Download ebooks file Toxins and other harmful compounds in foods 1st edition sikorski all chapters
Toxins and other harmful compounds in foods 1st Edition Sikorski
Visit to download the full and correct content document: https://textbookfull.com/product/toxins-and-other-harmful-compounds-in-foods-1st-edi tion-sikorski/
More products digital (pdf, epub, mobi) instant download maybe you interests ...
Natural Poisons and Venoms Plant Toxins Polyketides
Phenylpropanoids and Further Compounds 1st Edition Teuscher
CRC Press is an imprint of Taylor & Francis Group, an Informa business
No claim to original U.S. Government works
Printed on acid-free paper
Version Date: 20160901
International Standard Book Number-13: 978-1-4987-4852-0 (Hardback)
This book contains information obtained from authentic and highly regarded sources. Reasonable efforts have been made to publish reliable data and information, but the author and publisher cannot assume responsibility for the validity of all materials or the consequences of their use. The authors and publishers have attempted to trace the copyright holders of all material reproduced in this publication and apologize to copyright holders if permission to publish in this form has not been obtained. If any copyright material has not been acknowledged please write and let us know so we may rectify in any future reprint.
Except as permitted under U.S. Copyright Law, no part of this book may be reprinted, reproduced, transmitted, or utilized in any form by any electronic, mechanical, or other means, now known or hereafter invented, including photocopying, microfilming, and recording, or in any information storage or retrieval system, without written permission from the publishers.
For permission to photocopy or use material electronically from this work, please access www.copyright. com (http://www.copyright.com/) or contact the Copyright Clearance Center, Inc. (CCC), 222 Rosewood Drive, Danvers, MA 01923, 978-750-8400. CCC is a not-for-profit organization that provides licenses and registration for a variety of users. For organizations that have been granted a photocopy license by the CCC, a separate system of payment has been arranged.
Trademark Notice: Product or corporate names may be trademarks or registered trademarks, and are used only for identification and explanation without intent to infringe.
Library of Congress Cataloging-in-Publication Data
Names: Witczak, Agata. | Sikorski, Zdzisław E.
Title: Toxins and other harmful compounds in foods / Agata Witczak and Zdzisław E. Sikorski.
Description: Boca Raton : CRC Press, 2017. | Series: Chemical and functional properties of food components series
Identifiers: LCCN 2016029520| ISBN 9781498748520 (hardback : alk. paper) | ISBN 9781498748537 (e-book)
LC record available at https://lccn.loc.gov/2016029520
Visit the Taylor & Francis Web site at http://www.taylorandfrancis.com
and the CRC Press Web site at http://www.crcpress.com
Kevin D. Welch, Stephen T. Lee, Daniel Cook, Benedict T. Green, and Kip E. Panter
Sui-Sheng T. Hua, Perng-Kuang Chang, and Jeffrey Palumbo
Waldemar D ą browski, Alicja Dłubała, and Izabela Helak
Chapter 10
Bła żej Kudłak, Monika Wieczerzak, and Jacek Namieś nik
Tine Fierens, Mirja Van Holderbeke, Arnout Standaert, Isabelle Sioen, and Stefaan De Henauw
Chapter 12
Agata Witczak
Chapter
Elż bieta Kucharska and Joanna Bober Chapter 14
Shilpi Gupta Dixit Chapter 15
Elż bieta Kucharska and Barbara Wróblewska
Chapter 16
Zdzisław E. Sikorski and Hanna Staroszczyk
Wolska and Maciej Tankiewicz
Gra ż yna Gał ęzowska and Lidia Wolska
Chapter 19
Stefan S. Smoczy ń ski
Series Preface
Toxins and Other Harmful Compounds in Foods is the 20th volume in the CRC series of Chemical and Functional Properties of Food Components. The aim of this series is to present the actual state of knowledge on the contents, chemistry, and functionality of the main food constituents, on the methods of food analysis, as well as on the effects of the interactions of the components in various conditions of processing and storage on the sensory and biological properties of food products. These particular volumes are devoted to the individual components such as proteins, lipids, saccharides, colorants, and avor compounds, to the effects of various environmental and breeding conditions on the quality of the raw materials (e.g., meat and seafood), to the factors affecting safety of foods, and to the role of crucial enzymatic and chemical reactions occurring during food storage, handling, and processing (e.g., hydrolysis, cross-linking, polymerization, or oxidation). The books are edited by renowned scientists according to strictly outlined rules. The individual chapters are prepared by specialists from Africa, Australia, Asia, Europe, and North America, who based them on their personal research and teaching experience, as well as on critical evaluation of the current literature. Because of the dedication of the authors, the chapters took several months to complete, and they present actual results of research.
Like other books in this series, Toxins and Other Harmful Compounds in Foods addresses some of the most pressing problems related to food economy and quality. It presents the occurrence of natural harmful chemical and biological factors in numerous raw materials, describes rational technological processes aimed at avoiding conditions and reactions leading to generation of toxic compounds, as well as adequate regulatory and control measures needed to produce safe food of high sensory quality.
Zdzisław E. Sikorski
Preface
Plants and animals have hardly been created intentionally to satisfy human needs for alimentation. Thus many of them contain not only proteins, lipids, saccharides, vitamins, other organic compounds, and mineral components valuable to people’s nutrition, but also various chemical substances that ful ll different functions in the living plants or animals that otherwise may be toxic or harmful to humans. Furthermore, pathogenic micro-organisms, parasites, compounds generated due to processing, additives used illegally, and environmental pollutants occurring in food raw materials and products may pose a health hazard to the consumers. Research on the presence and properties of these harmful components/pollutants serves the purpose of minimizing the danger to human health. These hazards can be eliminated by limiting the maximal tolerable contents of the harmful elements and compounds, as well as by setting high standards of hygiene and rational processing parameters. The presently available methods make it possible to precisely analyze the composition of raw materials and products, enable the positioning of any particular components in the structure of the tissues, determine the concentration in the order of pg/g, speciation of pollutants, and running online effective control of the safety of food. The information presented in this volume should help the reader to understand the real hazards related to the presence and toxicity of harmful compounds in food raw materials and products. Sound knowledge on the occurrence and effects of toxins and other harmful compounds may help all those involved in the production, processing, and distribution of food to decrease the incidents of food-borne poisonings and help the educated consumers to rationally select their food products on the market.
The main idea of this book has been to present up-to-date knowledge on the occurrence, structure, and properties of harmful components in foods, the mode of action of these compounds in the human organism, on the possibilities to detect them, and on the procedures applied to eliminate the health hazards caused by food toxins and other noxious constituents. The chapters have been written by renowned specialists on food chemistry, toxicology, and microbiology. The information available in current world literature has been critically evaluated and presented in a very concise and user-friendly form. In most chapters, only the pertinent bibliographic sources have been cited, although the large number of new developments in some areas of research made it dif cult to keep the lists of references really short.
The rst chapter presents the factors that affect the health hazards caused by food toxins and other harmful compounds. Chapters 2 through 4 deal with the occurrence and effects of natural toxins of plant origin and marine phycotoxins. Chapter 5 describes the health hazards caused by biogenic amines that are found predominantly in sh and fermented products. Mycotoxins and bacterial toxins are discussed in Chapters 6 and 7. Pollution of foods as a result of human activities and environmental effects is presented in Chapters 8, 9, 11, 12, 14, and 17. The role of phytoestrogens and allergens, as well as the epidemiological and medical impact of contamination by viruses’ transmission via food and water, is discussed in Chapters 10, 13, and 15. The risks and bene ts of processing are presented in Chapter 16. The methods of
detection of harmful compounds and the international regulations established to control harmful food contaminations are presented in Chapters 18 and 19.
As the editors of this volume, we acknowledge with thanks the valuable contributions of the authors. Our thanks are especially due to those colleagues who prepared their chapters ahead of time, thus giving the editors a chance to check the material thoroughly.
We dedicate this volume to all people working in the whole food chain whose efforts serve the purpose of increasing food safety.
Agata Witczak and Zdzisław E. Sikorski Szczecin and Gdan´sk, Poland
Editors
Agata Witczak, PhD, DSc, earned her BS and MS at the Technical University, Szczecin, Poland, her PhD at the Agricultural University, Szczecin, and her DSc at the West Pomeranian University of Technology (ZUT), Szczecin. She serves as a vice dean for the quality of education, and for the eld of study of management of food safety and quality, at the Faculty of Food Sciences and Fisheries, ZUT. She is a member of the American Chemical Society and the Polish Society of Food Technologists, and an expert at the Sectorial Centre of Competence for the Food Industry at the Regional Centre for Innovation and Technology Transfer, ZUT. She is a chemist and toxicologist who researches persistent organic pollutants (POPs) in environmental and food safety studies. Dr. Witczak is involved in the risk assessment from xenobiotics distribution and transfer in the environment. She evaluates the effects of technological processes, including culinary processing, on POPs content in foodstuff. She is an author/coauthor of more than 70 original papers in Polish and international journals, and a coauthor of a number of unpublished works made for industrial entities and environmental protection units. She also reviews articles for prestigious magazines. Dr. Witczak is a member of the Committee of Analytical Chemistry, the Polish Academy of Sciences.
