Preparative isolation of oleocanthal, tyrosol, and hydroxytyrosol from olive oil by HPCCC

Adhami, Hamid-Reza; Zehl, Martin; Dangl, Christina; Dorfmeister, Dominic; Stadler, Marco; Urban, Ernst; Hewitson, Peter; Ignatova, Svetlana; Krenn, Liselotte

doi:10.1016/j.foodchem.2014.08.079

Cited by 37 publications

(30 citation statements)

References 35 publications

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“…An efficient method of high-speed CCC using a solvent system composed of butanol-water-acetic acid (1 : 1 : 0.1) and coupled with post-column online evaluation was developed to screen, isolate, and identify the major antidiabetic compounds present in the leaves of Olea europaea L. (Oleaceae) [22]. Moreover, the purification of TYR, HT, and a mixture of oleocanthal isomers by a two-step high-performance CCC procedure involving the use of heptane-EtOAc-MeOH-H 2 O mixtures in normal-phase and reverse-phase modes has been proposed [23]. In the field of by-product valorization, three works have comprised countercurrent chromatography utilization for the recovery of pure compounds.…”

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confidence: 99%

Development of a Sustainable Procedure for the Recovery of Hydroxytyrosol from Table Olive Processing Wastewater Using Adsorption Resin Technology and Centrifugal Partition Chromatography

et al. 2015

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The present endeavor aims to establish a novel procedure, applicable to the extraction and isolation of hydroxytyrosol from table olive processing wastewater. A two-step chromatographic separation is presented using non-ionic absorbent resin for the recovery of its phenolic content, followed by purification of hydroxytyrosol with centrifugal partition chromatography. Two table olive processing wastewaters, obtained from Kalamon and Amfissis olive varieties, were used. In the extracts obtained after resin treatment, the hydroxytyrosol content was determined by high-performance liquid chromatography with diode-array detection to be 4.05% and 10.10%, respectively. The extract from Amfissis table olive processing wastewater was further processed with preparative centrifugal partition chromatography for the purification of hydroxytyrosol. High-performance liquid chromatography analysis revealed that the isolated compound was >95% purity.

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Development of a Sustainable Procedure for the Recovery of Hydroxytyrosol from Table Olive Processing Wastewater Using Adsorption Resin Technology and Centrifugal Partition Chromatography

et al. 2015

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“…The olive oil-derived compounds (uvaol, erythrodiol, maslinic acid, oleanolic acid, betulinic acid, oleuropein, 3-hydroxytyrosol, and chlorogenic acid) were supplied by Sigma-Aldrich (Vienna, Austria). Oleocanthal (>80% purity) was isolated from olive oil as recently described (Adhami et al, 2015) and was and kindly provided by Prof. Liselotte Krenn (University of Vienna). Bovine serum albumin (BSA-fatty acid free) was from Roth (Karlsruhe, Germany).…”

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confidence: 99%

Erythrodiol, an Olive Oil Constituent, Increases the Half-Life of ABCA1 and Enhances Cholesterol Efflux from THP-1-Derived Macrophages

et al. 2017

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Cholesterol efflux (ChE) from macrophages is an initial step of reverse cholesterol transport (RCT). The ATP-binding cassette transporter A1 (ABCA1) is a key transporter for ChE and its increased expression is regarded to attenuate atherosclerosis. Thus, the identification and characterization of molecules raising ABCA1 and thereby stimulating ChE is of pharmacological relevance. In this study, we tested dietary compounds from olive oil for their capacity of enhancing cellular ABCA1 protein level. We identified erythrodiol (Olean-12-ene-3β,28-diol) as an ABCA1 stabilizer and revealed its positive influence on ChE in THP-1-derived human macrophages. Among the nine tested compounds from olive oil, erythrodiol was the sole compound raising ABCA1 protein level (at 10 μM). None of the tested compounds impaired viability of THP-1 macrophages from 5 to 20 μM as determined by resazurin conversion. Western blot analyses of key membrane transporters contributing to ChE showed that the protein level of ABCG1 and scavenger receptor class B member 1 (SR-B1) remain unaffected by erythrodiol. Besides, erythrodiol (10 μM) did not influence the mRNA level of ABCA1, ABCG1, and SR-B1, as determined by quantitative reverse transcription PCR, but significantly inhibited the degradation of ABCA1 as evident by an increased half-life of the protein in the presence of cycloheximide, an inhibitor of de novo protein synthesis. Therefore, erythrodiol promotes ChE from THP-1-derived human macrophages by stabilizing the ABCA1 protein. This bioactivity makes erythrodiol a good candidate to be further explored for therapeutic or preventive application in the context of atherosclerosis.

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“…The new resulting cells can form a malignant tumor (neoplasm) or spread through the body and form metastases. Oleocanthal is a phenolic compound in the composition of olive oil 2,3 , has been implicated in the health benefits associated with diets rich in extra virgin olive oil EVOO; a powerful antioxidant 4 ; Non-Steroidal Anti-Inflammatory Drugs (NSAIDs) 5 .…”

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confidence: 99%

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2017

IJPSR

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This study was carried out with goal to predict the inhibition of Aurora Kinase B by a series of Oleocanthal by molecular modeling. During last year's Kinases Aurora were emerged like one of the important targets of drug in several pharmaceutical companies and industries of research and it plays a main function in the regulation of the mitosis and the cytocinèse 1 and for this reason one inhibited these Kinases Aurora B with a series of oleocanthal derivatives as legand can simultaneously induce the autophagy and apoptose in the tumoral cells. To understand the complexation mechanisms in the biological system call was made at the molecular docking, we used MOE software. was optimized geometries of all ligands, in result, the calculation of the score of energy was made to form the complex and identify the interactions in the two media a solvated (water solution) and the other unsolvated in the end we find that the ligands L5 and L6 haves the lowest energies.

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Preparative isolation of oleocanthal, tyrosol, and hydroxytyrosol from olive oil by HPCCC

Cited by 37 publications

References 35 publications

Development of a Sustainable Procedure for the Recovery of Hydroxytyrosol from Table Olive Processing Wastewater Using Adsorption Resin Technology and Centrifugal Partition Chromatography

Development of a Sustainable Procedure for the Recovery of Hydroxytyrosol from Table Olive Processing Wastewater Using Adsorption Resin Technology and Centrifugal Partition Chromatography

Erythrodiol, an Olive Oil Constituent, Increases the Half-Life of ABCA1 and Enhances Cholesterol Efflux from THP-1-Derived Macrophages

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