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oleuropein
INDUSTRIAL CROPS AND PRODUCTS · 2020 · IF 4.244

Ultrasound-assisted deep eutectic solvent extraction of echinacoside and oleuropein from Syringa pubescens Turcz.

Xinsheng Wang,Yanfang Wu,Jie Li,Aoxiang Wang,Guangyao Li,Xueli Ren,Weiping Yin

In this work, deep eutectic solvents (DESs) were synthesized using ultrasound-assisted and stirring heating methods. DES combined with ultrasonic-assisted extraction (UAE) was proposed for the efficient extraction of glycosides from Syringa pubescens Turcz. A series of DES systems were used to evaluate the extraction efficiency of glycosides in S. pubescens . The DES composed of choline chloride/glycerol extracted higher than those of conventional solvents and other DESs. The extraction procedure of DES-UAE was optimized using response surface methodology. The extraction solvent was choline chloride-glycerol formed a DES with the mole ratio of 1:2 with 20 % of water content. The optimum conditions for echinacoside (ECH) and oleuropein (OLE) were ultrasound power of 200 W, extraction temperature of 68 °C, solvent to solid ratio of 20:1 mL/g and the extraction time of 45 min. Furthermore, the DES with 30 % water content can be used as dilution solvent before HPLC analysis of DES extract. In addition, the enrichment of ECH and OLE from DES extract was achieved using HPD-450 macroporous resin, with the recoveries of 80.04 % and 86.21 %, respectively.

CAS / MDL: 82854-37-3 32619-42-4
研究领域: 植物化学 · 分析化学
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INTERNATIONAL IMMUNOPHARMACOLOGY · 2017 · IF 2.956

Oleuropein prevents the development of experimental autoimmune myocarditis in rats

Jia-Ying Zhang,Zheng Yang,Kun Fang,Zhan-Li Shi,Dan-Hong Ren,Jing Sun

Oleuropein (OLE) is a natural secoiridoid that is derived from Olea europaea . OLE possesses cardioprotective effects in experimental models of hypertension, myocardial infarction, atherosclerosis and hyperlipidaemia . In the present study, the effects of OLE on experimental autoimmune myocarditis (EAM) were evaluated. EAM in rats were induced by subcutaneous injections of porcine cardiac myosin . Cardiac function parameters, myocardial pathology, myocardial inflammatory cell infiltration and nuclear factor kappa-B (NF-κB) expression were measured. Our data showed that the postmyocarditis rats exhibited increased left ventricular end systolic diameters, left ventricular end diastolic diameters, left ventricular end-diastolic pressures (LVEDP), and decreased ejection fractions . However, OLE significantly suppressed these changes in EAM rats. Histological analysis revealed that myosin induced miliary foci of discolouration on endocardial surfaces and extensive myocardial injuries with inflammatory cell infiltration were significantly improved by OLE therapy. A definitive positive correlation between the histological scores and LVEDP was observed. Moreover, OLE inhibited CD4 + , CD8 + cells and macrophage infiltration in myocardium and decreased the serum production of tumour necrosis factor-a (TNF-a), interleukin-1β (IL-1β) and IL-6 in EAM rats. Expectedly, the myocardial levels of NF-κB p65, p-IκBa, IKKa were significantly attenuated by OLE, indicating the inhibitory effects of OLE on the NF-κB pathway. Furthermore, OLE decreased the myocardial expressions of phosphorylated-p38 MAPK , phosphorylated-ERK, and did not change the levels of p38 MAPK and ERK in EAM rats. Collectively, our results suggest that OLE effectively prevents the development of myocarditis , at least in part, by inhibiting the MAPKs and NF-κB mediated inflammatory responses.

研究领域: 药理学 · 免疫学 · 心脏病学
✓ 已验证 DOI PubMed 高影响因子
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Drug Design Development and Therapy · 2023 · IF 4.8

Evaluation of Chitosan-Oleuropein Nanoparticles on the Durability of Dentin Bonding

