Abstract
Nowadays, the relationship between environment and public health must be studied through molecular epidemiology techniques which needs of increasingly sensitive instruments able to detect the smaller exposure and the smaller biological effects. These instruments are the biomarkers, and each type of them indicates, for preventive purposes, a particular stage of the biochemical pathway that, from exposure, can lead to disease through absorption, metabolic activation, and possible covalent bonds with DNA and proteins. Oxidative stress is a typical condition that falls under the description of semispecific biomarkers of effect, highlighting, at the meantime, a prepathological condition. This last is due to a biological damage occurring when oxidants exceed the level of antioxidant defenses producing a physiological unbalance which is indicative of a risky condition. The resulting damage to cells and organs may activate and/or accelerate disease processes.
Isoprostanes (IsoPs) are a group of prostaglandin-like compounds resulting from the peroxidation process of arachidonic acid induced by reactive oxygen species (ROS). These can contribute to the impairment of the chemical and physical properties of cell membranes that give rise to the oxidative damage. Isoprostanes can be grouped into four subfamilies, depending on where the radical link took place in the chain. Among all the isoprostanes, the F2-isoprostanes are the more stable molecules, detectable in all human tissues and biological fluids, including plasma, urine, bronchoalveolar lavage fluid, cerebrospinal fluid, and bile. The presence of isoprostanes in biological fluids and in human tissues is crucial because it describes a lipid peroxidation not completely contrasted by the antioxidant defenses. Due to their stability, the isoprostanes quantification, for example, in urine, can be adopted as a useful and sensitive marker of systemic oxidative stress resulting from an inflammatory response. The F2-isoprostanes allow to evaluate the oxidative lesions in a number of human diseases including atherosclerosis, Alzheimer, and lung disease. Oxidative stress increases in asthmatics and in subjects suffering from chronic obstructive pulmonary disease (COPD). Also for these reasons, isoprostanes have been proposed as a biomarker for inflammation of the airways and for the diagnosis of asthma. The 15-F2t-isoprostane is used also in epidemiological studies aiming to prove a relationship between the risk of developing chronic diseases and the action of free radicals arising from tobacco smoking and of occupational and environmental exposure to inhaled formaldehyde.
The quantification of isoprostanes has opened up new areas of investigation regarding the role of free radicals in human physiology and pathology and in the strategies of primary prevention.
Access this chapter
Tax calculation will be finalised at checkout
Purchases are for personal use only
Abbreviations
- 15-F2t-IsoP:
-
15-F2t-isoprostanes
- FA:
-
Formaldehyde
- IsoP:
-
Isoprostanes
- LPO:
-
Lipid Peroxidation
- ROS:
-
Reactive Oxygen Species
References
Aggarwal S, Moodley YP, Thompson PJ, Misso NL. Prostaglandin E2 and cysteinyl leukotriene concentrations in sputum: association with asthma severity and eosinophilic inflammation. Clin Exp Allergy J Br Soc Allergy Clin Immunol. 2010;40:85–93.
Ahmad A, Shameem M, Husain Q. Relation of oxidant-antioxidant imbalance with disease progression in patients with asthma. Ann Thorac Med. 2012;7:226–32.
Angelopoulou R, Lavranos G, Manolakou P. ROS in the aging male: model diseases with ROS-related pathophysiology. Reprod Toxicol Elmsford N. 2009;28:167–71.
Auerbach A, Hernandez ML. The effect of environmental oxidative stress on airway inflammation. Curr Opin Allergy Clin Immuno. 2012;12:133–9.
Baraldi E, Carraro S, Alinovi R, Pesci A, Ghiro L, Bodini A, Piacentini G, Zacchello F, Zanconato S. Cysteinyl leukotrienes and 8-isoprostane in exhaled breath condensate of children with asthma exacerbations. Thorax. 2003;58:505–9.
Barreto M, Villa MP, Olita C, Martella S, Ciabattoni G, Montuschi P. 8-Isoprostane in exhaled breath condensate and exercise-induced bronchoconstriction in asthmatic children and adolescents. Chest. 2009;135:66–73.
