Abstract
The photosensitizing perylenequinone toxin elsinochrome A (EA) is produced in culture by the bindweed biocontrol fungus Stagonospora convolvuli LA39 where it apparently plays a pathogenicity related role. We investigated the fate of EA with reference to its stability under different temperature and light conditions. EA remained stable when boiled in water at 100°C for 2 h. Similarly, exposing EA to 3–27°C in the dark for up to 16 weeks did not affect its stability either in dry or in aqueous form. However, results from irradiation experiments indicate that direct photolysis may be a significant degradation pathway for EA in the environment. EA either in dry form or dissolved in water was degraded by different irradiation wavelengths and intensities, with degradation plots fitting a first order rate kinetics. EA degraded faster if exposed in aqueous form, and at higher quantum flux density (μmol s−1 m−2). Sunlight was more effective in degrading EA than artificial white light and ultraviolet radiations (UV-A or UV-B). Exposing EA to natural sunlight, particularly, during the intense sunshine (1,420–1,640 μmol −1 m−2) days of 30 July to 5 August 2004 in Zurich caused the substance to degrade rapidly with half-life under such condition only 14 h. This implies that should EA gets into the environment, particularly on exposed environmental niches, such as on plant surfaces through biocontrol product spray, or released from shed diseased leaves, it may have no chance of accumulating to ‘level of concern’. Furthermore, a toxicity assay using Trichoderma atroviride P1 as biosensor showed that photo-degraded EA was not toxic, indicating that no stable toxic by-products were left.
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Abramson, D.: 1998, ‘Mycotoxin formation and environmental factors,’ in Mycotoxins in Agriculture and Food Safety, Singha, K.K. and Bhatnagar, D. (eds.), Marcel Dekker, New York, pp. 255–277
Ahonsi, M.O., Maurhofer, M., Boss, D., and Défago, G.: 2005, ‘Relationship between Aggressiveness of Stagonospora sp. Isolates on Field and Heldge Bindweeds, and In Vitro Production of Fungal Metabolites Cercosporin, Elsinochrome A and Leptosphaerodione,’ European Journal of Plant Pathology 111, 203–215
Anthanasopoulos, P.E., Kyriakidis, V., and Stavropoulos, P.: 2004, ‘A study on the environmental degradation of pesticides azinphos methyl and parathion methyl,’ Journal of Environmental Science and Health: Part B-Pesticides, Food Contaminations, and Agricultural Wastes B39, 297–309
Arnone, A., Merlini, L., Mondellil, R., Nasini, G., Ragg, E. and Scaglioni, L.: 1993, ‘Structure, conformational Analysis and Absolute configuration of the perylenequinone pigments elsinochromes B1, B2, C1 and C2,’ Gazetta Chimica Italiana 123, 131–136
Balis, C. and Payne, M.G.: 1971, ‘Triglycerides and cercosporin from Cercospora beticola: Fungal Growth and Cercosporin Production,’ Phytopathology 61, 1477–1484
Ballio, A.: 1991, ‘Non-host-selective fungal phytotoxins-bio-chemical aspects of their mode of action,’ Experientia 47, 782–790
Batchvarova, R.B., Reddy, V.S., and Benett, J.: 1992, ‘Cellular Resistance in Rice to Cercosporin, a Toxin of Cercospora,’ Phytopathology 82, 642–646
Bennett, G.A. and Richard, J.L.: 1996, ‘Influence of processing on Fusarium mycotoxins in contaminated Grains,’ Food Technology 50, 235–238
Biggs, W.W.: 1985, ‘Radiation Measurement,’ In LI-1000 Datalogger Instruction Manual, Software Ver. 1.02, Publication No. 8510-51, LI-COR, inc., Lincoln, Nebraska
Bove, F.J.: 1970, The Story of Ergot. S. Karger, New York
Carson, R.: 1962, Silent Spring. Houghton Mifflin Co., Boston
Chen, C.T., Nakanishi, K., and Natori, S.: 1966, ‘Biosynthesis of Elsinochrome A, the Perylenequinone from Elsinoe spp. 1,’ Chemical and Pharmaceutical Bulletin 14, 1434–1437
Chu, F.S. and Li, G.Y.: 1994, ‘Simultaneous Occurrence of Fumonisin B1 and other mycotoxins in moldy corn collected from people’s Republic of China in Regions of High Incidences of Esophageal Cancer,’ Applied and Environmental Microbiology 60, 847–852.
