Chebulagic acid (BioDeep_00000003754)

 

Secondary id: BioDeep_00000177221, BioDeep_00000230706

PANOMIX_OTCML-2023


代谢物信息卡片


chebulagic acid

化学式: C41H30O27 (954.097443)
中文名称: 诃子鞣酸
谱图信息: 最多检出来源 Escherichia coli(natural_products) 50%

Reviewed

Last reviewed on 2024-09-27.

Cite this Page

Chebulagic acid. BioDeep Database v3. PANOMIX ltd, a top metabolomics service provider from China. https://query.biodeep.cn/s/chebulagic_acid (retrieved 2024-11-08) (BioDeep RN: BioDeep_00000003754). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

分子结构信息

SMILES: C1C2C3C(C(C(O2)OC(=O)C4=CC(=C(C(=C4)O)O)O)OC(=O)C5=CC(=C(C6=C5C(C(C(=O)O3)CC(=O)O)C(C(=O)O6)O)O)O)OC(=O)C7=CC(=C(C(=C7C8=C(C(=C(C=C8C(=O)O1)O)O)O)O)O)O
InChI: InChI=1S/C41H30O27/c42-13-1-8(2-14(43)24(13)49)35(56)68-41-34-33-31(64-39(60)12(6-19(47)48)22-23-11(38(59)67-34)5-17(46)27(52)32(23)65-40(61)30(22)55)18(63-41)7-62-36(57)9-3-15(44)25(50)28(53)20(9)21-10(37(58)66-33)4-16(45)26(51)29(21)54/h1-5,12,18,22,30-31,33-34,41-46,49-55H,6-7H2,(H,47,48)

描述信息

D000970 - Antineoplastic Agents > D059003 - Topoisomerase Inhibitors > D059004 - Topoisomerase I Inhibitors
D004791 - Enzyme Inhibitors > D016859 - Lipoxygenase Inhibitors
Chebulagic acid is a COX-LOX dual inhibitor isolated from the fruits of Terminalia chebula Retz, on angiogenesis. Chebulagic acid is a M2 serine to asparagine 31 mutation (S31N) inhibitor and influenza antiviral. Chebulagic acid also against SARS-CoV-2 viral replication with an EC50 of 9.76 μM.
Chebulagic acid is a COX-LOX dual inhibitor isolated from the fruits of Terminalia chebula Retz, on angiogenesis. Chebulagic acid is a M2 serine to asparagine 31 mutation (S31N) inhibitor and influenza antiviral. Chebulagic acid also against SARS-CoV-2 viral replication with an EC50 of 9.76 μM.

Chebulagic acid. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=23094-71-5 (retrieved 2024-09-27) (CAS RN: 23094-71-5). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

同义名列表

3 个代谢物同义名

chebulagic acid; CID 442674; CID 250397



数据库引用编号

13 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)

