methyl glycyrrhetate β-D-galactoside

• 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: methyl glycyrrhetate β-D-galactoside
• 英文别名: methyl glycyrrhetinate β-D-galactoside；methyl 3β-(β-D-galactopyranosyloxy)-11-oxo-olean-12-en-30-oate；glycyrrhetinic acid methyl ester-β-D-galactopyranoside；18βH-glycyrrhetic acid methyl ester β-D-galactopyranoside；3-O-(β-D-galactopyranosyl)-18β-glycyrrhetic acid methyl ester；methyl (2S,4aS,6aR,6aS,6bR,8aR,10S,12aS,14bR)-2,4a,6a,6b,9,9,12a-heptamethyl-13-oxo-10-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,4,5,6,6a,7,8,8a,10,11,12,14b-dodecahydro-1H-picene-2-carboxylate
• 化学式: C₃₇H₅₈O₉
• 分子量: 646.862
• InChiKey: QHCVXOFJCANAHD-PLWHCFEASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  46
• 可旋转键数：
  5
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  143
• 氢给体数：
  4
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  glycyrrhetinic acid methyl ester-β-D-2,3,4,6-tetra-O-benzoyl galactopyranoside 在 sodium methylate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 5.0h， 以36.12%的产率得到methyl glycyrrhetate β-D-galactoside
  参考文献：
  名称：

  甘草次酸甲酯糖苷α-葡萄糖苷酶的合成及抑制作用

  摘要：

  摘要 研究了甘草次酸甲酯苷的合成和对α-葡萄糖苷酶的抑制作用。将甘草次酸的羧基甲基化，在羟基上引入葡萄糖和半乳糖，得到化合物7和12。化合物1，2，7，12和甘草酸（GL）它们对α葡萄糖苷酶抑制活性进行评价。其结果，化合物1，2，7，12和GL均显示显著α葡萄糖苷酶抑制活性和IC 50值分别为 0.465、1.352、0.759、0.687 和 2.085 mM，并作为非竞争性抑制剂。所述化合物的活性2，7，12比化合物低1，但比GL显著高。因此得出结论，甘草次酸经化学修饰后结构的变化对生物活性有一定的影响，其中羧基、羟基和引入的单糖种类的变化是影响因素。

  DOI：

  10.1080/14786419.2019.1639181

文献信息

• Synthesis and anti-HIV activity of triterpene 3-O-galactopyranosides, analogs of glycyrrhizic acid
  作者：L. A. Baltina、L. A. Baltina、R. M. Kondratenko、O. A. Plyasunova、S. A. Nepogodiev、R. A. Field

  DOI：10.1007/s10600-010-9679-1

  日期：2010.9

  A new method for synthesizing triterpene 3-O-galactosides, analogs of glycyrrhizic acid (GA) based on 18βglycyrrhetic acid (GLA) methyl esters and 18,19-dehydro-GLA, using 2,3,4,6-tetra-O-acetyl-a-Dgalactopyranosyl bromide as the glycosyl donor, I–Br promoter, and 4-Å molecular sieves was developed. The method could produce primarily 3-O-α-D- or β-D-galactopyranosides depending on the reaction conditions. The 3-O-α-D-galactopyranoside of GLA exhibited an index of selectivity (IS) 2.9 times greater than that of GA for inhibition of accumulation of virus-specific protein p24 of HIV-1. β-D-Galactopyranoside of GLA was more cytotoxic for MT-4 cells and exhibited weak anti-HIV-1 activity.

  一种使用2,3,4,6-四-O-合成三萜3-O-半乳糖苷、基于18β甘草次酸(GLA)甲酯和18,19-脱氢-GLA的甘草酸(GA)类似物的新方法开发了乙酰-α-D吡喃半乳糖基溴作为糖基供体、I-Br促进剂和4-Å分子筛。根据反应条件，该方法可以主要产生 3-O-α-D- 或 β-D-吡喃半乳糖苷。 GLA的3-O-α-D-吡喃半乳糖苷在抑制HIV-1的病毒特异性蛋白p24的积累方面表现出比GA高2.9倍的选择性指数(IS)。 GLA 的 β-D-吡喃半乳糖苷对 MT-4 细胞具有更强的细胞毒性，并且表现出较弱的抗 HIV-1 活性。
• A simple method of synthesis of triterpene glycosides similar to glycyrrhizic acid and their hepatoprotective activity in vitro
  作者：L. R. Mikhailova、L. A. Baltina、L. A. Baltina、R. M. Kondratenko、S. A. Nepogodiev、R. A. Field、O. Kunert、M. Ch. Yin

  DOI：10.1134/s1068162009050136

  日期：2009.9

  A simplified method of synthesis of triterpene 1,2-trans-glycosides was developed using the glycosylation of glycyrrhetic acid (GLA) and 18,19-dehydro-GLA by beta-pyranose peracetates in the presence of SnCl4 and molecular sieves 4 . The synthesized glycosides exhibited hepatoprotective activity toward the human hepatoma HepG2 cell line on the model of alcohol hepatitis and decreased the level of TNF-[alpha] protein.
• A “natural” approach: Synthesis and cytoxicity of monodesmosidic glycyrrhetinic acid glycosides
  作者：Stefan Schwarz、Bianka Siewert、Nuno M. Xavier、Ana R. Jesus、Amélia P. Rauter、René Csuk

  DOI：10.1016/j.ejmech.2013.11.024

  日期：2014.1

  Several pentacyclic triterpenoic acids have shown noteworthy antitumor activity, among them betulinic acid as well as oleanolic acid and derivatives thereof. Glycyrrhetinic acid (GA) exhibits some cytotoxic activity albeit this compound is not as active as betulinic acid, but GA came in the focus of scientific interest since it triggers apoptosis in tumor cells. In addition, it can be extracted from the roots of liquorice in high yields. Previous studies revealed that the introduction of an extra hydrophilic moiety increases the cytotoxicity of these compounds. Thus, a series of GA glycosides was prepared utilizing hexoses as well as pentoses (in D- and L-configuration) by using glycosyl trichloroacetimidates and TMSOTf as catalyst. The compounds were screened for cytotoxic activity against seven human cancer cell lines and the not malignant murine cell line NIH 3T3using a photometric SRB assay. The compounds trigger apoptosis as shown from extra trypan blue and acridine orange/ethidium bromide staining. (C) 2013 Elsevier Masson SAS. All rights reserved.
• Structure—activity relationships of synthetic methyl glycyrrhetate glycosides
  作者：Masayuki Takechi、Yasuo Tanaka

  DOI：10.1016/s0031-9422(00)95086-6

  日期：1993.3

  Of 15 synthetic methyl glycyrrhetate glycosides, the monoglycosides having CH2OH-6 or Me-6 in their sugar moieties and the diglycosides having a (1-->4) linkage between the sugar residues showed higher haemolytic activities than the others. The beta-maltoside and beta-lactoside exhibited much stronger antifungal activities against Trichophyton mentagrophytes than the others. However, none of them exhibited antibacterial activity against Staphylococcus aureus or Bacillus subtilis.