Shuya Zhao,Yunyang Zhang,Yun Chen,Xianghui Xing,Yu Wang,Guofeng Wu

Purpose To evaluate the effects of dentin pretreatment with chitosan-loaded oleuropein nanoparticles (CONPs) on the durability of resin–dentin bonding interfaces.Methods Eighty freshly extracted non-carious human third molars were randomly divided into four groups (n = 20 each): a de-ionized water (DW) group, a chitosan (CS) group, a chlorhexidine (CHX) group and a CONP group. The dentin in the DW, CS, CHX, and CONP groups were pretreated with de-ionized water, 1.0 mg/L CS solution, 2% chlorhexidine solution, and CONP suspension (prepared with 100 mg/L oleuropein), respectively, followed by the universal adhesive and resin composites. The bonded teeth of each group were randomly divided into two subgroups: an immediate subgroup and an aged subgroup. The bonded teeth of each group were then cut into the bonded beams. We measured their microtensile bond strength (μTBS), observed the characteristics of bonding interface by atomic force microscope, calculated the percentage of silver particles in a selected area for interfacial nanoleakage analysis, and evaluated the endogenous gelatinase activity within the bonding interface for in-situ zymogram analysis. Data were analyzed with two-way ANOVA and LSD multiple comparison test (P < 0.05).Results Regardless of after 24 h or after thermocycling, CONP exhibited better μTBS (P < 0.05) than the other three groups except that there was not a statistical significance (P > 0.05) in the CONP and CHX groups after 24 h. Besides, the CONP group presented significantly higher modulus of elasticity in the hybrid layers (P < 0.05), lower expression of nanoleakage (P < 0.05), and better inhibitory effect of matrix metalloproteinases than the other three groups before and after thermocycling.Conclusion Altogether, the CONPs had the potential to act as a dentin primer, which could effectively improve the dentin-resin binding durability.

CAS / MDL: 9012-76-4
研究领域: 牙科学 · 材料科学 · 生物医学工程
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DRUG DEVELOPMENT RESEARCH · 2025 ·Vol. 86 ·期 7 ·e70171 · IF 4.2

Oleuropein Modulates Mitophagy and Metabolism in Cardiomyocyte Via the PINK1/Parkin Signaling Pathway

Hao Ling,Chunli Song

‌Oleuropein (OLEU), a natural polyphenol, exhibits cardioprotective potential through mitochondrial modulation, yet its precise mechanisms remain elusive. This study elucidates OLEU's role in alleviating oxidative stress and regulating mitochondrial quality control via the PINK1/Parkin pathway. In vitro, H9C2 cardiomyocytes exposed to H₂O₂-induced oxidative stress were treated with OLEU (0–200 μM), and analyses included cell viability, ROS, SOD, MDA, ΔΨm, ATP, PINK1/Parkin expression and detection of Mitophagic Flux. In vivo, myocardial infarction (MI) was induced in SD rats via coronary ligation, followed by OLEU administration, with assessments of cardiac function, histopathology, and mitophagy using echocardiography, electron microscopy, immunohistochemistry and immunofluorescence. Results showed that OLEU (≤200 μM) dose-dependently restored cell viability, reduced ROS, and normalized SOD/MDA ( p < 0.05), while mitigating ΔΨm collapse and ATP depletion, indicating enhanced mitochondrial bioenergetics. OLEU upregulated PINK1/Parkin, promoting mitophagic clearance of damaged mitochondria, and metabolomic analysis revealed modulation of arginine/proline and lipid pathways. In MI rats, OLEU attenuated ROS, preserved myocardial structure, and improved cardiac function, supported by elevated mitophagy in electron microscopy. These findings demonstrate that OLEU protects cardiomyocytes by suppressing oxidative stress, stabilizing mitochondrial integrity, and activating PINK1/Parkin-mediated mitophagy, highlighting its therapeutic potential for myocardial injury and mitochondrial dysfunction.

CAS / MDL: 338967-87-6
研究领域: 心血管病学 · 分子生物学 · 药理学 · 线粒体生物学 · 氧化应激
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MOLECULES · 2015 ·Vol. 20 ·期 2 ·2903-2921 · IF 2.416

Enzymatic Hydrolysis of Oleuropein from Olea europea (Olive) Leaf Extract and Antioxidant Activities