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

  • Daniel Pushparaju Yeggoni, Manjunath Meti, Rajagopal Subramanyam. Chebulinic and chebulagic acid binding with serum proteins: biophysical and molecular docking approach. Journal of biomolecular structure & dynamics. 2022 Apr; ?(?):1-16. doi: 10.1080/07391102.2022.2060862. [PMID: 35403561]
  • Ganesh Vasu, Ramalingam Sundaram, Karuppiah Muthu. Chebulagic acid attenuates HFD/streptozotocin induced impaired glucose metabolism and insulin resistance via up regulations of PPAR γ and GLUT 4 in type 2 diabetic rats. Toxicology mechanisms and methods. 2022 Mar; 32(3):159-170. doi: 10.1080/15376516.2021.1976333. [PMID: 34470562]
  • Vishal S Patil, Darasaguppe R Harish, Umashankar Vetrivel, Subarna Roy, Sanjay H Deshpande, Harsha V Hegde. Hepatitis C Virus NS3/4A Inhibition and Host Immunomodulation by Tannins from Terminalia chebula: A Structural Perspective. Molecules (Basel, Switzerland). 2022 Feb; 27(3):. doi: 10.3390/molecules27031076. [PMID: 35164341]
  • Ruikun Du, Laura Cooper, Zinuo Chen, Hyun Lee, Lijun Rong, Qinghua Cui. Discovery of chebulagic acid and punicalagin as novel allosteric inhibitors of SARS-CoV-2 3CLpro. Antiviral research. 2021 06; 190(?):105075. doi: 10.1016/j.antiviral.2021.105075. [PMID: 33872675]
  • Maggie C Duncan, Pascal Amoa Onguéné, Ibuki Kihara, Derrick N Nebangwa, Maya E Naidu, David E Williams, Aruna D Balgi, Kerstin Andrae-Marobela, Michel Roberge, Raymond J Andersen, Masahiro Niikura, Fidele Ntie-Kang, Ian Tietjen. Virtual Screening Identifies Chebulagic Acid as an Inhibitor of the M2(S31N) Viral Ion Channel and Influenza A Virus. Molecules (Basel, Switzerland). 2020 Jun; 25(12):. doi: 10.3390/molecules25122903. [PMID: 32599753]
  • Chandran S Abhinand, Prabhakaran A Athira, Sasikumar J Soumya, Perumana R Sudhakaran. Multiple Targets Directed Multiple Ligands: An In Silico and In Vitro Approach to Evaluating the Effect of Triphala on Angiogenesis. Biomolecules. 2020 01; 10(2):. doi: 10.3390/biom10020177. [PMID: 31979409]
  • Palika Wetchakul, Jo Aan Goon, Ademola Ezekiel Adekoya, Opeyemi Joshua Olatunji, Sutticha Ruangchuay, Patcharawalai Jaisamut, Acharaporn Issuriya, Nongluk Kunworarath, Surasak Limsuwan, Sasitorn Chusri. Traditional tonifying polyherbal infusion, Jatu-Phala-Tiga, exerts antioxidant activities and extends lifespan of Caenorhabditis elegans. BMC complementary and alternative medicine. 2019 Aug; 19(1):209. doi: 10.1186/s12906-019-2626-1. [PMID: 31409340]
  • Ying Lu, Huiyu Yan, Shiyong Teng, Xige Yang. A liquid chromatography-tandem mass spectrometry method for preclinical pharmacokinetics and tissue distribution of hydrolyzable tannins chebulinic acid and chebulagic acid in rats. Biomedical chromatography : BMC. 2019 Mar; 33(3):e4425. doi: 10.1002/bmc.4425. [PMID: 30397912]
  • Sivasankar Shanmuganathan, Narayanasamy Angayarkanni. Chebulagic acid and Chebulinic acid inhibit TGF-β1 induced fibrotic changes in the chorio-retinal endothelial cells by inhibiting ERK phosphorylation. Microvascular research. 2019 01; 121(?):14-23. doi: 10.1016/j.mvr.2018.09.001. [PMID: 30189210]
  • Sivasankar Shanmuganathan, Narayanasamy Angayarkanni. Chebulagic acid Chebulinic acid and Gallic acid, the active principles of Triphala, inhibit TNFα induced pro-angiogenic and pro-inflammatory activities in retinal capillary endothelial cells by inhibiting p38, ERK and NFkB phosphorylation. Vascular pharmacology. 2018 09; 108(?):23-35. doi: 10.1016/j.vph.2018.04.005. [PMID: 29678603]
