Degradation mechanism of cyanobacterial toxin cylindrospermopsin by hydroxyl radicals in homogeneous UV/H2O2 process

Environmental Science and Technology

Volumn 48, Issue 8, 2014, Pages 4495-4504

  He, Xuexiang ^a,d   Zhang, Geshan ^a   De La Cruz, Armah A ^b   O'Shea, Kevin E ^c   Dionysiou, Dionysios D ^a,d  

^a UNIVERSITY OF CINCINNATI   (United States)

^b U S ENVIRONMENTAL PROTECTION AGENCY   (United States)

^c FLORIDA INTERNATIONAL UNIVERSITY   (United States)

^d UNIVERSITY OF CYPRUS   (Cyprus)

Author keywords

[No Author keywords available]

Indexed keywords

DEGRADATION; MASS SPECTROMETRY;

ADVANCED OXIDATION PROCESS; CYANOBACTERIAL TOXINS; CYLINDROSPERMOPSIN; DEGRADATION MECHANISM; EXTENDED REACTIONS; HYDROXYL RADICALS; NATURAL-WATER MATRICES; REACTIVE OXYGEN SPECIES;

BYPRODUCTS;

ALKALOID; CYLINDROSPERMOPSIN; GUANIDINE; HYDROXYL RADICAL; SULFATE; URACIL; WATER;

ALKALOID; BIODEGRADATION; CYANOBACTERIUM; FRAGMENTATION; HOMOGENEITY; HYDROGEN PEROXIDE; HYDROXYL RADICAL; OXIDATION; OXYGEN; TOXIN; ULTRAVIOLET RADIATION;

ARTICLE; CHEMICAL STRUCTURE; CYANOBACTERIUM; DEGRADATION KINETICS; DEHYDROGENATION; MASS SPECTROMETRY; NONHUMAN; OXIDATION; PHOTOCHEMISTRY; REACTION ANALYSIS; REACTION TIME; RING OPENING; ULTRAVIOLET RADIATION; WATER QUALITY;

ALKALOIDS; BACTERIAL TOXINS; BIODEGRADATION, ENVIRONMENTAL; FILTRATION; HYDROGEN PEROXIDE; HYDROXYL RADICAL; KINETICS; MARINE TOXINS; MICROCYSTINS; OHIO; OXIDATION-REDUCTION; SILICON DIOXIDE; SULFATES; ULTRAVIOLET RAYS; URACIL; WATER QUALITY;

EID: 84898863557     PISSN: 0013936X     EISSN: 15205851     Source Type: Journal    
DOI: 10.1021/es403732s     Document Type: Article

References (54)

