DOCSLIB.ORG

Qualitative Phenolic Profile (HPLC- L

Total Page：16

File Type：pdf, Size：1020Kb

Download full-text PDF Read full-text
Qualitative Phenolic Profile (HPLC- L 04-Gomez:gomez 9-06-2011 16:39 Pagina 22 L AVORO ORIGINALE A.M. G ÓMEZ -C ARAVACA 1, 2 , Qualitative phenolic profile (HPLC- L. C ERRETANI 1, DAD-MS) from olive oil mill waste A. S EGURA -C ARRETERO 2, waters at different states of storage and A. F ERNÁNDEZ -G UTIÉRREZ 2, G. L ERCKER 1, evaluation of hydrolysis process as a T. G ALLINA TOSCHI 1 pretreatment to recover their antioxidants PROGRESS IN NUTRITION Summary VOL . 13 , N. 1, 22-30, 2011 Olive oil mill waste water (OOMWW) represents a waste that it is gene - rated during the extraction process of olive oil from olives and it is an im - TITOLO portant environmental problem because of the huge volume generated in Profilo fenolico qualitativo the mills. Nevertheless, it is highlighted in literature the high concentra - (HPLC-DAD-MS) di acque tion of antioxidants, especially phenolic compounds, in the OOMWW. reflue di vegetazione Principally, the qualitative phenolic profiles of OOMWW differ depen - dell’industria olearia a diversi ding on the technological process of production of olive oil and the time stadi di conservazione e of storage. The aim of this work was to compare qualitatively the pheno - valutazione dell’idrolisi quale lic profile of OOMWW by HPLC-DAD-MS. Glucosilated secoiridoids pretrattamento per il recupero as oleuropein and ligstroside, their aglycon derivatives and simple phenols degli antiossidanti were the principal compounds found in these matrixes. Furthermore, dif - ferent hydrolysis reactions have been studied for the phenolic fraction in the oleuropein standard as well as in the OOMWW samples. These steps KEY WORDS Olive, olive oil mill waste waters, have been evaluated as pretreatment for the selection and a possible sub - antioxidants, phenols sequent recovery of most interesting phenolic compounds as hydroxytyro - sol that has been proved to possess an important antioxidant activity PAROLE CHIAVE Oliva, acque reflue, antiossidanti, Riassunto fenoli Le acque reflue di vegetazione (AV) dell’industria olearia rappresentano un rifiuto generato dal processo di estrazione dell’olio dalle olive e pertan - to sono un problema ambientale per l’elevato volume generato presso gli impianti di produzione. Tuttavia, è nota dalla letteratura, l’elevata concen - 1 Department of Analytical trazione nelle AV di composti antiossidanti a struttura fenolica. I profili Chemistry, Faculty of Sciences, fenolici qualitativi delle AV differiscono principalmente in funzione delle University of Granada, condizioni di produzione e delle modalità e tempi di conservazione. Que - C/Fuentenueva s/n, E-18071 sto lavoro ha l’obiettivo di confrontare qualitativamente i profili fenolici Granada, Spain delle AV mediante analisi HPLC-DAD-MS. Nelle acque reflue di vege - 2 Department of Food Science, tazione appena prodotte sono state ritrovate principalmente secoiridoidi University of Bologna, Piazza glicosilati (oleuropeina e ligstroside) nonché le loro forme derivate aglico - Goidanich 60, I-47521 Cesena (FC), Italy niche e basse concentrazioni di fenoli semplici. Allo stesso tempo sullo standard puro di oleuropeina e sugli stessi campioni di AV sono state in - Indirizzo per la corrispondenza: dagate diverse modalità di idrolisi della frazione fenolica. Tale operazione Dr. A.M. Gómez-Caravaca è stata valutata come pretrattamento per la selezione e l’eventuale succes - Tel. +390547338117 E-mail: [email protected] or sivo recupero dei composti fenolici di maggiore interesse come [email protected] l’idrossitirosolo al quale è riconosciuta una elevata attività antiossidante. 