Jiao-Jiao Yuan,Cheng-Zhang Wang,Jian-Zhong Ye,Ran Tao,Yu-Si Zhang

Oleuropein (OE), the main polyphenol in olive leaf extract, is likely to decompose into hydroxytyrosol (HT) and elenolic acid under the action of light, acid, base, high temperature. In the enzymatic process, the content of OE in olive leaf extract and enzyme are key factors that affect the yield of HT. A selective enzyme was screened from among 10 enzymes with a high OE degradation rate. A single factor (pH, temperature, time, enzyme quantity) optimization process and a Box-Behnken design were studied for the enzymatic hydrolysis of 81.04% OE olive leaf extract. Additionally, enzymatic hydrolysis results with different substrates (38.6% and 81.04% OE) were compared and the DPPH antioxidant properties were also evaluated. The result showed that the performance of hydrolysis treatments was best using hemicellulase as a bio-catalyst, and the high purity of OE in olive extract was beneficial to biotransform OE into HT. The optimal enzymatic conditions for achieving a maximal yield of HT content obtained by the regression were as follows: pH 5, temperature 55 °C and enzyme quantity 55 mg. The experimental result was 11.31% ± 0.15%, and the degradation rate of OE was 98.54%. From the present investigation of the antioxidant activity determined by the DPPH method, the phenol content and radical scavenging effect were both decreased after enzymatic hydrolysis by hemicellulase. However, a high antioxidant activity of the ethyl acetate extract enzymatic hydrolysate (IC50= 41.82 μg/mL) was demonstated. The results presented in this work suggested that hemicellulase has promising and attractive properties for industrial production of HT, and indicated that HT might be a valuable biological component for use in pharmaceutical products and functional foods.Keywords:Olea europeaL.;hydroxytyrosol;oleuropein;enzymatic hydrolysis;hemicellulase

CAS / MDL: 1898-66-4 9001-73-4
研究领域: 植物化学 · 食品科学 · 药理学
✓ 已验证 产品关联 DOI PubMed 高影响因子
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JOURNAL OF CHROMATOGRAPHY A · 2025 · IF 4

HSCCC-Tchebichef moment regression approach for enhanced quantification of oleuropein in olive leaf extracts

Jules Muhire,Fu-xin Zhang,Bao-qian Liu,Jinxia Hu,Xiaofang Wang,Dong Pei,Duo-Long Di

Oleuropein, a major bioactive phenolic compound from olive leaves, has attracted considerable interest for its health benefits. Targeted fractionation of oleuropein from crude extracts is hampered by the co-existence of numerous structurally similar metabolites, making conventional chromatographic separation inefficient. Here we describe, for the first time, a compact predictive framework that combines high-speed countercurrent chromatography (HSCCC), discrete Tchebichef moment (TM) feature extraction, and stepwise regression (SR) modelling to quantify oleuropein. Olive leaves were extracted with 80 % ethanol, and the crude extract was subjected to continuous-injection HSCCC in reverse‑phase mode using an ethyl acetate-petroleum ether-water (6:0.06:7) solvent system. HPLC analysed the resulting fractions and reference standards. Chromatograms were converted into two-dimensional matrices from which TMs up to the 20th order were computed. Forward stepwise regression identified a small set of TM coefficients that correlated strongly with oleuropein concentration and yielded a linear predictive model with high accuracy ( R 2 > 0.99). In comparison to the MCR-ALS, the TM-based model achieved superior predictive performance using fewer parameters. The integrated HSCCC-TM-SR approach provides a rapid and scalable method for quantifying oleuropein and may be extended to other complex natural products.

CAS / MDL: 32619-42-4
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JOURNAL OF FOOD BIOCHEMISTRY · 2015 ·Vol. 39 ·期 5 ·566-574 · IF 0.741

Purification, Dynamic Changes and Antioxidant Activities of Oleuropein in Olive (Olea Europaea L.) Leaves

Wu Zun-Qiu,Yue Gui-Zhou,Zhu Qing-Ping,Jiang You-Jun,Tang Kai-Yu,Chen Hua-Ping,Yang Ze-Shen,Huang Qian-Ming

Oleuropein was extracted from olive leaves by ultrasonic-assisted method and purified by silica gel column chromatography. The sample was identified as oleuropein by UV, infrared, mass spectroscopy and nuclear magnetic resonance spectroscopy analysis. Oleuropein and total phenolic contents over a year were determined by high-performance liquid chromatography and Folin–Ciocalteu methods. The results showed that 13.52% of pure oleuropein was found with a high purity of 96.54% and purification efficiency of 78.49%. Oleuropein and total phenolic contents of different olive varieties were quite different, but both had similar trends over the year. Five methods, including DPPH (2,2-diphenyl-1-picrylhydrazyl), ABST (2,2′-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid) diammonium salt), ferric reducing antioxidant power, total reducing power and nitrite-scavenging ability, were used to evaluate the antioxidant activities of oleuropein, and the IC 50 were 34.54 ± 0.14 μg/mL, 18.79 ± 0.82 μg/mL, 75.32 ± 1.83 μg/mL, 13.80 ± 0.68 μg/mL and 1.00 ± 0.08 mg/mL, respectively. Practical Applications This study provides information on the changes in contents including oleuropein and total phenolics in a year to help understand the relationship between content of oleuropein and various influencing factors. Currently, the metabolic pathways of oleuropein are not clear. These results provide information for the study of the metabolism of phenolic compounds in olive and promote research at the molecular level. Oleuropein occupies a large proportion of total polyphenols in olive and can be to be purified by silica gel column chromatography with high purification efficiency for industrial production and laboratory production. In addition, the comprehensive evaluation of activity in vitro shows that oleuropein is more useful than BHT (2,6-di- tert -butyl-4-methylphenol) for the application in food and human health.

