Olives and Olive Oil in Health and Disease Prevention This page intentionally left blank Olives and Olive Oil in Health and Disease Prevention Edited by Victor R. Preedy Dept Nutrition and Dietetics, Nutritional Sciences Division, School of Biomedical & Health Sciences, King’s College London, Franklin-Wilkins Building, London, UK Ronald Ross Watson University of Arizona Division of Health Promotion Sciences Mel and Enid Zuckerman College of Public Health, and School of Medicine, Arizona Health Sciences Center, Tucson, AZ, USA AMSTERDAM • BOSTON • HEIDELBERG • LONDON • NEW YORK • OXFORD • PARIS SAN DIEGO • SAN FRANCISCO • SINGAPORE • SYDNEY • TOKYO Academic Press is an imprint of Elsevier Academic Press is an imprint of Elsevier 32 Jamestown Road, London NW1 7BY, UK 30 Corporate Drive, Suite 400, Burlington, MA 01803, USA 525 B Street, Suite 1900, San Diego, CA 92101-4495, USA First edition 2010 Copyright © 2010 Elsevier Inc. All rights reserved with the exception of: Chapter 68, Crown Copyright © 2009. Published by Elsevier Inc. All rights reserved No part of this publication may be reproduced, stored in a retrieval system or transmitted in any form or by any means electronic, mechanical, photocopying, recording or otherwise without the prior written permission of the publisher Permissions may be sought directly from Elsevier’s Science & Technology Rights Department in Oxford, UK: phone ( (cid:2) 44) (0) 1865 843830; fax ( (cid:2) 44) (0) 1865 853333; email: [email protected] . Alternatively, visit the Science and Technology Books website at www.elsevierdirect.com/ rights for further information Notice No responsibility is assumed by the publisher for any injury and/or damage to persons or property as a matter of products liability, negligence or otherwise, or from any use or operation of any methods, products, instructions or ideas contained in the material herein. Because of rapid advances in the medical sciences, in particular, independent verification of diagnoses and drug dosages should be made British Library Cataloguing-in-Publication Data A catalogue record for this book is available from the British Library Library of Congress Cataloging-in-Publication Data A catalog record for this book is available from the Library of Congress ISBN : 978-0-12-374420-3 For information on all Academic Press publications visit our website at www.elsevierdirect.com Typeset by Macmillan Publishing Solutions www.macmillansolutions.com Printed and bound in United States of America 10 11 12 13 10 9 8 7 6 5 4 3 2 1 Contents Preface xv 7 . The Effect of the Ripening Process of List of Contributors xvii the Olive Fruit on the Chlorophyll and Abbreviations xxix Carotenoid Fractions of Drupes and Virgin Oils 59 Maria -Jose Motilva and Maria-Paz Romero Section 1 General Aspects of Olives and Olives and Olive Oil Olive Oil 1 8 . Influence of the Crushing System: Phenol Content in Virgin Olive Oil 1 .1 The Plant, Production, Olives and Produced from Whole and Olive Oil and Their Detailed De-stoned Pastes 69 Characterization 3 Paolo Amirante, Maria Lisa Clodoveo, Antonia Tamborrino, Alessandro Leone and The Plant and Production Alistair G. Paice 1 . Table Olives: Varieties and 9 . The Malaxation Process: Influence Variations 5 on Olive Oil Quality and the Effect Luis Rejano, Alfredo Monta ñ o, of the Control of Oxygen Francisco Javier Casado, Antonio Higinio S á nchez Concentration in Virgin and Antonio de Castro Olive Oil 77 2 . Olive Genomics 17 A ntonia Tamborrino, Maria Lisa Clodoveo, Alessandro Leone, Paolo Amirante and Corrado Fogher, Matteo Busconi, Luca Sebastiani Alistair G. Paice and Tania Bracci 3 . Current Initiatives in Proteomics of the 10 . Influence of Different Centrifugal Olive Tree 25 Extraction Systems on Antioxidant Wei Wang, Fuju Tai and Xiuli Hu Content and Stability of