22 04-Gomez:gomez 9-06-2011 16:39 Pagina 23 PROGRESS IN NUTRITION 1/2011 Introduction tioxidant activity makes them in - hydrolysis reactions were studied teresting for the food, pharmaceu - using oleuropein as standard and Olive oil mill waste water tical and cosmetic industry. Be - better results were apply to the (OOMWW) represents the main cause of that, to reutilize them, OOMWW phenolic samples. environmental problem in the oli - their extraction from OOMWW The aim of this treatment was to ve oil production process. 100 kg is a very important objective that evaluate the hydrolysis and to use of olives are necessary to produce also helps to diminish the volume it as a pretreatment for the selec - just 10-20 kg of olive oil, but it re - of olive oil industry by-products. tion and a possible subsequent re - sults in a huge amount of Many phenolic compounds have covery of most interesting pheno - OOMWW (40-100 kg been identified in OOMWW, al - lic compounds as hydroxytyrosol OOMWW) (1) that depends on though the phenolic fraction is very (HYTY) that has been proved to the olive cultivar, ripening index, different from that of olive fruit. possess an important antioxidant time of storage and quantity of OOMWW presents a high con - activity. water added during the olive oil centration of secoiridoids derivati - extraction process. ves, such as hydroxytyrosol, and the The treatment of OOMWW is dialdehydic form of decarboxy - Material and methods extremely difficult due to its large methyl oleuropein aglycone (1). volume and the high concentra - The profile of OOMWW is cha - Samples tion of organic matter (BOD va - racterized by a great complexity (9). ries between 15000 and 50000 A wide variety of methods have Three different OOMWWs that mg/L and COD can reach values been suggested for the treatment vary on the state of storage and the of around 250 g/L). Its principal of OOMWW, such as compo - ripeness of the olives were studied: components are polysaccharides, sting (10), anaerobic digestion OOMWW just produced from sugars, polyphenols, polyalcohols, (11), aerobic treatment (12), mi - fresh olives (AV1), OOMWW proteins,organic acids, and oil (2). xing with municipal wastewater just produced from very ripe olives Moreover, OOMWW contains (13), direct land application (irri - (AV2) and OOMWW from very considerable amounts of suspen - gation) (14), chemical oxidation in ripe olives and storage during three ded solids that may reach up to combination with biological treat - months (AV3). 190 g/L. Despite that, one of the ment (15) or adsorption (2), and major factors of the environmental even the utilization of fungi spe - Extraction of polar phenolic fraction problems caused by the cies (16). However, these metho - OOMWW is the high concentra - dologies had given rise to decom - Phenolic compounds were extrac - tion of polyphenols, because they position or destruction of the phe - ted from OOMWW by a liquid- present phytotoxicity (3, 4), toxi - nolic compounds contained on it liquid extraction method. 10 mL city against aquatic organisms (5), and not to their exploitation. of sample were centrifuged at or suppression of soil microorga - In this work the phenolic profile of 3500 rpm during 10 min. After nisms (6) and are difficult to de - three different OOMWWs concer - that, they were washed twice with compose (7,8). Although polyphe - ning their state of storage were stu - 15 mL of hexane in order to re - nols constitute an important envi - died by HPLC-DAD-MS (TOF, move lipids. The extraction was ronmental problem, their high an - time of flight). After that, different carried out with 20 mL of ethyl 23 04-Gomez:gomez 9-06-2011 16:39 Pagina 24 VOLUME 13 acetate for three times. Finally, the HPLC-DAD-MS(TOF) equip - USA). Parameters for analysis we - ethyl acetate fraction was evapora - ped with a reverse phase C18 Lu - re set using negative ion mode ted under vacuum and then the naTM column according to Ro - with spectra acquired over a mass dry residue was redissolved in 1 tondi et al. (17). Phenolic com - range from m/z 50–1000. The op - mL MeOH/H 2O (50/50). pounds were tentatively identified timum values of the ESI-MS based on their UV-vis and mass parameters were: capillary voltage, Acid and basic hydrolysis spectra obtained by HPLC- +4.5 kV; drying gas temperature, DAD-MS(TOF). 