glycyrrhizic acid 30-O-methyl ester | 77345-89-2

• 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 30-O-methyl ester
• 英文别名: glycyrrhizic acid 30-methyl ester；glycyrrhizin monomethyl ester；monomethyl glycyrrhizate；(2S,3S,4S,5R,6R)-6-[(2R,3R,4S,5S,6S)-2-[[(3S,4aR,6aR,6bS,8aS,11S,12aR,14aR,14bS)-11-methoxycarbonyl-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
• CAS: 77345-89-2
• 化学式: C₄₃H₆₄O₁₆
• 分子量: 836.972
• InChiKey: CAKDFKUXFMLCAR-ILVQQCHOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  59
• 可旋转键数：
  8
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  256
• 氢给体数：
  7
• 氢受体数：
  16

反应信息

• 作为反应物：
  描述：

  glycyrrhizic acid 30-O-methyl ester 在 硫酸 作用下， 以 1,4-二氧六环 为溶剂， 反应 2.0h， 以6 mg的产率得到(3beta,20beta)-3-羟基-11-氧代-齐墩果-12-烯-29-酸甲酯
  参考文献：
  名称：

  Kitagawa, Isao; Kamigauchi, Toshiyuki; Ohmori, Hidenobu, Chemical and pharmaceutical bulletin, 1980, vol. 28, # 10, p. 3078 - 3086

  摘要：

  DOI：
• 作为产物：
  描述：

  (3beta,20beta)-20-羧基-11-氧代-30-去甲齐墩果-12-烯-3-基 2-O-beta-D-吡喃葡糖基-beta-D-吡喃葡糖苷酸 在 氢氧化钾 作用下， 以 甲醇 、 乙醚 为溶剂， 反应 15.0h， 生成 glycyrrhizic acid 30-O-methyl ester
  参考文献：
  名称：

  Kitagawa, Isao; Kamigauchi, Toshiyuki; Ohmori, Hidenobu, Chemical and pharmaceutical bulletin, 1980, vol. 28, # 10, p. 3078 - 3086

  摘要：

  DOI：

文献信息

• Synthesis and immunomodulating activity of new glycopeptides of glycyrrhizic acid containing residues of L-glutamic acid
  作者：R. M. Kondratenko、L. A. Baltina、L. A. Baltina、N. Zh. Baschenko、G. A. Tolstikov

  DOI：10.1134/s1068162006060136

  日期：2006.12

  glycopeptide with three residues of Glu(OH)-OMe at a dose of 2 mg/kg stimulated the production of antibody-forming cells in mouse spleen in comparison with the control. The GA glycopeptide containing Glu residues only in the GA carbohydrate part turned out to be an immunosuppressor. The glycopeptide of the 30-methyl ester of GA with residues of free Glu in its carbohydrate part increased the hemagglutinine

  在N-羟基苯并三唑或N-羟基琥珀酰亚胺存在下，使用N，N'-二环己基碳二亚胺合成了含有Glu残基的甘草酸（GA）的新糖肽及其α-甲基酯，γ-甲基酯和α，γ-二甲基酯。 。取决于试剂的比例和反应条件，在GA的所有三个COOH基团上或在GA碳水化合物部分的COOH基团上均观察到酰胺键的形成。与对照组相比，具有2 mg / kg剂量的Glu（OH）-OMe的三个残基的GA糖肽刺激了小鼠脾脏中抗体形成细胞的产生。仅在GA碳水化合物部分中含有Glu残基的GA糖肽被证明是免疫抑制剂。在口服剂量为2和10 mg / kg时，GA的30甲基酯的糖肽在其碳水化合物部分带有游离Glu残基，可提高血凝素滴度。所有研究的化合物对小鼠的迟发型超敏反应几乎没有作用。
• Synthetic studies on the relationship between anti-HIV activities and micelle forming abilities of various alkylated glycyrrhetinate diglycoside sodium sulfates and related compounds
  作者：S Saito、T Furumoto、M Ochiai、A Hosono、H Hoshino、U Haraguchi、R Ikeda、N Shimada

