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| Targets |
Chebulic acid targets oxidative stress-related enzymes (SOD, CAT, GPx) - enhances enzyme [4]
Chebulic acid acts on advanced glycation endproduct (AGE) formation pathway - inhibits AGE-induced RAGE (receptor for AGEs) activation [3] Chebulic acid modulates inflammatory signaling pathways (NF-κB, MAPK) - suppresses pathway activation [1][3][5] |
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| ln Vitro |
1. Alveolar epithelial cell protection:
- Chebulic acid (10, 20, 40 μM) significantly increased viability of urban particulate matter (UPM)-exposed alveolar epithelial cells (A549) in a concentration-dependent manner (MTT assay) [1] - Chebulic acid reduced UPM-induced intracellular ROS generation and MDA levels, while increasing SOD and CAT activities in A549 cells [1] - Chebulic acid downregulated UPM-induced pro-inflammatory cytokines (TNF-α, IL-6, IL-1β) mRNA and protein expression via inhibiting NF-κB and MAPK pathways [1] 2. Endothelial cell dysfunction improvement: - Chebulic acid (5, 10, 20 μM) inhibited AGE-induced endothelial cell (HUVECs) apoptosis, as evidenced by reduced caspase-3 activity and TUNEL-positive cells [3] - Chebulic acid attenuated AGE-induced ROS production and NADPH oxidase activation in HUVECs, and restored NO production and eNOS activity [3] - Chebulic acid suppressed AGE-induced RAGE expression and downstream NF-κB p65 phosphorylation in HUVECs [3] 3. Hepatocyte antioxidant protection: - Chebulic acid (10, 25, 50 μM) protected isolated rat hepatocytes against H2O2-induced oxidative damage, increasing cell viability and reducing LDH leakage [4] - Chebulic acid enhanced SOD, CAT, and GPx activities, and decreased MDA and GSSG levels in H2O2-treated hepatocytes [4] - Chebulic acid inhibited H2O2-induced hepatocyte apoptosis by reducing Bax/Bcl-2 ratio and caspase-3 activation [4] |
| ln Vivo |
1. Ischemia-reperfusion (I/R) injury attenuation in diabetic rats:
- Chebulic acid (25, 50 mg/kg, p.o.) administered for 14 days prior to I/R surgery significantly reduced serum AST, ALT, LDH, and CK-MB levels in streptozotocin-induced diabetic rats [2] - Chebulic acid restored antioxidant status in diabetic I/R rats by increasing SOD, CAT, GPx activities and GSH levels, while decreasing MDA and NO levels in liver and heart tissues [2] - Chebulic acid attenuated I/R-induced inflammatory response in diabetic rats by reducing TNF-α, IL-1β, and ICAM-1 expression in tissues [2] 2. Hepatoprotective activity: - Chebulic acid (10, 20, 40 mg/kg, p.o.) administered for 7 days protected mice against CCl4-induced liver injury, as shown by reduced serum ALT, AST, and ALP levels [5] - Chebulic acid alleviated CCl4-induced hepatic oxidative stress by increasing SOD, CAT, GPx activities and decreasing MDA content in liver tissue [5] - Chebulic acid suppressed CCl4-induced hepatic inflammation via inhibiting NF-κB p65 nuclear translocation and reducing TNF-α, IL-6, and COX-2 expression [5] - Chebulic acid attenuated CCl4-induced hepatocyte apoptosis by downregulating Bax, caspase-3, caspase-9 expression and upregulating Bcl-2 expression [5] |
| Enzyme Assay |
1. Antioxidant enzyme activity assay:
- Tissue/cell homogenates are prepared and centrifuged to obtain supernatant [2][4][5] - Supernatant is incubated with specific substrates for SOD, CAT, and GPx respectively [2][4][5] - SOD activity is measured by monitoring the inhibition of nitrite formation from hydroxylamine hydrochloride [2][4][5] - CAT activity is determined by measuring the decomposition of H2O2 at 240 nm [2][4][5] - GPx activity is assayed by detecting the oxidation of NADPH at 340 nm [2][4][5] 2. AGE formation inhibition assay: - Bovine serum albumin (BSA) is incubated with glucose in the presence or absence of Chebulic acid at 37°C for 4 weeks [3] - Fluorescence intensity of AGE-BSA is measured at excitation 370 nm and emission 440 nm to evaluate AGE formation [3] - The inhibition rate of Chebulic acid on AGE formation is calculated compared to the control group [3] 3. Caspase-3 activity assay: - Cell/tissue lysates are prepared and incubated with caspase-3 substrate (Ac-DEVD-pNA) at 37°C for 2 hours [3][4][5] - The absorbance of released p-nitroaniline is measured at 405 nm to determine caspase-3 activity [3][4][5] |
| Cell Assay |
1. Alveolar epithelial cell (A549) protection assay:
