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Fátima Peres, Luisa L Martins, Miguel Mourato, Conceição Vitorino, Paulo Antunes, Suzana Ferreira-Dias
In this study, the lipophilic and hydrophilic phenol composition of virgin olive oils (VOO) obtained from olives from two of the most important Portuguese cultivars ('Galega Vulgar' and 'Cobrançosa'), harvested at different ripening stages and under two irrigation schemes (rain fed and irrigated), was evaluated. Phenolic alcohols (hydroxytyrosol and tyrosol), phenolic acids and derivatives and flavonoids (luteolin and apigenin), as well as tocopherols were quantified. Lipophilic (>300mgkg(-1)) and hydrophilic phenols (>600mgkg(-1)) were present in high contents in both VOO, for early ripening stages...
November 15, 2016: Food Chemistry
Amir Ben Mansour, Boutheina Gargouri, Eleni Melliou, Prokopios Magiatis, Mohamed Bouaziz
BACKGROUND: Olive oil contains compounds with interesting biological activities which are influenced by the cultivar, the geographic origin and other factors. The aims of this work were to (1) investigate these factors in Neb Jmel olive oil from various Tunisian origins; (2) determine the influence of geographic conditions on phenolic composition of Neb Jmel olive oil and consequently on the antioxidant compounds; and (3) verify whether oils could be discriminated based on geographical origin...
October 2016: Journal of the Science of Food and Agriculture
Agnieszka Filipek, Monika E Czerwińska, Anna K Kiss, Małgorzata Wrzosek, Marek Naruszewicz
BACKGROUND: Oleacein (dialdehydic form of decarboxymethyl elenolic acid linked to hydroxytyrosol; 3,4-DHPEA-EDA) have been proven to possess antioxidant and anti-inflammatory activity. PURPOSE: In this study, we examined whether oleacein could increase CD163 and IL-10 receptor expression as well as HO-1 intracellular secretion in human macrophages. METHODS: Effect of oleacein (10 and 20 μmol/l) or oleacein together with complexes of haemoglobin (Hb) and haptoglobin 1-1 (Hp11) or haptoglobin 2-2 (Hp22) on expression of IL-10 and CD163 receptor was determined by Flow Cytometry...
December 15, 2015: Phytomedicine: International Journal of Phytotherapy and Phytopharmacology
Elena Antonini, Alfonso Farina, Emanuele Salvatore Scarpa, Alessandra Frati, Paolino Ninfali
In this investigation, 14 extra virgin olive oils (EVOOs), produced with Leccino and Raggiola olive cultivars, by a new two-way (2W) decanter were compared with 14 EVOOs produced by means of a conventional three-way (3W) decanter. The 2W EVOOs had higher phenol concentrations, as shown by high-performance liquid chromatography/diode array detection (HPLC-DAD) analysis and yielded a higher extraction of the 3,4-DHPEA-EDA (oleacein), 3,4-DHPEA-EA (oleuropein aglycone) and p-HPEA-EDA (oleocanthal). The concentrations of lignans, (+)-pinoresinol and (+)-1-acetoxypinoresinol, detected by HPLC-FLD equipment, were higher in the 2W EVOOs than they were in EVOOs produced using the 3W system...
2016: International Journal of Food Sciences and Nutrition
Aránzazu García, Elisa Rodríguez-Juan, Guillermo Rodríguez-Gutiérrez, José Julian Rios, Juan Fernández-Bolaños
Deep eutectic solvents (DESs) are "green" solvents, applied in this study for the extraction of phenolic compounds from virgin olive oil (VOO). Different combinations of DES consisting of choline chloride (ChCl) in various mixing ratios with sugars, alcohols, organic acids, and urea, as well as a mixture of three sugars were used. The yields of the DES extractions were compared with those from conventional 80% (v/v) methanol/water. DES showed a good solubility of phenolic compounds with different polarities...
