AFLATOXINS – BIOCHEMISTRY AND MOLECULAR BIOLOGY Edited by Ramón Gerardo Guevara-González Aflatoxins – Biochemistry and Molecular Biology Edited by Ramón Gerardo Guevara-González Published by InTech Janeza Trdine 9, 51000 Rijeka, Croatia Copyright © 2011 InTech All chapters are Open Access articles distributed under the Creative Commons Non Commercial Share Alike Attribution 3.0 license, which permits to copy, distribute, transmit, and adapt the work in any medium, so long as the original work is properly cited. After this work has been published by InTech, authors have the right to republish it, in whole or part, in any publication of which they are the author, and to make other personal use of the work. Any republication, referencing or personal use of the work must explicitly identify the original source. Statements and opinions expressed in the chapters are these of the individual contributors and not necessarily those of the editors or publisher. No responsibility is accepted for the accuracy of information contained in the published articles. The publisher assumes no responsibility for any damage or injury to persons or property arising out of the use of any materials, instructions, methods or ideas contained in the book. Publishing Process Manager Petra Nenadic Technical Editor Teodora Smiljanic Cover Designer Jan Hyrat Image Copyright Juan Gaertner, 2010. Used under license from Shutterstock.com First published September, 2011 Printed in Croatia A free online edition of this book is available at www.intechopen.com Additional hard copies can be obtained from orders@intechweb.org Aflatoxins – Biochemistry and Molecular Biology, Edited by Ramón Gerardo Guevara-González p. cm. ISBN 978-953-307-395-8 free online editions of InTech Books and Journals can be found at www.intechopen.com Contents Preface IX Part 1 Biosynthesis and Biotransformation 1 Chapter 1 Biotransformation of Aflatoxin B1 and Its Relationship with the Differential Toxicological Response to Aflatoxin in Commercial Poultry Species 3 Gonzalo J. Diaz and Hansen W. Murcia Chapter 2 Control of Aflatoxin Biosynthesis in Aspergilli 21 Kenneth C. Ehrlich, Perng-Kuang Chang, Jiujiang Yu, Jeffrey W. Cary and Deepak Bhatnagar Chapter 3 Aflatoxin Biosynthetic Pathway and Pathway Genes 41 Jiujiang Yu and Kenneth C. Ehrlich Chapter 4 Conserved Regulatory Mechanisms Controlling Aflatoxin and Sterigmatocystin Biosynthesis 67 Ana M. Calvo and Sourabh Dhingra Part 2 Biomarkers and Breeding 89 Chapter 5 Identification of Gene Markers in Aflatoxin-Resistant Maize Germplasm for Marker-Assisted Breeding 91 Robert L. Brown, Abebe Menkir, Zhi-Yuan Chen, Meng Luo and Deepak Bhatnagar Chapter 6 Biomarkers of Aflatoxin Exposure and Its Relationship with the Hepatocellular Carcinoma 107 Alessandra Vincenzi Jager, Fernando Silva Ramalho, Leandra Náira Zambelli and Carlos Augusto Fernandes Oliveira Chapter 7 The Use of Proteomics as a Novel Tool in Aflatoxin Research 127 E. Razzazi-Fazeli, M. Rizwan, C. Mayrhofer and K. Nöbauer VI Contents Chapter 8 Genetic Resistance to Drought in Maize and Its Relationship in Aflatoxins Production 151 Ramón Gerardo Guevara-González, Angela María Chapa-Oliver, Laura Mejía-Teniente, Irineo Torres-Pacheco, Moises Alejandro Vazquez-Cruz, Juan Jesús Cervantes-Landaverde, Ricardo Ernesto Preciado-Ortiz and Ernesto Moreno- Martinez Part 3 Pathogenesis and Toxicology 161 Chapter 9 The Molecular Pathogenesis of Aflatoxin with Hepatitis B Virus-Infection in Hepatocellular Carcinoma 163 Hai-Xia Cao and Jian-Gao Fan Chapter 10 A Comprehensive Review of Male Reproductive Toxic Effects of Aflatoxin 177 Mohammad A. Akbarsha, Faisal Kunnathodi and Ali A. Alshatwi Chapter 11 Aflatoxicosis in Layer and Breeder Hens 203 Milad Manafi Chapter 12 Aflatoxins and Aflatoxicosis in Human and Animals 221 D. Dhanasekaran, S. Shanmugapriya, N. Thajuddin and A. Panneerselvam Chapter 13 Aflatoxins and Their Impact on