Basu S. F2-isoprostanes in human health and diseases: from molecular mechanisms to clinical implications. Antioxid Redox Signal. 2008;10:1405–34.
Basu S. Fatty acid oxidation and isoprostanes: oxidative strain and oxidative stress. Prostaglandins Leukot Essent Fatty Acids. 2010;82:219–25.
Block G, Dietrich M, Norkus EP, Morrow JD, Hudes M, Caan B, Packer L. Factors associated with oxidative stress in human populations. Am J Epidemiol. 2002;156:274–85.
Bodini A, Peroni D, Vicentini L, Loiacono A, Baraldi E, Ghiro L, Corradi M, Alinovi R, Boner AL, Piacentini GL. Exhaled breath condensate eicosanoids and sputum eosinophils in asthmatic children: a pilot study. Pediatr Allergy Immunol Off Publ Eur Soc Pediatr Allergy Immunol. 2004;15:26–31.
Bono R, Degan R, Pazzi M, Romanazzi V, Rovere R. Benzene and formaldehyde in air of two Winter Olympic venues of “Torino 2006.” Environ Int. 2010a;36:269–75.
Bono R, Romanazzi V, Munnia A, Piro S, Allione A, Ricceri F, Guarrera S, Pignata C, Matullo G, Wang P, Giese RW, Peluso M. Malondialdehyde-deoxyguanosine adduct formation in workers of pathology wards: the role of air formaldehyde exposure. Chem Res Toxicol. 2010b;23:1342–8.
Bono R, Bellisario V, Romanazzi V, Pirro V, Piccioni P, Pazzi M, Bugiani M, Vincenti M. Oxidative stress in adolescent passive smokers living in urban and rural environments. Int J Hyg Environ Health. 2014;217:287–93.
Bono R, Tassinari R, Bellisario V, Gilli G, Pazzi M, Pirro V, Mengozzi G, Bugiani M, Piccioni P. Urban air and tobacco smoke as conditions that increase the risk of oxidative stress and respiratory response in youth. Environ Res. 2015;137C:141–146.
Campos C, Guzmán R, López-Fernández E, Casado Á. Urinary biomarkers of oxidative/nitrosative stress in healthy smokers. Inhal Toxicol. 2011;23:148–56.
Comhair SAA, Erzurum SC. Redox control of asthma: molecular mechanisms and therapeutic opportunities. Antioxid Redox Signal. 2010;12:93–124.
Corrêa SM, Martins EM, Arbilla G. Formaldehyde and acetaldehyde in a high traffic street of Rio de Janeiro, Brazil. Atmos Environ. 2003;37:23–9.
De Bont R, van Larebeke N. Endogenous DNA damage in humans: a review of quantitative data. Mutagenesis. 2004;19:169–85.
Dean RT, Gieseg S, Davies MJ. Reactive species and their accumulation on radical-damaged proteins. Trends Biochem Sci. 1993;18:437–41.
Delfino RJ, Staimer N, Vaziri ND. Air pollution and circulating biomarkers of oxidative stress. Air Qual Atmos Health. 2010;4:37–52.
Dworski R, Murray JJ, Roberts 2nd LJ, Oates JA, Morrow JD, Fisher L, Sheller JR. Allergen-induced synthesis of F(2)-isoprostanes in atopic asthmatics. Evidence for oxidant stress. Am J Respir Crit Care Med. 1999;160:1947–51.
Fitzpatrick AM, Teague WG, Holguin F, Yeh M, Brown LA, Severe Asthma Research Program. Airway glutathione homeostasis is altered in children with severe asthma: evidence for oxidant stress. J Allergy Clin Immunol. 2009;123:146–152 e8.
Flyvholm MA, Andersen P. Identification of formaldehyde releasers and occurrence of formaldehyde and formaldehyde releasers in registered chemical products. Am J Ind Med. 1993;24:533–52.
Godish T. Effect of ambient environmental factors on indoor formaldehyde levels. Atmos Environ. 1989a;23:1695–8.