Virgin Olive Oil 85 4 . Chemometric Classification of Cultivars Paolo Amirante, Maria Lisa Clodoveo, of Olives: Perspectives on Portuguese Alessandro Leone, Antonia Tamborrino and Olives 33 Vinood B. Patel Joaquim C.G. Esteves da Silva 11 . A Marker of Quality of Olive Oils: The 5 . Effect of Climatic Conditions on Expression of Oleuropein 95 Quality of Virgin Olive Oil 43 Giovanni Sindona Mar í a -Paz Romero and Mar í a-Jos é Motilva 6 . Influence of Irrigation Management and 12 . Olive Oil Authenticity Evaluation Ripening on Virgin Olive Oil Quality by Chemical and Biological and Composition 51 Methodologies 101 Giuseppe Fregapane, Aurora G ó mez-Rico and Miguel A. Faria, Sara C. Cunha, Alistair G. Paice Maria Desamparados Salvador and Maria Beatriz P.P. Oliveira v vi Contents The Detailed Characterization of Olives and 20 . Phenolic Profiles of Portuguese Olives: Olive Products Cultivar and Geographics 177 Rosa M. Seabra, Paula B. Andrade, 13 . Ripening of Table Olives: Patr í cia Valent ã o, Miguel Faria, Alistair G. Paice and Use of Magnetic Resonance Maria Beatriz P.P. Oliveira Imaging (MRI) 109 21 . Low-level Free Phenols in Sicilian Maria Antonietta Brescia and Antonio Sacco Olive Oils 187 14 . NMR and Olive Oils: A Geographical Marcello Saitta, Giuseppa Di Bella, Characterization 117 Vincenzo Lo Turco, Giovanna Loredana La Torre Luisa Mannina and Anna Laura Segre † and Giacomo Dugo 15 . NMR and Olive Oils: A Characterization 22 . Volatile Compounds in Australian Olive According to the Cultivar 125 Oils: How Different Are They From Luisa Mannina and Anna Laura Segre † Other Oils 201 Curtis Kalua, Paul Prenzler, Danielle Ryan and 16 . Geographical Characterization of Kevin Robards Olive Oil by Means of Multivariate Classification: Application of 23 . Sterols and Non-steroidal CAIMAN 129 Triterpenoids of the Developing Davide Ballabio and Roberto Todeschini Olive Fruit 211 Na ï m Stiti, Sa ï da Triki and Marie-André e Hartmann 17 . Non-conventional Parameters for Quality Evaluation of Refined Olive Oil 24 . A Comparison of the Volatile and Olive Oil Commercial Classes 139 Compounds, in Spanish-style, Tommaso Gomes, Vito Michele Paradiso and Greek-style and Castelvetrano-style Debora Delcuratolo Green Olives of the Nocellara del Belice Cultivar: Alcohols, Aldehydes, 18 . Classification of Sicilian Olive Oils Ketones, Esters and Acids 219 According to Heavy Metal and Nadia Sabatini Selenium Levels Using Canonical Discriminant Analysis (CDA) 155 25 . Polyphenol Oxidase and Oleuropein Lara La Pera, Giacomo Dugo, in Olives and their Changes During Vincenzo Lo Turco, Rossana Rando and Giuseppa Di Bella Olive Ripening 233 Francisca Ortega-Garc í a, Santos Blanco, M. Á ngeles Peinado and Juan Perag ó n 1 .2 Components of Olives and Olive Plant Product and Uses 165 26 . Major and Minor Lipid Constituents of Cornicabra Virgin Olive Oil and the Lipids , Phenolics and Other Organics and Influence of Crop Season Changes 239 Volatiles M. Desamparados Salvador and Giuseppe Fregapane 19 . Polyphenols in Olive Oil: 27 . Phytosterol Classes in Olive Oils The Importance of Phenolic and their Analysis by Common Compounds in the Chemical Chromatographic Methods 249 Composition of Olive Oil 167 Sodeif Azadmard-Damirchi and Paresh C. Dutta Antonio Segura-Carretero, Javier Men é ndez-Men é ndez and 28 . Extraction of Oleuropein and Related Alberto Fern á ndez-Guti é rrez Phenols from Olive Leaves and Branches 259 †deceased. M .D. Luque de Castro and F. Priego Capote Contents vii 29 . The Occurrence of the Biogenic Amine 37 . Olive Biophenols and Conventional Melatonin in Olive Oil: Implications in Biotechnology from Mediterranean Health and Disease Prevention 275 Aliment Culture 333 Rafael Fern á ndez-Montesinos, Ganapathy Sivakumar and Nicola A. Uccella Cristina de la Puerta, Pedro P. Garc