Glycyrrhetinic Acid (BioDeep_00000410561)

   

PANOMIX_OTCML-2023 Volatile Flavor Compounds natural product


代谢物信息卡片


(2S,4aS,6aS,6bR,10S,12aS,14bS)-10-hydroxy-2,4a,6a,6b,9,9,12a-heptamethyl-13-oxo-3,4,5,6,6a,7,8,8a,10,11,12,14b-dodecahydro-1H-picene-2-carboxylic acid

化学式: C30H46O4 (470.3395916)
中文名称: 甘草次酸(α型)
谱图信息: 最多检出来源 Viridiplantae(plant) 98.73%

分子结构信息

SMILES: C1[C@@]2(C)[C@@]([H])(CC[C@]3(C)[C@]2([H])C(=O)C=C2[C@@]4([H])C[C@](C(O)=O)(C)CC[C@]4(C)CC[C@@]32C)C(C)(C)[C@@H](O)C1
InChI: InChI=1S/C30H46O4/c1-25(2)21-8-11-30(7)23(28(21,5)10-9-22(25)32)20(31)16-18-19-17-27(4,24(33)34)13-12-26(19,3)14-15-29(18,30)6/h16,19,21-23,32H,8-15,17H2,1-7H3,(H,33,34)/t19-,21+,22+,23-,26-,27+,28+,29-,30-/m1/s1

描述信息

Origin: Plant; SubCategory_DNP: Triterpenoids
18α-Glycyrrhetinic acid, a diet-derived compound, is an inhibitor of NF-kB and an activator of proteasome, which serves as pro-longevity and anti-aggregation factor in a multicellular organism. 18α-Glycyrrhetinic acid induces apoptosis[1][2].
18α-Glycyrrhetinic acid, a diet-derived compound, is an inhibitor of NF-kB and an activator of proteasome, which serves as pro-longevity and anti-aggregation factor in a multicellular organism. 18α-Glycyrrhetinic acid induces apoptosis[1][2].

同义名列表

8 个代谢物同义名

(2S,4aS,6aS,6bR,10S,12aS,14bS)-10-hydroxy-2,4a,6a,6b,9,9,12a-heptamethyl-13-oxo-3,4,5,6,6a,7,8,8a,10,11,12,14b-dodecahydro-1H-picene-2-carboxylic acid; Glycyrrhetinic Acid; (18alpha)-3beta-Hydroxy-11-oxoolean-12-en-30-oic acid; 18alpha-Glycyrrhetinic acid; 18α-GLYCYRRHETINIC ACID; 18alpha-Glycyrrhetic acid; 18α-Glycyrrhetinic acid; Glycyrrhetinate



数据库引用编号

18 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(0)

BioCyc(0)

PlantCyc(0)

代谢反应

0 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(0)

WikiPathways(0)

Plant Reactome(0)

INOH(0)

PlantCyc(0)

COVID-19 Disease Map(0)

PathBank(0)

PharmGKB(0)

30 个相关的物种来源信息

在这里通过桑基图来展示出与当前的这个代谢物在我们的BioDeep知识库中具有相关联信息的其他代谢物。在这里进行关联的信息来源主要有：

  • PubMed: 来源于PubMed文献库中的文献信息，我们通过自然语言数据挖掘得到的在同一篇文献中被同时提及的相关代谢物列表，这个列表按照代谢物同时出现的文献数量降序排序，取前10个代谢物作为相关研究中关联性很高的代谢物集合展示在桑基图中。
  • NCBI Taxonomy: 通过文献数据挖掘，得到的代谢物物种来源信息关联。这个关联信息同样按照出现的次数降序排序，取前10个代谢物作为高关联度的代谢物集合展示在桑吉图上。
  • Chemical Taxonomy: 在物质分类上处于同一个分类集合中的其他代谢物
  • Chemical Reaction: 在化学反应过程中，存在为当前代谢物相关联的生化反应过程中的反应底物或者反应产物的关联代谢物信息。

