Chebulinic acid
Chebulinic acid (CAS 18942-26-2), a hydrolyzable tannin isolated from Terminalia chebula, exhibits diverse biological activities, including enzyme inhibition, cellular regulation, and modulation of physiological functions [1–5].
Chebulinic acid demonstrates potent inhibitory activity against non-receptor protein tyrosine phosphatases, particularly PTPN9 and PTPN11, with IC₅₀ values of 34 nM and 37 nM, respectively. In cellular assays, 5 μM chebulinic acid significantly enhances glucose uptake in 3T3-L1 preadipocytes and selectively induces apoptosis in HL-60 and NB4 acute promyelocytic leukemia cells (IC₅₀ = 7.5 μM and 5 μM, respectively), while exhibiting minimal effects on K562 chronic myeloid leukemia cells (IC₅₀ > 60 μM) [2].
Chebulinic acid also confers cytoprotection against oxidative stress. At 25 μM, it reduces reactive oxygen species (ROS) production induced by glyceraldehyde-derived advanced glycation end products in HUVECs and mitigates glutamate-induced ROS accumulation and cell death in HT22 hippocampal cells [3,4]. Additionally, it displays gastroprotective effects, inhibiting H⁺/K⁺-ATPase (IC₅₀ = 65.01 μg/ml) and protecting gastric mucosa in rat ulcer models by decreasing gastric acidity and enhancing mucus secretion [5].
References:
[1] Yoon SY, Kang HJ, Ahn D, Hwang JY, Kwon SJ, Chung SJ. Identification of chebulinic acid as a dual targeting inhibitor of protein tyrosine phosphatases relevant to insulin resistance. Bioorg Chem. 2019 Sep;90:103087. doi: 10.1016/j.bioorg.2019.103087. Epub 2019 Jul 2. PMID: 31284101.
[2]Chhabra S, Mishra T, Kumar Y, Thacker G, Kanojiya S, Chattopadhyay N, Narender T, Trivedi AK. Chebulinic Acid Isolated From the Fruits of Terminalia chebula Specifically Induces Apoptosis in Acute Myeloid Leukemia Cells. Phytother Res. 2017 Dec;31(12):1849-1857. doi: 10.1002/ptr.5927. Epub 2017 Sep 18. PMID: 28921713.
[3] Lee HS, Koo YC, Suh HJ, Kim KY, Lee KW. Preventive effects of chebulic acid isolated from Terminalia chebula on advanced glycation endproduct-induced endothelial cell dysfunction. J Ethnopharmacol. 2010 Oct 5;131(3):567-74. doi: 10.1016/j.jep.2010.07.039. Epub 2010 Jul 24. PMID: 20659546.
[4] Song JH, Shin MS, Hwang GS, Oh ST, Hwang JJ, Kang KS. Chebulinic acid attenuates glutamate-induced HT22 cell death by inhibiting oxidative stress, calcium influx and MAPKs phosphorylation. Bioorg Med Chem Lett. 2018 Feb 1;28(3):249-253. doi: 10.1016/j.bmcl.2017.12.062. Epub 2017 Dec 29. PMID: 29317168.
[5] Mishra V, Agrawal M, Onasanwo SA, Madhur G, Rastogi P, Pandey HP, Palit G, Narender T. Anti-secretory and cyto-protective effects of chebulinic acid isolated from the fruits of Terminalia chebula on gastric ulcers. Phytomedicine. 2013 Apr 15;20(6):506-11. doi: 10.1016/j.phymed.2013.01.002. Epub 2013 Feb 23. PMID: 23462212.
| Storage | Desiccate at -20°C away from light |
| M.Wt | 956.68 |
| Cas No. | 18942-26-2 |
| Formula | C41H32O27 |
| Chemical Name | 2-((3S,3aS,4S,7R,8R,10S,11R,17S)-3,15,16-trihydroxy-2,5,13-trioxo-10,17-bis((3,4,5-trihydroxybenzoyl)oxy)-8-(((3,4,5-trihydroxybenzoyl)oxy)methyl)-2,3,3a,4,5,7,8,10,11,13-decahydro-7,11-methano[1,4,7]trioxacyclotridecino[11,10,9-de]chromen-4-yl)acetic aci |
| SDF | Download SDF |
| Canonical SMILES | OC1=C(O)C(O)=CC(C(OC[C@@H]2[C@@H](OC3=O)[C@H](OC(C4=CC(O)=C(O)C(O)=C4)=O)[C@@H](OC(C5=CC(O)=C(O)C6=C5[C@H]([C@@H]3CC(O)=O)[C@H](O)C(O6)=O)=O)[C@H](OC(C7=CC(O)=C(O)C(O)=C7)=O)O2)=O)=C1 |
| Shipping Condition | Small Molecules with Blue Ice, Modified Nucleotides with Dry Ice. |
| General tips | We do not recommend long-term storage for the solution, please use it up soon. |
Quality Control & MSDS
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Purity = 98.00%
- COA (Certificate Of Analysis)
- MSDS (Material Safety Data Sheet)
Chemical structure