í a-Luna, Russel J. Reiter and David Pozo Non Fruit Aspects Including Mill Wastewater 30 . Olive Biophenols as Food Supplements and Additives 283 38 . Production of Triterpene Acids by Antonella De Leonardis and Vincenzo Macciola Cell-suspension Cultures of Olea europaea 341 Metals , Electrolytes and Other Yutaka Orihara and Yutaka Ebizuka Components 39 . Bioactive Ingredients in Olive 31 . Chemical Composition of Fermented Leaves 349 Green Olives: Acidity, Salt, Moisture, Maria Z. Tsimidou and Vassiliki T. Papoti Fat, Protein, Ash, Fiber, Sugar, and 40 . Phenolic Compounds in Olive Oil Mill Polyphenol 291 Wastewater 357 Alfredo Monta ñ o, Antonio Higinio S á nchez, Jos é S. Torrecilla Antonio L ó pez-L ó pez, Antonio de Castro and Luis Rejano 1 .3 Stability, Microbes, Contaminants 32 . Some Metals in Table Olives 299 and Adverse Components and Yasemin Sahan Processes 367 33 . Olive Cultivar, Period of Harvest, and Environmental Pollution on the Bacterial and Fungal and Other Microbial Contents of Cu, Cd, Pb, and Zn: Italian Aspects Perspectives 307 41 . Lactic Acid Bacteria in Table Olive Alberto Angioni Fermentation 369 34 . Trace Components in Italian Virgin Cinzia L. Randazzo, Rajkumar Rajendram and Cinzia Caggia Olive Oils 313 Giovanni Sindona and Antonio Tagarelli 42 . Understanding and Optimizing the Microbial Degradation of Olive Oil: 35 . Inorganic Anions in Olive Oils: A Case Study with the Thermophilic Application of Suppressed Ion Bacterium Geobacillus thermoleovorans Exchange Chromatography (IEC) for IHI-91 377 the Analysis of Olive Oils Produced Peter Becker from De-stoned Olives and Traditional Extraction Methods 317 43 . Degradation of Phenolic Compounds Lara La Pera, Teresa Maria Pellican ò, Found in Olive Products by Pellicano Vincenzo Lo Turco, Giuseppa Di Bella Lactobacillus plantarum Strains 387 and Giacomo Dugo Jos é María Landete, H é ctor Rodr í guez, Jos é Antonio Curiel, Blanca de las Rivas, 36 . Purification and Characterization F é lix L ó pez de Felipe and Rosario Mu ñ oz of Olive ( Olea europaea L.) Peroxidases 325 44 . Microbial Colonization of Naturally Jorge A. Saraiva, C.S. Cl á udia, S. Nunes and Fermented Olives 397 Manuel A. Coimbra C .C. Tassou, E.Z. Panagou and G.-J.E. Nychas viii Contents 45 . O ccurrence of Aflatoxin B in the 54 . P olycyclic Aromatic Hydrocarbons (PAH) 1 Greek Virgin Olive Oil: Estimation of in Olive Oils and Other Vegetable Oils; the Daily Exposure 407 Potential for Carcinogenesis 489 Panagiota Markaki Isabel Mafra, Joana S. Amaral and M. Beatriz P.P. Oliveira Pesticides and Adulterants 55 . M ineral Paraffins in Olives and Olive Oils 499 46 . Fenthion, Dimethoate and Other Sabrina Moret, Tiziana Populin and Pesticides in Olive Oils of Organic and Lanfranco S. Conte Conventional Cultivation 415 Aristidis M. Tsatsakis and Ioannis N. Tsakiris 1 .4 Analytical Methods 507 47 . Residues of Pesticides and Polycyclic Natural Components Aromatic Hydrocarbons in Olive and Olive-Pomace Oils by Gas 56 . A nalytical Determination of Chromatography/Tandem Mass Polyphenols in Olive Oil 509 Spectrometry 425 Antonio Segura-Carretero, Alegr í a Carrasco- Evaristo Ballesteros and Natividad Ramos-Martos Pancorbo, Alessandra Bendini, Lorenzo Cerretani and Alberto Fern á ndez-Guti é rrez 48 . Acephate and Buprofezin Residues in 57 . E lectronic Tongues Purposely Designed Olives and Olive Oil 437 for the Organoleptic Characterization Pierluigi Caboni and Paolo Cabras of Olive Oils 525 Mar í a L. Rodr í guez-M é ndez, C. Apetrei and 49 . O live Oil Adulteration with Hazelnut Jos é A. De Saja Oil and Analytical Approaches for Its Detection 441 58 . D etermination of Olive Oil Parameters Dimitrios Zabaras by Near Infrared Spectrometry 533 Sergio Armenta, Javier Moros, Salvador Garrigues 50 . O live Oil Adulteration with Sunflower and