点击图上的相关代谢物的名称，可以跳转到相关代谢物的信息页面。



文献列表

  • Jianan Wei, Junhong Zhang, Fengju Hu, Wenjuan Zhang, Yunshan Wu, Bo Liu, Yue Lu, Li Li, Ling Han, Chuanjian Lu. Anti-psoriasis effect of 18β-glycyrrhetinic acid by breaking CCL20/CCR6 axis through its vital active group targeting GUSB/ATF2 signaling. Phytomedicine : international journal of phytotherapy and phytopharmacology. 2024 Jun; 128(?):155524. doi: 10.1016/j.phymed.2024.155524. [PMID: 38552435]
  • Ibrahim Bayav, Ekrem Darendelioğlu, Cuneyt Caglayan. 18β-Glycyrrhetinic acid exerts cardioprotective effects against BPA-induced cardiotoxicity through antiapoptotic and antioxidant mechanisms. Journal of biochemical and molecular toxicology. 2024 Feb; 38(2):e23655. doi: 10.1002/jbt.23655. [PMID: 38348715]
  • Bo-Wen Pan, Liang-Liang Zheng, Yang Shi, Zhang-Chao Dong, Ting-Ting Feng, Jian Yang, Ying Wei, Ying Zhou. Synthesis and Antiviral and Antitumor Activities of Novel 18β-Glycyrrhetinic Acid Derivatives. International journal of molecular sciences. 2023 Oct; 24(19):. doi: 10.3390/ijms241915012. [PMID: 37834459]
  • Hanyue Luo, Caishi Zhang, Lujuan He, Zefang Lin, Ji-Chun Zhang, Qi Qi, Jia-Xu Chen, Wei Yao. 18β-glycyrrhetinic acid ameliorates MPTP-induced neurotoxicity in mice through activation of microglial anti-inflammatory phenotype. Psychopharmacology. 2023 Jul; ?(?):. doi: 10.1007/s00213-023-06415-6. [PMID: 37436491]
  • Xia Li, Xiao-Ling Ma, Yi Nan, Yu-Hua Du, Yi Yang, Dou-Dou Lu, Jun-Fei Zhang, Yan Chen, Lei Zhang, Yang Niu, Ling Yuan. 18β-glycyrrhetinic acid inhibits proliferation of gastric cancer cells through regulating the miR-345-5p/TGM2 signaling pathway. World journal of gastroenterology. 2023 Jun; 29(23):3622-3644. doi: 10.3748/wjg.v29.i23.3622. [PMID: 37398884]
  • Xia Li, Yuhua Du, Shicong Huang, Yi Yang, Doudou Lu, Junfei Zhang, Yan Chen, Lei Zhang, Yi Nan, Ling Yuan. Exploring the molecular mechanism of glycyrrhetinic acid in the treatment of gastric cancer based on network pharmacology and experimental validation. Aging. 2023 May; 15(9):3839-3856. doi: 10.18632/aging.204718. [PMID: 37171392]
  • W Caré, G Grenet, C Schmitt, S Michel, J Langrand, G Le Roux, D Vodovar. [Adverse effects of licorice consumed as food: An update]. La Revue de medecine interne. 2023 Mar; ?(?):. doi: 10.1016/j.revmed.2023.03.004. [PMID: 37005098]
  • Hany Khalil, Alaa H Nada, Hoda Mahrous, Amr Hassan, Patricia Rijo, Ibrahim A Ibrahim, Dalia D Mohamed, Fawziah A Al-Salmi, Doaa D Mohamed, Ahmed I Abd Elmaksoud. Amelioration effect of 18β-Glycyrrhetinic acid on methylation inhibitors in hepatocarcinogenesis -induced by diethylnitrosamine. Frontiers in immunology. 2023; 14(?):1206990. doi: 10.3389/fimmu.2023.1206990. [PMID: 38322013]
  • Fanli Shi, Ruilong Li, Wenjing Wang, Xiangyu Yu, Fenxia Zhu, Yiping Huang, Jing Wang, Zhenhai Zhang. Carboxymethyl starch as a solid dispersion carrier to enhance the dissolution and bioavailability of piperine and 18β-glycyrrhetinic acid. Drug development and industrial pharmacy. 2023 Jan; 49(1):30-41. doi: 10.1080/03639045.2023.2182120. [PMID: 36803327]