研究领域: 植物化学 · 食品科学 · 分子生物学
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PARTICULATE SCIENCE AND TECHNOLOGY · 2025 · IF 1.5

Biomimic oleuropein-loaded mesoporous polydopamine nanocomposite in injectable hydrogels inhibits cell apoptosis and antioxidant for myocardial infarction

Tianyi Ma,Ming Huo,Ruinan Xing

This study addressed the fabrication of mesoporous polydopamine nanoparticles (MPD NPs) by an emulsion-induced interface assembly technique, followed by the incorporation of oleuropein (OLE) into MPD NPs via electrostatic attraction, resulting in OLE@MPD NPs. In the post-myocardial infarction (MI) context, these therapies were explicitly designed to eradicate reactive oxygen species (ROS) and promote MI healing. We additionally integrated them with a thermosensitive chitosan (CH) hydrogel (HGL) to generate an injectable composite hydrogel (OLE@MPD/CH HGL). Through in vitro tests, the OLE@MPD/CH HGL demonstrated remarkable ROS-scavenging capability in H9C2 cells subjected to oxidative stress and effectively inhibited their apoptosis. This study introduces an innovative method to enhance MI therapy by utilizing the OLE@MPD/CH HGL. This OLE@MPD/CH HGL efficiently diminishes localized oxidative stress caused by ROS and activates the HO-1/Nrf2 signaling pathway.

研究领域: 生物医学工程 · 纳米医学 · 心血管研究 · 药物递送 · 生物材料
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INTERNATIONAL JOURNAL OF FOOD SCIENCE AND TECHNOLOGY · 2024 · IF 2.6

Characterisation of chitosan coating incorporated with oleuropein and its effects on the quality of refrigerated chicken breasts

Weiping Guo,Yunfeng Xu,Xiangxiang He,Jiakang Wang,Jinle Xiang,Peiyan Li,Denglin Luo

Summary The stability, microstructure and antioxidant capacity of the composite coating solution of chitosan (CS) and oleuropein (OLE, 0.08–0.32%, w/v) were estimated by zeta potential, rheological properties, scanning electron microscope and 2,2-diphenyl-1-picrylhydrazyl radical scavenging assays. Effects of the composite coating on refrigerated chicken breasts were evaluated by microbial, chemical and sensory assays. The results revealed that the coating solutions were stable, intact and exhibited good antioxidant activities. When chicken samples were stored at 4 °C for 12 days, the microbial population treated with CS + OLE decreased to 5.43–7.59 log CFU g −1 compared with the control (8.41 log CFU g −1 ). The increase in pH values, total volatile base nitrogen and thiobarbituric acid reactive substances contents, and drip loss rate of chicken samples had also been deferred. Overall, the results indicated that it was feasible to apply CS with OLE to extend the shelf life of chicken breasts.

CAS / MDL: 76-03-9 504-17-6
研究领域: 食品科学 · 生物技术 · 微生物学
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MOLECULES · 2022 ·Vol. 27 ·期 16 ·5077 · IF 4.927

Stability, Antioxidant Activity and Intestinal Permeation of Oleuropein Inclusion Complexes with Beta-Cyclodextrin and Hydroxypropyl-Beta-Cyclodextrin