Zdzis ław E. Sikorski, PhD, DSc, earned his BS, MS, PhD, and DSc at the Gda ńsk University of Technology (GUT), and Dr honoris causa at the Agricultural University, Szczecin, Poland. He is a fellow of the International Academy of Food Science and Technology and an honorary professor emeritus of GUT. He gained industrial experience in breweries, sh-, meat-, and vegetable-processing plants, and on a deep-sea shing trawler. He was the founder, professor, and head of the Department of Food Chemistry and Technology, GUT, served there 5 years as dean of the Faculty of Chemistry, was chairman of the Committee of Food Technology and Chemistry of the Polish Academy of Sciences, chaired the scienti c board of the Sea Fisheries Institute in Gdynia, and was an elected member of the Main Council of Science and Tertiary Education in Poland. He also worked for several years as a postdoc/researcher/professor at Ohio State University, Columbus; CSIRO in Hobart, Australia; DSIR in Auckland, New Zealand; and National Taiwan Ocean University, Keelung, Taiwan. His research was focused mainly on food smoking and freezing and functional properties of food proteins. He is an author/coauthor of 210 journal papers, published 19 books, wrote 18 chapters on marine food science and food chemistry for other books, and holds several patents.
Contributors
Hassan Abdel-Gawad
Chemical Industries Division
National Research Centre
Giza, Egypt
Joanna Bober
Department of Medical Chemistry
Pomeranian Medical University in Szczecin
Szczecin, Poland
Perng-Kuang Chang
USDA-ARS
Southern Regional Research Center
New Orleans, Louisiana
Daniel Cook
USDA Agricultural Research Service Poisonous Plant Research Laboratory
Logan, Utah
Waldemar D ąbrowski
Department of Applied Microbiology and Biotechnology
West Pomeranian University of Technology
Szczecin, Poland
Stefaan De Henauw
Ghent University
Department of Public Health Ghent, Belgium
Shilpi Gupta Dixit
All India Institute of Medical Sciences
Jodhpur, Rajasthan, India
Alicja Dłubała
Department of Applied Microbiology and Biotechnology
West Pomeranian University of Technology Szczecin, Poland
Tine Fierens
Unit of Environmental Risk and Health
Flemish Institute for Technological Research (VITO NV)
Belgium
Gra ż yna Gałęzowska Department of Environmental Toxicology
Medical University of Gda ńsk
Gda ńsk, Poland
Benedict T. Green
USDA Agricultural Research Service Poisonous Plant Research Laboratory Logan, Utah
Gustaaf M. Hallegraeff
Institute for Marine and Antarctic Studies (IMAS) University of Tasmania Hobart, Australia
Izabela Helak Department of Applied Microbiology and Biotechnology
West Pomeranian University of Technology Szczecin, Poland
Sui-Sheng T. Hua
USDA-ARS
Western Regional Research Center
Albany, New York
Sevim Köse
Faculty of Marine Sciences
Karadeniz Technical University
Trabzon, Turkey
Roman Kotłowski Department of Microbiology
Gda ńsk University of Technology
Gda ńsk, Poland
El żbieta Kucharska Department of Human Nutrition
West Pomeranian University of Technology
Szczecin, Poland
Bła żej Kudłak Department of Analytical Chemistry
Gda ńsk University of Technology
Gda ńsk, Poland
Stephen T. Lee
USDA Agricultural Research Service Poisonous Plant Research Laboratory
Logan, Utah
Jacek Namie śnik
Department of Analytical Chemistry
Gda ńsk University of Technology
Gda ńsk, Poland
Jeffrey Palumbo
USDA-ARS
Western Regional Research Center
Albany, New York
Kip E. Panter
USDA Agricultural Research Service Poisonous Plant Research Laboratory
Logan, Utah
Mikołaj Protasowicki
West Pomeranian University of Technology
Szczecin, Poland
Zdzisław E. Sikorski
Department of Food Chemistry, Technology, and Biotechnology
Gda ńsk University of Technology
Gda ńsk, Poland
Isabelle Sioen
Ghent University
Ghent, Belgium
Stefan S. Smoczy ń ski University of Warmia and Mazury in Olsztyn Olsztyn, Poland
Arnout Standaert
Unit of Environmental Risk and Health
Flemish Institute for Technological Research (VITO NV)
Belgium
Hanna Staroszczyk
Department of Chemistry, Technology, and Food Biotechnology
Gda ńsk University of Technology
Gda ńsk, Poland
Maciej Tankiewicz
Department of Environmental Toxicology
Medical University of Gda ńsk
Gda ńsk, Poland
Mirja Van Holderbeke
Unit of Environmental Risk and Health
Flemish Institute for Technological Research (VITO NV)
Belgium
Kevin D. Welch
USDA Agricultural Research Service Poisonous Plant Research Laboratory Logan, Utah
Monika Wieczerzak
Department of Food Chemistry, Technology, and Biotechnology
Gda ńsk University of Technology
Gda ńsk, Poland
Agata Witczak Department of Toxicology
West Pomeranian University of Technology Szczecin, Poland
Lidia Wolska Department of Environmental Toxicology
Medical University of Gda ńsk
Gda ńsk, Poland
Barbara Wróblewska Polish Academy of Sciences Olsztyn, Poland
1 Problems of Food Safety
Waldemar Da ˛ browski and Agata Witczak
CONTENTS
1.1
1.3The
1.4Changes
1.5Xenobiotics
1.6
1.1 INTRODUCTION
Knowledgeable consumers expect not only high sensory quality of food, but also need the elimination of risks from frequently dangerous microbial, biological, and chemical contamination. Microbial contamination results from negligence during the transport, storage, and production stages, as well as from genetic variability and metabolic exibility of micro-organisms. An example of such exibility is the bacterium Escherichia coli. These micro-organisms were characterized many years ago as human and animal commensals or pathogens. They were categorized into 6 groups and 190 serotypes. In 2011, a new strain of E. coli occurred in Germany—a highly pathogenic, enteroaggregative strain of serotype O104:H4 that caused an outbreak involving 3842 cases of human infections, including 51 deaths. The disease resulted from the consumption of contaminated sprouted fenugreek seeds (Beutin and Martin 2012). More than 800 people infected had symptoms of hemolytic uremic syndrome, which may lead to loss of kidney functions. Apart from Germans, there were also residents of other countries, especially France, Denmark, and Sweden, among the infected people. The contaminated seeds were probably imported from Egypt. The major causes of the outbreak were globalization of raw materials, lack of adequate hygienic standards in mass production, and international migrations of people. Chemical contamination may also result from negligence during production, but its major cause is the widespread chemicalization of the natural and human environment. Improvements in analytical and diagnostic methods, including meta-analysis, cohort studies, and randomization, enable detection of previously unknown hazards and causes of human health disorders. Improved analytical methods, including the introduction of high-performance gas and liquid chromatography, in particular coupled with mass spectrometry, enable detection of compounds that were undetectable by conventional analytical methods. For example, some foods regarded
as strongly healthy have been found to contain hazardous compounds such as 3-monochloropropane-1,2-diol in soya sauces or carbamates in pickled products. Today most hazardous chemicals penetrate human organisms via the alimentary tract, and inadequate nutrition is regarded among the major pathogenic factors.
1.2 CHANGES IN FOOD PRODUCTION AND NUTRITION
Changes in food production involve the following:
•Concentration of production in factories of increasing processing ef ciency
•Changed production methods
•Increased number and more types of products
•Increased number and more types of unconventional foods (from other regions of the world)
Increased production ef ciency in a food-processing factory contributes to increased production, which signi cantly increases the number of consumers, and thus enlarges the risk from any production negligence. The consolidation of dairy plants in Poland (creamery and cheese-making industry) may be cited as an example. Currently, there are nearly 250,000 consumers to one creamery.
Changes in production methods concern various aspects, for example, changed sterilization methodology, where technologies of high-pressure, high-voltage electric impulses, or light impulses are introduced instead of thermal sterilization. Another example of threat associated with changes in production methods is hydroponic production of sprouts. In 1996, 6,000 children from Sakai, Japan, got infected after eating radish sprouts contaminated by enterohemorrhagic E. coli of 0157:H7 serotype. A similar big outbreak triggered by sprouts contaminated by E. coli 0104:H4 occurred in Germany in 2011. According to Meathead Goldwyn, “raw sprouts may be the riskiest food in the world” (http://amazingribs.com/blog/ raw_sprout_are_risky.html).
