Betulinic acid
(Synonyms: 白桦脂酸; Lupatic acid; Betulic acid) 目录号 : GC10480
白桦脂酸（Betulinic acid）是一种天然的五环三萜类化合物，是真核细胞拓扑异构酶I的抑制剂，IC50值为5μM。
Cas No.:472-15-1
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >98.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
| 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. | |
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.
白桦脂酸（Betulinic acid）是一种天然的五环三萜类化合物，是真核细胞拓扑异构酶I的抑制剂，IC50值为5μM[1]。Betulinic acid具有抗炎，抗疟疾，抗艾滋病和抗肿瘤等活性[2]。Betulinic acid可以抑制α-葡萄糖苷酶，IC50值为10.6μM[3]。
在体外，Betulinic acid（7.5μM）处理小鼠下丘脑细胞系（mHypoE-46）神经元10h，显著抑制了蛋白酪氨酸磷酸酶1B（PTP1B）的酶活性，抑制率达35%[4]。Betulinic acid（10-160μM）处理MDA-MB-231细胞24或48h，以时间和剂量依赖性方式抑制了细胞活力，降低了细胞的Bcl-2表达，诱导了细胞的超微结构变化[5]。
在体内，Betulinic acid（50mg/kg）通过口服治疗视网膜缺血模型小鼠，可防止视网膜GCL细胞丢失和视神经轴突丢失，部分阻断视网膜小动脉内皮功能障碍，抑制视网膜血管中的ROS产生，并增强抗氧化酶SOD3和HO-1的mRNA 表达[6]。Betulinic acid（30mg/kg）通过口服治疗结肠炎小鼠，显著预防腹泻和出血等结肠病理变化，降低了亚硝酸盐、丙二醛、过氧化物酶和脂质过氧化物水平，提高了超氧化物歧化酶、过氧化氢酶和谷胱甘肽水平[7]。
| Cas No. | 472-15-1 | SDF | |
| 别名 | 白桦脂酸; Lupatic acid; Betulic acid | ||
| 化学名 | (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 | ||
| 分子式 | C30H48O3 | 分子量 | 456.7 |
| 溶解度 | ≥ 22.85 mg/mL in DMSO, ≥ 9.62 mg/mL in EtOH with ultrasonic and warming | 储存条件 | 4°C, protect from light |
| General tips | 请根据产品在不同溶剂中的溶解度选择合适的溶剂配制储备液；一旦配成溶液，请分装保存，避免反复冻融造成的产品失效。 储备液的保存方式和期限：-80°C 储存时，请在 6 个月内使用，-20°C 储存时，请在 1 个月内使用。 为了提高溶解度，请将管子加热至37℃，然后在超声波浴中震荡一段时间。 |
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| Shipping Condition | 评估样品解决方案：配备蓝冰进行发货。所有其他可用尺寸：配备RT，或根据请求配备蓝冰。 | ||
| 制备储备液 | |||
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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 |
| 第一步：请输入基本实验信息（考虑到实验过程中的损耗，建议多配一只动物的药量） | ||||||||||
| 给药剂量 | mg/kg |  |
动物平均体重 | g | |
每只动物给药体积 | ul | |
动物数量 | 只 |
| 第二步：请输入动物体内配方组成（配方适用于不溶于水的药物；不同批次药物配方比例不同，请联系GLPBIO为您提供正确的澄清溶液配方） | ||||||||||
| % DMSO % % Tween 80 % saline | ||||||||||
| 计算重置 | ||||||||||
计算结果:
工作液浓度： mg/ml；
DMSO母液配制方法： mg 药物溶于 μL DMSO溶液（母液浓度 mg/mL，
体内配方配制方法：取 μL DMSO母液，加入 μL PEG300，混匀澄清后加入μL Tween 80，混匀澄清后加入 μL saline，混匀澄清。
1. 首先保证母液是澄清的；
2.
一定要按照顺序依次将溶剂加入，进行下一步操作之前必须保证上一步操作得到的是澄清的溶液，可采用涡旋、超声或水浴加热等物理方法助溶。
3. 以上所有助溶剂都可在 GlpBio 网站选购。