Hui Liu,Jinhua Luo,Ping Yang,Xiulan Yang,Jun Yan,Qian Yao

Compared to beta-cyclodextrins (beta-CD), hydroxypropyl-beta-cyclodextrins (HP-beta-CD) are a more popular material used to prepare inclusion complexes due to their superior solubility and intestinal absorption. In this study, oleuropein (OL) inclusion complexes with beta-CD (beta-CD:OL) and HP-beta-CD (HP-beta-CD:OL) were prepared and the formation of inclusion complexes was validated by IR, PXRD, and DSC. A phase solubility test showed that the lgK(25 °C) and binding energy of beta-CD:OL and HP-beta-CD:OL was 2.32 versus 1.98, and −6.1 versus −24.66 KJ/mol, respectively. Beta-CD:OL exhibited a more powerful effect than HP-beta-CD:OL in protecting OL from degradation upon exposure to light, high temperature and high humidity. Molecular docking, peak intensity of carbonyls in IR, and ferric reducing power revealed that beta-CD:OL formed more hydrogen bonds with the unstable groups of OL. Both inclusion complexes significantly enhanced the solubility, intestinal permeation and antioxidant activity of OL (p< 0.05). Though HP-beta-CD:OL had higher solubility and intestinal absorption over beta-CD:OL, the difference was not significant (p> 0.05). The study implies that lower binding energy is not always associated with the higher stability of a complex. Beta-CD can protect a multiple-hydroxyl compound more efficiently than HP-beta-CD with the intestinal permeation comparable to HP-beta-CD complex.Keywords:oleuropein;beta-CD;hydroxypropyl-beta-CD;stability;intestinal permeation

研究领域: 药剂学 · 食品科学 · 生物化学
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JOURNAL OF FOOD BIOCHEMISTRY · 2018 ·Vol. 42 ·期 3 ·e12517 · IF 1.552

Phenolic composition of oleuropein extract after enzymatic process by HPLC-MS and their antioxidant and antibacterial activities

Jiao-Jiao Yuan,Jun-Ling Tu,Frank G. F. Qin,Yong-Jun Xu,Bing Li

Oleuropein is an antioxidant olive constituent, but it is liable to degrade into hydroxytyrosol. Oleuropein extract was hydrolyzed by hemicellulase and the results presented that 14 phenols were identified in the ethyl acetate extract of enzymatic hydrolysate by HPLC-MS. Antioxidant activities (DPPH, ABTS, total reducing power, FRAP, and Fe 2+ chelating ability) of phenols were all added with the samples concentration increased, and dose–effect relationship also existed. 14 phenols all possessed certain inhibition effect against selected bacteria, and they had better inhibition effect against tested Gram-positive bacterium ( Staphylococcus aureus ) than Gram-negative bacterium ( Escherichia coli ). Finally, hydroxytyrosol, oleuropein, eugenol, caffeic acid, and 3,4-dihydroxybenzoic acid could present excellent antioxidant and antibacterial effect, and the two activities mainly had close relationship. Practical applications From the previous study we could know enzymatic biotransformation from oleuropein to HT was a promising method. Therefore, HT preparation from enzyme has attracted great attention of researcher. If that, a lot of enzymatic hydrolysate would be produced in the process. So, present study was to use fully the ethyl acetate extract of enzymatic hydrolysate, and to determine the chemical composition of phenolic compounds in EAE by HPLC-MS, and to evaluate their antioxidant and antimicrobial capacity. The result was shown that phenols of oleuropein extract after enzymatic process, therefore, may be suitable as a source of powerful antioxidants and bacteriostatic due to their stronger antioxidant and antibacterial activities. They could be widely applied in functional food industry for preservation.

研究领域: 食品科学 · 植物化学 · 生物技术
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COLLOIDS AND SURFACES A-PHYSICOCHEMICAL AND ENGINEERING ASPECTS · 2021 · IF 4.539

Isolation and purification of oleuropein from olive leaves using boric acid affinity resin and a novel solvent system

Baoqian Liu,Jianfei Liu,Dongdong Huang,Dong Pei,Jianteng Wei,Duolong Di

Oleuropein is an important natural compound with many biological activities. How to get high purity oleuropein is an urgent issue to be solved. This study provided a method for separating and purifying high purity oleuropein from olive leaves using boric acid affinity resin and a novel solvent system. And the experimental kinetic and adsorption isotherm data of boric acid affinity resin were well–fitted pseudo–first–order kinetic model and Langmuir isotherm model, respectively. The dynamic desorption experiments showed that ethanol was the most efficient eluent while had the lowest oleuropein purity. However, after the novel solvent system treated only one cycle of adsorption and desorption , the purity of oleuropein increased by 5.55 folds from 12.31 ± 0.42% – 68.30 ± 2.08 %. The results can guide the separation and purification of high purity catechol natural products using boric acid affinity resin and mixed solvent systems.

研究领域: 植物化学 · 天然产物分离纯化 · 药用植物研究
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