190°C; drying gas flow, 9 L/min; Four different kind of hydrolyses The HPLC system was coupled to and nebulizing gas pressure, 2 bar. were studied: strong and weak acid a Bruker Daltonik microTOF External calibration was perfor - hydrolyses, basic hydrolysis and mass spectrometer (Bruker Dalto - med using a sodium formiate so - enzymatic hydrolysis. nik, Bremen, Germany) using an lution injected at the beginning of Three modalities of strong acid orthogonal electrospray interface the run and all the spectra were hydrolyses were performed: 0.5 M (ESI) (model G1607A from Agi - calibrated prior to the polyphenol HCl/H 2SO4 2 h stirring at 80ºC; lent Technologies, Palo Alto, CA, identification. 1 M HCl/H 2SO4 2 h stirring and 1 M HCl/H 2SO4 22 min ultra - Figura 1 - Decrease of oleuropein after hydrolysis Vs time of hydrolysis. sounds. a) hydrolysis with HCl, b) hydrolysis with citric acid. The weak acid hydrolysis was car - ried out using a saturated solution of citric acid in MeOH/H 2O du - ring 6 h at 80ºC. The basic hydrolysis was carried out in the following way: 2 M NaOH/KOH during 4h stirring, after that it was acidified with HCl until pH=1. Finally, the sam - ple was extracted with diethyl ether/ethyl acetate. To perform the enzymatic hydroly - sis 1 mg oleuropein (Ol) in sodium acetate buffer 0.1 M, pH=5.5 and 5 mg β-glucosidase (from almonds) ≥ 6 units/mg were heated at 37ºC in a water bath during 1 h. Chromatographic procedure Determination of the phenolic fraction was performed using an 24 04-Gomez:gomez 9-06-2011 16:39 Pagina 25 PROGRESS IN NUTRITION 1/2011 The accurate mass data for the Figura 2 - Changes in the concentration of oleuropein and hydroxytyrosol du - molecular ions were processed ring the HCl hydrolysis at different times. using the software Data Analysis 3.4 (Bruker Daltonik), which pro - vided a list of possible elemental formulas by using the Generate Molecular Formula TM editor.
Load more

Recommended publications
  • Valorisation of Olea Europaea L. Olive Leaves Through the Evaluation of Their Extracts: Antioxidant and Antimicrobial Activity
    foods Article Valorisation of Olea europaea L. Olive Leaves through the Evaluation of Their Extracts: Antioxidant and Antimicrobial Activity Mónica Sánchez-Gutiérrez 1,2,* , Isabel Bascón-Villegas 1,2 , Alejandro Rodríguez 2 , Fernando Pérez-Rodríguez 1, África Fernández-Prior 3 , Antonio Rosal 4 and Elena Carrasco 1 1 Food Science and Technology Department, Universidad de Córdoba, Darwin Building, 14014 Córdoba, Spain; [email protected] (I.B.-V.); [email protected] (F.P.-R.); [email protected] (E.C.) 2 BioPrEn Group, Chemical Engineering Department, Universidad de Córdoba, Marie-Curie Building, 14014 Córdoba, Spain; [email protected] 3 Instituto de la Grasa, Consejo Superior de Investigaciones Científicas (CSIC), Campus Universitario Pablo de Olavide, Edificio 46, Ctra. de Utrera, km. 1, 41013 Seville, Spain; [email protected] 4 Molecular Biology and Biochemical Engineering Department, Campus Universitario Pablo de Olavide, Edificio 46, Ctra. de Utrera, km. 1, 41013 Seville, Spain; [email protected] * Correspondence: [email protected] Abstract: Olea europaea L. leaves constitute a source of bioactive compounds with recognized benefits for both human health and technological purposes. In the present work, different extracts from olive leaves were obtained by the application of two extraction methods, Soxhlet and microwave-assisted extraction (MAE), and six solvents (distilled water, ethanolic and glycerol mixtures solvents). MAE Citation: Sánchez-Gutiérrez, M.; was applied under 40, 60 and 80 ◦C for 3, 6.5 and 10 min. The effect of the extraction method, solvent Bascón-Villegas, I.; Rodríguez, A.; and treatment factors (the latter in MAE) on the total phenol content (TPC), the antioxidant activity Pérez-Rodríguez, F.; Fernández-Prior, Á.; Rosal, A.; Carrasco, E.
