Betulinic acid (Synonyms: Lupatic Acid, NSC 113090) |
| カタログ番号GC10480 |
胆汁酸に似た植物トリテルペノイド
Products are for research use only. Not for human use. We do not sell to patients.
Cas No.: 472-15-1
Sample solution is provided at 25 µL, 10mM.
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Betulinic acid is a natural pentacyclic triterpenoid compound and an inhibitor of eukaryotic topoisomerase I with an IC50 value of 5 μM[1]. Betulinic acid has anti-inflammatory, anti-malarial, anti-AIDS and anti-tumor activities[2]. Betulinic acid can inhibit α-glucosidase with an IC50 value of 10.6 μM[3].
In vitro, betulinic acid (7.5 μM) treatment of mouse hypothalamic cell line (mHypoE-46) neurons for 10 h significantly inhibited the enzymatic activity of protein tyrosine phosphatase 1B (PTP1B) by 35%[4]. Betulinic acid (10-160 μM) treatment of MDA-MB-231 cells for 24 or 48 h inhibited cell viability in a time- and dose-dependent manner, reduced Bcl-2 expression in cells, and induced ultrastructural changes in cells[5].
In vivo, oral administration of betulinic acid (50 mg/kg) to treat retinal ischemia model mice prevented retinal GCL cell loss and optic nerve axon loss, partially blocked retinal arteriolar endothelial dysfunction, inhibited ROS production in retinal blood vessels, and enhanced the mRNA expression of antioxidant enzymes SOD3 and HO-1[6]. Oral administration of betulinic acid (30 mg/kg) to treat colitis mice significantly prevented colon pathological changes such as diarrhea and bleeding, reduced nitrite, malondialdehyde, peroxidase and lipid peroxide levels, and increased superoxide dismutase, catalase and glutathione levels[7].
References:
[1] Chowdhury A R, Mandal S, Mittra B, et al. Betulinic acid, a potent inhibitor of eukaryotic topoisomerase I: identification of the inhibitory step, the major functional group responsible and development of more potent derivatives[J]. Medical Science Monitor, 2002, 8(7): BR254-BR260.
[2] Drąg-Zalesińska M, Borska S. Betulin and its derivatives–precursors of new drugs[J]. World Scientific News, 2019, 127(3): 123-138.
[3] Ding H, Wu X, Pan J, et al. New insights into the inhibition mechanism of betulinic acid on α-glucosidase[J]. Journal of agricultural and food chemistry, 2018, 66(27): 7065-7075.
[4] Jin T, Yu H, Huang X F. Selective binding modes and allosteric inhibitory effects of lupane triterpenes on protein tyrosine phosphatase 1B[J]. Scientific Reports, 2016, 6(1): 20766.
[5] Gao Y, Ma Q, Ma Y B, et al. Betulinic acid induces apoptosis and ultrastructural changes in MDA-MB-231 breast cancer cells[J]. Ultrastructural Pathology, 2018, 42(1): 49-54.
[6] Musayeva A, Unkrig J C, Zhutdieva M B, et al. Betulinic acid protects from ischemia-reperfusion injury in the mouse retina[J]. Cells, 2021, 10(9): 2440.
[7] Kalra J, Lingaraju M C, Mathesh K, et al. Betulinic acid alleviates dextran sulfate sodium-induced colitis and visceral pain in mice[J]. Naunyn-Schmiedeberg's Archives of Pharmacology, 2018, 391: 285-297.
| Cell experiment [1]: | |
Cell lines | Mouse hypothalamic cell line (mHypoE-46) neurons |
Preparation Method | Lupeol (28 μM) and betulinic acid (7.5 μM) were applied to the mHypoE-46 cell line for 10 h. The cells were collected for western blot and immunoprecipitation analysis. |
Reaction Conditions | 7.5μM; 10h |
Applications | Lupeol and betulinic acid significantly inhibited the enzymatic activity of protein tyrosine phosphatase 1B (PTP1B) by 35%. |
| Animal experiment [2]: | |
Animal models | Male C57Bl/6J mice |
Preparation Method | One day before induction of retinal ischemia (I/R), mice received 50 mg/kg body weight of betulinic acid or DMSO by gavage. 24 hours later, mice received a second dose of betulinic acid or vehicle solution, followed by anesthesia with xylocaine and ketamine to induce retinal ischemia. For the next seven days, mice received betulinic acid or vehicle solution once a day. Mice were sacrificed on day 8 for further studies. |
Dosage form | 50mg/kg; p.o. |
Applications | Following I/R, betulinic acid prevented retinal GCL cell loss and optic nerve axon loss, partially blocked retinal arteriolar endothelial dysfunction, inhibited ROS production in retinal vessels, and enhanced the mRNA expression of antioxidant enzymes SOD3 and HO-1. |
References: [1] Jin T, Yu H, Huang X F. Selective binding modes and allosteric inhibitory effects of lupane triterpenes on protein tyrosine phosphatase 1B[J]. Scientific Reports, 2016, 6(1): 20766. [2]Musayeva A, Unkrig J C, Zhutdieva M B, et al. Betulinic acid protects from ischemia-reperfusion injury in the mouse retina[J]. Cells, 2021, 10(9): 2440. | |
| Cas No. | 472-15-1 | SDF | |
| 同義語 | Lupatic Acid, NSC 113090 | ||
| Chemical Name | (1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-9-hydroxy-5a,5b,8,8,11a-pentamethyl-1-prop-1-en-2-yl-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13,13a,13b-hexadecahydrocyclopenta[a]chrysene-3a-carboxylic acid | ||
| Canonical SMILES | CC(=C)C1CCC2(C1C3CCC4C5(CCC(C(C5CCC4(C3(CC2)C)C)(C)C)O)C)C(=O)O | ||
| Formula | C30H48O3 | M.Wt | 456.7 |
| 溶解度 | ≥ 22.85 mg/mL in DMSO, ≥ 9.62 mg/mL in EtOH with ultrasonic and warming | Storage | 4°C, protect from light |
| General tips | Please select the appropriate solvent to prepare the stock solution according to the
solubility of the product in different solvents; once the solution is prepared, please store it in
separate packages to avoid product failure caused by repeated freezing and thawing.Storage method
and period of the stock solution: When stored at -80°C, please use it within 6 months; when stored
at -20°C, please use it within 1 month. To increase solubility, heat the tube to 37°C and then oscillate in an ultrasonic bath for some time. |
||
| Shipping Condition | Evaluation sample solution: shipped with blue ice. All other sizes available: with RT, or with Blue Ice upon request. | ||
| Prepare stock solution | |||
|
1 mg | 5 mg | 10 mg |
| 1 mM | 2.1896 mL | 10.9481 mL | 21.8962 mL |
| 5 mM | 0.4379 mL | 2.1896 mL | 4.3792 mL |
| 10 mM | 0.219 mL | 1.0948 mL | 2.1896 mL |
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Method for preparing in vivo formulation: Take μL DMSO master liquid, next addμL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O, mix and clarify.
Method for preparing in vivo formulation: Take μL DMSO master liquid, next add μL Corn oil, mix and clarify.
Note: 1. Please make sure the liquid is clear before adding the next solvent.
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Quality Control & SDS
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- Purity: >98.00%
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Average Rating: 5 (Based on Reviews and 30 reference(s) in Google Scholar.)
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