- A549 cells are cultured in DMEM medium supplemented with fetal bovine serum and antibiotics [1] - Cells are pre-treated with Chebulic acid (10, 20, 40 μM) for 2 hours, then exposed to UPM (100 μg/ml) for 24 hours [1] - Cell viability is detected by MTT assay, ROS generation by DCFH-DA staining, and MDA level by thiobarbituric acid reaction method [1] - TNF-α, IL-6, IL-1β mRNA expression is analyzed by RT-PCR, and protein levels by Western blot [1] 2. Endothelial cell (HUVECs) dysfunction assay: - HUVECs are cultured in EBM-2 medium and pre-treated with Chebulic acid (5, 10, 20 μM) for 1 hour, then incubated with AGE-BSA (100 μg/ml) for 24 hours [3] - Cell apoptosis is evaluated by TUNEL staining and caspase-3 activity assay [3] - ROS production is measured by DCFH-DA staining, NO level by Griess reagent, and eNOS activity by colorimetric assay [3] - RAGE and NF-κB p65 protein expression is detected by Western blot [3] 3. Hepatocyte oxidative damage assay: - Isolated rat hepatocytes are suspended in Williams' medium E and pre-treated with Chebulic acid (10, 25, 50 μM) for 30 minutes, then exposed to H2O2 (0.5 mM) for 1 hour [4] - Cell viability is determined by trypan blue exclusion test, and LDH leakage by colorimetric assay [4] - SOD, CAT, GPx activities and MDA, GSSG levels are measured using respective assay kits [4] - Bax and Bcl-2 protein expression is analyzed by Western blot [4] |
| Animal Protocol |
1. Diabetic rat I/R injury model:
- Streptozotocin (60 mg/kg, i.p.) is injected into Wistar rats to induce diabetes (blood glucose >250 mg/dl) [2] - Chebulic acid is dissolved in 0.5% carboxymethyl cellulose (CMC) and administered orally at doses of 25, 50 mg/kg once daily for 14 days [2] - On day 14, rats are anesthetized, and hepatic/renal I/R injury is induced by clamping the hepatic portal vein/renal pedicle for 30 minutes followed by reperfusion for 24 hours [2] - Blood samples and liver/heart tissues are collected for biochemical and histological analysis [2] 2. Mouse CCl4-induced liver injury model: - BALB/c mice are divided into control, CCl4, and Chebulic acid treatment groups (10, 20, 40 mg/kg) [5] - Chebulic acid is dissolved in 0.5% CMC and administered orally once daily for 7 days [5] - On day 7, mice are injected with CCl4 (1 ml/kg, i.p., 10% in olive oil) 2 hours after the last Chebulic acid administration [5] - After 24 hours, blood samples and liver tissues are collected for serum biochemical, histological, and molecular biological analysis [5] |
| References |
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| Additional Infomation |
Chebulic acid has been reported to exist in Terminalia citrina, Phyllanthus emblica, and Terminalia chebula, and there is relevant data. Chebulic acid is a natural phenolic acid isolated from the fruit of Terminalia chebula Retz. [3][4][5] Chebulic acid mainly exerts its biological activity through antioxidant, anti-inflammatory, and anti-apoptotic mechanisms. [1][2][3][4][5] Chebulic acid has potential protective effects against oxidative stress-related diseases, including respiratory diseases, cardiovascular diseases, and liver diseases. [1][2][3][4][5]
|
| Molecular Formula |
C14H12O11
|
|---|---|
| Molecular Weight |
356.2385
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| Exact Mass |
356.038
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| CAS # |
23725-05-5
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| PubChem CID |
71308174
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| Appearance |
White to off-white solid powder
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| Density |
1.882
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| Boiling Point |
755.9±60.0 °C(Predicted)
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| LogP |
-0.8
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| Hydrogen Bond Donor Count |
6
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| Hydrogen Bond Acceptor Count |
11
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| Rotatable Bond Count |
5
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| Heavy Atom Count |
25
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| Complexity |
587
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| Defined Atom Stereocenter Count |
3
|
| SMILES |
C1=C2C(=C(C(=C1O)O)O)[C@@H]([C@H](OC2=O)C(=O)O)[C@H](CC(=O)O)C(=O)O
|
| InChi Key |
COZMWVAACFYLBI-XJEVXTIOSA-N
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| InChi Code |
InChI=1S/C14H12O11/c15-5-1-4-7(10(19)9(5)18)8(3(12(20)21)2-6(16)17)11(13(22)23)25-14(4)24/h1,3,8,11,15,18-19H,2H2,(H,16,17)(H,20,21)(H,22,23)/t3-,8-,11-/m0/s1
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| Chemical Name |
(2S)-2-[(3S,4S)-3-carboxy-5,6,7-trihydroxy-1-oxo-3,4-dihydroisochromen-4-yl]butanedioic acid
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| HS Tariff Code |
2934.99.9001
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| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
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| Solubility (In Vitro) |
DMSO : ~250 mg/mL (~701.77 mM)
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|---|---|
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.17 mg/mL (6.09 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 21.7 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 2.17 mg/mL (6.09 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 21.7 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 2.8071 mL | 14.0355 mL | 28.0710 mL | |
| 5 mM | 0.5614 mL | 2.8071 mL | 5.6142 mL | |
| 10 mM | 0.2807 mL | 1.4035 mL | 2.8071 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
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