3-beta-hydroxy-11-oxo-18-alpha-olean-12-en-30-oicacid
18alpha-Glycyrrhetinic acid
CAS: 1449-05-4
Molecular Formula: C30H46O4
3-beta-hydroxy-11-oxo-18-alpha-olean-12-en-30-oicacid - Names and Identifiers
3-beta-hydroxy-11-oxo-18-alpha-olean-12-en-30-oicacid - Physico-chemical Properties
| Molecular Formula | C30H46O4 |
| Molar Mass | 470.69 |
| Density | 492.11°C (rough estimate) |
| Melting Point | 331-333°C |
| Boling Point | 492.11°C (rough estimate) |
| Solubility | Methanol, chloroform |
| Appearance | White powder |
| Storage Condition | 2-8℃ |
| Sensitive | Sensitive to air |
| Refractive Index | 1.48 |
| MDL | MFCD00064897 |
| Physical and Chemical Properties | Bioactive glycyr Rheic acid, a triterpene aglycone component of the natural product glycyrrhizic acid, has significant anti-proliferative and apoptosis-inducing activity in cancer cell lines. |
3-beta-hydroxy-11-oxo-18-alpha-olean-12-en-30-oicacid - Risk and Safety
| Hazard Symbols | Xn - Harmful |
| Risk Codes | 22 - Harmful if swallowed |
3-beta-hydroxy-11-oxo-18-alpha-olean-12-en-30-oicacid - Reference
| Reference Show more | 1. Ji Wanli, Zhou Zehua, Wang Tingting, an Yi, Liang Yi, Wang Xinhong. Analysis of chemical constituents of banxia Xiexin decoction based on UPLC-LTQ-Orbitrap-MS method [J]. Journal of Pharmaceutical Analysis, 2020,40(10):1736-1750. 2. [IF = 3.935] Yi Tao et al."Development and validation of an UHPLC-MS/MS approach for simultaneous quantitative assessment of five bioactive saponins in rat plasma: 3. [IF = 3.922] Wei Wang et al." Peony-Glycyrrhiza decection, an Herbal Preparation, Inhibits Clozapine Metabolism via Cytochrome P450s, but Not Flavin-Containing Monooxygenase in In Vitro Models."Drug Metab Dispos. 2015 Jul;43(7):1147-1153 4. [IF=3.645] Yi Tao et al."UHPLC-MS/MS quantification combined with chemometrics for the comparative analysis of different batches of raw and wine-processed Dipsacus asper."J Sep Sci. 2017 Apr;40(8):1686-1693 5. [IF=3.205] Yi Tao et al."Pharmacokinetic comparisons of six components from raw and vinegar-processed Daphne genkwa aqueous extracts following oral administration in rats by employing UHPLC-MS/MS approaches."J Chromatogr B. 2018 Mar;1079:34 6. [IF=3.205] Yi Tao et al."A simple and sensitive LC-MS/MS approach for simultaneous quantification of six bioactive compounds in rats following oral administration of aqueous extract and ultrafine powder of Astragalus propinquus: Application to a comparative pharmaco 7. [IF=3.205] Yi Tao et al."Comparative pharmacokinetic analysis of extracts of crude and wine-processed Dipsacus asper in rats by a sensitive ultra performance liquid chromatography-tandem mass spectrometry approach."J Chromatogr B. 2016 Nov;1036-1037:33 8. [IF=3.205] Yi Tao et al."Integrating UHPLC-MS/MS quantification and DAS analysis to investigate the effects of wine-processing on the tissue distributions of bioactive constituents of herbs in rats: Exemplarily shown for Dipsacus asper."J Chromatogr B. 2017 Jun;1055 9. [IF=3.046] Liwei Dong et al."Echinacoside induces apoptotic cancer cell death by inhibiting the nucleotide pool sanitizing enzyme MTH1."Oncotargets Ther. 2015; 8: 3649-3664 10. [IF=5.64] Ting Li et al."Dynamic Changes in Endophytic Microorganisms and Metabolites During Natural Drying of Licorice."Front Microbiol. 2021; 12: 740721 11. [IF=4.749] Bin Wei et al."Highly Selective Entrapment of His-Tagged Enzymes on Superparamagnetic Zirconium-Based MOFs with Robust Renewability to Enhance pH and Thermal Stability."Acs Biomater Sci Eng. 2021;7(8):3727-3736 12. [IF=4.032] Qiu-yue Xiao et al."A network pharmacology-based study on key pharmacological pathways and targets of Qi Fu Yin acting on Alzheimer's disease."Exp Gerontol. 2021 Jul;149:111336 13. [IF=3.69] Qian Zhang et al."Qishen Granule alleviates endoplasmic reticulum stress-induced myocardial apoptosis through IRE-1-CRYAB pathway in myocardial ischemia."J Ethnopharmacol. 2020 Apr;252:112573 14. [IF=3] Tao-Guang HUO et al."Liver metabonomics study on the protective effect of glycyrrhetinic acid against realgar-induced liver injury."Chin J Nat Medicines. 2020 Feb;18:138 15. [IF=2.877] Wanli Ji et al."Identifying the active compounds and mechanism of action of Banxia Xiexin decoction for treating ethanol-induced chronic gastritis using network pharmacology combined with UPLC-LTQ-Orbitrap MS."Comput Biol Chem. 2021 Aug;93:107535 16. [IF=5.34] Dong Shao et al."Identification of the active compounds and functional mechanisms of Jinshui Huanxian formula in pulmonary fibrosis by integrating serum pharmacochemistry with network pharmacology."PHYTOMEDICINE. 2022 Jul;102:154177 |
3-beta-hydroxy-11-oxo-18-alpha-olean-12-en-30-oicacid - Effect of gap junction blocker 18 α-glycyrrhetinic acid on proliferation of rat vascular smooth muscle cells
from VIP
Author:
Lingling Wu , Zhong Hua , Wang en help , Donna , Li Jiawei , He Fang