    [Show full text]
  • Targeted and Untargeted Metabolomics to Explore the Bioavailability of the Secoiridoids from a Seed/Fruit Extract (Fraxinus Angu
    Article Targeted and Untargeted Metabolomics to Explore the Bioavailability of the Secoiridoids from a Seed/Fruit Extract (Fraxinus angustifolia Vahl) in Human Healthy Volunteers: A Preliminary Study Rocío García-Villalba 1, Francisco A. Tomás-Barberán 1, Pascale Fança-Berthon 2, Marc Roller 2, Pilar Zafrilla 3, Nicolas Issaly 4 and María-Teresa García-Conesa 1,* Received: 9 November 2015 ; Accepted: 4 December 2015 ; Published: 11 December 2015 Academic Editor: Emilie Combet 1 Research Group on Quality, Safety and Bioactivity of Plant Foods, Department Food Science and Technology, Centro de Edafología y Biología Aplicada del Segura (CEBAS)–Consejo Superior de Investigaciones Científicas (CSIC), P. O. Box 164, Campus de Espinardo, Murcia 30100, Spain; [email protected] (R.G.-V.); [email protected] (F.A.T.-B.) 2 Naturex SA, Site d’AgroParc, BP 1218, 84911 Avignon Cedex 9, France; [email protected] (P.F.-B.); [email protected] (M.R.) 3 Department of Food Technology and Nutrition, Catholic University of San Antonio, Campus de los Jerónimos, N˝ 135, Guadalupe, Murcia 30107, Spain; [email protected] 4 Naturex Spain SL, Autovia A3, Salida343, Camino de Torrent s/n, Quart de Poblet, Valencia 46930, Spain; [email protected] * Correspondence: [email protected]; Tel.: +34-968-396-276; Fax: +34-968-396-102 Abstract: The bark, seeds, fruits and leaves of the genus Fraxinus (Oleaceae) which contain a wide range of phytochemicals, mostly secoiridoid glucosides, have been widely used in folk medicine against a number of ailments, yet little is known about the metabolism and uptake of the major Fraxinus components.
    [Show full text]
  • The Biological Activities of Oleocanthal from a Molecular Perspective
    nutrients Review The Biological Activities of Oleocanthal from a Molecular Perspective Kok-Lun Pang 1 and Kok-Yong Chin 2,* 1 Biomedical Science Programme, School of Diagnostic and Applied Health Sciences, Faculty of Health Sciences, Universiti Kebangsaan Malaysia, Kuala Lumpur 50300, Malaysia; [email protected] 2 Department of Pharmacology, Universiti Kebangsaan Malaysia Medical Centre, Cheras 56000, Malaysia * Correspondence: [email protected]; Tel.: +60-16-708-2900 Received: 10 April 2018; Accepted: 3 May 2018; Published: 6 May 2018 Abstract: Oleocanthal is a minor constituent of olive oil with strong anti-inflammatory activities. Since the pathogenesis of many chronic diseases involves inflammatory and oxidative components, oleocanthal is a promising agent to prevent these conditions. This review aimed to summarise the current beneficial health effects of oleocanthal and the molecular basis of its biological actions. The anti-inflammatory, antioxidative, antimicrobial, anticancer and neuroprotective activities of oleocanthal have been examined by previous studies. Of these, studies on the anticancer effects have been the most extensive. Oleocanthal was reported to suppress melanoma, breast, liver, and colon cancer cells. Neurological studies focused on the effects of oleocanthal against Alzheimer’s disease. Oleocanthal improved clearance of the amyloid beta protein from neurons and reduced the inflammation of astrocytes. Despite the positive results, validation of the biological effects of oleocanthal in animal disease models is limited and should be emphasized in the future. As a conclusion, oleocanthal may act together with other bioactive compounds in olive oil to achieve its therapeutic potential. The use of oleocanthal alone as a single therapeutic measure awaits validation from future studies.
