Oleuropein aglycone
(Synonyms: 3,4-DHPEA-EA) 目录号 : GC49815
A polyphenol with diverse biological activities
Cas No.:31773-95-2
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >95.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
Oleuropein aglycone is a polyphenol and an aglycone form of oleuropein that has been found in extra virgin olive oil and has diverse biological activities.1,2,3,4 It is formed from oleuropein via enzymatic, acidic, or acetyl hydrolysis.1 Dietary administration of oleuropein aglycone (50 mg/kg of food) increases the number of neuronal autophagic vesicles and reverses cognitive deficits in a TgCRND8 transgenic mouse model of Alzheimer’s disease.2 It also decreases cortical and hippocampal levels of histone deacetylase 2 (HDAC2) and restores long-term potentiation in the same model. Oleuropein aglycone increases urinary norepinephrine, as well as interscapular brown adipose tissue epinephrine and UCP1 protein levels, and decreases plasma leptin levels and total abdominal cavity adipose tissue weight in a rat model of high-fat diet-induced obesity.3 It also reduces lung neutrophil infiltration, lipid peroxidation, and IL-1β levels in a mouse model of carrageenan-induced pleurisy.4
1.Xu, F., Li, Y., Zheng, M., et al.Structure properties, acquisition protocols, and biological activities of oleuropein aglyconeFront. Chem.6239(2018) 2.Cordero, J.G., GarcÍa-Escudero, R., Avila, J., et al.Benefit of oleuropein aglycone for Alzheimer’s disease by promoting autophagyOxid. Med. Cell. Longev.5010741(2018) 3.Oi-Kando, Y., Iwasaki, Y., Nakamura, T., et al.Oleuropein aglycone enhances UCP1 expression in brown adipose tissue in high-fat-diet-induced obese rats by activating β-adrenergic signalingJ. Nutr. Biochem.40209-218(2017) 4.Impellizzeri, D., Esposito, E., Mazzon, E., et al.The effects of oleuropein aglycone, an olive oil compound, in a mouse model of carrageenan-induced pleurisyClin. Nutr.30(4)533-540(2011)
| Cas No. | 31773-95-2 | SDF | Download SDF |
| 别名 | 3,4-DHPEA-EA | ||
| Canonical SMILES | OC1=CC(CCOC(C[C@@H]2C(C(OC)=O)=CO[C@H](/C2=C/C)O)=O)=CC=C1O | ||
| 分子式 | C19H22O8 | 分子量 | 378.4 |
| 溶解度 | Acetonitrile: slightly soluble,Ethanol: slightly soluble w/ sonication | 储存条件 | -20°C |
| 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 | 2.6427 mL | 13.2135 mL | 26.4271 mL |
| 5 mM | 0.5285 mL | 2.6427 mL | 5.2854 mL |
| 10 mM | 0.2643 mL | 1.3214 mL | 2.6427 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。
Potential Therapeutic Effects of Oleuropein aglycone in Alzheimer's Disease
Curr Pharm Biotechnol 2016;17(11):994-1001.PMID:27455905DOI:10.2174/1389201017666160725120656.
Alzheimer's disease (AD) is an age-associated neurodegenerative amyloid disease and is considered a social and clinical problem the last decades, particularly in the Western countries. Amyloid diseases are characterized by the deposition of typically aggregated protein/peptides in tissues that are associated with brain degeneration and progressive cognitive impairment. The amyloid plaques and neurofibrillary tangles arise as a result of self-assembly into fibrillar material of amyloid-β protein and hyperphosphorylated tau, respectively. Moreover, mounting evidence shows that oxidative and nitrosative stress plays a central role in the pathogenesis of neurodegenerative disorders such as AD. Oleuropein belongs to a specific group of polyphenols, the secoiridoids, which are abundant in Oleaceae. Oleuropein aglycone is abundant in extra virgin olive oil and it is generated as a product of a glucosidase released when olive fruits are crushed. This secoiridoid compound has radical-scavenging activity and antioxidative effects and it is considered a promising target to prevent amyloid toxicity as an inhibitor of the oligomer nucleation and growth. The neuroprotective and antioxidant effects of flavonoids have been found to strongly depend on their structure and functional groups. Oleuropein aglycone counteracts amyloid aggregation and toxicity affecting different pathways: amyloid precursor protein processing, amyloid-β peptide and tau aggregation, autophagy impairment, and neuroinflammation. In the current work, available literature on Oleuropein aglycone effects as antioxidant and inhibitor of amyloid deposits in AD is reviewed. Moreover, we discuss the chemistry, food sources and bioavailability of Oleuropein aglycone.
Oleuropein aglycone and polyphenols from olive mill waste water ameliorate cognitive deficits and neuropathology
Br J Clin Pharmacol 2017 Jan;83(1):54-62.PMID:27131215DOI:10.1111/bcp.12993.
