Reversible redox chemistry of quinones: Impact on biogeochemical cycles

Chemosphere

Volumn 77, Issue 4, 2009, Pages 451-458

  Uchimiya, Minori ^a   Stone, Alan T ^a  

^a The Johns Hopkins University   (United States)

Author keywords

Benzoquinone; Catechol; Electron shuttle; Hydroquinone; Natural organic matter; Semiquinone radical

Indexed keywords

ADDITION REACTIONS; BIOGEOCHEMISTRY; ELECTRON TRANSITIONS; FREE RADICAL REACTIONS; MOLECULES; PHENOLS; SULFUR COMPOUNDS; THERMODYNAMICS;

BENZOQUINONES; CATECHOL; ELECTRON SHUTTLE; HYDROQUINONE; NATURAL ORGANIC MATTERS; SEMIQUINONE RADICALS;

QUINONE;

AROMATIC NITRO COMPOUND; CATECHOL DERIVATIVE; EXPLOSIVE; HYDROQUINONE DERIVATIVE; NATURAL ORGANIC MATTER; QUINONE DERIVATIVE;

AROMATIC HYDROCARBON; BIODEGRADATION; BIOGEOCHEMICAL CYCLE; CATALYSIS; FREE RADICAL; ORGANIC MATTER; ORGANIC POLLUTANT; REACTION KINETICS; REDOX POTENTIAL; THERMODYNAMICS;

ADDITION REACTION; AUTOOXIDATION; BIODEGRADATION; BIOGEOCHEMICAL CYCLE; CATALYSIS; CHEMICAL STRUCTURE; ELECTRON TRANSPORT; ENVIRONMENTAL IMPACT; NONHUMAN; OXIDATION REDUCTION POTENTIAL; OXIDATION REDUCTION REACTION; REVIEW; SOIL CHEMISTRY; SOIL MICROFLORA; THERMODYNAMICS;

EID: 70349210072     PISSN: 00456535     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.chemosphere.2009.07.025     Document Type: Review

References (87)

