Auraptene
(Synonyms: 橙皮油素) 目录号 : GC42873
A coumarin derivative with anti-inflammatory and chemopreventative activity
Cas No.:495-02-3
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >99.50%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
Auraptene is a coumarin derived from citrus plants that bears a geranyloxyl moiety at its C-7. It has anti-inflammatory, anti-carcinogenic, anti-bacterial, neuroprotective, and hepatoprotective activities. It inhibits leukocyte activation and induces phase II enzymes during the initiation phase of carcinogenesis. When examined for its potential use in Alzheimer's disease treatment, auraptene was shown to inhibit β-secretase (BACE1) activity with an IC50 value of 345.1 μM.
| Cas No. | 495-02-3 | SDF | |
| 别名 | 橙皮油素 | ||
| Canonical SMILES | O=C1C=CC2=C(C=C(OC/C=C(C)/CC/C=C(C)\C)C=C2)O1 | ||
| 分子式 | C19H22O3 | 分子量 | 298.4 |
| 溶解度 | DMF: 14 mg/ml,DMF:PBS(pH7.2) (1:2): 0.3 mg/ml,DMSO: 12 mg/ml,Ethanol: 12 mg/ml | 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 | 3.3512 mL | 16.756 mL | 33.5121 mL |
| 5 mM | 0.6702 mL | 3.3512 mL | 6.7024 mL |
| 10 mM | 0.3351 mL | 1.6756 mL | 3.3512 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。
A Review of Auraptene as an Anticancer Agent
Front Pharmacol 2021 Jun 22;12:698352.PMID:34239445DOI:10.3389/fphar.2021.698352.
Auraptene is a bioactive monoterpene coumarin isolated from Citrus aurantium and Aegle marmelos that belong to the Rutaceae family. Auraptene can modulate intracellular signaling pathways that control cell growth, inflammation and apoptosis and can exert pharmacological properties such as anti-bacterial, anti-fungal, antileishmania and anti-oxidant activity. Auraptene had inhibitory and chemo-preventive effects on the proliferation, tumorigenesis and growth of several cancer cell lines through increase in the activity of glutathione S-transferase, formation of DNA adducts and reduction of the number of aberrant crypt foci. Auraptene exhibits anticancer effects via targeting different cell signaling pathways such as cytokines, genes modulating cellular proliferation, growth factors, transcription factors and apoptosis. The present review is a detailed survey of scientific researches on the cytotoxicity and anticancer activity of Auraptene on cancer cells and tumor bearing animals.
A review of the pharmacological and therapeutic effects of Auraptene
Biofactors 2019 Nov;45(6):867-879.PMID:31424600DOI:10.1002/biof.1550.
There is a growing awareness in herbal medications as they are usually safe and devoid of significant adverse effects. Auraptene is a natural bioactive monoterpene coumarin ether and is consumed all over the world. There is growing evidence of the therapeutic benefits of Auraptene. Auraptene, also known as Auraptene and 7-geranyloxycoumarin, is a bioactive monoterpene coumarin from Rutaceae family, which is isolated from Citrus aurantium (Seville orange) and Aegle marmelos (bael fruit). Auraptene is a highly pleiotropic molecule, which can modulate intracellular signaling pathways that control inflammation, cell growth, and apoptosis. It has a potential therapeutic role in the prevention and treatment of various diseases due to its anti-inflammatory and antioxidant activities as well as its excellent safety profile. In the present article, various pharmacological and therapeutic effects of Auraptene were reviewed. Different online databases using keywords such as Auraptene, therapeutic effects and pharmacological effects were searched until the end of September 2018, for this purpose. Auraptene has been suggested to be effective in the treatment of a broad range of disorders including inflammatory disorders, dysentery, wounds, scars, keloids, and pain. In addition, different studies have demonstrated that Auraptene possesses numerous pharmacological properties including anti-inflammatory, anti-oxidative, anti-diabetic, anti-hypertensive and anti-cancer as well as neuroprotective effects. The present review provides a detailed survey of scientific researches regarding pharmacological properties and therapeutic effects of Auraptene.
Auraptene and Its Role in Chronic Diseases
Adv Exp Med Biol 2016;929:399-407.PMID:27771936DOI:10.1007/978-3-319-41342-6_19.