Ready-to-eat food products are growing in number and variety. Such foods usually require heating before serving. In the case of dumplings, the most appropriate procedure is processing in boiling water. Consumers, however, usually prefer microwave heating, which does not fully prevent the risk of infection with some kinds of pathogens (Szymczak and Dąbrowski 2015).
On the market, there are more and more food products from all over the world. Surimi crabsticks or Japanese sushi have become quite widespread. Their production on Asiatic markets is usually combined with centuries-long tradition. However, starting their mass production in distant countries may be hazardous. Recently in Europe, a red rice appeared, also called “red koji,” “red Chinese rice,” or “red mold rice.” This rice has been produced in China for centuries, with the use of molds Monascus purpureus. As early as in the fteenth century, Chinese pharmacopeia described health-promoting properties of this rice, as it regulates consumers’ lipid metabolism due to the presence of monacolin—a precursor of statins. However, some Monascus strains produce citrinin, an extremely harmful hepatonephrotoxin, which may produce dramatic health effects in consumers when the control of import is inadequate.
1.3 THE GLOBALIZATION OF FOOD PRODUCTION
Globalization is a process of changes in societies and economies, leading to an increasing interrelationship and integration of countries, societies, economies, and cultures. This integration applies to economic issues in particular. In Europe, it was initiated by establishing the European Free Trade Association (EFTA) in 1960. A free trade area among EFTA member states was formed in 1968. In 1992, the European Economic Community (EEC) and EFTA reached an agreement and formed a common free trade area for all goods. This agreement entered into force on January 1, 1994, and established the European Economic Area. In 1980, the United Nations Convention on Contracts for the International Sale of Goods (CISG) was signed in Vienna, which is a multilateral international treaty on the rules of international sale of goods. Until 2010, the convention had been rati ed by 77 states. These agreements promote, among others, international food trade, which is also facilitated by opened boarders in the European Union (EU), the Customs Union abolishing customs duties within the EU, and the rapid development of road, sea, and air transport. All this strongly in uences the development of the food industry and related food safety, as well as increasingly complex cross-border ows of raw materials and nished products (Hawkes 2006). Areas previously free from some hazards are currently exposed to the import of foods, often from different climate zones, contaminated by unknown types of micro-organisms. This poses an additional risk, especially for children, for example, due to the occurrence of viral diarrhea of unknown origin. Closer attention is also paid to adequate conditions of transportation and storage, especially considering the long logistic chains. A classic example of improper production and transportation was the case when in 1960 more than 100,000 turkeys on poultry farms in England died as a result of intoxication by feed contaminated by an a atoxin from imported peanuts.
1.4 CHANGES IN PUBLIC HEALTH AND DIETARY HABITS
Health condition of a society is proportional to its wealth. The wealthier a society is, the more valued is human health and life (http://www.who.int/health-accounts/ ghed/en/). These theses can be based not only on data on the expenditures of individual countries on disease prevention and treatment, but also on the comparison of infant mortality and average life expectancy. This stimulates medicine development and contributes to continuous introduction of new drugs. The effects are not only positive, but also negative. Among negative ones, there is suppressed immunity in patients due to frequent use of anticancer and immunosuppressive drugs. These medicines are widely used in therapies against cancer, autoimmune diseases, and allergies, as well as in patients after an organ transplant. As a result of the pharmacotherapy, there are an increasing number of people with suppressed immunity, for which an infection with even trivial micro-organisms may be life threatening. Therefore, even micro-organisms of low pathogenicity, when present in food, may pose a health risk. Moreover, the progress of civilization increases the number of allergic people. Previously, natural selection eliminated a large part of the population with this genetic predisposition. Asthmatic children usually died as a result of
secondary pneumonia. Currently, they reach the reproductive age, and for both parents with allergies, the likelihood of having an allergic child increases by 20% –30%. Food allergies affect 4% –6% of children and 2% –3% of adults (Sicherer and Samson 2014). For these people, even trace amounts of allergens in food can be of dramatic consequences. The fact has been imposing increasingly rigorous “allergic hygiene” standards upon food manufacturers, so that nally a food allergy hazard analysis and critical control points (HACCP) system has been developed.
Increased risk for human health from food consumption is also associated with changing life styles, consumption patterns, and dietary habits. We live faster and differently. Many people eat out, which is a consequence of working time duration, and sometimes also of travel-to-work time. At home, a large number of families have made drastic changes in their dietary habits. Excessive amounts of crisps, chips, and other junk foods and beverages excessively sweetened with glucose–fructose syrup are consumed. As a result, a massive increase in obesity has occurred among the people of developed countries, followed by an increase in diabetes and cardiovascular diseases. Certain foods, for example, harden vegetable fats containing trans-fatty acids, which are formed during the partial hydrogenation of vegetable oils. Transfats double the risk of breast cancer and increase the level of bad cholesterol, lowdensity lipoprotein (LDL), which translates into an increased risk of atherosclerotic diseases. Denmark and Canada, in an attempt to solve this problem, require food manufacturers to report data on trans-fat content in their products on product labels and to reduce the content.
1.5 XENOBIOTICS IN THE ENVIRONMENT AND FOOD
Food safety should be a guarantee that no adverse effects occur in the human body after food ingestion. Over the centuries, humans have learned to avoid certain plant and animal species—recognized as inedible or even poisonous (Wilcock et al. 2004). Potential contaminants in foodstuff may be of a natural origin (e.g., bacterial and fungal toxins, amygdalin, and solanine) or may be absorbed from the polluted environment (e.g., nitrates (V), nitrates (III), heavy metals—lead, cadmium, mercury, residues of fertilizers and pesticides, dioxins, phthalates, and residues of veterinary drugs). Contaminants that accumulate in the organisms are considered as the most dangerous. A wide use of antibiotics in animal husbandry also became a serious problem, as it contributed to the transfer of antibiotic resistance from animals to humans. Signi cant sources of food contamination also include substances formed during technological processing and storage. This group consists of mycotoxins, nitrosamines, acrolein, epoxides, and other compounds.
Another group of food contaminants consists of foreign substances introduced to food products during technological processing. The group includes cleaning agents, preservatives, sweeteners, dyers, and chemical contaminants passing to food from the packaging and equipment.
A majority of chemical contaminants detected in foods are dif cult or even impossible to avoid. These include certain metals, nitrates, N-nitroso compounds, pesticides, dioxins, dibenzofurans, PAHs, and other polyhalogenated polycyclic
aromatic compounds. An important group is constituted by halogenated aromatic hydrocarbons, classi ed as persistent organic pollutants (POPs).
Some of the substances mentioned earlier (pesticide residues, dioxins, polychlorinated biphenyls, and other POPs) have been detected for many years in both aquatic and terrestrial environment worldwide, which is re ected in their constant, although gradually decreasing, presence in food.
1.6 CONCLUSIONS
Food safety, according to the Food and Agriculture Organization, is an important component of food security, that is, physical and economical access to food for each resident. Ensuring food safety is closely related to minimizing the risk of any side effects in the human body.
Food safety is an area of increasing global interest because of its direct impact on human health. Safe food is food that comes from a clean, unpolluted natural environment. Since 1960s, health hazards have been regarded not only in terms of microbiological, but also chemical food contamination. Currently, health quality and safety of food are among the most important criteria for consumers’ assessment of food. For this reason, food quality assessment covers not only functional, sensory, esthetic, and hygienic aspects, but also the content of foreign chemicals (xenobiotics) in the product that may endanger human safety.
As shown in numerous studies, incorrect culinary or technological processing or improper storage may result in the formation of toxic compounds in foods, including acrolein, nitrosamines, and mycotoxins.
The most dangerous risks associated with the majority of xenobiotics are their carcinogenicity, teratogenicity, and endocrine-disrupting activity.
Among numerous chemical hazardous to human health, the leading ones are some of the natural substances, for example, mycotoxins, as well as anthropogenic compounds, which are environmental pollutants, or deliberately used chemicals, or by-products in various processes, for example, dioxins, dibenzofurans, pesticides, polychlorinated biphenyls, nitrates, and heavy metals.
At present, the problem of food contamination has become an important issue for food processing companies. It is re ected in the introduction of a “farm-to-table” system, which enables the control of the product since the very moment of raw materials harvesting, and further at all stages of production. Drawbacks to modern food production also include an extended way from raw materials to nished products, resulting from the phenomenon of globalization and multistage production of foods, for example, convenience foods.
Worth emphasizing is the fact that the occurrence of some groups of toxic compounds (pharmaceuticals, pesticides, additives, and preservatives) in food may be avoided or reduced to an acceptable level, provided that food security systems (e.g., HACCP, good manufacturing practice, and good hygiene practice) are appropriately implemented and used. A greater concern for food safety is also re ected in the introduction of increasingly stringent standards on acceptable levels of toxic chemicals in various types of foods.
