Oxidative Stress and Antioxidant Defenses in Biology Oxidative Stress and Antioxidant Defenses in Biology edited by SamiAhmad CHAPMAN & HALL IGJp An International Thomson Publishing Company New York • Albany • Bonn • Boston • Cincinnati • Detroit • London • Madrid • Melbourne • Mexico City • Pacific Grove • Paris· San Francisco • Singapore • Tokyo • Toronto • Washington Cover design: Andrea Meyer, emDASH inc. Copyright © 1995 Softcover reprint of the hardcover 1st edition 1995 By Chapman & Hall A division of International Thomson Publishing Inc. I(j)P The ITP logo is a trademark under license For more information, contact: Chapman & Hall Chapman & Hall One Penn Plaza 2-6 Boundary Row New York, NY 10119 London SEI 8HN International Thomson Publishing International Thomson Editores Berkshire House 168-173 Campos Eliseos 385, Piso 7 High Holborn Col. 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Includes bibliographical references and index. ISBN-13: 978-1-4615-9691-2 e-ISBN-13: 978-1-4615-9689-9 DOl: 10.1007/978-1-4615-9689-9 1. Active oxygen-Pathophysiology. 2. Antioxidants. I. Ahamd, Sarni. R8170.094 1995 574.2' 19214-dc20 94-13342 CIP Please send your order for this or any Chapman & Hall book to Chapman & Hall, 29 West 35th Street, New York, NY 10001, Attn: Customer Service Department. You may also call our Order Department at 1-212-244-3336 or fax your purchase order to 1-800-248-4724. For a complete listing of Chapman & Hall's titles, send your requests to Chapman & Hall, Dept. BC, One Penn Plaza, New York, NY 10119. Contents Contributors ................................................ x Preface .................................................... xi List of Abbreviations ..................................... xviii 1 Mechanisms of oxygen activation and reactive oxygen species detoxification Enrique Cadenas Introduction ............................................. 1 Chemistry of reactive oxygen species ...................... 4 Biological sources of free radicals ......................... 18 The reactivity of free radicals with non-enzymic small molecular antioxidants ................................... 25 Primary antioxidant defenses ............................. 25 Secondary antioxidant defenses ........................... 40 Oxidants and antioxidants ............................... 42 Summary ............................................... 45 References .............................................. 46 2 Pathophysiology and reactive oxygen metabolites Yan Chen, Allen M. Miles and Mathew B. Grisham Introduction ............................................ 62 Ischemia and repufusion injury ........................... 63 Inflammatory bowel disease .............................. 74 Arthritis ................................................ 80 Central nervous system injury ............................ 81 Acute renal failure ...................................... 84 Sickle cell anemia ....................................... 84 Cancer ................................................. 86 Summary ............................................... 87 References .............................................. 88 v vi Contents 3 Free radical mechanisms of oxidative modification of low density lipoprotein (or the rancidity of body fat) Balaraman Kalyanaraman Introduction ............................................ 96 Oxidative modification of low density lipoprotein and its relevance to atherogenesis ........................ 97 Effect of supplementation with antioxidant ................ 98 Inhibition of LDL oxidation by phenolic antioxidants ....... 98 Summary .............................................. 113 References ............................................. 114 4 Synthetic pro-oxidants: drugs, pesticides and other environmental pollutants Sidney J. Stohs Introduction .......................................... 117 Halogenated alkanes and alkenes ........................ 119 Dioxin and its bioisosteres .............................. 122 Halogenated cyclic pesticides ............................ 129 Phorbol esters ......................................... 135 Paraquat and diquat .................................... 137 Quinones .............................................. 141 Quinolones ............................................ 149 Transition metals and cation complexes .................. 151 Miscellaneous inducers of oxidative stress ................ 161 Summary and conclusions .............................. 165 References ............................................. 167 5 Metabolic detoxification of plant pro-oxidants May R. Berenbaum Introduction ........................................... 181 Detoxification of photos ensitizers ........................ 183 Metabolism of redox-active proo xidants .................. 200 Contents vii Summary and conclusions .............................. 203 References ............................................. 204 6 Antioxidant mechanisms of secondary natural products Richard A. Larson Introduction ........................................... 210 Kinetics of antioxidation ................................ 212 Antioxidants as reducing agents ......................... 215 Antioxidants as radical quenchers ....................... 217 Antioxidants as singlet oxygen quenchers ................ 225 Antioxidants as metal Ion complexing agents ............. 229 Synergistic effects ...................................... 231 Summary .............................................. 232 References ............................................. 233 7 Antioxidant mechanisms of enzymes and proteins Sami Ahmad 7.1 Introduction ......................................... 238 Primary antioxidant enzymes ............................ 240 Ancillary antioxidant enzymes ........................... 259 Antioxidant proteins .................................... 262 Summary .............................................. 265 References ............................................. 265 8 Antioxidant defenses of Escherichia coli and Salmonella typhimurium Richard D. Cunningham and Holly Ahern Introduction ........................................... 