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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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Antioxidants · 2021 ·Vol. 10 ·期 11 ·1697 · IF 6.313

Oleuropein Enhances Stress Resistance and Extends Lifespan via Insulin/IGF-1 and SKN-1/Nrf2 Signaling Pathway in Caenorhabditis elegans

Shiling Feng,Chunyan Zhang,Tao Chen,Lijun Zhou,Yan Huang,Ming Yuan,Tian Li,Chunbang Ding

Oleuropein (OLE) is a secoiridoid glycoside that mainly exists in olives with multifaceted health benefits. The present study aimed to investigate the stress resistance and lifespan extension effects of OLE inCaenorhabditis elegans. The results showed that OLE could significantly prolong the lifespan ofC. elegansby 22.29%. Treatment with OLE also significantly increased the survival rates of worms against lethal heat shock and oxidative stress. Meanwhile, OLE supplementation increased the expression and activity of antioxidant enzymes and suppressed the generation of malondialdehyde in nematodes. In addition, the results from mutants implied that OLE might mediate longevity and stress resistance via DAF-16/FoxO, which played a vital role in the insulin/IGF-1 signaling (IIS) pathway. To further identify the molecular targets of OLE, mRNA level and loss-of-function mutants of IIS-associated genes were investigated. The data revealed that OLE activated IIS by down-regulating the upstream components,daf-2andage-1. Furthermore, another stress response and longevity pathway in parallel to DAF-16, SKN-1/Nrf2, was also shown to involve in OLE-induced beneficial effects. Collectively, these results provide the theoretical basis that OLE could enhance the stress resistance and increase the lifespan ofC. elegansthrough the IIS and SKN-1/Nrf2 signaling pathways.Keywords:oleuropein;Caenorhabditis elegans;longevity;stress resistance

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Journal of Functional Foods · 2023 · IF 5.6

Oleuropein and its hydrolysate from extra virgin olive oil inhibit breast cancer cells proliferation interfering with the PI3K-AKT signal pathway

Shuyan Han,Hongmei Hou,Yiren Zhang,Zhongxiang Fang,Yun Li,Le Zhang,Yandan Wang,Shijia Zhang,Hui Zhang,Qingzhe Jin,Gangcheng Wu,Xingguo Wang

Naturally existing polyphenols in virgin olive oil possess significative biological activities and are potential nutraceutical therapeutic for breast cancer. In the present study, we investigated the anti-breast cancer activity of oleuropein and its hydrolysates, and further explored their molecular mechanisms. A similar cellular viability was observed in MCF-7 and MDA-MB-231 cells both treated with oleocanthal (3 μg/mL), hydroxytyrosol (30 μg/mL) and oleuropein (200 μg/mL) showed the same cellular viability, indicating oleocanthal structure may be the main structural component part of the physiological activity of oleuropein. Results showed that olive polyphenols produced reactive oxygen species and suppressed breast cancer cells. For flow cytometry analysis, the three polyphenols impacted the MCF-7 cell and MDA-MB-231 cycle, stagnated in the G1 phase and S phase, respectively, via reducing Cyclin D protein expression and promoting cell apoptosis. The pro-apoptosis, anti-proliferation capacity and delaying cell cycle of the three olive oil polyphenols could be achieved through the PI3K-AKT signaling pathway, mainly inhibited phosphorylation of AKT, PI3K protein.

CAS / MDL: 10597-60-1 32619-42-4
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PHYTOCHEMICAL ANALYSIS · 2021 ·Vol. 32 ·期 6 ·1074-1081 · IF 3.373

Response surface methodology optimised solvothermal system enables an efficient extraction of echinacoside and oleuropein from Syringa pubescens Turcz

Yanfang Wu,Yindi Chu,Qinyu Yang,Mengjia Li,Miao Yu,Ruixue Deng,Kun Liu,Xinsheng Wang,Enguo Fan