  • Ajay Kesharwani, Suja Kizhiyedath Polachira, Reshmi Nair, Aakanksha Agarwal, Nripendra Nath Mishra, Satish Kumar Gupta. Anti-HSV-2 activity of Terminalia chebula Retz extract and its constituents, chebulagic and chebulinic acids. BMC complementary and alternative medicine. 2017 Feb; 17(1):110. doi: 10.1186/s12906-017-1620-8. [PMID: 28196487]
  • Kai Lu, Sujit Basu. The natural compound chebulagic acid inhibits vascular endothelial growth factor A mediated regulation of endothelial cell functions. Scientific reports. 2015 Apr; 5(?):9642. doi: 10.1038/srep09642. [PMID: 25859636]
  • Shanmuganathan Sivasankar, Ramu Lavanya, Pemaiah Brindha, Narayanasamy Angayarkanni. Aqueous and alcoholic extracts of Triphala and their active compounds chebulagic acid and chebulinic acid prevented epithelial to mesenchymal transition in retinal pigment epithelial cells, by inhibiting SMAD-3 phosphorylation. PloS one. 2015; 10(3):e0120512. doi: 10.1371/journal.pone.0120512. [PMID: 25793924]
  • Gangadharan Leela Shyni, Sasidharan Kavitha, Sasidharan Indu, Anil Das Arya, Sasidharan Suseela Anusree, Vadavanath Prabhakaran Vineetha, Sankar Vandana, Andikannu Sundaresan, Kozhiparambil Gopalan Raghu. Chebulagic acid from Terminalia chebula enhances insulin mediated glucose uptake in 3T3-L1 adipocytes via PPARγ signaling pathway. BioFactors (Oxford, England). 2014 Nov; 40(6):646-57. doi: 10.1002/biof.1193. [PMID: 25529897]
  • Won Jeong Lee, Jae Sun Moon, Sung In Kim, Young Tae Kim, Oyekanmi Nash, Yong-Sun Bahn, Sung Uk Kim. Inhibition of the calcineurin pathway by two tannins, chebulagic acid and chebulanin, isolated from Harrisonia abyssinica Oliv. Journal of microbiology and biotechnology. 2014 Oct; 24(10):1377-81. doi: 10.4014/jmb.1405.05030. [PMID: 25001554]
  • Naresh Kumar, D Gangappa, Geetika Gupta, Roy Karnati. Chebulagic acid from Terminalia chebula causes G1 arrest, inhibits NFκB and induces apoptosis in retinoblastoma cells. BMC complementary and alternative medicine. 2014 Aug; 14(?):319. doi: 10.1186/1472-6882-14-319. [PMID: 25169718]
  • Kenneth T Kongstad, Sileshi G Wubshet, Ane Johannesen, Lasse Kjellerup, Anne-Marie Lund Winther, Anna Katharina Jäger, Dan Staerk. High-resolution screening combined with HPLC-HRMS-SPE-NMR for identification of fungal plasma membrane H(+)-ATPase inhibitors from plants. Journal of agricultural and food chemistry. 2014 Jun; 62(24):5595-602. doi: 10.1021/jf501605z. [PMID: 24830509]
  • Yoko Miyasaki, John D Rabenstein, Joshua Rhea, Marie-Laure Crouch, Ulla M Mocek, Patricia Emmett Kittell, Margie A Morgan, Wesley Stephen Nichols, M M Van Benschoten, William David Hardy, George Y Liu. Isolation and characterization of antimicrobial compounds in plant extracts against multidrug-resistant Acinetobacter baumannii. PloS one. 2013; 8(4):e61594. doi: 10.1371/journal.pone.0061594. [PMID: 23630600]
  • Baoru Yang, Maaria Kortesniemi, Pengzhan Liu, Maarit Karonen, Juha-Pekka Salminen. Analysis of hydrolyzable tannins and other phenolic compounds in emblic leafflower (Phyllanthus emblica L.) fruits by high performance liquid chromatography-electrospray ionization mass spectrometry. Journal of agricultural and food chemistry. 2012 Sep; 60(35):8672-83. doi: 10.1021/jf302925v. [PMID: 22889097]
  • Indu Sasidharan, A Sundaresan, V M Nisha, Mahesh S Kirishna, K G Raghu, P Jayamurthy. Inhibitory effect of Terminalia chebula Retz. fruit extracts on digestive enzyme related to diabetes and oxidative stress. Journal of enzyme inhibition and medicinal chemistry. 2012 Aug; 27(4):578-86. doi: 10.3109/14756366.2011.603130. [PMID: 22512724]
