glycyrrhizic acid

• 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: glycyrrhizic acid
• 英文别名: glycyrrhizin；(2S,3S,4S,5R,6R)-6-[(3R,4S,5S,6S)-2-[[(3S,4aR,6aR,6bS,8aS,11S,12aR,14aR,14bS)-11-carboxy-4,4,6a,6b,8a,11,14b-heptamethyl-14-oxo-2,3,4a,5,6,7,8,9,10,12,12a,14a-dodecahydro-1H-picen-3-yl]oxy]-6-carboxy-4,5-dihydroxyoxan-3-yl]oxy-3,4,5-trihydroxyoxane-2-carboxylic acid
• 化学式: C₄₂H₆₂O₁₆
• 分子量: 822.945
• InChiKey: LPLVUJXQOOQHMX-ZHSSTXRASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  58
• 可旋转键数：
  7
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  267
• 氢给体数：
  8
• 氢受体数：
  16

反应信息

• 作为反应物：
  描述：

  glycyrrhizic acid 在 盐酸 作用下， 以 水 、 溶剂黄146 为溶剂， 反应 1.0h， 以72%的产率得到甘草次酸
  参考文献：
  名称：

  18α-甘草次酸单葡糖醛酸苷通过抑制NF-κB和MAPK信号通路作为抗炎药

  摘要：

  基于甘草甜素的SAR分析，发现了18α-甘草次酸单葡糖苷酸（18α-GAMG）对LPS诱导的RAW264.7细胞中NO和IL-6产生具有强烈抑制作用。Western印迹和免疫荧光结果表明18α-GAMG降低了LPS刺激的RAW264.7细胞中iNOS，COX-2和MAPKs的表达以及NF-κB的激活。进一步的体内结果表明，18α-GAMG可以显着改善CCl 4诱导的肝纤维化的病理变化。

  DOI：

  10.1039/c7md00210f
• 作为试剂：
  描述：

  环戊二烯 、 3-phenyl-1-(2-pyridyl)prop-2-en-1-one 在 Cu(C₁₂H₇N₂NH₂)⁽²⁺⁾ 、 glycyrrhizic acid 作用下， 以 水 为溶剂， 反应 24.0h， 以92%的产率得到(3-phenylbicyclo[2.2.1]hept-5-en-2-yl)(pyridin-2-yl)methanone
  参考文献：
  名称：

  基于甘草酸的自组装螺旋纳米结构作为不对称Diels-Alder反应的支架

  摘要：

  摘要甘草酸（GA）作为一种传统草药，可以在水中自组装成螺旋状纳米纤维。形成的螺旋纳米结构可用作不对称Diels-Alder反应的支架。通过与一系列非手性铜配体共组装，GA螺旋纳米结构的手性可转移至催化位点，所得组装体对Diels-Alder反应的催化表现出适度的对映选择性。

  DOI：

  10.1016/j.cclet.2019.02.015

文献信息

• UGT73F17, a new glycosyltransferase from <i>Glycyrrhiza uralensis</i>, catalyzes the regiospecific glycosylation of pentacyclic triterpenoids
  作者：Junbin He、Kuan Chen、Zhi-min Hu、Kai Li、Wei Song、Li-yan Yu、Chung-Hang Leung、Dik-Lung Ma、Xue Qiao、Min Ye

  DOI：10.1039/c8cc04215b

  日期：——

  The regiospecific glycosylation of pentacyclic triterpenoids by UGT73F17, a new glycosyltransferase from Glycyrrhiza uralensis, is highlighted. UGT73F17 exhibited strict substrate specificity toward the carboxyl group at C-30/C-29 of pentacyclic triterpenoids, and showed high promiscuity to sugar donors. UGT73F17 represents the first identified triterpenoid 30/29-O-glycosyltransferase, and could be

  突出了UGT73F17（一种来自甘草的新糖基转移酶）对五环三萜类化合物的区域特异性糖基化作用。UGT73F17对五环三萜类化合物的C-30 / C-29处的羧基表现出严格的底物特异性，并与糖供体高度混杂。UGT73F17代表第一个鉴定出的三萜类30 / 29- O-糖基转移酶，可以用作合成糖基酯皂苷的有效生物催化剂。
• Oleanane-type Triterpene Glucuronides from the Roots of<i>Glycyrrhiza uralensis</i>Fischer
  作者：Yun-Feng Zheng、Lian-Wen Qi、Xiao-Bing Cui、Guo-Ping Peng、Yong-Bo Peng、Mei-Ting Ren、Xiao-Lan Cheng、Ping Li

  DOI：10.1055/s-0029-1240907

  日期：2010.9

  Investigation of characteristic constituents of the roots of Glycyrrhiza uralensis Fischer led to isolation of four new triterpene glucuronides, namely uralsaponins C–F (1–4), an artificial product, namely the methyl ester of glycyrrhizin (5), as well as six known triterpene glucuronides (6–11). These new compounds were identified by 1D and 2D NMR spectroscopic analysis. The cytotoxicity of the selected compounds and their aglycones were evaluated against HeLa and MCF-7 cancer cell lines, and the preliminary structure-activity relationship was also elucidated.

  通过对 Glycyrrhiza uralensis Fischer 根部特征成分的研究，分离出了四种新的三萜葡糖苷酸（即 uralsaponins C-F (1-4)）、一种人工产物（即甘草苷的甲酯 (5)）以及六种已知的三萜葡糖苷酸 (6-11)。这些新化合物是通过一维和二维核磁共振光谱分析确定的。评估了所选化合物及其苷元对 HeLa 和 MCF-7 癌细胞株的细胞毒性，并初步阐明了其结构-活性关系。
• Synthesis of amino acid conjugates of glycyrrhizic acid using N-hydroxyphthalimide and N,N'-dicyclohexylcarbodiimide
  作者：L. A. Baltina、A. I. Fairushina、L. A. Baltina

  DOI：10.1134/s1070363215120129

  日期：2015.12

  Synthesis of amino acid conjugates of glycyrrhizic acid with the use of N-hydroxyphthalimide, N,N'-dicyclohexylcarbodiimide, and tert-butyl esters of L-amino acids (valine, isoleucine, phenylalanine, and methionine) was performed followed by deprotection with trifluoroacetic acid. The target amino acid conjugates were isolated by column chromatography on silica gel in 40-45% yield. The structure of the prepared compounds was confirmed by IR and C-13 NMR spectroscopy.
• USE OF GLYCYRRHETINIC ACID, GLYCYRRHIZIC ACID AND RELATED COMPOUNDS FOR MITIGATION AND/OR TREATMENT OF PNEUMONITIS/PNEUMONIA/PULMONARY FIBROSIS INDUCED BY VIRUS INFECTION AND/OR BY CHEMICAL OR BIOLOGICAL AGENTS
  申请人：ZHANG Lurong

  公开号：US20210244691A1

  公开（公告）日：2021-08-12

  The present invention pertains to novel uses of glycyrrhetinic acid (GA), glycyrrhizic acid (GR) and related compounds for mitigation and/or treatment of pneumonitis/pneumonia/pulmonary fibrosis induced by various chemicals/bioagents and/or pathogens, such as anti-cancer therapies and/or virus. Also embodied are therapeutic uses of prodrugs, metabolites, derivatives (e.g., acids, esters and ethers), and salts of glycyrrhetinic acid (GA) and glycyrrhizic acid (GR) in a form of drugs, health products, foods or food additives.