  • Yamei Jiang, Chengzhe Cai, Pingbao Zhang, Yongsheng Luo, Jingjing Guo, Jiawei Li, Ruiming Rong, Yi Zhang, Tongyu Zhu. Transcriptional profile changes after treatment of ischemia reperfusion injury-induced kidney fibrosis with 18β-glycyrrhetinic acid. Renal failure. 2022 Dec; 44(1):660-671. doi: 10.1080/0886022x.2022.2061998. [PMID: 35699239]
  • Cuneyt Caglayan, Fatih Mehmet Kandemir, Adnan Ayna, Cihan Gür, Sefa Küçükler, Ekrem Darendelioğlu. Neuroprotective effects of 18β-glycyrrhetinic acid against bisphenol A-induced neurotoxicity in rats: involvement of neuronal apoptosis, endoplasmic reticulum stress and JAK1/STAT1 signaling pathway. Metabolic brain disease. 2022 08; 37(6):1931-1940. doi: 10.1007/s11011-022-01027-z. [PMID: 35699857]
  • Zhangting Wang, Jiang Ma, Yisheng He, Kai-Kei Miu, Sheng Yao, Chunping Tang, Yang Ye, Ge Lin. Nrf2-mediated liver protection by 18β-glycyrrhetinic acid against pyrrolizidine alkaloid-induced toxicity through PI3K/Akt/GSK3β pathway. Phytomedicine : international journal of phytotherapy and phytopharmacology. 2022 Jul; 102(?):154162. doi: 10.1016/j.phymed.2022.154162. [PMID: 35598524]
  • Jia-Ling Wang, Hui Liu, Zhi-Cheng Jing, Fang Zhao, Ru Zhou. 18β-Glycyrrhetinic acid ameliorates endoplasmic reticulum stress-induced inflammation in pulmonary arterial hypertension through PERK/eIF2α/NF-κB signaling. The Chinese journal of physiology. 2022 Jul; 65(4):187-198. doi: 10.4103/0304-4920.354801. [PMID: 36073567]
  • Ling Yuan, Yi Yang, Xia Li, Xin Zhou, Yu-Hua Du, Wen-Jing Liu, Lei Zhang, Lei Yu, Ting-Ting Ma, Jia-Xin Li, Yan Chen, Yi Nan. 18β-glycyrrhetinic acid regulates mitochondrial ribosomal protein L35-associated apoptosis signaling pathways to inhibit proliferation of gastric carcinoma cells. World journal of gastroenterology. 2022 Jun; 28(22):2437-2456. doi: 10.3748/wjg.v28.i22.2437. [PMID: 35979263]
  • K Buvanesvaragurunathan, J Ganesh, S Nagul Kumar, V Porchezhiyan, A Radha, P Azhahianambi, P Pandikumar, S Ignacimuthu. In vitro growth inhibitory effect of selected 18β-glycyrrhetinic acid esters on Theileriaannulata. Experimental parasitology. 2022 May; 236-237(?):108258. doi: 10.1016/j.exppara.2022.108258. [PMID: 35421387]
  • Xiaoyan Wang, Fang Xie, Xiaofeng Zhou, Ting Chen, Ye Xue, Wei Wang. 18β-Glycyrrhetinic acid inhibits the apoptosis of cells infected with rotavirus SA11 via the Fas/FasL pathway. Pharmaceutical biology. 2021 Dec; 59(1):1098-1105. doi: 10.1080/13880209.2021.1961821. [PMID: 34411493]
  • Ibtesam S Alanazi, Mohamed Emam, Mabrouk Elsabagh, Saad Alkahtani, Mohamed M Abdel-Daim. The protective effects of 18β-glycyrrhetinic acid against acrylamide-induced cellular damage in diabetic rats. Environmental science and pollution research international. 2021 Nov; 28(41):58322-58330. doi: 10.1007/s11356-021-14742-4. [PMID: 34117542]
  • Tao Yang, Jing Zhou, Lei Fang, Minmin Wang, Maimaitiyiming Dilinuer, Aikemu Ainiwaer. Protection function of 18β-glycyrrhetinic acid on rats with high-altitude pulmonary hypertension based on 1H NMR metabonomics technology. Analytical biochemistry. 2021 10; 631(?):114342. doi: 10.1016/j.ab.2021.114342. [PMID: 34419454]