    [Show full text]
  • Quantitation of Oleuropein and Related Phenolics in Cured Spanish-Style Green, California- Style Black Ripe, and Greek-Style Natural Fermentation Olives
    UC Davis UC Davis Previously Published Works Title Quantitation of Oleuropein and Related Phenolics in Cured Spanish-Style Green, California- Style Black Ripe, and Greek-Style Natural Fermentation Olives. Permalink https://escholarship.org/uc/item/3t34332d Journal Journal of agricultural and food chemistry, 66(9) ISSN 0021-8561 Authors Johnson, Rebecca Melliou, Eleni Zweigenbaum, Jerry et al. Publication Date 2018-03-01 DOI 10.1021/acs.jafc.7b06025 Peer reviewed eScholarship.org Powered by the California Digital Library University of California Article Cite This: J. Agric. Food Chem. 2018, 66, 2121−2128 pubs.acs.org/JAFC Quantitation of Oleuropein and Related Phenolics in Cured Spanish-Style Green, California-Style Black Ripe, and Greek-Style Natural Fermentation Olives † ‡ § Rebecca Johnson, Eleni Melliou, Jerry Zweigenbaum, and Alyson E. Mitchell* † Department of Food Science and Technology, University of California, Davis, One Shields Avenue, Davis, California 95616, United States ‡ Department of Pharmacognosy and Natural Products Chemistry, Faculty of Pharmacy, University of Athens, Panepistimiopolis Zografou, GR-15771 Athens, Greece § Agilent Technologies, 2850 Centerville Road, Wilmington, Delaware 19808, United States *S Supporting Information ABSTRACT: Oleuropein, ligstroside, and related hydrolysis products are key contributors to olive bitterness, and several of these phenolics are implicated in the prevention of lifestyle age-related diseases. While table olive processing methods are designed to reduce oleuropein, the impact of processing on ligstroside and related hydrolysis products (e.g., oleacein, oleocanthal, hydroxytyrosol glucoside, ligstroside aglycone, and oleuropein aglycone) is relatively unknown. Herein, levels of these com- pounds were measured in Spanish-style green (SP), Californian-style black ripe (CA), and Greek-style natural fermentation (GK) olives using rapid ultrahigh-performance liquid chromatography (UHPLC) tandem mass spectrometry (MS/MS).
    [Show full text]
  • Exploratory Analysis of Commercial Olive-Based Dietary Supplements Using Untargeted and Targeted Metabolomics
    Supplementary Material Exploratory analysis of commercial olive-based dietary supplements using untargeted and targeted metabolomics Mar Garcia-Aloy 1, Nelli Groff 1, Domenico Masuero 1, Mauro Nisi 2, Antonio Franco 3, Furio Battelini 2, Urska Vrhovsek 1 and Fulvio Mattivi 1,4,* 1 Metabolomics Unit, Food Quality and Nutrition Department, Research and Innovation Centre Fondazione Edmund Mach, San Michele all'Adige, Italy 2 Agraria Riva del Garda S.C.A., Riva del Garda, Italy 3 Ethifenol S.R.L., Bergamo, Italy 4 Department of Cellular, Computational and Integrative Biology - CIBIO, University of Trento, San Michele all'Adige, Italy Garcia-Aloy et al. – Supplementary Material 2 of 34 Table S1. Unknown compounds detected in study samples. C Compound Formula RT Ions LI C203 Unknown 001 (glucoside) C12H23NO7 78 294.1551 [M+H]+ IV C204 Unknown 002 (glucoside) C14H26O8 82 323.1704 [M+H]+ IV C205 Unknown 003 (glucoside) C13H18O8 96 347.0982 [M-H+HCOOH]- IV C206 Unknown 004 glucoside C15H24O8 257 377.1453 [M-H+HCOOH]-; 333.1546 [M+H]+; 350.1812 [M+NH4]+; 153.091 [M+H-hexose-H2O]+ IV C207 Unknown 004 C9H14O3 282 171.1015 [M+H]+; 172.1049 13C[M+H]+; 188.1283 [M+NH4]+; 153.091 [M+H-H2O]+; 111.0803 [M+H-C2H4O2]+ IV C208 Unknown 005 (glucoside) C18H30O11 278 467.1769 [M-H+HCOOH]-; 468.1803 13C[M-H+HCOOH]-; 423.1862 [M+H]+; 440.2126 [M+NH4]+; 441.2163 13C[M+NH4]+; 261.1335 [M+H- IV hexose]+; 243.1228 [M+H-hexose-H2O]+ C209 Unknown 006 (glucoside) C19H30O8 287 387.2015 [M+H]+ IV C210 Unknown 007 (glucoside) C19H32O9 316 403.1974 [M-H]-; 422.2386 [M+NH4]+
