and GA-derivatives towards 11 beta-hydroxysteroid dehydrogenase (11 beta-HSD) was investigated. Novel compounds with modi. cations at positions C-3, C-11 and C-29 of the GA skeleton were prepared. Single crystal X-ray diffraction data of selected substances are reported and discussed. (C) 2009 Elsevier Ltd. All rights reserved.