  • V Patil, A Bandivadekar, D Debjani. Inhibition of Propionibacterium acnes lipase by extracts of Indian medicinal plants. International journal of cosmetic science. 2012 Jun; 34(3):234-9. doi: 10.1111/j.1468-2494.2012.00706.x. [PMID: 22268921]
  • Yuttana Sudjaroen, William E Hull, Gerhard Erben, Gerd Würtele, Supranee Changbumrung, Cornelia M Ulrich, Robert W Owen. Isolation and characterization of ellagitannins as the major polyphenolic components of Longan (Dimocarpus longan Lour) seeds. Phytochemistry. 2012 May; 77(?):226-37. doi: 10.1016/j.phytochem.2011.12.008. [PMID: 22277734]
  • Yongxin Li, Shanjiang Yu, Dong Liu, Peter Proksch, Wenhan Lin. Inhibitory effects of polyphenols toward HCV from the mangrove plant Excoecaria agallocha L. Bioorganic & medicinal chemistry letters. 2012 Jan; 22(2):1099-102. doi: 10.1016/j.bmcl.2011.11.109. [PMID: 22196120]
  • Vijaya Ravinayagam, Ravindran Jaganathan, Sachdanandam Panchanadham, Shanthi Palanivelu. Potential Antioxidant Role of Tridham in Managing Oxidative Stress against Aflatoxin-B(1)-Induced Experimental Hepatocellular Carcinoma. International journal of hepatology. 2012; 2012(?):428373. doi: 10.1155/2012/428373. [PMID: 22518320]
  • Yi-Na Huang, Dong-Dong Zhao, Bo Gao, Kai Zhong, Rui-Xue Zhu, Yan Zhang, Wang-Jun Xie, Li-Rong Jia, Hong Gao. Anti-hyperglycemic effect of chebulagic acid from the fruits of Terminalia chebula Retz. International journal of molecular sciences. 2012; 13(5):6320-6333. doi: 10.3390/ijms13056320. [PMID: 22754367]
  • Hsin-Ying Chuang, Lean-Teik Ng, Liang-Tzung Lin, Jung-San Chang, Jen-Yang Chen, Ta-Chen Lin, Chun-Ching Lin. Hydrolysable tannins of tropical almond show antifibrotic effects in TGF-β1-induced hepatic stellate cells. Journal of the science of food and agriculture. 2011 Dec; 91(15):2777-84. doi: 10.1002/jsfa.4521. [PMID: 21725979]
  • Joon Ha Park, Han Seung Joo, Ki-Yeon Yoo, Bich Na Shin, In Hye Kim, Choong Hyun Lee, Jung Hoon Choi, Kyunghee Byun, Bonghee Lee, Soon Sung Lim, Myong Jo Kim, Moo-Ho Won. Extract from Terminalia chebula seeds protect against experimental ischemic neuronal damage via maintaining SODs and BDNF levels. Neurochemical research. 2011 Nov; 36(11):2043-50. doi: 10.1007/s11064-011-0528-9. [PMID: 21667226]
  • Surender Singh, Vinod Nair, Y K Gupta. Antiarthritic activity of majoon suranjan (a polyherbal Unani formulation) in rat. The Indian journal of medical research. 2011 Sep; 134(?):384-8. doi: ". [PMID: 21985823]
  • Anh Thu Pham, Karl Egil Malterud, Berit Smestad Paulsen, Drissa Diallo, Helle Wangensteen. DPPH radical scavenging and xanthine oxidase inhibitory activity of Terminalia macroptera leaves. Natural product communications. 2011 Aug; 6(8):1125-8. doi: . [PMID: 21922915]
  • Xiuping Chen, Fangyun Sun, Lifeng Ma, Jinhua Wang, Hailin Qin, Guanhua Du. In vitro evaluation on the antioxidant capacity of triethylchebulate, an aglycone from Terminalia chebula Retz fruit. Indian journal of pharmacology. 2011 May; 43(3):320-3. doi: 10.4103/0253-7613.81508. [PMID: 21713099]
  • Sunil Kumar, Smita Narwal, Vipin Kumar, Om Prakash. α-glucosidase inhibitors from plants: A natural approach to treat diabetes. Pharmacognosy reviews. 2011 Jan; 5(9):19-29. doi: 10.4103/0973-7847.79096. [PMID: 22096315]