Human and Animal Health: An Emerging Problem 255 Eva G. Lizárraga-Paulín, Ernesto Moreno-Martínez and Susana P. Miranda-Castro Part 4 Miscellaneous 283 Chapter 14 Aflatoxins: Mechanisms of Inhibition by Antagonistic Plants and Microorganisms 285 Mehdi Razzaghi-Abyaneh, Masoomeh Shams-Ghahfarokhi and Perng-Kuang Chang Chapter 15 The Evolutionary Dynamics in the Research on Aflatoxins During the 2001-2010 Decade 305 Martín G. Theumer and Héctor R. Rubinstein Chapter 16 Binding of Aflatoxin B 1 to Lactic Acid Bacteria and Saccharomyces cerevisiae in vitro: A Useful Model to Determine the Most Efficient Microorganism 323 Romina P. Pizzolitto, Dante J. Bueno, María R. Armando, Lilia Cavaglieri, Ana M. Dalcero and Mario A. Salvano Chapter 17 The Population Dynamics of Aflatoxigenic Aspergilli 347 Geromy G. Moore, Shannon B. Beltz, Ignazio Carbone, Kenneth C. Ehrlich and Bruce W. Horn Contents VII Chapter 18 Aflatoxin in Agricultural Commodities and Herbal Medicine 367 Mehrdad Tajkarimi, Mohammad Hossein Shojaee, Hassan Yazdanpanah and Salam A. Ibrahim Chapter 19 A Review of Aflatoxin M 1 , Milk, and Milk Products 397 Hamid Mohammadi Chapter 20 Aflatoxins: Contamination, Analysis and Control 415 Giniani Carla Dors, Sergiane Souza Caldas, Vivian Feddern, Renata Heidtmann Bemvenuti, Helen Cristina dos Santos Hackbart, Michele Moraes de Souza, Melissa dos Santos Oliveira, Jaqueline Garda-Buffon, Ednei Gilberto Primel and Eliana Badiale-Furlong Chapter 21 Estimated Daily Intake of Aflatoxin M 1 in Thailand 439 Nongluck Ruangwises, Piyawat Saipan and Suthep Ruangwises Chapter 22 Influence of Soluble Feed Proteins and Clay Additive Charge Density on Aflatoxin Binding in Ingested Feeds 447 William F. Jaynes and Richard E. Zartman Preface Aflatoxins are produced by Aspergillus flavi group species and are thought to be one of the most cancerous natural substances known. Economically and biologically the most important fungal species able to produce the aflatoxins are Aspergillus flavus and Aspergillus parasiticus. The biosynthesis of aflatoxins, as all secondary metabolites, is strongly dependent on growth conditions such as substrate composition or physical factors like pH, water activity, temperature or modified atmospheres. Depending on the particular combination of external growth parameters the biosynthesis of aflatoxin can either be completely inhibited, albeit normal growth is still possible or the biosynthesis pathway can be fully activated. Knowledge about these relationships enables an assessment of which parameter combinations can control aflatoxin biosynthesis or which are conducive to phenotypic aflatoxin production. All these aspects are fascinating and strongly growing in knowledge based on the work of excellent researchers as those invited to write every chapter presented in this book. Finally, this book is an attempt to provide a wide and current approach of top studies in aflatoxins biochemistry and molecular biology, as well as some general aspects to researchers interested in this field. Dr. Ramon Gerardo Guevara-Gonzalez Professor Biosystems Engineering Group School of Engineering Queretaro Autonomous University Queretaro, Qro, Mexico [...]... as AFB1-dhd) and AFB1 consumption in turkey, quail, duck and chicken microsomal incubations (left) and relationship between AFBO formation (measured as AFB1-GSH) and AFB1 consumption (right) 10 Aflatoxins – Biochemistry and Molecular Biology Both biotransformation variables (AFBO formation and AFB1 disappearance) correlate well with the in vivo sensitivity observed for turkeys, quail and chickens... hydroxylated metabolites AFM1 and AFQ1 can also undergo the cytosolic reduction of the C1 carbonyl group in a reaction analogous to the reduction of AFB1 to AFL The reduced metabolites of AFM1 and AFQ1 have been named aflatoxicol M1 (Salhab et al., 1977; Loveland et al., 1983) and aflatoxicol H1 (Salhab & Hsieh, 1975), respectively