  DOI：10.1016/0223-5234(96)89163-x

  日期：1996.1

  Sodium sulfates 11-14, 29-32, 35 and 37 of various alkyl glycyrrhizin and related compounds were synthesized. In vitro anti-HIV activities of the sulfates were compared to the activities of glycyrrhizin 1 in the inhibition of replications of HTLV-III and GUN-4. The activities of the sulfates were increased 11.1, 15.2, 9.1 and 5.0 times for 11-14, 100.0, 125.5, 83.3 and 11.6 times for 29-32, and 11.6 and 50.0 times for 35 and 37. From the relationship between CMC values and anti-HIV activities of the sulfates, it appeared that the sulfates exhibiting more potent antiviral activities had higher micelle forming abilities. Sodium sulfates having a triterpenoid or steroid ring in the molecule showed more potent activities than those of thioglycosides which had no such ring. From the investigation of syncytium formation, we suggest that the active sulfates inhibited HIV-1 infection early in the replication cycle of the virus.
• The Synthesis and Antiviral Activity of Glycyrrhizic Acid Conjugates with α-D-Glucosamine and Some Glycosylamines
  作者：R. M. Kondratenko、L. A. Baltina、S. R. Mustafina、E. V. Vasil'eva、R. Pompei、D. Deidda、O. A. Plyasunova、A. G. Pokrovskii、G. A. Tolstikov

  DOI：10.1023/b:rubi.0000030135.97089.37

  日期：2004.5

  Glycyrrhizic acid and its 30-methyl ester were conjugated with 2-amino-1,3,4,6-tetra-O-acetyl-2-deoxy-alpha-D-glucopyranose, 2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyl amine, 2,3,4-tri-O-acetyl-alpha-L-arabinopyranosyl amine, 2-acetamido-2-deoxy-beta-D-glucopyranosyl amine, and beta-D-galactopyranosyl amine using N,N-'dicyclohexylcarbodiimide and its mixtures with N-hydroxybenzotriazole. Structures of the conjugates were confirmed by IR, UV, H-1, and C-13 NMR spectroscopy. The glycoconjugate with the residues of 2-acetamido-2-deoxy-beta-D-glucopyranosyl amine in the carbohydrate part of its molecule exhibited antiviral activity (ID50 4 mug/ml) toward the herpes simplex type 1 virus (HSV-1) in the VERO cell culture. Two compounds demonstrated anti-HIV-1 activity (50-70% inhibition of p24) in a culture of MT-4 cells at concentrations of 0.5-20 mug/ml.
• Mannosylated saponins based on oleanolic and glycyrrhizic acids. Towards synthetic colloidal antigen delivery systems
  作者：Alison M. Daines、Ben W. Greatrex、Colin M. Hayman、Sarah M. Hook、Warren T. McBurney、Thomas Rades、Phillip M. Rendle、Ian M. Sims

  DOI：10.1016/j.bmc.2009.05.043

  日期：2009.7

  Immunostimulatory saponin based colloidal antigen delivery systems show promise as adjuvants for subunit vaccines. For this reason, allyl oleanolate was glycosylated at the 3-position using trichloroacetimidate donors to give monodesmodic saponins following deprotection. Bisdesmodic saponins were synthesized by double glycosylation at the 3- and 28-positions of oleanolic acid. When formulated together with cholesterol and phospholipids, ring-like, helical and rod-like nanostructures were formed depending on the saponin concentrations used. As an indication of adjuvant activity, the ability of these formulations, and the saponins by themselves, to induce dendritic cell maturation was measured, but no significant activity was observed. (C) 2009 Elsevier Ltd. All rights reserved.
• Baltina; Ryzhova; Vasil'eva, Russian Journal of Bioorganic Chemistry, 1996, vol. 22, # 12, p. 810 - 814
  作者：Baltina、Ryzhova、Vasil'eva、Tolstikov、Sakhautdinova、Lazareva、Kondratenko

  DOI：——

  日期：——