Aim: In TgCRND8 (Tg) mice we checked the dose-response effect of diet supplementation with Oleuropein aglycone (OLE) at 12.5 or 0.5 mg kg-1 of diet. We also studied the effects of dietary intake of the mix of polyphenols present in olive mill waste water administered at a total dose as high as the highest dose of OLE (50 mg kg-1 of diet) previously investigated. Methods: Four month-old Tg mice were equally divided into four groups and treated for 8 weeks with a modified low fat (5.0%) AIN-76 A diet (10 g day-1 per mouse) as such, supplemented with OLE (12.5 or 0.5 mg kg-1 of diet) or with a mix of polyphenols (50 mg kg-1 of diet) found in olive mill waste water. Behavioural performance was evaluated by the step down inhibitory avoidance and object recognition tests. Neuropathology was analyzed by immunohistochemistry. Results: OLE supplementation at 12.5 mg kg-1 of diet and the mix of polyphenols was found to improve significantly cognitive functions of Tg mice (P < 0.0001). Aß42 and pE-3Aß plaque area and number were significantly reduced in the cortex by OLE and in the cortex and hippocampus by the mix of polyphenols (P < 0.01, P < 0.001 and P < 0.0001). Similar autophagy induction was found in the brain cortex of differently treated mice. Conclusion: Our results extend previous data showing that the effects of OLE on behavioural performance and neuropathology are dose-dependent and not closely related to OLE by itself. In fact, diet supplementation with the same dose of a mix of polyphenols found in olive mill waste water resulted in comparable neuroprotection.
Benefit of Oleuropein aglycone for Alzheimer's Disease by Promoting Autophagy
Oxid Med Cell Longev 2018 Feb 20;2018:5010741.PMID:29675133DOI:10.1155/2018/5010741.
Alzheimer's disease is a proteinopathy characterized by accumulation of hyperphosphorylated Tau and β-amyloid. Autophagy is a physiological process by which aggregated proteins and damaged organelles are eliminated through lysosomal digestion. Autophagy deficiency has been demonstrated in Alzheimer's patients impairing effective elimination of aggregates and damaged mitochondria, leading to their accumulation, increasing their toxicity and oxidative stress. In the present study, we demonstrated by microarray analysis the downregulation of fundamental autophagy and mitophagy pathways in Alzheimer's patients. The benefits of the Mediterranean diet on Alzheimer's disease and cognitive impairment are well known, attributing this effect to several polyphenols, such as Oleuropein aglycone (OLE), present in extra virgin olive oil. OLE is able to induce autophagy, achieving a decrease of aggregated proteins and a reduction of cognitive impairment in vivo. This effect is caused by the modulation of several pathways including the AMPK/mTOR axis and the activation of autophagy gene expression mediated by sirtuins and histone acetylation or EB transcription factor. We propose that supplementation of diet with extra virgin olive oil might have potential benefits for Alzheimer's patients by the induction of autophagy by OLE.
Structure Properties, Acquisition Protocols, and Biological Activities of Oleuropein aglycone
Front Chem 2018 Aug 13;6:239.PMID:30151359DOI:10.3389/fchem.2018.00239.
Oleuropein aglycone, which is the major phenolic component of extra virgin olive oil, is gaining popularity and importance in scientific and public communities. This paper summarizes the structure properties, acquisition protocols, and biological activities of Oleuropein aglycone. There are three hydrolytic methods used to obtain Oleuropein aglycone from oleuropein-enzymatic hydrolysis, acid hydrolysis, and acetal hydrolysis. Enzymatic hydrolysis can be achieved with exogenous enzymes and endogenous enzymes. In addition, the diverse pharmacological effects of Oleuropein aglycone are summaried. These pharmacological effects include anti-Alzheimer's disease, anti-breast cancer, anti-inflammatory, anti-hyperglycemic, anti-oxidative, and lipid-lowering properties. Therefore, we can use hydrolysis and biological activities to study Oleuropein aglycone in the future.
Oleuropein aglycone: A Possible Drug against Degenerative Conditions. In Vivo Evidence of its Effectiveness against Alzheimer's Disease
J Alzheimers Dis 2015;45(3):679-88.PMID:25649656DOI:10.3233/JAD-142850.
The amyloid plaques and neurofibrillary tangles found in the Alzheimer's disease (AD) brain arise as a result of self-assembly into fibrillar material of amyloid-β protein (Aβ) and hyperphosphorylated tau, respectively, through a pathological process starting with the appearance of aggregation nuclei and neurotoxic oligomers. Accordingly, the search of inhibitors of oligomer nucleation and growth is considered a promising target to prevent amyloid toxicity. In recent years, a number of dietary factors including antioxidants, vitamins, and polyphenols have been characterized for their ability to protect cells stressed by several factors including the presence of amyloid deposits as well as to inhibit amyloid self-assembly and cytotoxicity and some of them are currently in clinical trial. The present review summarizes the findings on the beneficial effects against neurodegeneration and other peripheral inflammatory and degenerative diseases of Oleuropein aglycone (OLE), a natural phenol abundant in the extra virgin olive oil. The data presently available suggest that OLE could provide a protective and therapeutic effect against a number of pathologies, including AD as well as obesity, type 2 diabetes, non-alcoholic hepatitis, and other natural or experimentally-induced pathological conditions. Such a protection could result, at least in part, in a remarkable improvement of the pathological signs arising from stress conditions including oxidative stress, an excessive inflammatory response, and the presence of cytotoxic aggregated material. In particular, the recent data on the cellular and molecular correlates of OLE neuroprotection suggest it could also play a therapeutic role against AD.