Introduction Syringa pubescens Turcz. was reported to be abundant in the Funiu Mountains of Henan Province and can be used to treat hepatitis and cirrhosis. In order to develop and utilise the resource, a fast and simple technique to extract bioactive compounds is needed. Objectives Our aims were to provide an extraction technique of glycosides from S. pubescens and study the antioxidant activity of this material. Methods Box–Behnken design (BBD) was employed with three factors at three levels. The process parameters such as ethanol concentration ( X 1 ), temperature ( X 2 ), and solvent–solid ratio ( X 3 ) could significantly influence efficiency and yield of target compounds. High-performance liquid chromatography (HPLC) was used to determine the content of glycosides. DPPH (α,α-diphenyl-β-picrylhydrazyl), ABTS (2,2'-azino-bis(3-ethylbenzothiazoline-6-sulphonic acid) and reducing power were used to evaluate the antioxidant activity of S. pubescens extract. Results The optimal parameters for the maximal extraction yield were obtained with ethanol concentration of 68%, temperature of 89°C, solvent–solid ratio of 46 mL/g, and time of 20 min. The S. pubescens extract showed strong antioxidant properties in vitro . Conclusion The findings indicated the potential application of solvothermal extraction method to extract bioactive compounds from S. pubescens Turcz. Furthermore, the S. pubescens extract could be used as an important resource of antioxidant activity.

CAS / MDL: 82854-37-3 32619-42-4
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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
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Natural Product Communications · 2020 · IF 0.468

Jasmine (Jasminum grandiflorum) Flower Extracts Ameliorate Tetradecanoylphorbol Acetate Induced Ear Edema in Mice

Dongli Li,Xiaodan Tang,Chang Liu,Huifang Li,Shuzhen Li,Shili Sun,Xi Zheng,Panpan Wu,Xuetao Xu,Kun Zhang,Hang Ma

Published data from in vitro assays support the anti-inflammatory effects of jasmine (Jasminum grandiflorum Linn.) but limited studies are reported in animal models. Herein, the anti-inflammatory effects of jasmine flower extracts (JFEs) including ethanol extract (JF-EE), petroleum ether extract (JF-PEE), ethyl acetate extract (JF-EAE), and n-butanol extract (JF-BE) were evaluated in a mouse ear edema model. Acute mouse ear skin inflammation was induced by tetradecanoylphorbol acetate (TPA; 125 µg/mL) and then treated with JFEs (100 mg/mL) or dexamethasone (DEX; 6.25 mg/mL; as a positive control). Jasmine flower extracts alleviated ear edema by reducing TPA-increased ear thickness and ear weight by 30.8% to 64.1% and 24.0% to 47.1%, respectively, whereas DEX showed comparable activity (by 71.8% and 49.1%, respectively). Their anti-inflammatory effects were supported by data from the immunohistochemical assays. Jasmine flower extracts reduced the inflammatory cells (from 5.5- to 9.5-fold) and the expressions of inflammation related enzymes including cyclooxygenase-2 and inhibitor of kappa-B kinase (from 1.9- to 2.8-fold and from 7.1- to 11.0-fold, respectively). Findings from this study showed that JFEs were able to ameliorate TPA-induced mouse skin inflammation. However, future studies on the underlying mechanisms of jasmine flower’s anti-inflammatory effects are warranted.

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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.

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Innovative Food Science & Emerging Technologies · 2017 · IF 2.573

Ultrasound-assisted enzyme catalyzed hydrolysis of olive waste and recovery of antioxidant phenolic compounds

Zhihong Wang,Chengzhang Wang,Changwei Zhang,Wenjun Li

The ultrasound-assisted enzyme hydrolysis (UAEH) procedure for extraction of phenolics from olive waste (OW) was established. The optimized conditions obtained with response surface methodology (RSM) were pH   5.75, treatment 40   min and temperature 55   °C, the yield obtained reached to 4.0%. The extraction kinetics model was fitted well to the ln ( C t / C 0 )   =   kt , and the rate constants ( k ) increased with the increased in the extraction temperature. Moreover, the values of k were higher and the activation energy was lower than ultrasound treatment alone. The thermodynamic parameters indicated the extraction process was easier under the UAEH. Compared with the petroleum ether and n-butyl alcohol, ethyl acetate extract fraction had high phenolic content (64.4   mg/g), especially hydroxytyrosol and tyrosol (17.2   mg/g and 14.1   mg/g), and exhibited excellent antioxidant activities in DPPH·, ABTS + ·and FRAP assay. These finding revealed that OW could be used for a enrich source of natural phenolic compounds for development of food industry. Industrial relevance Olive waste (OW) has been widely paid attention as sources of high-added value compounds, such as phenolic which can be obtained by the several methods. And phenolic extract as a food additive can not only improve the sensory quality of food, but also can enhance antioxidant capacity in fatty food matrices. Moreover, the use of this extract has better economic benefits than synthetic additives usually used in food industry. In this study, a novel green, simple and efficient technology was employed to extract the phenolic compounds, which was suitable for large-scale industrial use. The results indicated that ultrasound-assisted enzyme hydrolysis (UAEH) has significant potential in the extraction process of phenolics from OW exhibiting higher phenolic yield in shorter extraction times.