April 15, 2016: Food Chemistry
Annekathrin Martina Keiler, Sefirin Djiogue, Tino Ehrhardt, Oliver Zierau, Leandros Skaltsounis, Maria Halabalaki, Günter Vollmer
Oleocanthal is a bioactive compound from olive oil. It has attracted considerable attention as it is anti-inflammatory, antiproliferative, and has been shown to possess neuroprotective properties in vitro and in vivo. Delineated from its polyphenolic structure, the aim of this study was to characterize oleocanthal towards estrogenic properties. This might contribute to partly explain the beneficial effects described for the Mediterranean diet. Estrogenic properties of oleocanthal were assessed by different methods: a) stimulation of reporter gene activity in MVLN or RNDA cells either expressing estrogen receptor α or β, b) stimulation of luciferase reporter gene activity in U2OS osteosarcoma cells expressing estrogen receptor α or β, and c) elucidation of the impact on estradiol-induced gene expression in U2OS cells transduced with both estrogen receptors...
September 2015: Planta Medica
Monika E Czerwińska, Marlena Ziarek, Agnieszka Bazylko, Ewa Osińska, Anna K Kiss
INTRODUCTION: The genus Ligustrum (Oleaceae) is distributed in Europe and Asia (south China and Korea), where it is used to prevent hypertension, sore throats, inflammation and diabetes. The main groups of compounds in extracts of Ligustrum vulgare are biologically active secoiridoids and phenylpropanoids. OBJECTIVES: The aim of the study was primarily the development and validation of a HPTLC-photodensitometry method for separation and determination of secoiridoids (oleacein, oleuropein) and phenylpropanoids (echinacoside) in different extracts prepared from leaves of L...
July 2015: Phytochemical Analysis: PCA
Marek Naruszewicz, Monika E Czerwińska, Anna K Kiss
Epidemiological studies suggest that the cardioprotective properties of olive oil, particularly extra-virgin type, result from a positive influence of its components, such as phenolic compounds, on the cardiovascular system. One of the most abundant phenolic compounds of extra virgin olive oil is the dialdehydic form of elenolic acid conjugated with 3, 4-(dihydroxyphenyl)ethanol (3, 4- DHPEA-EDA), also known as oleacein. Due to its abundance in olive oil, it may play a special role in decreasing the progression of atherosclerosis...
2015: Current Pharmaceutical Design
Isabella Vulcano, Maria Halabalaki, Leandros Skaltsounis, Markus Ganzera
The first CE procedure for the quantitative determination of pharmacologically relevant secoiridoids in olive oil, oleocanthal and oleacein, is described. Together with their precursors tyrosol and hydroxytyrosol they could be baseline separated in less than 15min using a borax buffer with pH 9.5, at 25kV and 30°C. Method validation confirmed that the procedure is selective, accurate (recovery rates from 94.0 to 104.6%), reproducible (σmax⩽6.8%) and precise (inter-day precision⩽6.4%), and that the compounds do not degrade quickly if non-aqueous acetonitrile is used as solvent...
February 15, 2015: Food Chemistry
Jörg Flemmig, Dorothea Rusch, Monika Ewa Czerwińska, Hans-Wilhelm Rauwald, Jürgen Arnhold
We investigated in vitro the ability of a standardised olive leaf dry extract (Ph. Eur.) (OLE) as well as of its single components to circumvent the hydrogen peroxide-induced inhibition of the hypothiocyanite-producing activity of lactoperoxidase (LPO). The rate of hypothiocyanite (⁻OSCN) formation by LPO was quantified by spectrophotometric detection of the oxidation of 5-thio-2-nitrobenzoic acid (TNB). By using excess hydrogen peroxide, we forced the accumulation of inactive enzymatic intermediates which are unable to promote the two-electronic oxidation of thiocyanate...
May 1, 2014: Archives of Biochemistry and Biophysics
Konstantina Vougogiannopoulou, Christelle Lemus, Maria Halabalaki, Carlo Pergola, Oliver Werz, Amos B Smith, Sylvie Michel, Leandros Skaltsounis, Brigitte Deguin
The dialdehydes oleacein (2) and oleocanthal (4) are closely related to oleuropein (1) and ligstroside (3), the two latter compounds being abundant iridoids of Olea europaea. By exploiting oleuropein isolated from the plant leaf extract, an efficient procedure has been developed for a one-step semisynthesis of oleacein under Krapcho decarbomethoxylation conditions. Highlighted is the fact that 5-lipoxygenase is a direct target for oleacein with an inhibitory potential (IC50: 2 μM) more potent than oleocanthal (4) and oleuropein (1)...