Godish T. Formaldehyde exposures from tobacco smoke: a review. Am J Public Health. 1989b;79:1044–5.
Griffiths HR. The influence of diet on protein oxidation. Nutr Res Rev. 2002;15:3–17.
Halliwell B. Lipid peroxidation, antioxidants and cardiovascular disease: how should we move forward? Cardiovasc Res. 2000;47:410–18.
Harman D. The aging process. Proc Natl Acad Sci U S A. 1981;78:7124–8.
IARC. Formaldehyde, 2-butoxyethanol and 1-tert-butoxypropan-2-ol. IARC monographs on the evaluation of carcinogenic risks to humans 2007/03/21 ed., vol. 88. Lyon: International Agency for Research on Cancer. 2006; p. 1–478.
Im H, Oh E, Mun J, Khim JY, Lee E, Kang HS, Kim E, Kim H, Won NH, Kim YH, Jung WW, Sul D. Evaluation of toxicological monitoring markers using proteomic analysis in rats exposed to formaldehyde. J Proteome Res. 2006;5:1354–66.
Kelly TJ, Smith DL, Satola J. Emission Rates of Formaldehyde from Materials and Consumer Products Found in California Homes. Environ Sci Technol. 1999;33:81–8.
Kono Y, Fridovich I. Superoxide radical inhibits catalase. J Biol Chem. 1982;257:5751–4.
Kum C, Kiral F, Sekkin S, Seyrek K, Boyacioglu M. Effects of xylene and formaldehyde inhalations on oxidative stress in adult and developing rats livers. Exp Anim Jpn Assoc Lab Anim Sci. 2007;56:35–42.
Li Y, Nie J, Beyea J, Rudra CB, Browne RW, Bonner MR, Mu L, Trevisan M, Freudenheim JL. Exposure to traffic emissions: associations with biomarkers of antioxidant status and oxidative damage. Environ Res. 2013;121:31–8.
Lykkesfeldt J. Malondialdehyde as biomarker of oxidative damage to lipids caused by smoking. Clin Chim Acta. 2007;380:50–8.
Marnett LJ. Lipid peroxidation-DNA damage by malondialdehyde. Mutat Res. 1999;424:83–95.
Migliore L, Coppede F. Environmental-induced oxidative stress in neurodegenerative disorders and aging. Mutat Res. 2009;674:73–84.
Milne GL, Musiek ES, Morrow JD. F2-isoprostanes as markers of oxidative stress in vivo: an overview. Biomark Biochem Indic Expo Response Susceptibility Chem. 2005;10 Suppl 1:S10–23.
Milne GL, Yin H, Brooks JD, Sanchez S, Jackson Roberts 2nd L, Morrow JD. Quantification of F2-isoprostanes in biological fluids and tissues as a measure of oxidant stress. Methods Enzymol. 2007;433:113–26.
Milne GL, Yin H, Morrow JD. Human biochemistry of the isoprostane pathway. J Biol Chem. 2008;283:15533–7.
Montuschi P, Corradi M, Ciabattoni G, Nightingale J, Kharitonov SA, Barnes PJ. Increased 8-isoprostane, a marker of oxidative stress, in exhaled condensate of asthma patients. Am J Respir Crit Care Med. 1999;160:216–20.
Morrow JD, Frei B, Longmire AW, Gaziano JM, Lynch SM, Shyr Y, Strauss WE, Oates JA, Roberts LJ. Increase in circulating products of lipid peroxidation (F2-isoprostanes) in smokers. Smoking as a cause of oxidative damage. N Engl J Med. 1995;332:1198–203.
Morrow JD, Zackert WE, Yang JP, Kurhts EH, Callewaert D, Dworski R, Kanai K, Taber DF, Moore K, Oates JA, Roberts LJ. Quantification of the major urinary metabolite of 15-F2t-isoprostane (8-iso-PGF2alpha) by a stable isotope dilution mass spectrometric assay. Anal Biochem. 1999;269:326–31.
Moulton PV, Yang W. Air pollution, oxidative stress, and Alzheimer’s disease. J Environ Public Health. 2012;2012:472751.