1. Bailey S.I., and Ritchie I.M. A cyclic voltammetric study of the aqueous electrochemistry of some quinones. Electrochim. Acta 30 (1985) 3-12
2. Bard A.J., and Faulkner L.R. Electrochemical Methods Fundamentals and Applications (2001), John Wiley & Sons, Inc., NY
3. Bishop C.A., and Tong L.K.J. The reversible addition of hydroxide ion to quinones. Tetrahedron Lett. 304 (1964) 3043-3048
4. Bishop C.A., and Tong L.K.J. Equilibria of substituted semiquinones at high pH. J. Am. Chem. Soc. 87 (1965) 501-505
5. Borraccino R.K.M., Giot R., Agathos S.N., Nyns E., Naveau H.P., and Pauss A. Abiotic transformation of catechol and 1-naphothol in aqueous solution: Influence of environmental factors. Water Res. 15 (2001) 3729-3737
6. Bruice P.Y. Organic Chemistry (1998), Prentice Hall, NJ
7. Brunmark A., and Cadenas E. Redox and addition chemistry of quinoid compounds and its biological implications. Free Radical Biol. Med. 7 (1989) 435-477
8. Carroll F.A. Perspectives on Structure and Mechanism in Organic Chemistry (1998), Brooks/Cole Publishing Company, Pacific Grove, CA
9. Cervantes-Carrillo, F.J., 2002. Quinones As Electron Acceptors and Redox Mediators For the Anaerobic Biotransformation of Priority Pollutants. Thesis Wageningen University, Wageningen, The Netherlands.
10. Chefetz B., and Xing B.S. Relative role of aliphatic and aromatic moieties as sorption domains for organic compounds: a review. Environ. Sci. Technol. 43 (2009) 1680-1688
11. Chiou C.T., Kile D.E., Brinton T.I., Malcolm R.L., Leenheer J.A., and MacCarthy P. A comparison of water solubility enhancements of organic solutes by aquatic humic materials and commercial humic acids. Environ. Sci. Technol. 21 (1987) 1231-1234
12. Clark W.M. Oxidation-Reduction Potentials of Organic Systems (1960), The Williams & Wilkins Company, Baltimore, MD
13. Colon D., Weber E.J., and Anderson J.L. Effect of natural organic matter on the reduction of nitroaromatics by Fe(II) species. Environ. Sci. Technol. 42 (2008) 6538-6543
14. Curtis G.P., and Reinhard M. Reductive dehalogenation of hexachlorethane, carbon tetrachloride, and bromoform by anthrahydroquinone disulfonate and humic acid. Environ. Sci. Technol. 28 (1994) 2393-2401
15. Dayan F.E., Romagni J.G., and Duke S.O. Investigating the mode of action of natural phytotoxins. J. Chem. Ecol. 26 (2000) 2079-2094
16. Deiana S., Gessa C., Marchetti M., and Usai M. Phenolic acid redox properties: pH influence on iron(III) reduction by caffeic acid. Soil Sci. Soc. Am. J. 59 (1995) 1301-1307
17. Doong R.A., and Chiang H.C. Transformation of carbon tetrachloride by thiol reductants in the presence of quinone compounds. Environ. Sci. Technol. 39 (2005) 7460-7468
18. Dunnivant F.M., and Schwarzenbach R.P. Reduction of substituted nitrobenzenes in aqueous solutions containing natural organic matter. Environ. Sci. Technol. 26 (1992) 2133-2141
19. Field J.A., Cervantes F.J., van der Zee F.P., and Lettinga G. Role of quinones in the biodegradation of priority pollutants: a review. Water Sci. Technol. 42 (2000) 215-222
20. Fu Q.S., Barkovskii A.L., and Adriaens P. Reductive transformation of dioxins: an assessment of the contribution of dissolved organic matter to dechlorination reactions. Environ. Sci. Technol. 33 (1999) 3837-3842
21. Glaus M.A., Hejiman C.G., Schwarzenbach R.P., and Zeyer J. Reduction of nitroaromatic compounds mediated by Streptomyces sp. exudates. Appl. Environ. Microbiol. 58 (1992) 1945-1951
22. Hakala J.A., Chin Y.P., and Weber E.J. Influence of dissolved organic matter and Fe(II) on the abiotic reduction of pentachloronitrobenzene. Environ. Sci. Technol. 41 (2007) 7337-7342
23. Hernandez M.E., and Newman D.K. Extracellular electron transfer. Cell. Mol. Life Sci. 58 (2001) 1562-1571
24. Holmes T.J., John V., Vennerstrom J., and Choi K.E. Solution characterization of carboxybenzoquinone and the isolation of derived quinhydrones. J. Org. Chem. 49 (1984) 4736-4738
25. Jiang J., and Kappler A. Kinetics of microbial and chemical reduction of humic substances: implications for electron shuttling. Environ. Sci. Technol. 42 (2008) 3563-3569
26. Jiang J., Bauer I., Paul A., and Kappler A. Arsenic redox changes by microbially and chemically formed semiquinone radicals and hydroquinones in a humic substance model quinone. Environ. Sci. Technol. 43 (2009) 3639-3645
27. Johnson J.M., Sharratt B.S., Reicosky D.C., and Lindstrom M.J. Impact of high-lignin fermentation byproduct on soils with contrasting soil organic carbon content. Soil Sci. Soc. Am. J. 71 (2007) 1151-1159
28. Kappler A., and Haderlein S.B. Natural organic matter as reductant for chlorinated aquatic pollutants. Environ. Sci. Technol. 37 (2003) 2714-2719
