5092-01-3Relevant academic research and scientific papers
Structure-based design of glycyrrhetinic acid derivatives as potent anti-sepsis agents targeting high-mobility group box-1
Wang, Yuanyuan,Yu, Zongmin,Yuan, Hu,Chen, Hao,Xie, Ning,Wang, Zhibin,Sun, Qingyan,Zhang, Weidong
, (2020/11/27)
Novel Glycyrrhetinic Acid (GA) derivatives with fused heterocycles on A ring were structure-based designed and synthesized. Their potential anti-inflammatory effects were investigated by a classical LPS stimulated macrophage model. Surface plasmon resonance (SPR) was used to verify the binding of GA analogues with HMGB1. A preliminary structure–activity relationship was summarized and an analogue GA-60 with ortho-methoxybenzyl pyrozole showed stronger anti-inflammatory effect and higher affinity for HMGB1 with a Kd value of 12.5 μM. In addition, this compound exhibited excellent inhibitory functions on NO (96%), TNF-α (94%), and IL-6 (100%), by interfering with phosphorylation of p38, ERK, JNK MAPKs, as well as that of NF-κB p65 and IKKα/β. Moreover, GA-60 extended the survival of either the classic CLP-induced or LPS-induced sepsis mouse models. Molecular modeling predictions further supported these findings, clearly indicating that inhibiting HMGB1 release, using fused heterocyclic GA derivatives, is a promising strategy for treatment of sepsis.
Synthesis and inhibition of α-glucosidase of methyl glycyrrhetinate glycosides
Zhang, Wei,Wang, He-Ying,Wang, Huai-Xu,Zhu, Zhen-Yuan
supporting information, p. 1874 - 1880 (2019/07/22)
The synthesis of the methyl glycyrrhetinate glycosides and inhibition of α-glucosidase were studied. The carboxyl group of glycyrrhetinic acid was methylated, and glucose and galactose were introduced into the hydroxyl group to obtain compounds 7 and 12.
Preparation method of 18 beta-methyl glycyrrhetinate
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Paragraph 0024; 0030-0063, (2021/11/27)
The invention provides a preparation method of 18 beta-methyl glycyrrhetinate, which comprises the following steps: taking 18 beta-glycyrrhetinic acid and trimethylsilyl diazomethane as raw materials, and reacting to prepare the 18 beta-methyl glycyrrhetinate. According to the invention, 18 beta-glycyrrhetinic acid is used as a starting material and is subjected to one-step methyl esterification reaction with trimethylsilyl diazomethane to obtain 18 beta-methyl glycyrrhetinate, the synthesis process is simple, the synthesis process conditions are mild, the yield is up to 99.2% or above, the product quality is good, and the content is greater than 99.5%. Besides, through selection of a plurality of parameters such as the solvent, the reaction time and the material dosage, the yield and the purity of the reaction are further improved, and a basis is provided for industrial production.
Quaternary ammonium glycyrrhetinic acid cationic surfactant as well as preparation method and application thereof (by machine translation)
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Paragraph 0041; 0043; 0044, (2020/05/01)
The invention discloses a quaternary ammonium glycyrrhetinic acid cationic surfactant and a preparation method and application. thereof, and the critical micelle concentration of the surfactant at room temperature is 5 × 10. - 4 mol/L, Can descend the surface tension from 72mN/m to 47mN/m. and, the surfactant has better regulation and control effect on the bouncing behavior of the liquid drop on the hydrophobic solid surface, and the surfactant concentration on the surface of the blade such as dive, PTFE can be 5 × 10 higher. - 4 At mol/L, can obviously inhibit the liquid drop bouncing, and realize better spreading. and, the quaternary ammonium glycyrrhetinic acid cationic surfactant in the invention can extend to various crop blades, such as wheat, rice, corn, cabbage and other blades, have great application prospects, in the field of agricultural industry. (by machine translation)
Synthesis and anti-hepaticfibrosis of glycyrrhetinic acid derivatives with inhibiting COX-2
Bai, Zhongjie,He, Dian,Mohammed, Eyad Abdulwhab Hamoud,Wang, Yanni,Wang, Zhen,Zhang, Qiuping,Zhao, Quanyi
, (2020/04/08)
Many tests have shown cyclooxygenase-2 (COX-2) was closely related to the activation of hepatic stellate cells (HSCs), which further promoting the onset and development of hepatic fibrosis. According to these research findings, a series of glycyrrhetinic acid derivatives were designed and synthesized. Meanwhile, their anti-hepaticfibrotic activities were evaluated in vitro and in vivo. Firstly, in the tests of the cell models, all the compounds displayed anti-proliferative effect on the HSC-T6 activated by (transforming growth factor beta) TGF-β1 (10 ng/mL). Among them, compounds 2 and 16 exhibited a stronger activity than the others, and their IC50 values were 17.6 μM and 30.3 μM, respectively; both of them were low toxicity to normal HSC-T6 cells and WI38 cells, and they inhibited the activated HSC-T6 cells proliferation by promoting apoptosis and resting them at the G0/G1 phase. Secondly, compounds 2 and 16 displayed strong inhibitory effect on activation of HSCs; they not only inhibited the expression of α-SMA and Col1 in the activated HSC-T6 cells, but also decreased the levels of COX-2, TGF-β1 and (reactive oxygen species) ROS in a concentration-dependent manner; they down-regulated the levels of three biomarkers in the process of test, but this decrease did not change linearly with the action time of compound. Thirdly, for the rats which induced with (carbon tetrachloride) CCl4, the symptoms of liver fibrosis in rats were significantly alleviated after successive administration the tested compound for 14d; the α-SMA level in liver tissue decreased in a concentration dependent manner; and the liver cell necrosis and the fat collagen fiber decreased significantly compared with the positive control group; furthermore, inflammatory infiltration was significantly lower than that of the control. This suggests the compounds possibly are candidates for hepatic fibrosis with promising application in clinic.