Abstract:
to investigate whether gap junction is involved in inhibiting the proliferation of rat vascular smooth muscle cells and the possible molecular mechanism, the experiment was divided into two groups: control group and 18 α-glycyrrhetinic acid (18 α-GA) group. MTT method and flow cytometry to detect cell proliferation activity, dye tracer molecular transfer method (scratch labeled dye transport method) to detect cell gap junction function, the expressions of Connexin 40(Cx40) and 43(Cx43) were detected by Western blotting. The results showed that:(1) compared with the control group, the A570 value and the proportion of S phase of cell cycle in 18α-GA group were decreased (P0.01), and the cell proliferation activity was weakened;(2) compared with the control group, 18α-GA group showed a significant decrease in the percentage of fluorescent dye transmission, and a significant decrease in the gap junction function (P0.01), there was no significant difference in the expression of Cx40 and total Cx43 protein in the 18α-GA group (P0.05), and the ratio of phosphorylated Cx43 to non phosphorylated Cx43 was significantly decreased (P0.01). Therefore, 18α-GA may inhibit the proliferation of vascular smooth muscle cells by down-regulating the expression of phosphorylated Cx43 protein in vascular smooth muscle cells, leading to the weakening of gap junctional intercellular communication.
stowed
Key words:
gap junctions proliferation vascular smooth muscle cells
DOI:
10.3969/j.issn.1007-7383.2013.05.014
cited:
year:
2013
Last Update：2024-01-02 23:10:35
3-beta-hydroxy-11-oxo-18-alpha-olean-12-en-30-oicacid - Study on preparation of optical isomer 18 α-glycyrrhetinic acid
from titanium academic
Author:
Cheng , wood-based Burley · ABS , Ma Hongyan
Abstract:
objective to optimize the preparation process of 18 α-glycyrrhetinic acid (18 α-GA) and characterize its structure. Methods natural Glycyrrhiza triterpene sapogenin 18 β-glycyrrhetinic acid (18 β-GA) was used as raw material, and its optical isomer 18 α-GA was prepared by step reaction method and one-pot method, respectively, the process and yield of the two preparation methods were investigated. The chemical structure was determined by conventional four spectroscopy. Results the total yield of the target compound was 45% by step reaction method, and the target product was directly prepared by one-pot method, the yield was 63%, the operation process was simplified, and the reaction time was shortened, the reaction yield was improved. The spectral characteristics and physicochemical properties of the target compound were described in detail. Conclusion The one-pot method for preparing 18 α-glycyrrhetinic acid has the advantages of simple operation and high yield. It is a good way to prepare 18 α-glycyrrhetinic acid with high optical purity.
Key words:
18 α-glycyrrhetinic acid; Preparation process; optimization
DOI:
10.3969/j.issn.1009-5551.2012.02.002
cited:
year:
2012
Last Update：2023-08-16 22:05:47
3-beta-hydroxy-11-oxo-18-alpha-olean-12-en-30-oicacid - Protective effect of 18 α-glycyrrhetinic acid on lipotoxicity induced by free fatty acids in HepG2 cells
from VIP
Author:
Cheng yuan , Li Juan , don , Tan yimin
Abstract:
Objective to investigate the protective effect of 18 α-glycyrrhetinic acid (18 α-GA) on free fatty acid (FFAs)-induced lipotoxicity in HepG2 cells and its molecular mechanism via mitochondrial pathway. Methods HepG2 cells were treated with 1 mmol/L FFAs, oleic acid (OA)-palmitic acid (PA)(2:1) to establish the steatosis model in vitro, model group and 18 α-glycyrrhetinic acid low, medium and high dose (10,20,40 μmol/L) group, positive drug (apoptosis inhibitor Z-VAD-FMK,10 μmol/L) the cell viability was detected by MTT assay, the apoptosis was observed by Hoechst33258 staining, the activation of Bax protein was observed by immunofluorescence staining, and the distribution of cytochrome C in mitochondria and cytoplasm was detected by Western blotting; caspase-3 enzyme activity assay kit was used to determine the intracellular Caspase-3 activity. Results 18 α-glycyrrhetinic acid could protect HepG2 cells from FFAs-induced decrease in viability and reduce the number of lipid apoptosis of HepG2 cells; 18 α-glycyrrhetinic acid could down-regulate the activation of Bax protein and reduce the release of cytochrome C, this prevented a dose-related increase in Caspase-3 activity. Conclusion 18 α-glycyrrhetinic acid has a protective effect on the lipotoxicity of HepG2 cells induced by FFAs, and its mechanism is related to the inhibition of mitochondrial apoptosis pathway.stowed
Key words:
18 α-glycyrrhetinic acid Free Fatty Acids mitochondria lipid apoptosis
DOI:
10.7501/j.issn.1674-5515.2020.07.002
year:
2020
Last Update：2023-08-16 22:05:47
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