At present, some risk is indicated with indiscriminate use of pesticides. Another important problem concerns malpractices in crop protection, usually resulting from disregarding the recommendations for proper use, which poses health risk to humans and animals. The size of population exposed to pesticides is dif cult to estimate. The most frequent effects include gastrointestinal dysfunctions, such as loss of appetite, nausea, dysgeusia, and vomiting, and also neurological disorders, such as headaches, dizziness, impaired balance, and hyperactivity (Gilden et al. 2010). Prenatal exposure to organophosphate pesticides may also signi cantly contribute to lower birth weights and decreased gestational ages (Rauch et al. 2012).
According to Sanghi et al. (2003), even low-dose exposures to chlorpyrifos during pregnancy and just after birth may inhibit DNA synthesis and reduce the number of neuronal cells in certain parts of the brain. It is suspected that even lowlevel exposure to chlorpyrifos early in life may adversely affect the function of the nervous system later in life.
Consumer education and reliable information on food composition from food manufacturers have become highly important because of potential hazards that may occur in both raw materials and processed food products.
REFERENCES
Beutin, L. and A. Martin. 2012. Outbreak of Shiga Toxin-Producing Escherichia coli (STEC) O104:H4 Infection in Germany Causes a Paradigm Shift with Regard to Human Pathogenicity of STEC Strains. Journal of Food Proteins 75(2): 408–418.
Gilden, R.C., K. Huf ing, and B. Sattler. 2010. Pesticides and Health Risks. Journal of Obstetric, Gynecologic, & Neonatal Nursing 39(1): 103–110.
Hawkes, C. 2006. Uneven Dietary Development: Linking the Policies and Processes of Globalization with the Nutrition Transition, Obesity and Diet-Related Chronic Diseases. Globalization and Health 2: 4.
Rauch, S.A., J.M. Braun, D.B. Barr, A.M. Calafat, J. Khoury, M.A. Montesano, K. Yolton, and B. Weight. 2012. Associations of Prenatal Exposure to Organophosphate Pesticide Metabolites with Gestational Age and Birth Weight. Environmental Health Perspectives 120(7): 1055–1060.
Sanghi, R., M.K.K. Pillai, T.R. Jayalekshmi, and A. Nair. 2003. Organochlorine and Organophosphorus Pesticide Residues in Breast Milk from Bhopal, Madhya Pradesh, India. Human & Experimental Toxicology 22(2): 73–76.
Sicherer, S.H. and H.A. Sampson. 2014. Food Allergy: Epidemiology, Pathogenesis, Diagnosis, and Treatment. Journal of Allergy and Clinical Immunology 133(2): 291–307.
Szymczak B. and W. Dąbrowski. 2015. Effect of Filling Type and Heating Method on Prevalence of Listeria species and L. monocytogenes in dumplings produced in Poland. Journal of Food Science 80(5): M1060–M1065.
Wilcock, A., M. Pun, J. Khanona, and M. Aung. 2004. Consumer Attitudes, Knowledge and Behaviour: A Review of Food Safety Issues. Trends in Food Science & Technology 15: 56–66.
2 Natural Toxins of Plant Origin (Phytotoxins)
Kevin D. Welch, Stephen T. Lee, Daniel Cook, Benedict T. Green, and Kip E. Panter
2.1 INTRODUCTION
Natural toxins, and speci cally those produced by plants, have multiple and diverse functions that can either be detrimental or bene cial to both animals and humans. It has been argued for decades that many of these compounds serve as a defense mechanism to protect plants against herbivory, predation, or disease (reviewed by Wink 1999). Secondary compounds can protect a plant in various ways by imparting bitterness or causing discomfort or some other negative cue to inhibit herbivory, or it may be overtly toxic thus killing the predator, debilitating it, or causing an inherent aversion to the plant.
Plant secondary compounds may have other signi cant survival roles such as signals to attract insects, birds, or other animals to enhance pollination and/or seed dispersal. In addition to any potential functions, secondary compounds may concomitantly serve a physiologic function such as protection against UV light or frost, or provide a function of nitrogen transport and storage. In several instances, compounds can serve multiple functions in the same plant. Anthocyanins or monoterpenes can be insect attractants in owers, but are insecticidal and antimicrobial at the same time in leaves (Wink 1999). Similarly, insects and other organisms have evolved with plants, thereby utilizing the protective mechanism of the plant. For example, a relationship between milkweeds and the Monarch butter y demonstrates such a relationship between a plant and an insect (Harborne 1993). The larvae of the Monarch butter y feed on milkweeds and accumulate cardenolides. Birds feeding on the caterpillar, pupa or adult, will vomit and subsequently become averted and thus avoid the Monarch butter ies. There are numerous other examples whereby plants, insects, large herbivores, and other organisms play an intertwined role in nature’s balance. Multiple functions are typical of plant compounds and do not contradict in any way their main role as chemical defense and signal-induction compounds. If a trait serves multiple functions in a given plant or animal, it is more likely to survive the rigors of natural selection.
In general, plant parts that are important for survival and reproduction, such as owers and seeds, will concentrate defense compounds. Consequently, compounds may be more rapidly synthesized or stored at certain stages of critical growth, that is, buds, young tissue, or seedlings. Many of these plant species rely on secondary compounds during early growth phase or seed phase, yet the vegetative and mature stages are protected by mechanical or morphological adaptations. Although plants have a limited capacity to replace or regenerate parts that are eaten, diseased, or damaged, secondary compounds are of major importance to promote survival.
The capacity for open growth and regeneration, which is prominent in perennials, allows for a margin of tolerance toward herbivores and microbes. While the role of secondary compounds in plant evolution is signi cant for survival, the impact on the health and wellbeing of man and animals may be bene cial or deleterious.
Over 100,000 secondary compounds have been identi ed including alkaloids, glycosides, proteins, polypeptides, amines and nonprotein amino acids, organic acids, alcohols, polyacetylenes, resinous toxins, and mineral toxins. For thousands of years, man has used some of these compounds as avors, dyes, fragrances, insecticides, hallucinogens, nutritional supplements, animal or human poisons, and therapeutic/pharmaceutical agents. Volumes have been written on the natural toxins of plants. While the negative impact of plant toxins on livestock and humans has been the most publicized, the diversity of these toxins and their potential as new pharmaceutical agents for the treatment of diseases in humans and animals has received widespread interest in modern society. Scientists are actively screening plants from all regions of the world for bioactivity and potential pharmaceuticals for the treatment or prevention of many diseases. This chapter will focus on plants and their toxins that have been researched at the USDA-Agricultural Research Service, Poisonous Plant Research Laboratory (PPRL) in Logan, Utah, with casual mention of other relevant toxins affecting animals and humans.
2.2 ALKALOIDS
2.2.1 IntroductIon
An alkaloid is a basic, nitrogen-containing compound generally found in higher plants. Pelletier (1983) suggested that an alkaloid is a cyclic compound containing nitrogen in a negative oxidation state, which is of limited distribution in living organisms. Pelletier’s de nition includes alkaloids with nitrogen as part of a heterocyclic system and extracyclic bound nitrogen.
Several thousand alkaloids have been identi ed and characterized in plants. Over 20% of higher plant families contain alkaloids, thus alkaloids are the most ubiquitous and signi cant class of plant toxins (Blackwell 1990). Although alkaloids have been suggested to be waste byproducts of plant metabolism, they may play a role in binding ionic nitrogen needed by seedlings. Alkaloids were initially associated with members of the plant kingdom, but more and more alkaloid compounds are being discovered in micro-organisms, fungi, marine invertebrates, insects, and higher animals (Roberts and Wink 1998). Many of these alkaloids have led to the discovery of new pharmaceuticals and the treatment of disease in man and animals.
Bitter alkaloids may have evolved a universal role in plant chemical defense as a feeding deterrent. Quinine, strychnine, and brucine are extremely bitter alkaloids. However, there are little data on animal/plant relationships that show bitterness is the only controlling factor in preventing herbivore ingestion of poisonous plants. There are many examples of animals eating plants that, in human terms, are “bitter as gall.” Wink et al. (1993) partially disproved the bitterness theory in a feeding trial with geese, in which the birds avoided essential oils but tolerated bitter alkaloids.
2.2.2 PIPerIdIne Alk AloIds
Piperidine alkaloids are widely distributed in nature, mostly in plants, but also in lower animals such as Nemertine worms. Of the hundreds of piperidine alkaloids known, most are derived by 1 of 3 biosynthetic pathways in the plant using the building blocks of lysine, acetate, or mevalonate as precursors (reviewed by Panter and Keeler 1989). The common nucleus of all piperidine alkaloids is the piperidine ring (Figure 2.1). Some of the more simple-structured piperidines follow the lysine and acetate pathways, while the more complex ones use mevalonate. Acetate-derived piperidine alkaloids are common in nature in plants and lower animals. For example, the simple piperidines in poison hemlock, gamma-coniceine and coniine, are acetate pathway derived. Likewise, anabaseine, also acetate pathway derived and a known tobacco alkaloid, has been identi ed as a poison gland product of Aphaenogaster ants and various 2,6-disubstituted piperidine alkaloids have been isolated from the re ant (Solenopsis saevissima), in which these alkaloids function as attractants (Roberts and Wink 1998). More than 100 different alkaloids (many of them piperidine) have been isolated from neotropical frogs of the Dendrobatidae family, and others have been identi ed in numerous microorganisms.