C3 and C20 diesterified glycyrrhetinic acid derivative, and preparation method and application thereof
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Paragraph 0064-0066; 0091, (2020/02/29)
The invention provides a C3 and C20 diesterified glycyrrhetinic acid derivative having a structure represented by formula I shown in the description, or a pharmaceutically acceptable salt, a solvate,an optical isomer or a polymorph thereof. Experimental results show that the C3 and C20 diesterified glycyrrhetinic acid derivative has a very good bacteriostatic effect on Staphylococcus aureus, caninhibit Staphylococcus aureus ATCC 6538, Staphylococcus aureus ATCC 12228 and Staphylococcus aureus ATCC 29213, and provides a new choice for anti-infective drugs for Staphylococcus aureus.
Pentacyclic triterpenoid glycyrrhetinic acid derivative as well as preparation method and application thereof
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Paragraph 0046; 0054; 0055, (2020/05/01)
The invention discloses a pentacyclic triterpenoid glycyrrhetinic acid derivative which has a structure as shown in a general formula 1 or a formula 7 in the specification, wherein each substituent isdefined in detail in the specification. The invention also discloses application of the pentacyclic triterpenoid glycyrrhetinic acid derivative in preparation of anti-HCV drugs. Huh7 cytotoxic activity results show that the pentacyclic triterpenoid glycyrrhetinic acid derivative is low in cytotoxicity and has research value. In-vitro anti-HCVcc result shows that glycyrrhetinic acid has relativelyweak anti-HCVcc activity, but the pentacyclic triterpenoid glycyrrhetinic acid derivative has relatively good anti-HCV activity.
Preparation method of glycyrrhetinic acid glucoside and application of glycyrrhetinic acid glucoside in sweetening agents
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Paragraph 0006; 0015-0017; 0025-0027, (2020/07/29)
The invention relates to a synthetic route of glycyrrhetinic acid glucoside and application of glycyrrhetinic acid glucoside in sweetening agents, and belongs to the field of synthesis of novel sweetening agents. The novel sweetening agent with higher swe
Synthesis and antitumor effects of novel 18β-glycyrrhetinic acid derivatives featuring an exocyclic α,β-unsaturated carbonyl moiety in ring A
Huang, Min,Gong, Ping,Wang, Yuetong,Xie, Xiaorui,Ma, Zhuangshi,Xu, Qihao,Liu, Dan,Jing, Yongkui,Zhao, Linxiang
, (2020/09/04)
A series of novel 18β-glycyrrhetinic acid (GA) derivatives featuring an exocyclic α,β-unsaturated carbonyl moiety in ring A were synthesized and evaluated for their antitumor activities. Compounds 5c and 5l showed stronger cytotoxicity than other compounds and reported GA analogue CDODA-Me (methyl 2-cyano-3,11-dioxo-18β-olean-1,12-dien-30-oate). 5c and 5l induced apoptosis in cancer cells accompanying with c-Flip reduction and Noxa induction, associated with decreased HDAC3 expression and increased acetylation of H3. 5l displayed better stability properties than 5c and CDODA-Me in microsomes and plasma, 5l also showed favorable pharmacokinetic profiles and inhibited tumor growth in mice. Compound 5l represents a new type of GA derivatives with improved antitumor activity.
Application of acetyl glycyrrhetinic acid methyl ester in preparation of medicine for treating viral hepatitis B
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Paragraph 0025; 0028-0031, (2020/11/25)
The invention relates to application of acetyl glycyrrhetinic acid methyl ester in preparation of a medicine for treating viral hepatitis B. Specifically, the invention provides an application of a compound shown as a formula (1), namely 3 beta-acetoxy-11-carbonyl oleanane-12-ene-30-carboxylic acid methyl ester, in preparation of a medicine for preventing and treating hepatitis B virus infection diseases. The compound shown in the formula (1) has remarkable activity of inhibiting HBeAg secreted by HepG2.2. 15 cells; under the concentration of 100 micrograms per milliliter, the intensity of inhibiting HBeAg secretion is 51.4% and is 3.78 times that of a positive control drug alpha-interferon (10000 units per milliliter) and 4.94 times that of lamivudine (100 micrograms per milliliter) respectively; under the concentration, the inhibition ratio of the lamivudine to HBV-DNA replication is 94.6%, and the inhibition strength (the inhibition ratio of 3-TC with the concentration of 100 micrograms per milliliter to HBV-DNA is 88.4%) of the lamivudine is higher than that of lamivudine with the same concentration and is 3.1 times that of high-concentration alpha-interferon (10000 units per milliliter). Therefore, the acetyl glycyrrhetinic acid methyl ester can be expected to be used for preparing non-nucleoside medicines for treating hepatitis B virus infection diseases; specifically, the compound can be used for preparing an HBV-DNA inhibitor and an HBeAg inhibitor, and the preparation method of the compound is simple in step, low in cost, wide in raw material source and easy for industrial production.