Miguel de la Guardia Cirugeda and Corn Oil Using Molecular 59 . D etermination of Olive Oil Acidity 545 Fluorescence Spectroscopy 451 Bet ü l Ö zt ü rk, Aysun Ankan and Durmus ¸ Ö zdemir Marcone Augusto Leal de Oliveira, Manoela Ruchiga Balesteros, Adriana Ferreira Faria and Fernando Antonio Simas Vaz Toxicology and Contaminants 60 . A pplication of the Electronic Nose in Olive Oil Analyses 553 51 B enzene, Toluene, Ethylbenzene, M . Stella Cosio, Simona Benedetti, Susanna (o-, m- and p-) Xylenes and Styrene in Buratti, Matteo Scampicchio and Saverio Mannino Olive Oil 463 Silvia L ó pez-Feria, Soledad C á rdenas and 61 . S qualene and Tocopherols in Olive Oil: Miguel Valcá rcel Importance and Methods of Analysis 561 Maria Z. Tsimidou 52 . T he Toxicity Profile of Hydrolyzed Aqueous Olive Pulp Extract 471 62 . A n Overview of the Chemometric Robert M. Diener and Mildred S. Christian Methods for the Authentication of the Geographical and Varietal Origin of 53 . P lasticizer in Olive Oils 481 Olive Oils 569 Giuseppa Di Bella, Lara La Pera, Vincenzo Lo Turco, Federico Marini, Remo Bucci, Antonio L. Magr ì and Donatella Pollicino and Giacomo Dugo Andrea D. Magr ì Contents ix 63 . C haracterization of Three Portuguese 71 . M ultiresidue Analysis of Low- and Varietal Olive Oils Based on Fatty Medium-polarity Pesticides in Olive Oil Acids, Triacylglycerols, Phytosterols by GC-MS/MS 667 and Vitamin E Profiles: Application of Alberto Marinas, Fernando Lafont, Mar í a A. Aramend í a, I.M. Garc í a, Jos é M. Marinas Chemometrics 581 and Francisco J. Urbano Joana S. Amaral, Isabel Mafra and M. Beatriz P.P. Oliveira 64 . L iquid Chromatography-Mass Section 2 Spectrometry Determination of Nutritional, Pharmacological and Sterols in Olive Oil 591 Metabolic Properties of Olives and Roberto Romero-Gonz á lez, Antonia Garrido Olive Oil 685 Frenich and Jos é Luis Mart í nez Vidal 65 . 13 C Nuclear Magnetic Resonance 2 .1 General Nutrition 687 Spectroscopy as a New Quantitative General Aspects and Changes in Food Method for Determining Fatty Acid Processing Positional Distribution in Olive Oil Triacylglycerols: Applications to Olive 72 . T rends in Olive Oil Production, Supply Oil Authenticity 603 and Consumption in Mediterranean Giovanna Vlahov Countries from 1961 to the Present Day 689 66 . E xtraction Techniques for the Analysis Genevieve Buckland and Carlos A. Gonz á lez of Virgin Olive Oil Aroma 615 Stefania Vichi 73 . T he Bioavailability of Olive Oil Phenolic Compounds 699 67 R apid Assays to Evaluate the Antioxidant Mar í a -Isabel Covas, Montserrat Fit ó , Capacity of Phenols in Virgin Olha Khymenets and Rafael de la Torre Olive Oil 625 Lorenzo Cerretani and Alessandra Bendini 74 . N utrient Profiles of Commercial Table Olives: Proteins and Vitamins 705 68 . P olycyclic Aromatic Hydrocarbons Antonio L ó pez-L ó pez, Alfredo Monta ñ o and (PAHs) in Olive Oil: Methodological Antonio Garrido-Fern á ndez Aspects of Analysis 637 75 . N utrient Profiles of Commercial Table Martin Rose Olives: Fatty Acids, Sterols, and Fatty Alcohols 7 15 Adverse Components Antonio L ó pez-L ó pez, Alfredo Monta ñ o and Antonio Garrido-Fern á ndez 69 . D etermination of Aflatoxins and Ochratoxin A in Olive Oil 645 76 . N utritional Properties of Extra Virgin Chiara Cavaliere, Patrizia Foglia, Roberto Samperi Olive Oils from the Emilia-Romagna and Aldo Laganà Region: Profiles of Phenols, Vitamins and Fatty Acids 725 70 . S ample Preparation Approaches for the Annalisa Rotondi and Chiara Lapucci Analysis of Pesticide Residues in Olives and Olive Oils 653 77 . T able Olives: A Carrier for Delivering Sara C. Cunha, Steven J. Lehotay, Probiotic Bacteria to Humans 735 Katerina Mastovska, Jos é O. Fernandes and Paola Lavermicocca, Mauro Rossi, Francesco Russo M. Beatriz P.P. Oliveira and Rajaventhan Srirajaskanthan