The piperidine alkaloids are historically signi cant because of the ancient Greek practice of executing criminals with poison-hemlock tea. Early literature refers to human poisoning more frequently than animal poisoning. Even today, accidental human poisonings occasionally occur; however, most current reports involve ingestion by livestock species. A human incident was reported by Frank et al. (1995) in which a 6-year-old boy and his father were successfully treated for accidental poisonhemlock poisoning. After ingesting young poison-hemlock leaves, the boy became unresponsive and was then hospitalized. After plant identi cation and appropriate hospital treatment, the boy recovered completely. One of the most famous historical accounts of poison hemlock is the execution of the philosopher Socrates, who was sentenced to death by drinking hemlock tea after he was convicted of introducing new divinities into the philosophy of that day. A historical account of Socrates’ death was published by Daugherty (1995).
FIGURE 2.1 Piperidine ring (a) and three functionalities of three carbons or larger that impart teratogenic activity, that is, coniine (R1), anabasine (R 2), and ammodendrine (R 3), respectively b, c, d.
In ancient times, Conium seed was collected green, dried, and stored to be used medicinally as a sedative. The dried leaf and juice of Conium maculatum were listed in pharmacopoeias of London and Edinburgh from 1864 to 1898, and the last of cial record appeared in Great Britain in the British Pharmaceutical Codex of 1934. Interest in the medicinal value of poison hemlock has declined because of the unpredictability of its effects. The unpredictability is now understood as the toxin pro le, and concentration in the plant and green seed can vary dramatically because of environmental factors or even diurnally. Poison hemlock also has historical signi cance to researchers because coniine was the rst alkaloid discovered in 1827 and rst synthesized in 1886 (Landenburg 1886; reviewed by Panter and Keeler 1989).
Poison hemlock contains three major and ve minor alkaloids. The toxicity and teratogenic effects of the three major alkaloids from poison hemlock have been compared (Figure 2.2). Gamma-coniceine usually predominates in early vegetative stages of plant growth, and coniine and N-methyl coniine usually predominate in seed and mature plant. Gamma-coniceine is the precursor to all the other poison-hemlock alkaloids. Gamma-coniceine is 7–8 times more toxic in a mammalian bioassay compared to coniine, which is 1.5–2 times more toxic than N-methyl coniine (Figure 2.2). The pharmacological activity is similar among these alkaloids but varies in potency because of structural differences. Pharmacological studies with Conium alkaloids have demonstrated that they act as stereoselective nicotinic acetylcholine receptor agonists (Lee et al. 2013). Peripheral actions on smooth muscle are initiated by ganglionic stimulation and subsequent receptor desensitization, which explains some of the early clinical signs of stimulation to the gastrointestinal (GI) tract and urinary system. Spinal re exes are later blocked, which has been attributed to the increased membrane permeability to potassium ions. Pharmacologically, the properties of all three alkaloids are very similar, except gamma-coniceine is more stimulatory to autonomic ganglia and N-methyl coniine has a greater desensitizing effect (Fodor and Colasanti 1985).
The teratogenic effects of poison hemlock are well known and have been described in cattle, sheep, goats, and pigs (Panter et al. 1999; Green et al. 2013a). Numerous eld cases of poisoning and subsequent malformations have been reported. The mechanism of action, susceptible stages of pregnancy, and detailed descriptions of the teratogenic effects have been reviewed by Panter et al. (2013b) and Green et al. (2013a, 2013b).
FIGURE 2.2 Three piperidine alkaloid teratogens from Conium maculatum (poison-hemlock) with accompanying LD50 as determined in a mouse bioassay: coniine (a), gamma-coniceine (b), and N-methyl coniine (c).
LD50 = 1.6
LD50 = 134.4 (a) (b)
FIGURE 2.3 Piperidine teratogens from Nicotiana glauca (anabasine [a]) and Lupinus formosus (ammodendrine [b]).
In addition to poison-hemlock alkaloids, Nicotiana species and certain lupine species also contain potent toxic and teratogenic piperidine alkaloids (Figure 2.3). All teratogenic piperidine alkaloids have certain structural characteristics that are required for induction of birth defects. The molecular structure includes a piperidine ring with a side chain of at least three carbons or larger attached to the ring adjacent to the nitrogen atom (Figure 2.1). The structural characteristics were rst proposed by Keeler and Balls (1978), and all experiments since that time have supported this theory. The structural requirement for teratogenicity is thought to occur because the alkaloids bind to the nicotinic acetylcholine receptors of the neuromuscular junction. Fetal clinical effects include a signi cant reduction in fetal movement during critical stages of gestation. Just as fetal movement helps prevent skeletal contracture malformations, fetal movement is critical in the prevention of cleft palate. The stage of gestation when the fetus is exposed to alkaloids is related to the type of malformation manifested. Malformations are the same and the mechanism of action is the same for all piperidine alkaloids possessing structural characteristics as discussed above. In addition to lupines, poison hemlock, and Nicotiana spp., other plant species of the genera Genista, Prosopis, Lobelia, Cytisus, Sophora, Pinus, Punica, Duboisia, Sedum, Withania, Carica, Hydrangea, Dichroa, Cassia, Ammondendron, Liparia, and Colidium contain potentially toxic and teratogenic piperidine alkaloids. Many plant species or varieties from these genera may be included in animal and human diets (Keeler and Crowe 1984).
2.2.3 QuInolIzIdIne Alk AloIds
Quinolizidine alkaloids are mainly found in genera of the Fabaceae (Legume) family, a large and commercially important family that contains hundreds of quinolizidine alkaloids. More than 150 quinolizidine alkaloids have been structurally identi ed and characterized in lupines alone (Kinghorn and Balandrin 1984). Signi cant genera containing quinolizidine alkaloids include Lupinus, Laburnum, Cytisus, Thermopsis, and Sophora. Most of these genera contain the teratogen anagyrine (Figure 2.4).
The common structural feature of quinolizidine alkaloids is a decalin ring system with a nitrogen atom at one vertex. Often a second or third nitrogen atom is incorporated into additional six-membered rings. Bicyclic, tricyclic, tetracyclic, and even more complex alkaloids with 5–10 rings have been characterized (Keeler 1989).
Lupinus spp. (lupines) contain both quinolizidine and piperidine alkaloids that are toxic and teratogenic. Eighteen western US lupine species have been reported to contain the teratogen anagyrine (Figure 2.4), with 14 of these containing teratogenic levels (Davis and Stout 1986). Two species, L. formosus and L. arbustus, contain teratogenic levels of the piperidine alkaloid ammodendrine (Figure 2.4; Panter et al. 1998). Lupine alkaloids are produced by leaf chloroplasts and are translocated via the phloem and stored in epidermal cells and in seeds (Wink et al. 1995).
Quinolizidine alkaloid content and pro le varies between lupine species and in individual plants depending on environmental conditions, season of the year, and stage of plant growth (Wink and Carey 1994). Alkaloid content (per gram of plant) may be highest during early growth stages, decreasing through the bud stage, and concentrating in the owers and maturing seeds. Seed pods contain high protein levels and high concentrations of alkaloids.
The effects of site and elevation on alkaloid content have been described by Carey and Wink (1994). Total alkaloid content decreases as elevation increases and was shown to be six times higher in plants at 2,700 m versus plants collected at 3,500 m. This phenomenon persisted even when seedlings from the highest and lowest elevations were grown under identical greenhouse conditions, thus suggesting evolutionary differences genetically.
2.2.3.1
Mechanism of Action
The proposed mechanism of action for lupine-induced malformations and cleft palate in cattle has been elucidated using a goat model. Using ultrasound imaging, Panter et al. (1990) hypothesized that the mechanism for induced contracture defects and cleft palate involves a chemically induced reduction in fetal movement much as one would expect with a sedative, neuromuscular blocking agent, or anesthetic. The proposed mechanism of action was supported by experiments using radio ultrasound where a direct relationship was recorded between reduced fetal activity and severity of contracture-type skeletal defects and cleft palate in sheep and goats (Panter et al. 1990; Weinzweig et al. 2008). Further research suggests that this inhibition of fetal movement must be over a protracted period of time during speci c stages of gestation.
FIGURE 2.4 Teratogenic quinolizidine alkaloid anagyrine from Lupinus spp.
Another random document with no related content on Scribd:
BORROW'S BIBLE IN SPAIN: The Journeys, Adventures, and Imprisonments of an Englishman, in an attempt to circulate the Scriptures in the Peninsula. By G B , Author of "The Gipsies of Spain." With a Biographical Introduction by the Editor, and Illustrations.