273 Direct defenses against oxidative stress .................. 274 Indirect defenses against oxidative stress ................. 281 Summary .............................................. 292 References ............................................. 292 viii Contents 9 Antioxidant defenses of plants and fungi David A. Dalton Introduction ........................................... 298 Sources of activated forms of oxygen .................... 300 Antioxidant defenses in chloroplasts ..................... 310 Antioxidant defenses in nitrogen fixation ................. 330 The role of catalase ..................................... 333 Stress and antioxidant defenses ......................... 335 Miscellaneous antioxidants in plants ..................... 335 Beneficial uses of active oxygen in plants ................. 337 Antioxidant defenses of fungi ........................... 339 Summary .............................................. 341 References ............................................. 342 10 Antioxidant defenses of vertebrates and invertebrates Gary W. Felton Introduction ........................................... 356 Avoidance of oxidative stress ............................ 357 Enzymatic removal of ROS .............................. 358 Prevention or interception of free radical processes ........ 386 Repair processes ....................................... 408 Summary and final comments .......................... .410 References ............................................. 412 11 Genetic regulation of antioxidant defenses in Escherichia coli and Salmonella typhimurium Holly Ahern and Richard P. Cunningham Introduction ........................................... 435 Response to oxidative stress ............................. 436 Response to H 0 The peroxide stimulon and 2 2: the oxyR regulon ....................................... 436 Response to Oi-: The superoxide stimulon and the soxRS regulon ...................................... 439 Contents ix Response to starvation/stationary phase stimulon and the katF regulon ................................... 441 Multi-layered regulation: sodA gene ...................... 442 Summary .............................................. 443 References ............................................. 443 Subject Index ............................................. 447 Cont ribu tors HOLLY AHERN GARY W. FELTON Department of Biological Sciences Department of Entomology State University of New York University of Arkansas at Albany Fayetteville, Arkansas 72703 New York 12222 MATHEW B. GRISHAM SAMI AHMAD Department of Physiology and Department of Biochemistry Biophysics University of Nevada Louisiana State University Reno, Nevada 89557-0014 Medical Center Shreveport, Louisiana 71130 MAY R. BERENBAUM Department of Entomology BALARAMAN KALYANARAMAN University of Illinois Biophysics Research Institute Urbana, Illinois 61801-3795 Medical College of Wisconsin Milwaukee, Wisconsin 53228 ENRIQUE CADENAS Institute for Toxicology and RICHARD A. LARSON Department of Molecular Institute For Environmental Studies Pharmacology & Toxicology University of Illinois University of Southern California Urbana, Illinois 61801 Los Angeles, California 90033 ALLEN M. MILES YAN CHEN Department of Physiology and Department of Physiology and Biophysics Biophysics Louisiana State Medical Center Louisiana State University Shreveport, Louisiana 71130 Medical Center SIDNEY J. STOHS Shreveport, Louisiana 71130 School of Pharmacy and Allied RICHARD P. CUNNINGHAM Health Professions Department of Biological Sciences Creighton University Health State University of New York Sciences Center at Albany Omaha, Nebraska 68178 New York 12222 DAVID A. DALTON Biology Department, Reed College Portland, Oregon 97202 x Preface The ground-state of molecular oxygen, O is essential to many 2, indispensible metabolic processes of all aerobic life forms ranging from prokaryotes, protists, plants, and fungi to animals. Research by mammalian toxicologists and clinicians has unravelled persua sive evidence that O dependence imposes universal toxicity to all 2 aerobic life processes. The basis of this paradox is that one-electron reduction of O generates the superoxide anion free radical, 2 0;-, from numerous biological sources; for example, redox-active autoxidizable molecules such as catecholamines, oxidoreductases, and subcellular organelles such as mitochondria, endoplasmic reti'C ulum (microsomes), nuclei, and chloroplasts. Oxygen is also acti vated in biologically relevant photosensitizing reactions to highly re active singlet oxygen, 10 2, In all biological systems, 0;- undergoes further reduction to H 0 2 2 via Fenton reaction to the hydroxyl radical, ·OH. These, and some other forms of activated O constitute reactive oxygen species (ROS) 2, and/or metabolites (ROM). Both 'OH and 10 are the most reactive 2 forms of ROS known and among their deleterious reactions are ox idation of proteins, DNA, steroidal compounds, and peroxidation of the cell membrane's unsaturated lipids to form unstable hydro peroxides. Their many breakdown products include malondialde hyde and hydroxynonenals that are themselves highly reactive and threaten cellular integrity and function. More importantly, they de compose to free radicals that can continue to propagate the vicious lipid peroxidation chain reaction. This is the so-called endogenous oxidative stress with which all aerobic organisms must cope. Thus the evolutionary process that in the first instance harnessed oxygen for the physiological support of aerobic organisms resulted in toxicity as a side effect of ROS attack, rendering them targets for peroxidative attack, cell and tissue degeneration and, ultimately, or ganismal death. Earlier texts have emphasized the nature of patho logical processes mediated by this stress which include the leakage of cell membranes, dysfunction of mitochondria, depletion of glu tathione and disturbed redox states of cells, and the depletion of ATP. These processes which affect cells and DNAs lead to aging, tumor promotion and cancer, inflammatory diseases, post-ischemic injury and numerous serious ailments. xi