Aflatoxicol H1 8 Aflatoxins – Biochemistry and Molecular Biology is a major metabolite... from AFB1, namely aflatoxins M1 (AFM1), Q1 (AFQ1), and B2a (AFB2a) (Fig 1) AFM1 was first isolated from the 6 Aflatoxins – Biochemistry and Molecular Biology milk of cows and rats fed AFB1-contaminated peanut meal and it was initially termed “milk toxin” (de Iongh et al., 1964) It was later discovered that AFM1 is not a metabolite exclusive of mammals and, in fact, it is produced by crude or isolated... aflatoxin B1 and blood components of various species in vitro: Interconversion of aflatoxin B1 and aflatoxicol in the blood Toxicology and Applied Pharmacology, Vol.67, No.2, (February 1983), pp 292-301, ISSN 0041-008X Leeson, S.; Diaz, G.J & Summers, J.D (1995) Poultry metabolic disorders and mycotoxins University Books, ISBN 0-9695600-1-1, Guelph, Canada 18 Aflatoxins – Biochemistry and Molecular Biology. .. matches: 24 Aflatoxins – Biochemistry and Molecular Biology AFL2G_11313 and AFL2G_06146 These may also bind to a TCGNxCGA DNA motif The C-terminal activation domain for AflR, like those of other C6-type transcription factors in fungi, has a high number (8/28) of acidic amino acids and (5/28) basic amino acids and is otherwise not distinctive The C-terminal 38 amino acid region (residues 40 8–4 44) also... dedicated peroxisomal vesicles (Roze et al., 2011) The ability to form and stabilize such vesicles could be critical to the coordination of the biosynthetic steps leading to AF formation All of these processes are illustrated in Figure 1 and are discussed in more detail below 22 Aflatoxins – Biochemistry and Molecular Biology Environmental and nutritional stimuli Receptor Proteins Import proteins HSPs PKs... transcriptional activation of later genes (ver1 and omtA) nor for aflR, but did upregulate expression of the polyketide synthase gene, pksA and nor1, two early genes necessary for the beginning steps in AF biosynthesis (Du et al., 2007) AflJ’s transcription was regulated by AflR in A flavus and A parasiticus An AflR-binding site near the 26 Aflatoxins – Biochemistry and Molecular Biology translational start site... constants KM and Vmax (left) and enzyme kinetics (right) of aflatoxin B1 epoxidation activity in liver microsomes of four poultry species Information for some CYP450 enzymes in turkey, chicken and quail can be found in the databases mentioned before (i.e UniProtKB and GeneBank) Sequences for turkey CYP1A5 and CYP3A37, chicken CYP1A1, CYP1A4, CYP1A5 and CYP3A80, and Japanese quail CYP1A1, CYP1A4 and CYP1A5... cytosolic NADPH-dependent enzyme that in the case of the chicken has an estimated molecular weight of 46.5 KDa and is inhibited by the 17-ketosteroids androsterone, dehydroisoandrosterone and estrone (Chen et al., 1981) Formation of AFL was first reported in chicken, duck, turkey and rabbit liver cytosol (Patterson & Roberts, 1971), and it also occurs in quail (Lozano & Diaz, 2006) However, little or no activity... differences in AFB1 biotransformation pathways among species The aim of the present chapter is to review the current knowledge on AFB1 biotransformation, with emphasis on 4 Aflatoxins – Biochemistry and Molecular Biology commercial poultry species, and to correlate this information with the in vivo susceptibility to AFB1 in these species 2 Biotransformation of aflatoxin B1 In general, the metabolism or biotransformation . AFLATOXINS – BIOCHEMISTRY AND MOLECULAR BIOLOGY Edited by Ramón Gerardo Guevara-González Aflatoxins – Biochemistry and Molecular Biology Edited. (AFQ1), and B 2a (AFB 2a ) (Fig. 1). AFM1 was first isolated from the Aflatoxins – Biochemistry and Molecular Biology 6 milk of cows and rats fed AFB1-contaminated peanut meal and it was. (Salhab et al., 1977; Loveland et al., 1983) and aflatoxicol H1 (Salhab & Hsieh, 1975), respectively. Aflatoxicol H1 Aflatoxins – Biochemistry and Molecular Biology 8 is a major metabolite