  • Shouyan Wu, Henglei Lu, Wenjie Wang, Luyao Song, Meng Liu, Yuhan Cao, Xinming Qi, Jianhua Sun, Likun Gong. Prevention of D-GalN/LPS-induced ALI by 18β-glycyrrhetinic acid through PXR-mediated inhibition of autophagy degradation. Cell death & disease. 2021 05; 12(5):480. doi: 10.1038/s41419-021-03768-8. [PMID: 33986260]
  • Kai-Xia Zhang, Peng-Ru Wang, Fei Chen, Xi-Jing Qian, Lin Jia, Xiao-Juan Liu, Lin Li, Yong-Sheng Jin. Synthesis and Anti-HCV Activities of 18β-Glycyrrhetinic Acid Derivatives and Their In-Silico ADMET Analysis. Current computer-aided drug design. 2021; 17(6):831-837. doi: 10.2174/1573409916666200827104008. [PMID: 32860363]
  • Min Huang, Ping Gong, Yuetong Wang, Xiaorui Xie, Zhuangshi Ma, Qihao Xu, Dan Liu, Yongkui Jing, Linxiang Zhao. Synthesis and antitumor effects of novel 18β-glycyrrhetinic acid derivatives featuring an exocyclic α,β-unsaturated carbonyl moiety in ring A. Bioorganic chemistry. 2020 10; 103(?):104187. doi: 10.1016/j.bioorg.2020.104187. [PMID: 32890994]
  • Meng Yang, Minyi Zhang, Qingli Liu, Tingting Xu, Tongling Huang, Dongsheng Yao, Chi-Wai Wong, Jinsong Liu, Min Guan. 18β-Glycyrrhetinic acid acts through hepatocyte nuclear factor 4 alpha to modulate lipid and carbohydrate metabolism. Pharmacological research. 2020 07; 157(?):104840. doi: 10.1016/j.phrs.2020.104840. [PMID: 32353589]
  • Xiaoli Cheng, Linwei Qiu, Fen Wang. 18α-Glycyrrhetinic acid (GA) ameliorates fructose-induced nephropathy in mice by suppressing oxidative stress, dyslipidemia and inflammation. Biomedicine & pharmacotherapy = Biomedecine & pharmacotherapie. 2020 May; 125(?):109702. doi: 10.1016/j.biopha.2019.109702. [PMID: 32106383]
  • Seon Yu Lee, Ji Hyun Jeong, Bo Na Kim, So Jung Park, Yang-Chun Park, Guk Yeo Lee. LC-MS/MS analysis of puerarin and 18β-glycyrrhetinic acid in human plasma after oral administration of Samso-eum and its application to pharmacokinetic study. Biomedical chromatography : BMC. 2020 Apr; 34(4):e4774. doi: 10.1002/bmc.4774. [PMID: 31813157]
  • Shao-Hua Xu, Hai-Lan Chen, Yong Fan, Wei Xu, Jian Zhang. Application of tandem biotransformation for biosynthesis of new pentacyclic triterpenoid derivatives with neuroprotective effect. Bioorganic & medicinal chemistry letters. 2020 02; 30(4):126947. doi: 10.1016/j.bmcl.2019.126947. [PMID: 31924497]
  • Haiming Chen, Huazhen Liu, Bin Tang, Yuchao Chen, Ling Han, Jingjie Yu, Yuhong Yan, Chuanjian Lu. The Protective Effects of 18β-Glycyrrhetinic Acid on Imiquimod-Induced Psoriasis in Mice via Suppression of mTOR/STAT3 Signaling. Journal of immunology research. 2020; 2020(?):1980456. doi: 10.1155/2020/1980456. [PMID: 32908937]
  • Meng Xiang, Xiang Zhou, Ting-Rong Luo, Pei-Yi Wang, Li-Wei Liu, Zhong Li, Zhi-Bing Wu, Song Yang. Design, Synthesis, Antibacterial Evaluation, and Induced Apoptotic Behaviors of Epimeric and Chiral 18β-Glycyrrhetinic Acid Ester Derivatives with an Isopropanolamine Bridge against Phytopathogens. Journal of agricultural and food chemistry. 2019 Dec; 67(48):13212-13220. doi: 10.1021/acs.jafc.9b06147. [PMID: 31702905]