"Lovers of good literature and cheap may be commended to the 'Minerva Library' edition of 'The Bible in Spain,' edited by Mr. G.T. Bettany. This is an excellent reprint, with neat binding, good type, and fair woodcuts."—Saturday Review.
VOLUME IV.—FOURTH EDITION.
EMERSON'S PROSE WORKS: The complete Prose Works of R W E . With a Critical Introduction by the Editor, and Portrait of the Author.
"The series, judging by the initial volumes, will be endowed with everything that makes reading pleasant and agreeable.... The printing is a marvel of clearness, the slurs that too often characterise cheap volumes being conspicuous by their absence.... The binding is both elegant and durable.... If the excellence of the first volumes is maintained in the future, the series will enjoy a success both widespread and prolonged."—City Press.
VOLUME V.—THIRD EDITION.
GALTON'S SOUTH AFRICA: The Narrative of an Explorer in Tropical South Africa: being an Account of a Visit to Damaraland in 1851. By F G , F.R.S. With a New Map and Appendix, together with a Biographical Introduction by the Editor, Portrait of Mr. Galton, and Illustrations. Containing also Vacation Tours in 1860 and 1861, by S G G , F G , F.R.S., and W.G. C , M.A.
"Be it understood the 'Minerva Library' presents itself in a form that even the lover of luxurious books could scarcely find fault with."— Warrington Guardian.
"The 'Minerva Library' will be hailed with delight, we are sure, by all readers."—The Weekly Times.
VOLUME VI.—THIRD EDITION.
THE BETROTHED LOVERS (I Promessi Sposi). By A M With a Biographical Introduction by the Editor, and Portrait of the Author.
Of this great Work G wrote:—"Manzoni's romance transcends all that we have knowledge of in this kind. I need only say that the internal part, all that comes from the core of the poet, is thoroughly perfect, and that the external part, all the notes of localities and so forth, is not a whit behind its great inner qualities.... The work gives us the pleasure of an absolutely ripe fruit."
VOLUME VII.—THIRD EDITION.
GOETHE'S FAUST (Complete). Translated in the Original Metres, with copious Critical and Explanatory Notes by B T With a Critical Introduction by the Editor, Portrait of G , and R ' Illustrations.
This is a full and complete reprint of B T ' unrivalled rendering of G ' masterpiece. It is published by special arrangement with M . B T , and contains the whole of the Translator's copious and extremely valuable Notes, Introductions, and Appendices.
VOLUME VIII.—SECOND EDITION.
WALLACE'S TRAVELS ON THE AMAZON: Travels on the Amazon and Rio Negro. By A R W , Author of "The Malay Archipelago," "Darwinism," etc. Giving an account of the Native Tribes, and Observations on the Climate, Geology, and Natural History of the Amazon Valley. With a Biographical Introduction, Portrait of the Author, and Illustrations.
"It would be impossible to overrate the service which Mr. Wallace, the co-discoverer of Darwinism, has done."—Times, September 11th, 1889.
VOLUME IX.—THIRD EDITION.
DEAN STANLEY'S LIFE OF DR. ARNOLD. The Life and Correspondence of Thomas Arnold, D.D. (Head-Master of Rugby School). By A P S , D.D., Dean of Westminster. With a Portrait of A , and Full Page Illustrations.
"One of the most remarkable and most instructive books ever published—a book for which Arnold himself left abundant materials in his voluminous correspondence, supplemented by a large quantity of miscellaneous matter added by his friend and former pupil, Dean Stanley."—Morning Advertiser.
VOLUME X.—SECOND EDITION.
POE'S TALES OF ADVENTURE, MYSTERY, AND IMAGINATION. By E A P . With a Biographical Introduction by the Editor, Portrait of the Author, and Illustrations.
"Contains over forty of Poe's marvellous stories, certainly among the most exciting and sensational tales ever written. The volume itself is a marvel, comprising, as it does, over 560 pages, strongly and neatly bound, for two shillings."—Newcastle Chronicle.
VOLUME XI.
COMEDIES BY MOLIÈRE: Including The Would-Be Gentleman; The Affected Young Ladies; The Forced Marriage; The Doctor by Compulsion; Scapin's Rogueries; The Blunderer; The School for Husbands; The School for Wives; The Miser; The Hypochondriac; The Misanthrope; The Blue-Stockings; Tartuffe, or the Hypocrite. Newly Translated by C M , M.A. The Translation revised by the Editor, with a Portrait of the Author, and Biographical Introduction.
VOLUME XII.
FORSTER'S LIFE OF GOLDSMITH: The Life and Times of Oliver Goldsmith. By J F , Author of "The Life of Charles Dickens," etc. With a Biography of
F by the Editor, and Numerous Illustrations by M , S , L , and Others.
VOLUME XIII.
LANE'S MODERN EGYPTIANS: The Manners and Customs of the Modern Egyptians. By E W L , Translator of "The Arabian Nights' Entertainments." With a Biographical Introduction by the Editor, Sixteen Full Page Plates, and Eighty Illustrations in the Text.
VOLUME XIV.
TORRENS' LIFE OF LORD MELBOURNE: Memoirs of William Lamb, Second Viscount Melbourne. By W.M. T . Revised by the Author. With an Introduction by the Editor, and Portrait of Melbourne.
VOLUME XV.
THACKERAY'S VANITY FAIR: A Novel Without a Hero. By W M T . With a Biographical Introduction by the Editor, Portrait of the Author, and Thirteen Full-Page Illustrations.
WARD, LOCK & CO., L , N Y , M . And at all Booksellers' and Railway Bookstalls.
STANDARD WORKS BY GREAT WRITERS.
THE WORLD LIBRARY OF STANDARD BOOKS.
A Series of Standard Works, including many of the acknowledged Masterpieces of Historical and Critical Literature, made more accessible than hitherto to the general reader by publication in a cheap form and at a moderate price.
Crown 8vo, cloth gilt or buckram, label on back, uncut edges.
1 Hallam's Constitutional History of England. With Lord M ' Essay on the same. 970 pp., 5s. L E , demy 8vo, 7s. 6d.; half-calf, 12s.
2 Hallam's Europe during the Middle Ages. By the Author of "The Constitutional History of England." 720 pp., 3s. 6d. L E , 894 pp., demy 8vo, 6s.; half-calf, 10s. 6d.
3 Hallam's Church and State. By the Author of "The Constitutional History of England." 400 pp., 2s. 6d.
4 The Wealth of Nations (Inquiry into the Nature and Causes of). By A S . 832 pp., 3s. 6d.; half-calf, 7s. 6d. L E , demy 8vo. 6s.; half-calf, 10s. 6d.
6 M'Culloch's Works: Principles of Political Economy, Notes, &c., to "Smith's Wealth of Nations," &c. 700 pp., 3s. 6d.
7 Adam Smith's Essays: Moral Sentiments, Astronomy, Physics, &c. 476 pp., 3s. 6d.
8 Hume's History of England. In Three Vols. 2,240 pp., 10s. 6d. L E , demy 8vo, 18s.; half-calf, 31s. 6d.
9 Hume's Essays: Literary, Moral, and Political. 3s. 6d.
10 Montaigne's Essays. Complete. 684 pp., 3s. 6d.; halfcalf, 7s. 6d. L E , 920 pp., 6s.; hf.-calf, 10s. 6d.
11 Warton's History of English Poetry, from the Eleventh to the Seventeenth Century. 1,032 pp., 6s.
12 The Court and Times of Queen Elizabeth. By L A . 530 pp., 3s. 6d.
13 Edmund Burke's Choice Pieces. Containing the Speech on the Law of Libel, Reflections on Revolution in France, on the Sublime and Beautiful, Abridgment of English History. 3s. 6d.
14 Herbert's Autobiography and History of England under Henry VIII. By Lord H of Cherbury. 770 pp., 3s. 6d.
15 Walpole's Anecdotes of Painting in England. By H W . 538 pp., 3s. 6d.
17 Locke's Essays: On Toleration, Education, Value of Money. 700 pp., 3s. 6d.
18 Bolingbroke on the Study and Use of History. 3s. 6d.
19 Essays on Beauty and Taste: On Beauty, by F , Lord J ; On Taste, by A A , LL.D. 324 pp., 3s. 6d.
20 Milton's Early Britain. With More's England under Richard III., and Bacon's England under Henry VIII., 430 pp., 3s. 6d.
21 Marvell's Poems and Satires. With Memoir of the Author. 3s. 6d.
22 Macaulay: Reviews, Essays, and Poems. 650 pp., 3s. 6d.; half-calf, 6s. L E , demy 8vo, 6s.
23 Sydney Smith's Essays, Social and Political. 3s. 6d.; L E , demy 8vo, 6s.
24 Lord Bacon. Proficience and Advancement of Learning, Historical Sketches and Essays. 530 pp., 3s. 6d.; half-calf, 6s.; L E , demy 8vo, 6s.