    [Show full text]
  • Tyrosol and Its Metabolites As Antioxidative and Anti-Inflammatory Molecules in Human Endothelial Cells†
    Postprint of Food Funct., 2017, 8, 2905-2914 DOI: 10.1039/C7FO00641A Tyrosol and its metabolites as antioxidative and anti-inflammatory molecules in human endothelial cells† Francisco J. G. Muriana *a, Sergio Montserrat-de la Paz a, Ricardo Lucas b, Beatriz Bermudez c, Sara Jaramillo d, Juan C. Morales , Rocio Abia a and Sergio Lopez *a aLaboratory of Cellular and Molecular Nutrition, Instituto de la Grasa (CSIC), Seville, Spain. E-mail: [email protected]; [email protected]; Fax: +34954616790; Tel: +34954611550 bDepartment of Biochemistry and Molecular Pharmacology, Instituto de Parasitologia y Biomedicina (CSIC), Granada, Spain cDepartment of Cell Biology, School of Biology (University of Seville), 41012 Seville, Spain dPhytochemicals and Food Quality Group, Instituto de la Grasa (CSIC), Seville, Spain Received 28th April 2017 , Accepted 3rd July 2017 First published on 4th July 2017 Tyrosol (Tyr) is a phenolic compound found in virgin olive oil. After ingestion, Tyr undergoes extensive first pass intestinal/hepatic metabolism. However, knowledge about the biological effects of Tyr metabolites is scarce. We chemically synthesized Tyr glucuronate (Tyr-GLU) and sulphate (Tyr-SUL) metabolites and explored their properties against oxidative stress and inflammation in TNF-α-treated human umbilical vein endothelial cells (hECs). Tyr and Tyr-SUL prevented the rise of reactive oxygen species, the depletion of glutathione, and the down-regulation of glutathione peroxidase 1, glutamate-cysteine ligase catalytic subunit, and heme oxygenase-1 genes. Tyr-SUL and to a lower extent Tyr and Tyr-GLU prevented the phosphorylation of NF-κB signaling proteins. Tyr-GLU and Tyr-SUL also prevented the over-expression of adhesion molecules at gene, protein, and secretory levels, and the adhesion (Tyr-SUL > Tyr-GLU) of human monocytes to hECs.
    [Show full text]
  • Oleuropein Hydrolysis in Natural Green Olives: Importance of the Endogenous Enzymes
    Accepted Manuscript Oleuropein Hydrolysis in Natural Green Olives: Importance of the Endogenous Enzymes Eva Ramírez, Manuel Brenes, Pedro García, Eduardo Medina, Concepción Romero PII: S0308-8146(16)30433-2 DOI: http://dx.doi.org/10.1016/j.foodchem.2016.03.061 Reference: FOCH 18945 To appear in: Food Chemistry Received Date: 5 January 2016 Revised Date: 11 March 2016 Accepted Date: 17 March 2016 Please cite this article as: Ramírez, E., Brenes, M., García, P., Medina, E., Romero, C., Oleuropein Hydrolysis in Natural Green Olives: Importance of the Endogenous Enzymes, Food Chemistry (2016), doi: http://dx.doi.org/ 10.1016/j.foodchem.2016.03.061 This is a PDF file of an unedited manuscript that has been accepted for publication. As a service to our customers we are providing this early version of the manuscript. The manuscript will undergo copyediting, typesetting, and review of the resulting proof before it is published in its final form. Please note that during the production process errors may be discovered which could affect the content, and all legal disclaimers that apply to the journal pertain. Oleuropein Hydrolysis in Natural Green Olives: Importance of the Endogenous Enzymes Eva Ramírez, Manuel Brenes, Pedro García, Eduardo Medina, Concepción Romero* Food Biotechnology Department, Instituto de la Grasa (IG-CSIC), Universidad Pablo de Olavide - Edificio 46 Ctra. de Utrera, km. 1- 41013, Seville (Spain) *Corresponding author. Tel.: +34 954611550; Fax: +34 954616790; E-mail address: [email protected] Running title: Oleuropein Hydrolysis: Importance of the Endogenous Enzymes 1 ABSTRACT The bitter taste of olives is mainly caused by the phenolic compound named oleuropein and the mechanism of its hydrolysis during the processing of natural green olives was studied.