  • Aranya Manosroi, Pensak Jantrawut, Hiroyuki Akazawa, Toshihiro Akihisa, Jiradej Manosroi. Biological activities of phenolic compounds isolated from galls of Terminalia chebula Retz. (Combretaceae). Natural product research. 2010 Dec; 24(20):1915-26. doi: 10.1080/14786419.2010.488631. [PMID: 21108118]
  • Uma Ranjan Lal, Shailendra Mani Tripathi, Sanjay M Jachak, Kamlesh Kumar Bhutani, Inder Pal Singh. Chemical changes during fermentation of Abhayarishta and its standardization by HPLC-DAD. Natural product communications. 2010 Apr; 5(4):575-9. doi: . [PMID: 20433076]
  • Takashi Yoshida, Yoshiaki Amakura, Morio Yoshimura. Structural features and biological properties of ellagitannins in some plant families of the order Myrtales. International journal of molecular sciences. 2010 Jan; 11(1):79-106. doi: 10.3390/ijms11010079. [PMID: 20162003]
  • S Kinoshita, Y Inoue, S Nakama, T Ichiba, Y Aniya. Antioxidant and hepatoprotective actions of medicinal herb, Terminalia catappa L. from Okinawa Island and its tannin corilagin. Phytomedicine : international journal of phytotherapy and phytopharmacology. 2007 Nov; 14(11):755-62. doi: 10.1016/j.phymed.2006.12.012. [PMID: 17293097]
  • Quanbin Han, Jingzheng Song, Chunfeng Qiao, Lina Wong, Hongxi Xu. Preparative isolation of hydrolysable tannins chebulagic acid and chebulinic acid from Terminalia chebula by high-speed counter-current chromatography. Journal of separation science. 2006 Jul; 29(11):1653-7. doi: 10.1002/jssc.200600089. [PMID: 16922284]
  • Akira Murakami, Hisashi Ishida, Kimie Kobo, Ikuyo Furukawa, Yasutaka Ikeda, Megumi Yonaha, Yohko Aniya, Hajime Ohigashi. Suppressive effects of Okinawan food items on free radical generation from stimulated leukocytes and identification of some active constituents: implications for the prevention of inflammation-associated carcinogenesis. Asian Pacific journal of cancer prevention : APJCP. 2005 Oct; 6(4):437-48. doi: . [PMID: 16435988]
  • Sang-Ik Lee, Pung-Mi Hyun, Seung-Hyung Kim, Kyoung-Shin Kim, Sang-Keun Lee, Byoung-Soo Kim, Pil Jae Maeng, Jong-Soon Lim. Suppression of the onset and progression of collagen-induced arthritis by chebulagic acid screened from a natural product library. Arthritis and rheumatism. 2005 Jan; 52(1):345-53. doi: 10.1002/art.20715. [PMID: 15641090]
  • Bruno Fogliani, Phila Raharivelomanana, Jean-Pierre Bianchini, Saliou Bouraïma-Madjèbi, Edouard Hnawia. Bioactive ellagitannins from Cunonia macrophylla, an endemic Cunoniaceae from New Caledonia. Phytochemistry. 2005 Jan; 66(2):241-7. doi: 10.1016/j.phytochem.2004.11.016. [PMID: 15652581]
  • Lih-Jeng Juang, Shuenn-Jyi Sheu, Ta-Chen Lin. Determination of hydrolyzable tannins in the fruit of Terminalia chebula Retz. by high-performance liquid chromatography and capillary electrophoresis. Journal of separation science. 2004 Jun; 27(9):718-24. doi: 10.1002/jssc.200401741. [PMID: 15387468]
  • Lan-zhen Zhang, Wen-hua Zhao, Ya-jian Guo, Guang-zhong Tu, Shu Lin, Lin-guang Xin. [Studies on chemical constituents in fruits of Tibetan medicine Phyllanthus emblica]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2003 Oct; 28(10):940-3. doi: . [PMID: 15620182]
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  • S Hamada, T Kataoka, J T Woo, A Yamada, T Yoshida, T Nishimura, N Otake, K Nagai. Immunosuppressive effects of gallic acid and chebulagic acid on CTL-mediated cytotoxicity. Biological & pharmaceutical bulletin. 1997 Sep; 20(9):1017-9. doi: 10.1248/bpb.20.1017. [PMID: 9331989]
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