  • Peng Zhang, Zhi Chang, Jiamei Yang, Jun Feng, Yang Yu, Yanmin Pei, Jialing Wang, Fang Zhao, Zhou Ru. Vasorelaxation effect of 18β-glycyrrhetinic acid on the thoracic aorta of rats: proposed mechanism. Die Pharmazie. 2019 12; 74(12):751-754. doi: 10.1691/ph.2019.9724. [PMID: 31907117]
  • Jennifer A Easton, Ahmad K Albuloushi, Miriam A F Kamps, Gladys H M R Brouns, Jos L V Broers, Barry J Coull, Vincent Oji, Michel van Geel, Maurice A M van Steensel, Patricia E Martin. A rare missense mutation in GJB3 (Cx31G45E) is associated with a unique cellular phenotype resulting in necrotic cell death. Experimental dermatology. 2019 10; 28(10):1106-1113. doi: 10.1111/exd.13542. [PMID: 29570224]
  • Juan Sun, Han-Yu Liu, Cheng-Zhi Lv, Jie Qin, Yuan-Feng Wu. Modification, Antitumor Activity, and Targeted PPARγ Study of 18β-Glycyrrhetinic Acid, an Important Active Ingredient of Licorice. Journal of agricultural and food chemistry. 2019 Aug; 67(34):9643-9651. doi: 10.1021/acs.jafc.9b03442. [PMID: 31390199]
  • A Kowalska, U Kalinowska-Lis. 18β-Glycyrrhetinic acid: its core biological properties and dermatological applications. International journal of cosmetic science. 2019 Aug; 41(4):325-331. doi: 10.1111/ics.12548. [PMID: 31166601]
  • Zih-Ying Li, Yu-Tang Tung, Sheng-Yi Chen, Gow-Chin Yen. Novel findings of 18β-glycyrrhetinic acid on sRAGE secretion through inhibition of transient receptor potential canonical channels in high-glucose environment. BioFactors (Oxford, England). 2019 Jul; 45(4):607-615. doi: 10.1002/biof.1517. [PMID: 31120605]
  • Boyi Fan, Baocheng Jiang, Sensen Yan, Bohui Xu, Huilian Huang, Guangtong Chen. Anti-Inflammatory 18β-Glycyrrhetinin Acid Derivatives Produced by Biocatalysis. Planta medica. 2019 Jan; 85(1):56-61. doi: 10.1055/a-0662-0296. [PMID: 30086557]
  • Shou-Yan Wu, Shi-Chao Cui, Le Wang, Yi-Ting Zhang, Xiao-Xia Yan, Heng-Lei Lu, Guo-Zhen Xing, Jin Ren, Li-Kun Gong. 18β-Glycyrrhetinic acid protects against alpha-naphthylisothiocyanate-induced cholestasis through activation of the Sirt1/FXR signaling pathway. Acta pharmacologica Sinica. 2018 Dec; 39(12):1865-1873. doi: 10.1038/s41401-018-0110-y. [PMID: 30061734]
  • Suat Kamisli, Osman Ciftci, Asli Taslidere, Nese Basak Turkmen, Cemal Ozcan. The beneficial effects of 18β-glycyrrhetinic acid on the experimental autoimmune encephalomyelitis (EAE) in C57BL/6 mouse model. Immunopharmacology and immunotoxicology. 2018 Aug; 40(4):344-352. doi: 10.1080/08923973.2018.1490318. [PMID: 30052483]
  • Jin Chen, Zhao-Qi Zhang, Jia Song, Qiu-Meng Liu, Chao Wang, Zhao Huang, Liang Chu, Hui-Fang Liang, Bi-Xiang Zhang, Xiao-Ping Chen. 18β-Glycyrrhetinic-acid-mediated unfolded protein response induces autophagy and apoptosis in hepatocellular carcinoma. Scientific reports. 2018 06; 8(1):9365. doi: 10.1038/s41598-018-27142-5. [PMID: 29921924]
  • Zehe Ge, Haipeng Diao, Xiaoli Ji, Qingping Liu, Xiaoyan Zhang, Qing Wu. Gap junctional intercellular communication and endoplasmic reticulum stress regulate chronic cadmium exposure induced apoptosis in HK-2 cells. Toxicology letters. 2018 May; 288(?):35-43. doi: 10.1016/j.toxlet.2018.02.013. [PMID: 29444456]