    [Show full text]
  • OLEUROPEIN and OLEUROPEIN AGLYCONE 1469 of These Compounds Might Help to Confer Those Health 4
    468/0LEOCANTHAL PDR FOR NUTRITIONAL SUPPLEMENTS INDICATIONS AND USAGE premium extra-virgin olive oil contains about nine milli- Olecocanthal, an olive polyphenol, has reported antioxida- grams of oleocanthal. The potency of oleocanthal and tive and antiinflammatory activity. One report stirred wide ibuprofen is approximately the same. Therefore, nine milli- interest in the substance by claiming it has ibuprofen-like grams of oleocanthal is approximately equal to nine milli- activity. In common with what has been claimed for other grams of ibuprofen, which is about 10% percent of a low olive polyphenols (see Hydroxytyrosol and Oleuropein), it dose (l00 milligrams) of ibuprofen. may have some cardioprotective and anticancer activity, as Dietary supplements of oleocanthal are currently well, although clinical evidence for this is lacking. unavailable. RESEARCH SUMMARY LITERATURE A brief communication in the journal Nature excited interest Andrewes p, Busch JL, de Joode T, et al. Sensory properties of in oleocanthal when researchers reported that this substance, virgin olive oil polyphenols: identification of deacetoxy- derived from newly pressed extra-virgin olive oil, has some ligstroside aglycon as a key contributor to pungency. Agric characteristics in common with the anti-inflammatory drug Food Chem. 2003;51(5):1415-1420. ibuprofen. They noted that both induce very similar stinging Beauchamp GK, Keast RS, Morel D, et al. Phytochemistry: sensations in the throat and thereafter determined that the ibuprofen-like activity in extra-virgin olive oil. Nature. two substances have structural and pharmacological similari- 2005;437(7055):45-46. ties. They found that oleocanthal, like ibuprofen, is an Fini L, Hotchkiss E, Fogliano V, et al.
    [Show full text]
  • Effect of Hydroxytyrosol and Olive Leaf Extract on 1,2-Dicarbonyl
    Food Chemistry 217 (2017) 602–609 Contents lists available at ScienceDirect Food Chemistry journal homepage: www.elsevier.com/locate/foodchem Effect of hydroxytyrosol and olive leaf extract on 1,2-dicarbonyl compounds, hydroxymethylfurfural and advanced glycation endproducts in a biscuit model ⇑ Marta Navarro, Francisco J. Morales Institute of Food Science, Technology and Nutrition (ICTAN-CSIC), Madrid, Spain article info abstract Article history: The antiglycative activity of hydroxytyrosol (HT) and olive leaf extract (OLE) was investigated in Received 7 May 2016 wheat-flour biscuits. Quercetin (QE) and gallic acid (GA) were used as reference of antiglycative activity Received in revised form 5 September 2016 of phenolic compounds. HT, OLE, QE and GA were added in the range of 0.25–0.75% (w/w). Samples were Accepted 6 September 2016 compared against a control recipe baked at 180 °C/20 min. HT biscuit was able to inhibit efficiently the Available online 7 September 2016 formation of hydroxymethylfurfural (HMF) and 3-deoxyglucosone (3-DG), as well as reduced the forma- tion of overall free fluorescent AGEs and pentosidine. The inhibition of the 3-DG and HMF formation was Chemical compounds: directly and significantly correlated under controlled baking conditions. However, samples formulated Methylglyoxal (PubChem CID: 880) with OLE exerted similar antiglycative capacity against pentosidine and Ne-carboxyethyl-lysine, Glyoxal (PubChem CID: 7860) 3-deoxyglucosone (PubChem CID: 114839) although the amount of HT in the biscuit was 100-fold lower than the biscuit formulated with HT. Hydroxymethylfurfural (PubChem CID: Methylglyoxal, 3-DG, and glyoxal were the predominant 1,2-dicarbonyl compounds after baking but only 237332) 3-DG was significantly reduced by HT.