1. Graham, J. L.; Loftin, K. A.; Meyer, M. T.; Ziegler, A. C. Cyanotoxin mixtures and taste-and-odor compounds in cyanobacterial blooms from the midwestern united states Environ. Sci. Technol. 2010, 44, 7361-7368
2. de la Cruz, A. A.; Antoniou, M. G.; Hiskia, A.; Pelaez, M.; Song, W.; O'Shea, K. E.; He, X.; Dionysiou, D. D. Can we effectively degrade microcystins?-implications on human health Anticancer Agents Med. Chem. 2011, 11, 19-37
3. Sharma, V. K.; Triantis, T. M.; Antoniou, M. G.; He, X.; Pelaez, M.; Han, C.; Song, W.; O'Shea, K. E.; De La Cruz, A. A.; Kaloudis, T.; Hiskia, A.; Dionysiou, D. D. Destruction of microcystins by conventional and advanced oxidation processes: A review Sep. Purif. Technol. 2012, 91, 3-17
4. de La Cruz, A. A.; Hiskia, A.; Kaloudis, T.; Chernoff, N.; Hill, D.; Antoniou, M. G.; He, X.; Loftin, K.; O'Shea, K.; Zhao, C.; Pelaez, M.; Han, C.; Lynch, T. J.; Dionysiou, D. D. A review on cylindrospermopsin: The global occurrence, detection, toxicity and degradation of a potent cyanotoxin Environ. Sci.: Processes Impacts 2013, 15, 1979-2003
5. Kinnear, S. Cylindrospermopsin: A decade of progress on bioaccumulation research Mar. Drugs 2010, 8, 542-564
6. Hawkins, P. R.; Runnegar, M. T. C.; Jackson, A. R. B.; Falconer, I. R. Severe hepatotoxicity caused by the tropical cyanobacterium (blue-green alga) Cylindrospermopsis raciborskii (Woloszynska) Seenaya and Subba Raju isolated from a domestic water supply reservoir Appl. Environ. Microbiol. 1985, 50, 1292-1295
7. Wormer, L.; Cirés, S.; Carrasco, D.; Quesada, A. Cylindrospermopsin is not degraded by co-occurring natural bacterial communities during a 40-day study Harmful Algae 2008, 7, 206-213
8. Moreira, C.; Azevedo, J.; Antunes, A.; Vasconcelos, V. Cylindrospermopsin: Occurrence, methods of detection and toxicology J. Appl. Microbiol. 2013, 114, 605-620
9. Štraser, A.; Filipic, M.; Žegura, B. Cylindrospermopsin induced transcriptional responses in human hepatoma HepG2 cells Toxicol. In Vitro 2013, 27, 1809-1819
10. Humpage, A. R.; Falconer, I. R. Oral toxicity of the cyanobacterial toxin cylindrospermopsin in male Swiss albino mice: Determination of no observed adverse effect level for deriving a drinking water guideline value Environ. Toxicol. 2003, 18, 94-103
11. Song, W.; Yan, S.; Cooper, W. J.; Dionysiou, D. D.; Oshea, K. E. Hydroxyl radical oxidation of cylindrospermopsin (cyanobacterial toxin) and its role in the photochemical transformation Environ. Sci. Technol. 2012, 46, 12608-12615
12. Onstad, G. D.; Strauch, S.; Meriluoto, J.; Codd, G. A.; Von Gunten, U. Selective oxidation of key functional groups in cyanotoxins during drinking water ozonation Environ. Sci. Technol. 2007, 41, 4397-4404
13. Acero, J. L.; Haderlein, S. B.; Schmidt, T. C.; Suter, M. J.; Von Gunten, U. MTBE oxidation by conventional ozonation and the combination ozone/hydrogen peroxide: Efficiency of the processes and bromate formation Environ. Sci. Technol. 2001, 35, 4252-4259
14. Ho, L.; Lambling, P.; Bustamante, H.; Duker, P.; Newcombe, G. Application of powdered activated carbon for the adsorption of cylindrospermopsin and microcystin toxins from drinking water supplies Water Res. 2011, 45, 2954-2964
15. He, X.; de la Cruz, A. A.; Dionysiou, D. D. Destruction of cyanobacterial toxin cylindrospermopsin by hydroxyl radicals and sulfate radicals using UV-254nm activation of hydrogen peroxide, persulfate and peroxymonosulfate J. Photochem. Photobiol. A 2013, 251, 160-166
16. 2 in synthetic and natural water samples Water Res. 2012, 46, 1501-1510
17. 2: Toward the generative mechanism and biological toxicity Water Res. 2013, 47, 3211-3219