25 Essays by Thomas de Quincey. Confessions of an Opium Eater, Letters to a Young Man, &c. 550 pp., 3s. 6d.; L E , demy 8vo, 6s.
26 Josephus (The Complete Works of). By W . Life and Marginal Notes. 810 pp., 3s. 6d. L E , 6s.
27 Paley's Works: "The Evidences of Christianity," "Horæ Paulinæ," and "Natural Theology." With Life and Notes. 3s. 6d.
28 Taylor's Holy Living and Dying. With Life, Introduction, and Notes. 2s. 6d.
29 Dean Milman's History of the Jews. 520 pp., 3s. 6d.
30 Macaulay: Reviews and Essays. Second Series. 2s. 6d.
31 Locke on the Human Understanding. 670 pp., 3s. 6d.; half-calf, 7s. 6d.
32 Plutarch's Lives. By L . 750 pp., 3s. 6d.; halfcalf, 7s. 6d.
33 Addison's Essays from "Spectator." 600 pp., 3s. 6d.
34 Shakespere's Complete Works. With Life and Glossary 1,000 pp., 3s. 6d. L E , 6s.
35 Cook's Boston Monday Lectures. 640 pp., 5s.
36 Todd's Complete Works. Sunday School Teacher, Lectures for Young Men, &c. 920 pp., 5s.
37 D'Aubigne's History of the Reformation. 870 pp., 3s. 6d.; half-calf, 7s. 6d.
38 The Arabian Nights' Entertainments. 430 pp., 3s. 6d.
39 Heroes for the Faith: Scottish Worthies who suffered during the Reformation. 3s. 6d.
40 Martyrs for the Truth. Last Words and Dying Testimonies of the Scottish Worthies. Revised, with Notes 3s. 6d.
43 Newman Smyth's Works. Containing "Old Faiths in New Light," "The Religious Feeling," and "Orthodox Theology." 3s. 6d.
44 Hallam's Literature of Europe during the 15th, 16th, and 17th Centuries. Complete. 900 pp., 5s.
45 Lamb's Essays of Elia and Eliana. 850 pp., 3s. 6d.
46 History of Rome. By D. R . Edited by H.W. D , Ph.D. 500 pp., 3s. 6d.
47 History of Greece. By D. R . Edited by H.W. D , Ph.D. 480 pp., 3s. 6d.
48 Palgrave's History of the Anglo-Saxons. 2s. 6d. WARD, LOCK & CO., London, Melbourne, and New York.
*** END OF THE PROJECT GUTENBERG EBOOK A DEAD MAN'S DIARY
***
Updated editions will replace the previous one—the old editions will be renamed.
Creating the works from print editions not protected by U.S. copyright law means that no one owns a United States copyright in these works, so the Foundation (and you!) can copy and distribute it in the United States without permission and without paying copyright royalties. Special rules, set forth in the General Terms of Use part of this license, apply to copying and distributing Project Gutenberg™ electronic works to protect the PROJECT GUTENBERG™ concept and trademark. Project Gutenberg is a registered trademark, and may not be used if you charge for an eBook, except by following the terms of the trademark license, including paying royalties for use of the Project Gutenberg trademark. If you do not charge anything for copies of this eBook, complying with the trademark license is very easy. You may use this eBook for nearly any purpose such as creation of derivative works, reports, performances and research. Project Gutenberg eBooks may be modified and printed and given away—you may do practically ANYTHING in the United States with eBooks not protected by U.S. copyright law. Redistribution is subject to the trademark license, especially commercial redistribution.
START: FULL LICENSE
THE FULL PROJECT GUTENBERG LICENSE
PLEASE READ THIS BEFORE YOU DISTRIBUTE OR USE THIS WORK
To protect the Project Gutenberg™ mission of promoting the free distribution of electronic works, by using or distributing this work (or any other work associated in any way with the phrase “Project Gutenberg”), you agree to comply with all the terms of the Full Project Gutenberg™ License available with this file or online at www.gutenberg.org/license.
Section 1. General Terms of Use and Redistributing Project Gutenberg™ electronic works
1.A. By reading or using any part of this Project Gutenberg™ electronic work, you indicate that you have read, understand, agree to and accept all the terms of this license and intellectual property (trademark/copyright) agreement. If you do not agree to abide by all the terms of this agreement, you must cease using and return or destroy all copies of Project Gutenberg™ electronic works in your possession. If you paid a fee for obtaining a copy of or access to a Project Gutenberg™ electronic work and you do not agree to be bound by the terms of this agreement, you may obtain a refund from the person or entity to whom you paid the fee as set forth in paragraph 1.E.8.
1.B. “Project Gutenberg” is a registered trademark. It may only be used on or associated in any way with an electronic work by people who agree to be bound by the terms of this agreement. There are a few things that you can do with most Project Gutenberg™ electronic works even without complying with the full terms of this agreement. See paragraph 1.C below. There are a lot of things you can do with Project Gutenberg™ electronic works if you follow the terms of this agreement and help preserve free future access to Project Gutenberg™ electronic works. See paragraph 1.E below.
1.C. The Project Gutenberg Literary Archive Foundation (“the Foundation” or PGLAF), owns a compilation copyright in the collection of Project Gutenberg™ electronic works. Nearly all the individual works in the collection are in the public domain in the United States. If an individual work is unprotected by copyright law in the United States and you are located in the United States, we do not claim a right to prevent you from copying, distributing, performing, displaying or creating derivative works based on the work as long as all references to Project Gutenberg are removed. Of course, we hope that you will support the Project Gutenberg™ mission of promoting free access to electronic works by freely sharing Project Gutenberg™ works in compliance with the terms of this agreement for keeping the Project Gutenberg™ name associated with the work. You can easily comply with the terms of this agreement by keeping this work in the same format with its attached full Project Gutenberg™ License when you share it without charge with others.
1.D. The copyright laws of the place where you are located also govern what you can do with this work. Copyright laws in most countries are in a constant state of change. If you are outside the United States, check the laws of your country in addition to the terms of this agreement before downloading, copying, displaying, performing, distributing or creating derivative works based on this work or any other Project Gutenberg™ work. The Foundation makes no representations concerning the copyright status of any work in any country other than the United States.
1.E. Unless you have removed all references to Project Gutenberg:
1.E.1. The following sentence, with active links to, or other immediate access to, the full Project Gutenberg™ License must appear prominently whenever any copy of a Project Gutenberg™ work (any work on which the phrase “Project Gutenberg” appears, or with which the phrase “Project Gutenberg” is associated) is accessed, displayed, performed, viewed, copied or distributed:
This eBook is for the use of anyone anywhere in the United States and most other parts of the world at no cost and with almost no restrictions whatsoever. You may copy it, give it away or re-use it under the terms of the Project Gutenberg License included with this eBook or online at www.gutenberg.org. If you are not located in the United States, you will have to check the laws of the country where you are located before using this eBook.
1.E.2. If an individual Project Gutenberg™ electronic work is derived from texts not protected by U.S. copyright law (does not contain a notice indicating that it is posted with permission of the copyright holder), the work can be copied and distributed to anyone in the United States without paying any fees or charges. If you are redistributing or providing access to a work with the phrase “Project Gutenberg” associated with or appearing on the work, you must comply either with the requirements of paragraphs 1.E.1 through 1.E.7 or obtain permission for the use of the work and the Project Gutenberg™ trademark as set forth in paragraphs 1.E.8 or 1.E.9.
1.E.3. If an individual Project Gutenberg™ electronic work is posted with the permission of the copyright holder, your use and distribution must comply with both paragraphs 1.E.1 through 1.E.7 and any additional terms imposed by the copyright holder. Additional terms will be linked to the Project Gutenberg™ License for all works posted with the permission of the copyright holder found at the beginning of this work.
1.E.4. Do not unlink or detach or remove the full Project Gutenberg™ License terms from this work, or any files containing a part of this work or any other work associated with Project Gutenberg™.
1.E.5. Do not copy, display, perform, distribute or redistribute this electronic work, or any part of this electronic work, without prominently displaying the sentence set forth in paragraph 1.E.1 with active links or immediate access to the full terms of the Project Gutenberg™ License.
1.E.6. You may convert to and distribute this work in any binary, compressed, marked up, nonproprietary or proprietary form, including any word processing or hypertext form. However, if you provide access to or distribute copies of a Project Gutenberg™ work in a format other than “Plain Vanilla ASCII” or other format used in the official version posted on the official Project Gutenberg™ website (www.gutenberg.org), you must, at no additional cost, fee or expense to the user, provide a copy, a means of exporting a copy, or a means of obtaining a copy upon request, of the work in its original “Plain Vanilla ASCII” or other form. Any alternate format must include the full Project Gutenberg™ License as specified in paragraph 1.E.1.