    [Show full text]
  • Type of the Paper (Article
    Supplementary Materials Evaluating Quality Parameters, the Metabolic Profile, and Other Typical Features of Selected Commercial Extra Virgin Olive Oils from Brazil Aline Gabrielle Alves de Carvalho 1, Lucía Olmo-García 2, Bruna Rachel Antunes Gaspar 1, Alegría Carrasco-Pancorbo 2,*,†, Vanessa Naciuk Castelo-Branco 3,† and Alexandre Guedes Torres 1, † 1 Laboratory of Nutritional Biochemistry and Food Science, Lipid Biochemistry and Lipidomics Laboratory, Institute of Chemistry, Federal University of Rio de Janeiro, Rio de Janeiro 21941-902, Brazil; [email protected] (A.G.A.d.C.); [email protected] (B.R.A.G.); [email protected] (A.G.T.) 2 Department of Analytical Chemistry, Faculty of Sciences, University of Granada, Ave. Fuentenueva s/n, E-18071 Granada, Spain; [email protected] (L.O.-G.); [email protected] (A.C.-P.) 3 Laboratory of Food Biotechnology, Fluminense Federal University, Niteroi 24230-340, RJ, Brazil; [email protected] (V.N.C.-B) * Correspondence: [email protected]; Tel.: +34-958-242-785 † These authors contributed equally to this work. 1 Figure S1a. Representative extracted ion chromatograms (EIC) of the studied EVOOs determined by RP-LC-MS. 1. Quinic acid; 2. Hydroxytyrosol; 3. Eudesmic acid; 4. Tyrosol; 5. Vanillic acid; 6. Decarboxymethyl elenolic acid; 7. p-Coumaric acid; 8. Vanillin; 9. Ferulic acid; 10. Desoxy elenolic acid; 11. Hydroxy elenolic acid; 12. Hydroxytyrosol acetate; 13. Elenolic acid; 14. Hydroxy decarboxymethyl oleuropein aglycone; 15. Decarboxymethyl oleuropein aglycone (isomer 1); 16. Luteolin; 17. Decarboxymethyl oleuropein aglycone (isomer 2); 18. Syringaresinol; 19. Oleuropein aglycone (isomer 1); 20. Pinoresinol; 21. 10-Hydroxy oleuropein aglycone 1; 22.
    [Show full text]
  • Olea Europaea L., Folium
    22 November 2011 EMA/HMPC/430506/2009 Committee on Herbal Medicinal Products (HMPC) Assessment report on Olea europaea L., folium Based on Article 16d(1), Article 16f and Article 16h of Directive 2001/83/EC as amended (traditional use) Final Herbal substance(s) (binomial scientific Olea europaea L. folium (olive leaf) name of the plant, including plant part) Herbal preparation(s) Herbal substance Fresh or dried leaves Herbal preparations Comminuted herbal substance (dried leaves) Powdered herbal substance (dried leaves) Pharmaceutical forms Herbal substance and comminuted herbal substance as herbal tea for oral use. Herbal preparation in solid dosage form for oral use. Rapporteur Dr Ioanna Chinou 7 Westferry Circus ● Canary Wharf ● London E14 4HB ● United Kingdom Telephone +44 (0)20 7418 8400 Facsimile +44 (0)20 7523 7051 E -mail [email protected] Website www.ema.europa.eu An agency of the European Union © European Medicines Agency, 2012. Reproduction is authorised provided the source is acknowledged. Table of contents Table of contents ................................................................................................................... 2 1. Introduction ....................................................................................................................... 3 1.1. Description of the herbal substance(s), herbal preparation(s) or combinations thereof .. 3 1.2. Information about products on the market in the Member States ............................... 6 1.3. Search and assessment methodology ....................................................................
    [Show full text]
  • Olea Europaea L
    Bruno et al. BMC Plant Biology (2019) 19:428 https://doi.org/10.1186/s12870-019-1969-6 RESEARCH ARTICLE Open Access Changes in gene expression and metabolic profile of drupes of Olea europaea L. cv Carolea in relation to maturation stage and cultivation area Leonardo Bruno1, Ernesto Picardi2,3, Marianna Pacenza1, Adriana Chiappetta1, Antonella Muto1, Olimpia Gagliardi1, Innocenzo Muzzalupo4, Graziano Pesole2,3 and Maria Beatrice Bitonti1* Abstract Background: Olive (Olea europaea L.) is an emblematic oil tree crop in the Mediterranean basin. Currently, despite olive features as a moderately thermophilic species, its cultivation is worldwide spreading due to the health-related impact of olive products on human nutrition. A point of concern for the expanding olive cultivation is related to the influence that, in addition to genotype, environmental factors exerts on drupe development and metabolism with consequent impact on fruit key traits. In this context, the aim of the present work was to gain further information on the genetic networks controlling drupe maturation phase and, mainly, on their modulation in response to environmental cues. Results: To achieve this goal, a comparative transcriptome-wide investigation was carried out on drupes of Olea europaea cultivar Carolea, collected from plants growing in areas at different altitude level and therefore experiencing different climatic conditions. Two maturation stages of drupe were analysed: green mature and turning-purple. Metabolic characterization of drupe was also performed. At both
    [Show full text]