18. Guzmán-Guillén, R.; Prieto, A. I.; González, A. G.; Soria-Díaz, M. E.; Cameán, A. M. Cylindrospermopsin determination in water by LC-MS/MS: Optimization and validation of the method and application to real samples Environ. Toxicol. Chem. 2012, 31, 2233-2238
19. Banker, R.; Carmeli, S.; Werman, M.; Teltsch, B.; Porat, R.; Sukenik, A. Uracil moiety is required for toxicity of the cyanobacterial hepatotoxin cylindrospermopsin J. Toxicol. Environ. Health A 2001, 62, 281-288
20. Norris, R. L.; Eaglesham, G. K.; Pierens, G.; Shaw, G. R.; Smith, M. J.; Chiswell, R. K.; Seawright, A. A.; Moore, M. R. Deoxycylindrospermopsin, an analog of cylindrospermopsin from cylindrospermopsis raciborskii Environ. Toxicol. 1999, 14, 163-165
21. Neumann, C.; Bain, P.; Shaw, G. Studies of the comparative in vitro toxicology of the cyanobacterial metabolite deoxycylindrospermopsin J. Toxicol. Environ. Health, Part A 2007, 70, 1679-1686
22. -) in aqueous solution J. Phys. Chem. Ref. Data 1988, 17, 513-886
23. Stadtman, E. R. Oxidation of free amino acids and amino acid residues in proteins by radiolysis and by metal-catalyzed reactions Annu. Rev. Biochem. 1993, 62, 797-821
24. Rejnek, J.; Hanus, M.; Kabelác, M.; Ryjácek, F.; Hobza, P. Correlated ab initio study of nucleic acid bases and their tautomers in the gas phase, in a microhydrated environment and in aqueous solution. Part 4. Uracil and thymine Phys. Chem. Chem. Phys. 2005, 7, 2006-2017
25. Jovanovic, S. V.; Simic, M. G. Mechanism of OH radical reactions with thymine and uracil derivatives J. Am. Chem. Soc. 1986, 108, 5968-5972
26. Prasanthkumar, K. P.; Suresh, C. H.; Aravindakumar, C. T. Theoretical study of the addition and abstraction reactions of hydroxyl radical with uracil Radiat. Phys. Chem. 2012, 81, 267-272
27. Thomas, J. K. Pulse radiolysis of aqueous solutions of methyl iodide and methyl bromide. The reactions of iodine atoms and methyl radicals in water J. Phys. Chem. 1967, 71, 1919-1925
28. Minakata, D.; Li, K.; Westerhoff, P.; Crittenden, J. Development of a group contribution method to predict aqueous phase hydroxyl radical (HO•) reaction rate constants Environ. Sci. Technol. 2009, 43, 6220-6227
29. Fujita, S.; Steenken, S. Pattern of hydroxyl radical addition to uracil and methyl- and carboxyl-substituted uracils. Electron transfer of hydroxyl adducts with N,N,N′,N′-tetramethyl-p-phenylenediamine and tetranitromethane J. Am. Chem. Soc. 1981, 103, 2540-2545
30. Burrows, C. J.; Muller, J. G. Oxidative nucleobase modifications leading to strand scission Chem. Rev. 1998, 98, 1109-1151
31. Merel, S.; Clément, M.; Mourot, A.; Fessard, V.; Thomas, O. Characterization of cylindrospermopsin chlorination Sci. Total Environ. 2010, 408, 3433-3442
32. Senogles, P.; Shaw, G.; Smith, M.; Norris, R.; Chiswell, R.; Mueller, J.; Sadler, R.; Eaglesham, G. Degradation of the cyanobacterial toxin cylindrospermopsin, from Cylindrospermopsis raciborskii, by chlorination Toxicon 2000, 38, 1203-1213
33. Antoniou, M. G.; Shoemaker, J. A.; De La Cruz, A. A.; Dionysiou, D. D. Unveiling new degradation intermediates/pathways from the photocatalytic degradation of microcystin-LR Environ. Sci. Technol. 2008, 42, 8877-8883
34. Szabö-Bárdos, E.; Markovics, O.; Horváth, O.; Toro, N.; Kiss, G. Photocatalytic degradation of benzenesulfonate on colloidal titanium dioxide Water Res. 2011, 45, 1617-1628
35. Olson, C. N.; Galloway, M. M.; Yu, G.; Hedman, C. J.; Lockett, M. R.; Yoon, T.; Stone, E. A.; Smith, L. M.; Keutsch, F. N. Hydroxycarboxylic acid-derived organosulfates: Synthesis, stability, and quantification in ambient aerosol Environ. Sci. Technol. 2011, 45, 6468-6474