Murphy DM, O’Byrne PM. Recent advances in the pathophysiology of asthma. Chest. 2010;137:1417–26.
Narumiya S. Molecular diversity of prostanoid receptors; subtypes and isoforms of prostaglandin E receptor. Adv Exp Med Biol. 1997;400A:207–13.
Nielsen GD, Wolkoff P. Cancer effects of formaldehyde: a proposal for an indoor air guideline value. Arch Toxicol. 2010;84:423–46.
Praticò D, Basili S, Vieri M, Cordova C, Violi F, Fitzgerald GA. Chronic obstructive pulmonary disease is associated with an increase in urinary levels of isoprostane F2alpha-III, an index of oxidant stress. Am J Respir Crit Care Med. 1998;158:1709–14.
Rager JE, Smeester L, Jaspers I, Sexton KG, Fry RC. Epigenetic changes induced by air toxics: formaldehyde exposure alters miRNA expression profiles in human lung cells. Environ Health Perspect. 2011;119:494–500.
Rahman I. The role of oxidative stress in the pathogenesis of COPD: implications for therapy. Treat Respir Med. 2005;4:175–200.
Roberts LJ, Reckelhoff JF. Measurement of F(2)-isoprostanes unveils profound oxidative stress in aged rats. Biochem Biophys Res Commun. 2001;287:254–6.
Rokach J, Kim S, Bellone S, Lawson JA, Praticò D, Powell WS, FitzGerald GA. Total synthesis of isoprostanes: discovery and quantitation in biological systems. Chem Phys Lipids. 2004;128:35–56.
Romanazzi V, Pirro V, Bellisario V, Mengozzi G, Peluso M, Pazzi M, Bugiani M, Verlato G, Bono R. 15-F2t isoprostane as biomarker of oxidative stress induced by tobacco smoke and occupational exposure to formaldehyde in workers of plastic laminates. Sci Total Environ. 2013;442:20–5.
Rossner Jr P, Svecova V, Milcova A, Lnenickova Z, Solansky I, Sram RJ. Seasonal variability of oxidative stress markers in city bus drivers. Part I. Oxidative damage to DNA. Mutat Res. 2008a;642:14–20.
Rossner Jr P, Svecova V, Milcova A, Lnenickova Z, Solansky I, Sram RJ. Seasonal variability of oxidative stress markers in city bus drivers. Part II. Oxidative damage to lipids and proteins. Mutat Res. 2008b;642:21–7.
Rossner Jr P, Rossnerova A, Sram RJ. Oxidative stress and chromosomal aberrations in an environmentally exposed population. Mutat Res. 2011;707:34–41.
Salo DC, Pacifici RE, Lin SW, Giulivi C, Davies KJ. Superoxide dismutase undergoes proteolysis and fragmentation following oxidative modification and inactivation. J Biol Chem. 1990;265:11919–27.
Salthammer T, Mentese S, Marutzky R. Formaldehyde in the indoor environment. Chem Rev. 2010;110:2536–72.
Schmid O, Speit G. Genotoxic effects induced by formaldehyde in human blood and implications for the interpretation of biomonitoring studies. Mutagenesis. 2007;22:69–74.
Schraufstatter I, Hyslop PA, Jackson JH, Cochrane CG. Oxidant-induced DNA damage of target cells. J Clin Invest. 1988;82:1040–50.
Shahid SK, Kharitonov SA, Wilson NM, Bush A, Barnes PJ. Exhaled 8-isoprostane in childhood asthma. Respir Res. 2005;6:79.
Slupphaug G, Kavli B, Krokan HE. The interacting pathways for prevention and repair of oxidative DNA damage. Mutat Res. 2003;531:231–51.
Souvignet C, Cracowski JL, Stanke-Labesque F, Bessard G. Are isoprostanes a clinical marker for antioxidant drug investigation?. Fundam Clin Pharmacol. 2000;14:1–10.
Speit G, Schutz P, Hogel J, Schmid O. Characterization of the genotoxic potential of formaldehyde in V79 cells. Mutagenesis. 2007;22:387–94.
