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Alternariol, a dibenzopyrone mycotoxin ofAlternaria spp., is a new photosensitizing and DNA cross-linking agent

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Summary

The mycotoxin alternariol (3,4′,5-trihydroxy-6′-methyldibenzo [a] pyrone) but not alternariol monomethyl ether (3,4′-dihydroxy-5-methoxy-6′-methyldibenzo [a] pyrone) is phototoxic toEscherichia coli in the presence of near UV light (320–400 nm). The phototoxicity bioassays with a DNA repair-deficient mutant ofE. coli suggested that DNA may be the molecular target for photo-induced toxicity of alternariol. Interactions between alternariol and double-stranded, supercoiled DNA suggest that alternariol interacts with DNA by intercalation. No DNA breakage was detected in this system; however, alternariol forms a complex and cross-links double-stranded DNA in near UV light. These results suggest that alternariol is a new phototoxic, DNA-intercalating agent and is a DNA cross-linking mycotoxin in near UV light.

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Authors and Affiliations

  1. Department of Botany, University of Toronto, M5S 1A1, Toronto, Ontario, Canada

    F. DiCosmo & N. A. Straus

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  1. F. DiCosmo
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  2. N. A. Straus
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Additional information

Acknowledgment. Dr Albert Stoessl (Agriculture Canada, London, Ontario, Canada) generously provided a mixture of alternariol and alternariol monomethyl ether, and made many helpful suggestions. Dr Ashwood-Smith (University of Victoria, Victoria, British Columbia, Canada) kindly supplied the microorganisms through Dr G.H.N. Towers (University of British Columbia, Vancouver). We gratefully acknowledge the gifts. It is a pleasure to acknowledge the able assistance of Mr S. Tallevi.

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DiCosmo, F., Straus, N.A. Alternariol, a dibenzopyrone mycotoxin ofAlternaria spp., is a new photosensitizing and DNA cross-linking agent. Experientia 41, 1188–1190 (1985). https://doi.org/10.1007/BF01951722

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