March 28, 2014: Journal of Natural Products
Monika E Czerwińska, Anna K Kiss, Marek Naruszewicz
Polyphenols, such as oleacein (3,4-DHPEA-EDA; 3,4-dihydroxyphenylethanol-elenolic acid dialdehyde), are believed to play a role in the prevention of cardiovascular diseases. Due to an increase of neutrophil mediators in acute myocardial infarction the aim of this study was to establish the effect of oleacein on neutral endopeptidase (NEP) activity and other functions of human neutrophils, such as elastase, MMP-9 and IL-8 production. The effect on CD62L and CD11b/CD18 expression on neutrophils was also determined...
June 15, 2014: Food Chemistry
Evangelia Karkoula, Angeliki Skantzari, Eleni Melliou, Prokopios Magiatis
A previously developed method for measurement of oleocanthal and oleacein in olive oil by quantitative (1)H NMR was expanded to include the measurement of the monoaldehydic forms of oleuropein and ligstroside aglycons. The method was validated and applied to the study of 340 monovarietal Greek and Californian olive oils from 23 varieties and for a 3-year period. A wide variation concerning the concentrations of all four secoiridoids was recorded. The concentration of each one ranged from nondetectable to 711 mg/kg and the sum of the four major secoiridoids (named as D3) ranged from nondetectable to 1534 mg/kg...
January 22, 2014: Journal of Agricultural and Food Chemistry
Andrzej Parzonko, Monika E Czerwińska, Anna K Kiss, Marek Naruszewicz
Endothelial progenitor cells (EPCs) are responsible for neovascularization of ischaemic tissue and may participate in re-endothelization of an injured arterial wall. There is evidence that angiotensin II, by an increase of gp91phox expression and induction of ROS generation, accelerates cell senescence and impairs functions of EPCs. Oleacein is a main phenolic compound from olive oil, whereas oleuropein is present in olive leaves. Both compounds possess antioxidative, hypotensive and anti-inflammatory properties and show beneficial activity on the cardiovascular system...
September 15, 2013: Phytomedicine: International Journal of Phytotherapy and Phytopharmacology
K Hansen, A Adsersen, S B Christensen, S R Jensen, U Nyman, U W Smitt
The aqueous extract of the leaves of Olea europaea and Olea lancea both inhibited Angiotensin Converting Enzyme (ACE) in vitro. A bioassay-directed fractionation resulted in the isolation of a strong ACE-inhibitor namely the secoiridoid 2-(3,4-dihydroxyphenyl)ethyl 4-formyl-3-(2-oxoethyl)-4 E-hexenoate (oleacein) (IC(50) = 26 μM). Five secoiridoid glycosides (oleuropein, ligstroside, excelcioside, oleoside 11-methyl ester, oleoside) isolated from Oleaceous plants showed no significant ACE-inhibition whereas, after enzymatic hydrolysis, the ACE-inhibition at 0...
March 1996: Phytomedicine: International Journal of Phytotherapy and Phytopharmacology
Evangelia Karkoula, Angeliki Skantzari, Eleni Melliou, Prokopios Magiatis
A new method for direct measurement of the oleocanthal and oleacein levels in olive oil by quantitative (1)H NMR was developed. The method was applied to the study of 175 monovarietal commercial Greek and California olive oil samples. The main findings were as follows: (1) There was a significant variation concerning the concentrations of oleocanthal and oleacein among the studied samples. Their concentrations ranged from nondetectable to 355 mg/kg and their sum (index D1) from 0 to 501 mg/kg. (2) There are olive varieties that independent of geographic origin and harvest time produce oil that contains both compounds in low levels...
November 28, 2012: Journal of Agricultural and Food Chemistry
B Somanadhan, U W Smitt, V George, P Pushpangadan, S Rajasekharan, J O Duus, U Nyman, C E Olsen, J W Jaroszewski
Bioactivity-guided fractionation of extracts of the aerial parts of Jasminum azoricum var. travancorense, using an in vitro ACE inhibition assay, led to isolation of three oligomeric, iridoid-type compounds, which were named sambacein I-III. Their structures are based on spectroscopic and chemical evidence. Similarly, fractionation of extracts of aerial parts of J. grandiflorum resulted in the isolation of the previously reported ACE inhibitor, oleacein. The IC50 values of purified ACE inhibitors were 26-36 microM...
April 1998: Planta Medica
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