Tabatabaie T, Floyd RA. Susceptibility of glutathione peroxidase and glutathione reductase to oxidative damage and the protective effect of spin trapping agents. Arch Biochem Biophys. 1994;314:112–19.
Uchiyama S, Inaba Y, Kunugita N. Determination of acrolein and other carbonyls in cigarette smoke using coupled silica cartridges impregnated with hydroquinone and 2,4-dinitrophenylhydrazine. J Chromatogr A. 2010;1217:4383–8.
Valko M, Rhodes CJ, Moncol J, Izakovic M, Mazur M. Free radicals, metals and antioxidants in oxidative stress-induced cancer. Chem Biol Interact. 2006;160:1–40.
Voynow JA, Kummarapurugu A. Isoprostanes and asthma. Biochim Biophys Acta. 2011;1810:1091–5.
Wedes SH, Khatri SB, Zhang R, Wu W, Comhair SA, Wenzel S, Teague WG, Israel E, Erzurum SC, Hazen SL. Noninvasive markers of airway inflammation in asthma. Clin Transl Sci. 2009;2:112–17.
Wolff SP, Dean RT. Fragmentation of proteins by free radicals and its effect on their susceptibility to enzymic hydrolysis. Biochem J. 1986;234:399–403.
Wolkoff P, Nielsen GD. Non-cancer effects of formaldehyde and relevance for setting an indoor air guideline. Environ Int. 2010;36:788–99.
Wood LG, Simpson JL, Hansbro PM, Gibson PG. Potentially pathogenic bacteria cultured from the sputum of stable asthmatics are associated with increased 8-isoprostane and airway neutrophilia. Free Radic Res. 2010;44:146–54.
Yang W, Omaye ST. Air pollutants, oxidative stress and human health. Mutat Res. 2009;674:45–54.
Yin K, Halushka PV, Yan YT, Wong PY. Antiaggregatory activity of 8-epi-prostaglandin F2 alpha and other F-series prostanoids and their binding to thromboxane A2/prostaglandin H2 receptors in human platelets. J Pharmacol Exp Ther. 1994;270:1192–6.
Zhang L, Freeman LE, Nakamura J, Hecht SS, Vandenberg JJ, Smith MT, Sonawane BR. Formaldehyde and leukemia: epidemiology, potential mechanisms, and implications for risk assessment. Environ Mol Mutagen. 2010a;51:181–91.
Zhang L, Tang X, Rothman N, Vermeulen R, Ji Z, Shen M, Qiu C, Guo W, Liu S, Reiss B, Freeman LB, Ge Y, Hubbard AE, Hua M, Blair A, Galvan N, Ruan X, Alter BP, Xin KX, Li S, Moore LE, Kim S, Xie Y, Hayes RB, Azuma M, Hauptmann M, Xiong J, Stewart P, Li L, Rappaport SM, et al.: Occupational exposure to formaldehyde, hematotoxicity, and leukemia-specific chromosome changes in cultured myeloid progenitor cells. Cancer Epidemiol Biomark Prev Publ Am Assoc Cancer Res Cosponsored Am Soc Prev Oncol 2010;19:80–88.
Author information
Authors and Affiliations
Corresponding author
Editor information
Editors and Affiliations
Rights and permissions
Copyright information
© 2015 Springer Science+Business Media Dordrecht
About this entry
Cite this entry
Bono, R., Romanazzi, V. (2015). Isoprostanes as Biomarkers of Disease and Early Biological Effect. In: Preedy, V., Patel, V. (eds) General Methods in Biomarker Research and their Applications. Biomarkers in Disease: Methods, Discoveries and Applications. Springer, Dordrecht. https://doi.org/10.1007/978-94-007-7696-8_25
Download citation
DOI: https://doi.org/10.1007/978-94-007-7696-8_25
Published:
Publisher Name: Springer, Dordrecht
Print ISBN: 978-94-007-7695-1
Online ISBN: 978-94-007-7696-8
eBook Packages: Biomedical and Life SciencesReference Module Biomedical and Life Sciences