29. Kappler A., Benz M., Schink B., and Brune A. Electron shuttling via humic acids in microbial iron(II) reduction in freshwater sediment. FEMS Microbiol. Ecol. 47 (2004) 85-92
30. Klapper L., McKnight D.M., Fulton J.R., Blunt-Harris E.L., Nevin K.P., Lovley D.R., and Hatcher P.G. Fulvic acid oxidation state detection using fluorescence spectroscopy. Environ. Sci. Technol. 36 (2002) 3170-3175
31. Kwon M.J., and Finneran K.T. Microbially mediated biodegradation of hexahydro-1,3,5-trinitro-1,3,5-triazine by extracellular electron shuttling compounds. Appl. Environ. Microbiol. 72 (2006) 5933-5941
32. LaKind J.S., and Stone A.T. Reductive dissolution of goethite by phenolic reductants. Geochim. Cosmochim. Acta 53 (1989) 961-971
33. Lee H., Dellatore S.M., Miller W.M., and Messersmith P.B. Mussel-inspired surface chemistry for multifunctional coatings. Science 318 (2007) 426-430
34. Lee H., Lee B.P., and Messersmith P.B. A reversible wet/dry adhesive inspired by mussels and geckos. Nature 448 (2007) 338-342
35. Lipczynska-Kochany E., and Bolton J.R. Flash photolysis/high-performance liquid chromatography method for studying the sequence of photochemical reactions: direct photolysis of phenol. Environ. Sci. Technol. 26 (1992) 2524-2527
36. Lovley D.R., Coates J.D., Blunt-Harris E.L., Phillips E.J.P., and Woodward J.C. Humic substances as electron acceptors for microbial respiration. Nature 382 (1996) 445-448
37. Marschner H. Mineral Nutrition of Higher Plants (1999), Academic Press, London, UK
38. Meisel D., and Fessenden R.W. Electron exchange and electron transfer of semiquinones in aqueous solutions. J. Am. Chem. Soc. 98 (1976) 7505-7510
39. Munday R. Authoxidation of naphthohydroquinone: Effects of pH, naphthoquinones and superoxide dismutase. Free Radical Res. 32 (2000) 245-253
40. Murphy E.M., Zachara J.M., Smith S.C., Phillips J.L., and Wietsma T.W. Interaction of hydrophobic organic compounds with mineral-bound humic substances. Environ. Sci. Technol. 28 (1994) 1291-1299
41. Musso H. Oxidative Coupling of Phenols. In: Taylor W.I., and Battersby A.R. (Eds) (1967), Marcel Dekker, Inc., New York 1-84
42. Neta P. The Chemistry of the Quinonoid Compounds. In: Patai S., and Rappoport Z. (Eds) (1988), Wiley-Interscience, NY 879-898
43. Neto L.M., Andriulo A.E., and Traghetta D.G. Effects of cultivation on ESR spectra of organic matter from soil size fractions of a Mollisol. Soil Sci. 157 (1994) 365-372
44. Nevin K.P., and Lovley D.R. Potential for nonenzymatic reduction of Fe(III) via electron shuttling in subsurface sediments. Environ. Sci. Technol. 34 (2000) 2472-2478
45. Newman D.K., and Kolter R. A role for excreted quinones in extracellular electron transfer. Nature 405 (2000) 94-97
46. Nurmi J.T., and Tratnyek P.G. Electrochemical properties of natural organic matter (NOM), fractions of NOM, and model biogeochemical electron shuttles. Environ. Sci. Technol. 36 (2002) 617-624
47. O'Loughlin E.J. Effects of electron transfer mediators on the bioreduction of lepidocrocite (g-FeOOH) by Shewanella putrefaciens CN32. Environ. Sci. Technol. 42 (2008) 6876-6882
48. O'Loughlin E.J., Burris D.R., and Delcomyn C.A. Reductive dechlorination of trichloroethene mediated by humic-metal complexes. Environ. Sci. Technol. 33 (1999) 1145-1147
49. Pandey A.K., Pandey S.D., and Misra V. Stability constants of metal-humic acid complexes and its role in environmental detoxification. Ecotoxicol. Environ. Saf. 47 (2000) 195-200
50. Papouchado L., Petrie G., Sharp J.H., and Adams R.N. Anodic hydroxylation of aromatic compounds. J. Am. Chem. Soc. 90 (1968) 5620-5621
51. Papouchado L., Petrie G., and Adams R.N. Anodic oxidation pathways of phenolic compounds. Part 1. Anodic hydroxylation reactions. J. Electroanal. Chem 38 (1972) 389-395
52. Patai S., and Rappoport S. The Chemistry of the Quinonoid Compounds (1988), Wiley, New York
53. Peretyazhko T., and Sposito G. Iron(III) reduction and phosphorous solubilization in humid tropical forest soils. Geochim. Cosmochim. Acta 69 (2005) 3643-3652
54. Peretyazhko T., and Sposito G. Reducing capacity of terrestrial humic acids. Geoderma 137 (2006) 140-146
55. Perlinger J.A., Angst W., and Schwarzenbach R.P. Kinetics of the reduction of hexachloroethane by juglone in solutions containing hydrogen. Environ. Sci. Technol. 30 (1996) 3408-3417
56. Perlinger J.A., Kalluri V.M., Venkatapathy R., and Angst W. Addition of hydrogen sulfide to juglone. Environ. Sci. Technol. 36 (2002) 2663-2669
57. Rakshit S., Uchimiya M., and Sposito G. Iron(III) bioreduction in soil in the presence of added humic substances. Soil Sci. Soc. Am. J. 73 (2009) 65-71
58. Ratasuk N., and Nanny M.A. Characterization and quantification of reversible redox sites in humic substances. Environ. Sci. Technol. 41 (2007) 7844-7850