  • Hidayat Hussain, Ivan R Green, Umair Shamraiz, Muhammad Saleem, Amin Badshah, Ghulam Abbas, Najeeb Ur Rehman, Muhammad Irshad. Therapeutic potential of glycyrrhetinic acids: a patent review (2010-2017). Expert opinion on therapeutic patents. 2018 05; 28(5):383-398. doi: 10.1080/13543776.2018.1455828. [PMID: 29558289]
  • Rosanna Marsella, Luisa Cornegliani, Ibrahim Ozmen, Mary Bohannon, Kim Ahrens, Domenico Santoro. Randomized, double-blinded, placebo-controlled pilot study on the effects of topical blackcurrant emulsion enriched in essential fatty acids, ceramides and 18-beta glycyrrhetinic acid on clinical signs and skin barrier function in dogs with atopic dermatitis. Veterinary dermatology. 2017 Dec; 28(6):577-e140. doi: 10.1111/vde.12467. [PMID: 28736984]
  • Yu-Qi Sun, Chun-Mei Dai, Yan Zheng, Shu-Dan Shi, Hai-Yang Hu, Da-Wei Chen. Binding effect of fluorescence labeled glycyrrhetinic acid with GA receptors in hepatocellular carcinoma cells. Life sciences. 2017 Nov; 188(?):186-191. doi: 10.1016/j.lfs.2017.07.032. [PMID: 28768154]
  • Ayman M Mahmoud, Omnia E Hussein, Walaa G Hozayen, Sanaa M Abd El-Twab. Methotrexate hepatotoxicity is associated with oxidative stress, and down-regulation of PPARγ and Nrf2: Protective effect of 18β-Glycyrrhetinic acid. Chemico-biological interactions. 2017 May; 270(?):59-72. doi: 10.1016/j.cbi.2017.04.009. [PMID: 28414158]
  • Rui He, Yongsong Xu, Jingjing Peng, Tingting Ma, Jing Li, Muxin Gong. The effects of 18β-glycyrrhetinic acid and glycyrrhizin on intestinal absorption of paeoniflorin using the everted rat gut sac model. Journal of natural medicines. 2017 Jan; 71(1):198-207. doi: 10.1007/s11418-016-1049-2. [PMID: 27747446]
  • Md Ataur Rahman, Kausik Bishayee, Khadija Habib, Ali Sadra, Sung-Oh Huh. 18α-Glycyrrhetinic acid lethality for neuroblastoma cells via de-regulating the Beclin-1/Bcl-2 complex and inducing apoptosis. Biochemical pharmacology. 2016 10; 117(?):97-112. doi: 10.1016/j.bcp.2016.08.006. [PMID: 27520483]
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  • Yi Zhu, Yong Gao, Caroline Tao, Mengle Shao, Shangang Zhao, Wei Huang, Ting Yao, Joshua A Johnson, Tiemin Liu, Aaron M Cypess, Olga Gupta, William L Holland, Rana K Gupta, David C Spray, Herbert B Tanowitz, Lei Cao, Matthew D Lynes, Yu-Hua Tseng, Joel K Elmquist, Kevin W Williams, Hua V Lin, Philipp E Scherer. Connexin 43 Mediates White Adipose Tissue Beiging by Facilitating the Propagation of Sympathetic Neuronal Signals. Cell metabolism. 2016 09; 24(3):420-433. doi: 10.1016/j.cmet.2016.08.005. [PMID: 27626200]
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  • Taotao Ma, Cheng Huang, Xiaoming Meng, Xiaofeng Li, Yilong Zhang, Shuai Ji, Jun Li, Min Ye, Hong Liang. A potential adjuvant chemotherapeutics, 18β-glycyrrhetinic acid, inhibits renal tubular epithelial cells apoptosis via enhancing BMP-7 epigenetically through targeting HDAC2. Scientific reports. 2016 05; 6(?):25396. doi: 10.1038/srep25396. [PMID: 27145860]
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