Auraptene (7-geranyloxycoumarin) is the best known and most abundant prenyloxycoumarin present in nature. It is synthesized by various plant species, mainly those of the Rutaceae and Umbeliferae (Apiaceae) families, comprising many edible fruits and vegetables such as lemons, grapefruit and orange. Auraptene has shown a remarkable effect in the prevention of degenerative diseases, in particular it has been reported to be one the most promising known natural chemopreventive agents against several types of cancer. The aim of this chapter is to review the effects of Auraptene in the prevention and treatment of different chronic diseases.
Protective Effects of Auraptene against Free Radical-Induced Erythrocytes Damage
J Pharmacopuncture 2022 Dec 31;25(4):344-353.PMID:36628343DOI:10.3831/KPI.2022.25.4.344.
Objectives: Auraptene is the most abundant natural prenyloxycoumarin. Recent studies have shown that it has multiple biological and therapeutic properties, including antioxidant properties. Erythrocytes are constantly subjected to oxidative damage that can affect proteins and lipids within the erythrocyte membrane and lead to some hemoglobinopathies. Due to the lack of sufficient information about the antioxidant effects of Auraptene on erythrocytes, this study intended to evaluate the potential of this compound in protecting radical-induced erythrocytes damages. Methods: The antioxidant activity of Auraptene was measured based on DPPH and FRAP assays. Notably, oxidative hemolysis of human erythrocytes was used as a model to study the ability of Auraptene to protect biological membranes from free radical-induced damage. Also, the effects of Auraptene in different concentrations (25-400 µM) on AAPH-induced lipid/protein peroxidation, glutathione (GSH) content and morphological changes of erythrocytes were determined. Results: Oxidative hemolysis and lipid/protein peroxidation of erythrocytes were significantly suppressed by Auraptene in a time and concentration-dependent manner. Auraptene prevented the depletion of the cytosolic antioxidant GSH in erythrocytes. Furthermore, it inhibited lipid and protein peroxidation in a time and concentration-dependent manner. Likewise, FESEM results demonstrated that Auraptene reduced AAPH-induced morphological changes in erythrocytes. Conclusion: Auraptene efficiently protects human erythrocytes against free radicals. Therefore, it can be a potent candidate for treating oxidative stress-related diseases.
Auraptene, a citrus peel-derived natural product, prevents myocardial infarction-induced heart failure by activating PPARα in rats
Phytomedicine 2022 Dec;107:154457.PMID:36223697DOI:10.1016/j.phymed.2022.154457.
Background: Auraptene derived from the peel of Citrus hassaku possesses anti-tumor, anti-inflammatory, and neuroprotective activities. Thus, it could be a valuable pharmacological alternative to treat some diseases. However, the therapeutic value of Auraptene for heart failure (HF) is unknown. Study design/methods: In cultured cardiomyocytes from neonatal rats, the effect of Auraptene on phenylephrine-induced hypertrophic responses and peroxisome proliferator-activated receptor-alpha (PPARα)-dependent gene transcriptions. To investigate whether Auraptene prevents the development of heart failure after myocardial infarction (MI) in vivo, Sprague-Dawley rats with moderate MI (fractional shortening < 40%) were randomly assigned for treatment with low- or high-dose Auraptene (5 or 50 mg/kg/day, respectively) or vehicle for 6 weeks. The effects of Auraptene were evaluated by echocardiography, histological analysis, and the measurement of mRNA levels of hypertrophy, fibrosis, and PPARα-associated genes. Results: In cultured cardiomyocytes, Auraptene repressed phenylephrine-induced hypertrophic responses, such as increases in cell size and activities of atrial natriuretic factor and endothelin-1 promoters. Auraptene induced PPARα-dependent gene activation by enhancing cardiomyocyte peroxisome proliferator-responsive element reporter activity. The inhibition of PPARα abrogated the protective effect of Auraptene on phenylephrine-induced hypertrophic responses. In rats with MI, Auraptene significantly improved MI-induced systolic dysfunction and increased posterior wall thickness compared to the vehicle. Auraptene treatment also suppressed MI-induced increases in myocardial cell diameter, perivascular fibrosis, and expression of hypertrophy and fibrosis response markers at the mRNA level compared with vehicle treatment. MI-induced decreases in the expression of PPARα-dependent genes were improved by Auraptene treatment. Conclusions: Auraptene has beneficial effects on MI-induced cardiac hypertrophy and left ventricular systolic dysfunction in rats, at least partly due to PPARα activation. Further clinical studies are required to evaluate the efficacy of Auraptene in patients with HF.