Chebulinic acid (BioDeep_00000003756)

 

Secondary id: BioDeep_00000230707

PANOMIX_OTCML-2023 natural product


代谢物信息卡片


2-[(4R,5S,7R,8R,11S,12S,13S,21S)-13,17,18-trihydroxy-2,10,14-trioxo-5,21-bis[(3,4,5-trihydroxybenzoyl)oxy]-7-[(3,4,5-trihydroxybenzoyl)oxymethyl]-3,6,9,15-tetraoxatetracyclo[10.7.1.14,8.016,20]henicosa-1(19),16(20),17-trien-11-yl]acetic acid

化学式: C41H32O27 (956.1130922)
中文名称: 诃子林鞣酸
谱图信息: 最多检出来源 Astragalus membranaceus(otcml) 10%

Reviewed

Last reviewed on 2024-09-27.

Cite this Page

Chebulinic acid. BioDeep Database v3. PANOMIX ltd, a top metabolomics service provider from China. https://query.biodeep.cn/s/chebulinic_acid (retrieved 2024-11-05) (BioDeep RN: BioDeep_00000003756). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

分子结构信息

SMILES: C1=C(C=C(C(=C1O)O)O)C(=O)OCC2C3C(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(=C7)O)O)O
InChI: InChI=1S/C41H32O27/c42-15-1-10(2-16(43)26(15)51)35(56)62-9-22-31-33(66-36(57)11-3-17(44)27(52)18(45)4-11)34(41(63-22)68-37(58)12-5-19(46)28(53)20(47)6-12)67-38(59)13-7-21(48)29(54)32-25(13)24(30(55)40(61)65-32)14(8-23(49)50)39(60)64-31/h1-7,14,22,24,30-31,33-34,41-48,51-55H,8-9H2,(H,49,50)

描述信息

Chebulinic acid. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=18942-26-2 (retrieved 2024-09-27) (CAS RN: 18942-26-2). 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

2-[(4R,5S,7R,8R,11S,12S,13S,21S)-13,17,18-trihydroxy-2,10,14-trioxo-5,21-bis[(3,4,5-trihydroxybenzoyl)oxy]-7-[(3,4,5-trihydroxybenzoyl)oxymethyl]-3,6,9,15-tetraoxatetracyclo[10.7.1.14,8.016,20]henicosa-1(19),16(20),17-trien-11-yl]acetic acid; Chebulinic acid; CID 250396



数据库引用编号

11 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)