Chu, F.S., Chang, C.C., Ashoor, S.H., and Prentice, N.: 1975, ‘Stability of aflatoxin B1 and ochratoxin Ain Brewing,’ Applied Microbiology 29, 313–316
Daub, M.E. and Ehrenshaft, M.: 1993, ‘The photoactivated toxin cercosporin as a tool in fungal photobiology,’ Physiologia Plantarum 89, 227–236
Daub, M.E. and Ehrenshaft, M: 2000, ‘The photoactive cercospora toxin cercosporin: Contributions to plant disease and fundamental Biology.’ Annual Review of Phytopathology 38, 461–490
Daub, M.E.: 1982, ‘Cercosporin, a photosensitizing toxin from Cercospora species,’ Phytopathology 72, 370–374
Jensen-Korte, U., Anderson, C., and Spiteller, M.: 1987, ‘Photodegradation of pesticides in the presence of humic substances,’ The Science of the Total Environment 62, 335–340
Joffe, A.Z.: 1986, Fusarium Species: Their Biology and Toxicology. John Wiley, New York
Katagi, T.: 2004, ‘Photodegradation of pesticides on plant and soil surfaces,’ Reviews of Environmental Contamination and Toxicology 182, 1–195
Lowes, K.F., Shearman, E.A., Payne, J., MacKenzie, D., Archer, D.B., Merry, R.J., and Gasson, M.J.: 2000, ‘Prevention of yeast spoilage in feed and food by the yeast mycocin HMK,’ Applied and Environmental Microbiology 66, 1066–1076
Lubulwa, A.S.G. and Davis, J.S.: 1994, ‘Estimating the social cost of the impacts of fungi and aflatoxins in maize and peanuts,’ in Highley, E., Wright, E.J., Banks, H.J. and Champ, B.R. (eds.), Stored Product Protection. CAB International, Wallingford, pp. 1017–1042
Ma, L., Tai, H., Li, C., Zhang, Y., Wang, Z.H., and Ji, W.Z.: 2003, ‘Photodynamic inhibitory effects of three perylenequinones on human colorectal carcinoma cell line and primate embryonic stem cell line,’ World Journal of Gastroenterology 9, 485–490
Meille, S.V., Malpezzi, L., Allegra, G., Nasini, G., and Weiss, U.: 1989, ‘Structure of Elsinochrome A: a Perylenequinone metabolite,’ Acta Crystallographica, Section C, Crystal Structure Communications 45, 628–632
Mitchell, T.K., Chilton, W.S., and Daub, M.E.: 2002, ‘Biodegradation of the polyketide toxin cercosporin,’ Applied and Environmental Microbiology 68, 4173–4181
Nicolet, B. and Tabacchi, R.: 1999, ‘Secondary metabolites produced by Stagonospora sp., a Potential Biocontrol Agent Against Bindweeds,’ In Lyr, H., Russell, P.E. and Sisler, H.D. (eds.), Modern Fungicides and Antifungal Compounds II. Intercept Limited, Andover, United Kingdom, pp. 469–476
Niu, J., Chen, J., Martens, D., Henkelmann, B., Quan, X., Yang, F., Seidlitz, H.K., and Schramm, K.-W.: 2004, ‘The role of UV-B on the degradation of PCDD/Fs and PAHs sorbed on surfaces of spruce (Picea abies (L.) Karst.) Needles,’ Science of the Total Environment 322, 231–241
Sanz-Asensio, J., Plaza-Medina, M., and Martinez-Soria, T.: 1997, ‘Kinetic study of the degradation of ethiofencarb in aqueous solutions,’ Pesticide Science 50, 187–194
Shotwell, O.L., Hesseltine, C.W., and Goulden, M.L.: 1969, ‘Ochratoxin A: Occurrence as natural contaminant of a corn sample,’ Applied Microbiology 17, 765–766
Shotwell, O.L., Hesseltine, C.W., Vandegraft, E.E., and Goulden, M.L.: 1971, ‘Survey of corn from different regions for aflatoxin, ochratoxin, and zearalenone,’ Cereal Science Today 16, 266–273
Stahl, W. and Sies, H.: 2002, ‘Introduction: Reactive Oxygen Species,’ Research Monographs: Reactive Oxygen Species, Instut für Physiologische Chemie 1, Heinrich-Heine-Universität Düsseldorf
Strasser, H., Vey, A., and Butt, T.M.: 2000, ‘Are there any risks in using entomopathogenic fungi for pest control, with particular Reference to the Bioactive Metabolites of Metarhizium, Tolypocladium and Beauveria species?,’ Biocontrol Science and Technology 10, 717–735
Tamaoki, T. and Nakano, H.: 1990, ‘Potent and specific inhibitors of protein kinase C of microbiologic origin,’ Biotechnology 8, 732–735
Tschen, J.S.M., Chen, L.L., Hsieh, S.T., and Wu, T.S.: 1997, ‘Isolation and phytotoxic effects of helvolic acid from plant pathogenic fungus Sarocladium oryzae,’ Botanical Bulletin of Academia Sinica 38, 251–256
Vink, J.P.M. and Vanderzee, S.E.A.T.: 1995, ‘Some physicochemical and environmental factors affecting transformation rates and sorption of the herbicide metamitron in soil,’ Pesticide Science 46, 113–119
Weiss, U., Merlini, L., and Nasini, G.: 1987, ‘Naturally occurring perylenequinones,’ in Progress in the Chemistry of Organic Natural Products. Herz, W., Grisebach, H., Kirby, G.W. and Tamm, C.H. (eds.), Springer-Verlag, Vienna 52, pp. 1–71
Yumbe-Guevara, B.E., Imoto, T., and Yoshizawa, T.: 2003, ‘Effects of heating procedures on deoxynivalenol, nivalenol and zearalenone levels in naturally contaminated barley and wheat,’ Food Additives and Contaminants 20, 1132–1140
Zepp, R.G. and Cline, D.M.: 1977, ‘Rates of direct photolysis in aquatic environment,’ Environmental Science and Technology 11, 359–366
Zepp, R.G., Callaghan, T.V., and Erickson, D.J.: 1995, ‘Effects of increased solar ultraviolet radiation on biogeochemical cycles,’ Ambio 24, 181–187
Zepp, R.G., Schlotzauer P.F., and Sink, R.M.: 1995, ‘Photosensitized Transformations Involving Electronic Energy Transfer in Natural Waters: Role of Humic Substances,’ Environmental Science and Technology 19, 74–81
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Ahonsi, M.O., Boss, D., Maurhofer, M. et al. Potential environmental fate of elsinochrome A, a perylenequinone toxin produced in culture by bindweed biocontrol fungus Stagonospora convolvuli LA39. Environmentalist 26, 183–193 (2006). https://doi.org/10.1007/s10669-006-7830-0
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DOI: https://doi.org/10.1007/s10669-006-7830-0