36. Kodama, M. Paralytic shellfish poisoning toxins: Biochemistry and origin Aqua-BioSci. Monogr. 2010, 3, 1-38
37. Hu, E.; Cheng, H.; Hu, Y. Microwave-induced degradation of atrazine sorbed in mineral micropores Environ. Sci. Technol. 2012, 46, 5067-5076
38. Zhao, Z.; Ueno, K.; Angell, C. A. High conductivity, and "dry" proton motion, in guanidinium salt melts and binary solutions J. Phys. Chem. B 2011, 115, 13467-13472
39. Morimoto, S.; Ito, T.; Fujita, S.; Nishimoto, S. A pulse radiolysis study on the reactions of hydroxyl radical and sulfate radical anion with guanidine derivatives in aqueous solution Chem. Phys. Lett. 2008, 461, 300-304
40. Ito, T.; Morimoto, S.; Fujita, S.; Nishimoto, S. Radical intermediates generated in the reactions of l-arginine with hydroxyl radical and sulfate radical anion: A pulse radiolysis study Radiat. Phys. Chem. 2009, 78, 256-260
41. Nukuna, B. N.; Goshe, M. B.; Anderson, V. E. Sites of hydroxyl radical reaction with amino acids identified by 2H NMR detection of induced 1H/2H exchange J. Am. Chem. Soc. 2001, 123, 1208-1214
42. Aschmann, S. M.; Arey, J.; Atkinson, R. Kinetics and products of the reaction of OH radicals with 3-methoxy-3-methyl-1-butanol Environ. Sci. Technol. 2011, 45, 6896-6901
43. Ta, N.; Hong, J.; Liu, T.; Sun, C. Degradation of atrazine by microwave-assisted electrodeless discharge mercury lamp in aqueous solution J. Hazard. Mater. 2006, 138, 187-194
44. Chen, C.; Yang, S.; Guo, Y.; Sun, C.; Gu, C.; Xu, B. Photolytic destruction of endocrine disruptor atrazine in aqueous solution under UV irradiation: Products and pathways J. Hazard. Mater. 2009, 172, 675-684
45. Nélieu, S.; Kerhoas, L.; Einhorn, J. Degradation of atrazine into ammeline by combined ozone/hydrogen peroxide treatment in water Environ. Sci. Technol. 2000, 34, 430-437
46. Darer, A. I.; Cole-Filipiak, N. C.; O'Connor, A. E.; Elrod, M. J. Formation and stability of atmospherically relevant isoprene-derived organosulfates and organonitrates Environ. Sci. Technol. 2011, 45, 1895-1902
47. Chiswell, R. K.; Shaw, G. R.; Eaglesham, G.; Smith, M. J.; Norris, R. L.; Seawright, A. A.; Moore, M. R. Stability of cylindrospermopsin, the toxin from the cyanobacterium, cylindrospermopsis raciborskii: Effect of pH, temperature, and sunlight on decomposition Environ. Toxicol. 1999, 14, 155-161
48. Shah, N. S.; He, X.; Khan, H. M.; Khan, J. A.; O'Shea, K. E.; Boccelli, D. L.; Dionysiou, D. D. Efficient removal of endosulfan from aqueous solution by UV-C/peroxides: A comparative study J. Hazard. Mater. 2013, 10.1016/j.jhazmat.2013.10.019
49. Samuni, A.; Neta, P. Hydroxyl radical reaction with phosphate esters and the mechanism of phosphate cleavage J. Phys. Chem. 1973, 77, 2425-2429
50. Nakamura, K.; Ienaga, K.; Yokozawa, T.; Fujitsuka, N.; Oura, H. Production of methylguanidine from creatinine via creatol by active oxygen species: Analyses of the catabolism in vitro Nephron 1991, 58, 42-46
51. Aoyagi, K.; Nagase, S.; Koyama, A.; Narita, M.; Tojo, S. Products of creatinine with hydroxyl radical as a useful marker of oxidative stress in vivo Methods Mol. Biol. 1998, 108, 157-164
52. Calza, P.; Medana, C.; Baiocchi, C.; Pelizzetti, E. Photo-induced transformation of methylguanidine derivatives on titanium dioxide Appl. Catal., B 2006, 63, 124-130
53. Garrison, W. M. Reaction mechanisms in the radiolysis of peptides, polypeptides, and proteins Chem. Rev. 1987, 87, 381-398
54. Liu, I.; Lawton, L. A.; Robertson, P. K. J. Mechanistic studies of the photocatalytic oxidation of microcystin-LR: An investigation of byproducts of the decomposition process Environ. Sci. Technol. 2003, 37, 3214-3219