14 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

  • Mohd Waseem, Shubhashis Das, Debarati Mondal, Monika Jain, Jitendra K Thakur, Naidu Subbarao. Identification of novel inhibitors against Med15a KIX domain of Candida glabrata. International journal of biological macromolecules. 2023 Dec; 253(Pt 2):126720. doi: 10.1016/j.ijbiomac.2023.126720. [PMID: 37678676]
  • Aashima, Mehak Rathi, Shilpi, Akash, Kamaljeet Kaur, Priyanka Kriplani, Kumar Guarve. Chebulinic Acid: An Incipient Anticancer Agent. Recent patents on anti-cancer drug discovery. 2023 Aug; ?(?):. doi: 10.2174/1574892819666230821110429. [PMID: 37605424]
  • Kriti Sharma, Shiv Kumar, Ravi Prakash, Sonu Khanka, Tripti Mishra, Rajat Rathur, Arpon Biswas, Sarvesh Kumar Verma, R S Bhatta, T Narender, Divya Singh. Chebulinic acid alleviates LPS-induced inflammatory bone loss by targeting the crosstalk between reactive oxygen species/NFκB signaling in osteoblast cells. Free radical biology & medicine. 2023 01; 194(?):99-113. doi: 10.1016/j.freeradbiomed.2022.11.026. [PMID: 36423891]
  • Naiju Thomas, Poonam Patil, Anjana Sharma, Sandeep Kumar, Vikas Kumar Singh, Kalichamy Alagarasu, Deepti Parashar, Suman Tapryal. Studies on the antiviral activity of chebulinic acid against dengue and chikungunya viruses and in silico investigation of its mechanism of inhibition. Scientific reports. 2022 06; 12(1):10397. doi: 10.1038/s41598-022-13923-6. [PMID: 35729191]
  • Eshetu M Bobasa, Anh Dao Thi Phan, Michael E Netzel, Daniel Cozzolino, Yasmina Sultanbawa. Hydrolysable tannins in Terminalia ferdinandiana Exell fruit powder and comparison of their functional properties from different solvent extracts. Food chemistry. 2021 Oct; 358(?):129833. doi: 10.1016/j.foodchem.2021.129833. [PMID: 33933967]
  • Xin-Hong Feng, Hai-Yan Xu, Jian-Ye Wang, Shen Duan, Ying-Chun Wang, Chao-Mei Ma. In vivo hepatoprotective activity and the underlying mechanism of chebulinic acid from Terminalia chebula fruit. Phytomedicine : international journal of phytotherapy and phytopharmacology. 2021 Mar; 83(?):153479. doi: 10.1016/j.phymed.2021.153479. [PMID: 33561764]
  • 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]
  • Min Wang, Yanru Li, Xianda Hu. Chebulinic acid derived from triphala is a promising antitumour agent in human colorectal carcinoma cell lines. BMC complementary and alternative medicine. 2018 Dec; 18(1):342. doi: 10.1186/s12906-018-2412-5. [PMID: 30587184]
  • 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]
  • Ji Hoon Song, Myoung-Sook Shin, Gwi Seo Hwang, Seong Taek Oh, Jung Jin Hwang, Ki Sung Kang. Chebulinic acid attenuates glutamate-induced HT22 cell death by inhibiting oxidative stress, calcium influx and MAPKs phosphorylation. Bioorganic & medicinal chemistry letters. 2018 02; 28(3):249-253. doi: 10.1016/j.bmcl.2017.12.062. [PMID: 29317168]
  • Indrani Kar, Rajagopal Chattopadhyaya. Effect of seven Indian plant extracts on Fenton reaction-mediated damage to DNA constituents. Journal of biomolecular structure & dynamics. 2017 Nov; 35(14):2997-3011. doi: 10.1080/07391102.2016.1244493. [PMID: 27691720]
  • 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]
  • 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]
  • Vaibhav Mishra, Manali Agrawal, Samuel Adetunji Onasanwo, Gaurav Madhur, Preeti Rastogi, Haushila Prasad Pandey, Gautam Palit, Tadigoppula Narender. Anti-secretory and cyto-protective effects of chebulinic acid isolated from the fruits of Terminalia chebula on gastric ulcers. Phytomedicine : international journal of phytotherapy and phytopharmacology. 2013 Apr; 20(6):506-11. doi: 10.1016/j.phymed.2013.01.002. [PMID: 23462212]
  • 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]
  • 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]
  • Kai Lu, Debanjan Chakroborty, Chandrani Sarkar, Tingting Lu, Zhiliang Xie, Zhongfa Liu, Sujit Basu. Triphala and its active constituent chebulinic acid are natural inhibitors of vascular endothelial growth factor-a mediated angiogenesis. PloS one. 2012; 7(8):e43934. doi: 10.1371/journal.pone.0043934. [PMID: 22937129]
  • 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]
  • 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]
  • Nahida Tabassum, Feroz Ahmad. Role of natural herbs in the treatment of hypertension. Pharmacognosy reviews. 2011 Jan; 5(9):30-40. doi: 10.4103/0973-7847.79097. [PMID: 22096316]
  • 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]
  • Hari Prasad Devkota, Purusotam Basnet, Shoji Yahara. A new phenolic compound, 4-dehydrochebulic acid-1,6-dimethyl ester from Sapium insigne leaves. Journal of natural medicines. 2010 Apr; 64(2):191-3. doi: 10.1007/s11418-009-0378-9. [PMID: 20037803]
  • V Maruthappan, K Sakthi Shree. Hypolipidemic activity of haritaki (terminalia chebula) in atherogenic diet induced hyperlipidemic rats. Journal of advanced pharmaceutical technology & research. 2010 Apr; 1(2):229-35. doi: ". [PMID: 22247850]
  • 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]
  • K K Dholwani, A K Saluja, A R Gupta, D R Shah. A review on plant-derived natural products and their analogs with anti-tumor activity. Indian journal of pharmacology. 2008 Mar; 40(2):49-58. doi: 10.4103/0253-7613.41038. [PMID: 21279166]
  • 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]
  • 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]
  • A Vonshak, O Barazani, P Sathiyamoorthy, R Shalev, D Vardy, A Golan-Goldhirsh. Screening South Indian medicinal plants for antifungal activity against cutaneous pathogens. Phytotherapy research : PTR. 2003 Nov; 17(9):1123-5. doi: 10.1002/ptr.1399. [PMID: 14595602]
  • 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]
  • Ammar Saleem, Michael Husheem, Pirkko Härkönen, Kalevi Pihlaja. Inhibition of cancer cell growth by crude extract and the phenolics of Terminalia chebula retz. fruit. Journal of ethnopharmacology. 2002 Aug; 81(3):327-36. doi: 10.1016/s0378-8741(02)00099-5. [PMID: 12127233]
  • Olga Silva, Eugénia Ferreira, M Vaz Pato, Manuela Caniça, Elsa T Gomes. In vitro anti-Neisseria gonorrhoeae activity of Terminalia macroptera leaves. FEMS microbiology letters. 2002 Jun; 211(2):203-6. doi: 10.1111/j.1574-6968.2002.tb11225.x. [PMID: 12076813]
  • G Ding, Y R Lu, C R Ji, Y Z Liu. [Analysis of tannins in Fructus Chebulae and its confusion varieties by HPCE]. Yao xue xue bao = Acta pharmaceutica Sinica. 2001 Apr; 36(4):292-5. doi: ". [PMID: 12580059]
  • G Ding, Y Liu, W Wang. [Assay of three hydrolyzable tannins in Fructus Chebulae from different habitats by RP-HPLC]. Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials. 2000 Jun; 23(6):328-30. doi: ". [PMID: 12575084]
  • K Schumacher. [Proceedings: Disorders in the cellular immunity]. Medizinische Klinik. 1975 Jun; 70(23):1009. doi: NULL. [PMID: 1636]