1.E.7. Do not charge a fee for access to, viewing, displaying, performing, copying or distributing any Project Gutenberg™ works unless you comply with paragraph 1.E.8 or 1.E.9.
1.E.8. You may charge a reasonable fee for copies of or providing access to or distributing Project Gutenberg™ electronic works provided that:
• You pay a royalty fee of 20% of the gross profits you derive from the use of Project Gutenberg™ works calculated using the method you already use to calculate your applicable taxes. The fee is owed to the owner of the Project Gutenberg™ trademark, but he has agreed to donate royalties under this paragraph to the Project Gutenberg Literary Archive Foundation. Royalty payments must be paid within 60 days following each date on which you prepare (or are legally required to prepare) your periodic tax returns. Royalty payments should be clearly marked as such and sent to the Project Gutenberg Literary Archive Foundation at the address specified in Section 4, “Information about donations to the Project Gutenberg Literary Archive Foundation.”
• You provide a full refund of any money paid by a user who notifies you in writing (or by e-mail) within 30 days of receipt that s/he does not agree to the terms of the full Project Gutenberg™ License. You must require such a user to return or destroy all
copies of the works possessed in a physical medium and discontinue all use of and all access to other copies of Project Gutenberg™ works.
• You provide, in accordance with paragraph 1.F.3, a full refund of any money paid for a work or a replacement copy, if a defect in the electronic work is discovered and reported to you within 90 days of receipt of the work.
• You comply with all other terms of this agreement for free distribution of Project Gutenberg™ works.
1.E.9. If you wish to charge a fee or distribute a Project Gutenberg™ electronic work or group of works on different terms than are set forth in this agreement, you must obtain permission in writing from the Project Gutenberg Literary Archive Foundation, the manager of the Project Gutenberg™ trademark. Contact the Foundation as set forth in Section 3 below.
1.F.
1.F.1. Project Gutenberg volunteers and employees expend considerable effort to identify, do copyright research on, transcribe and proofread works not protected by U.S. copyright law in creating the Project Gutenberg™ collection. Despite these efforts, Project Gutenberg™ electronic works, and the medium on which they may be stored, may contain “Defects,” such as, but not limited to, incomplete, inaccurate or corrupt data, transcription errors, a copyright or other intellectual property infringement, a defective or damaged disk or other medium, a computer virus, or computer codes that damage or cannot be read by your equipment.
1.F.2. LIMITED WARRANTY, DISCLAIMER OF DAMAGES - Except for the “Right of Replacement or Refund” described in paragraph 1.F.3, the Project Gutenberg Literary Archive Foundation, the owner of the Project Gutenberg™ trademark, and any other party distributing a Project Gutenberg™ electronic work under this agreement, disclaim all liability to you for damages, costs and
expenses, including legal fees. YOU AGREE THAT YOU HAVE NO REMEDIES FOR NEGLIGENCE, STRICT LIABILITY, BREACH OF WARRANTY OR BREACH OF CONTRACT EXCEPT THOSE PROVIDED IN PARAGRAPH 1.F.3. YOU AGREE THAT THE FOUNDATION, THE TRADEMARK OWNER, AND ANY DISTRIBUTOR UNDER THIS AGREEMENT WILL NOT BE LIABLE TO YOU FOR ACTUAL, DIRECT, INDIRECT, CONSEQUENTIAL, PUNITIVE OR INCIDENTAL DAMAGES EVEN IF YOU GIVE NOTICE OF THE POSSIBILITY OF SUCH DAMAGE.
1.F.3. LIMITED RIGHT OF REPLACEMENT OR REFUND - If you discover a defect in this electronic work within 90 days of receiving it, you can receive a refund of the money (if any) you paid for it by sending a written explanation to the person you received the work from. If you received the work on a physical medium, you must return the medium with your written explanation. The person or entity that provided you with the defective work may elect to provide a replacement copy in lieu of a refund. If you received the work electronically, the person or entity providing it to you may choose to give you a second opportunity to receive the work electronically in lieu of a refund. If the second copy is also defective, you may demand a refund in writing without further opportunities to fix the problem.
1.F.4. Except for the limited right of replacement or refund set forth in paragraph 1.F.3, this work is provided to you ‘AS-IS’, WITH NO OTHER WARRANTIES OF ANY KIND, EXPRESS OR IMPLIED, INCLUDING BUT NOT LIMITED TO WARRANTIES OF MERCHANTABILITY OR FITNESS FOR ANY PURPOSE.
1.F.5. Some states do not allow disclaimers of certain implied warranties or the exclusion or limitation of certain types of damages. If any disclaimer or limitation set forth in this agreement violates the law of the state applicable to this agreement, the agreement shall be interpreted to make the maximum disclaimer or limitation permitted by the applicable state law. The invalidity or unenforceability of any provision of this agreement shall not void the remaining provisions.
1.F.6. INDEMNITY - You agree to indemnify and hold the Foundation, the trademark owner, any agent or employee of the Foundation, anyone providing copies of Project Gutenberg™ electronic works in accordance with this agreement, and any volunteers associated with the production, promotion and distribution of Project Gutenberg™ electronic works, harmless from all liability, costs and expenses, including legal fees, that arise directly or indirectly from any of the following which you do or cause to occur: (a) distribution of this or any Project Gutenberg™ work, (b) alteration, modification, or additions or deletions to any Project Gutenberg™ work, and (c) any Defect you cause.
Section 2. Information about the Mission of Project Gutenberg™
Project Gutenberg™ is synonymous with the free distribution of electronic works in formats readable by the widest variety of computers including obsolete, old, middle-aged and new computers. It exists because of the efforts of hundreds of volunteers and donations from people in all walks of life.
Volunteers and financial support to provide volunteers with the assistance they need are critical to reaching Project Gutenberg™’s goals and ensuring that the Project Gutenberg™ collection will remain freely available for generations to come. In 2001, the Project Gutenberg Literary Archive Foundation was created to provide a secure and permanent future for Project Gutenberg™ and future generations. To learn more about the Project Gutenberg Literary Archive Foundation and how your efforts and donations can help, see Sections 3 and 4 and the Foundation information page at www.gutenberg.org.
Section 3. Information about the Project Gutenberg Literary Archive Foundation
The Project Gutenberg Literary Archive Foundation is a non-profit 501(c)(3) educational corporation organized under the laws of the state of Mississippi and granted tax exempt status by the Internal Revenue Service. The Foundation’s EIN or federal tax identification number is 64-6221541. Contributions to the Project Gutenberg Literary Archive Foundation are tax deductible to the full extent permitted by U.S. federal laws and your state’s laws.
The Foundation’s business office is located at 809 North 1500 West, Salt Lake City, UT 84116, (801) 596-1887. Email contact links and up to date contact information can be found at the Foundation’s website and official page at www.gutenberg.org/contact
Section 4. Information about Donations to the Project Gutenberg Literary Archive Foundation
Project Gutenberg™ depends upon and cannot survive without widespread public support and donations to carry out its mission of increasing the number of public domain and licensed works that can be freely distributed in machine-readable form accessible by the widest array of equipment including outdated equipment. Many small donations ($1 to $5,000) are particularly important to maintaining tax exempt status with the IRS.
The Foundation is committed to complying with the laws regulating charities and charitable donations in all 50 states of the United States. Compliance requirements are not uniform and it takes a considerable effort, much paperwork and many fees to meet and keep up with these requirements. We do not solicit donations in locations where we have not received written confirmation of compliance. To SEND DONATIONS or determine the status of compliance for any particular state visit www.gutenberg.org/donate.
While we cannot and do not solicit contributions from states where we have not met the solicitation requirements, we know of no
prohibition against accepting unsolicited donations from donors in such states who approach us with offers to donate.
International donations are gratefully accepted, but we cannot make any statements concerning tax treatment of donations received from outside the United States. U.S. laws alone swamp our small staff.
Please check the Project Gutenberg web pages for current donation methods and addresses. Donations are accepted in a number of other ways including checks, online payments and credit card donations. To donate, please visit: www.gutenberg.org/donate.
Section 5. General Information About Project Gutenberg™ electronic works
Professor Michael S. Hart was the originator of the Project Gutenberg™ concept of a library of electronic works that could be freely shared with anyone. For forty years, he produced and distributed Project Gutenberg™ eBooks with only a loose network of volunteer support.
Project Gutenberg™ eBooks are often created from several printed editions, all of which are confirmed as not protected by copyright in the U.S. unless a copyright notice is included. Thus, we do not necessarily keep eBooks in compliance with any particular paper edition.
Most people start at our website which has the main PG search facility: www.gutenberg.org.
This website includes information about Project Gutenberg™, including how to make donations to the Project Gutenberg Literary Archive Foundation, how to help produce our new eBooks, and how to subscribe to our email newsletter to hear about new eBooks.