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EUROPEAN JOURNAL OF LIPID SCIENCE AND TECHNOLOGY · 2018 ·Vol. 120 ·期 5 ·1700471 · IF 2.2

W/O Nano-Emulsions with Olive Leaf Phenolics Improved Oxidative Stability of Sacha Inchi Oil

Lingyi Liu,Zhou Jin,Min Wang,Wangyang Shen,Zhenzhou Zhu,Zhan Wang,Lianliang Liu

Natural phenolic compounds have been drawn a wide attention to replace the synthesis antioxidants due to the food safety issues, while, natural phenolic compounds are usually polyhydroxy derivatives which exhibit hydrophilic capacity, limiting their applications directly in lipid systems. In this work, olive leaf phenolics (OLP) are extracted by ultrasound from five cultivars and the optimal cultivar is chosen to prepare W/O nano-emulsions of Sacha Inchi oil (SIO, containing more than 90% polyunsaturated fatty acids). The droplet size could reach 2.15 ± 0.13 nm and remaines stable without phase separation during 30-day storage. Oxidative stabilities of SIO containing 0.02%, 0.05%, and 0.1% OLP (w/w) are evaluated by Rancimat test and accelerated storage test. The release of OLP by preparation of W/O nano-emulsions is capable of controlling the oxidative progress of SIO, by prolonging the induction time, preventing the production of primary and secondary oxidative products and also the deterioration of polyunsaturated fatty acids and tocopherols. Practical Applications : Sacha Inchi oil (SIO) contains approximately 90% of polyunsaturated fatty acids (PUFAs) associated with poor oxidative stability. Olive leaf phenolics (OLP) are considered as a great and cheap source of natural phenolic compounds. This study aimes to select the optimum source of OLP from five cultivars and to prepare a W/O nano-emulsion of OLP. By diluting the W/O nano-emulsion of OLP into SIO, effect of different concentrations OLP on the oxidative stability of SIO is evaluated through thermal oxidative stability and storage oxidative stability in an accelerated storage test. Results indicate that the capacity of OLP to retard the SIO oxidation depends on the incorporated concentration, which means that it is doable to adopt OLP, an abundant and cheap material, to improve the stability of edible oil with high PUFAs in the industry. Olive leaf phenolics are extracted and detected to prepare an efficient and stable W/O nano-emulsion; By diluting W/O nano-emulsion into Sacha Inchi oil, oxidative stability of the high content PUFAs oil is improved.

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COLLOIDS AND SURFACES A-PHYSICOCHEMICAL AND ENGINEERING ASPECTS · 2025 · IF 5.4

The Pd nanoparticles-modified porphyrin metal-organic framework as highly efficient oxidase mimics for colorimetric quantification and discrimination of oleuropein

Yueping You,Yi Wang,Meiyi Liang,Chenglin Wu,Zhiheng Huang,Jinlin Guo,Hulan Chen,Yu Fan

Given the limitations associated with conventional methods for oleuropein (OLE) analysis, such as their high cost, lengthy analysis time, and complex sample preparation procedures, this study proposed a novel colorimetric sensing assay based on nanozyme technology, with a specific focus on PCN-224-Pd composite materials. PCN-224 exhibited distinctive structural characteristics and possessed a substantial specific surface area, making it an ideal dispersion platform for Pd nanoparticles. This effectively enhanced the catalytic activity and stability of the nanozyme. Technologies such as transmission electron microscopy (TEM), X-ray photoelectron spectroscopy (XPS), inductively coupled plasma optical emission spectrometry (ICP-OES), and fourier-transform infrared spectroscopy (FTIR) were employed to comprehensively characterize the morphology, structure, and composition of the synthesized PCN-224-Pd. Experimental characterizations revealed that PCN-224-Pd exhibited high affinity and the origin of PCN-224-Pd as oxidase mimics was likely dependent on the conversion of dissolved oxygen to 1 O 2 and •OH. Under optimal catalytic conditions, we developed a colorimetric sensing assay for oleuropein with an extended linear range (0.1–400 μg/mL) and an impressively low detection limit (9.7 ng/mL). These results indicated that the PCN-224-Pd based method held immense potential for practical applications as it could serve as a visual inspection technique for detecting oleuropein.

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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.

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