59. Rau J., Knackmuss H.J., and Stolz A. Effects of different quinoid redox mediators on the anaerobic reduction of azo dyes by bacteria. Environ. Sci. Technol. 36 (2002) 1497-1504
60. Raymond K.N., Miller G., and Matzanke B.F. Complexation of iron by siderophores: a review of their solution and structural chemistry and biological function. Top. Curr. Chem. 123 (1984) 49-102
61. Roginsky V.A., and Barsukova T. Kinetics of oxidation of hydroquinones by molecular oxygen. Effect of superoxide dismutase. J. Chem. Soc., Perkin Trans. 2 157 (2000) 1575-1582
62. Roginsky V.A., Pisarenko L.M., Bors W., Michel C., and Saran M. Comparative pulse radiolysis studies of alkyl- and methoxy-substituted semiquinone formed from quinones and hydroquinones. J. Chem. Soc., Faraday Trans. 94 (1998) 1835-1840
63. Roginsky V.A., Pisarenko L.M., Bors W., and Michel C. The kinetics and thermodynamics of quinone-semiquinone-hydroquinone systems under physiological conditions. J. Chem. Soc., Perkin Trans. 2 (1999) 871-876
64. Royer R.A., Burgos W.D., Fisher A.S., Unz R.F., and Dempsey B.A. Enhancement of biological reduction of hematite by electron shuttling and Fe(II) complexation. Environ. Sci. Technol. 36 (2002) 1939-1946
65. Rubin E.M. Genomics of cellulosic biofuels. Nature 454 (2008) 841-845
66. Salloum M.J., Chefetz B., and Hatcher P.G. Phenanthrene sorption by aliphatic-rich natural organic matter. Environ. Sci. Technol. 36 (2002) 1953-1958
67. Schwarzenbach R.P., Stierli R., Lanz K., and Zeyer J. Quinone and iron porphyrin mediated reduction of nitroaromatic compounds in homogeneous aqueous-solution. Environ. Sci. Technol. 24 (1990) 1566-1574
68. Scott D.T., McKnight D.M., Blunt-Harris E.L., Kolesar S.E., and Lovley D.R. Quinone moieties act as electron acceptors in the reduction of humic substances by humics-reducing microorganisms. Environ. Sci. Technol. 32 (1998) 2984-2989
69. Skotnicka-Pitak J., Khunjar W.O., Love N.G., and Aga D.S. Characterization of metabolites formed during the biotransformation of 17a-ethinylestradiol by Nitrosomonas europaea in batch and continuous flow bioreactors. Environ. Sci. Technol. 43 (2009) 3549-3555
70. Sposito G. The Chemistry of Soils (1989), Oxford University Press, New York, NY
71. Stumm W., and Morgan J.J. Aquatic Chemistry (1996), Wiley-Interscience, NY
72. Sutton R., and Sposito G. Molecular structure in soil humic substances: the new view. Environ. Sci. Technol. 39 (2005) 9009-9015
73. Thomson R.H. Studies in the juglone series. III. Addition reactions. J. Org. Chem. 16 (1951) 1082-1090
74. Thomson R.H. Naturally Occurring Quinones IV Recent Advances (1997), Blackie A&P, NY
75. 13C NMR investigation of hydroxylamine-derivatized humic substances. Environ. Sci. Technol. 26 (1992) 107-116
76. Thorn K.A., Pettigrew P.J., and Goldenberg W.S. Covalent binding of aniline to humic substances.2. N-15 NMR studies of nucleophilic addition reactions. Environ. Sci Technol. 30 (1996) 2764-2775
77. Thorn K.A., Pennington J.C., Kennedy K.R., Cox L.G., Hayes C.A., and Porter B.E. N-15 NMR study of the immobilization of 2,4- and 2,6-dinitrotoluene in aerobic compost. Environ. Sci. Technol. 42 (2008) 2542-2550
78. Tratnyek P.G., and Macalady D.L. Abiotic reduction of nitro aromatic pesticides in anaerobic laboratory systems. J. Agric. Food Chem. 37 (1989) 248-254
79. Turick D.E., Tisa L.S., and Caccavo F. Melanin production and use as a soluble electron shuttle for Fe(III) oxide reduction and as a terminal electron acceptor by Shewanella algae BrY. Appl. Environ. Microbiol. 68 (2002) 2436-2444
80. Uchimiya M., and Stone A.T. Aqueous oxidation of substituted dihydroxybenzenes by substituted benzoquinones. Environ. Sci. Technol. 40 (2006) 3515-3521
81. Uchimiya M., and Stone A.T. Redox reactions between iron and quinones: thermodynamic constraints. Geochim. Cosmochim. Acta 70 (2006) 1388-1401
82. Van der Zee F.R., and Cervantes F.J. Impact and application of electron shuttles on the redox (bio)transformation of contaminants: a review. Biotechnol. Adv. 27 (2009) 256-277
83. Van Puyvelde L., Bosselaers J., Stevens C., De Kimpe N., Van Gestel J., and Van Damme P. Phytotoxins from the leaves of Laggera decurrens. J. Agric. Food Chem. 47 (1999) 2116-2119
84. Vyvyan J.R. Allelochemicals as leads for new herbicides and agrochemicals. Tetrahedron 58 (2002) 1631-1646
85. Weber E.J., Spidle D.L., and Thorn K.A. Covalent binding of aniline to humic substances. 1. Kinetic studies. Environ. Sci Technol. 30 (1996) 2755-2763
86. Youngblood M.P. Kinetics and mechanism of the addition of sulfite to p-benzoquinone. J. Org. Chem. 51 (1986) 1981-1985
87. Zhang H.C., and Weber E.J. Elucidating the role of electron shuttles in reductive transformations in anaerobic sediments. Environ. Sci. Technol. 43 (2009) 1042-1048