Comparative studies on microbial and chemical modifications of trichothecene mycotoxins.
The microbial modification of several trichothecene mycotoxins by trichothecene-producing strains of Fusarium nivale and F. solani was studied. These results were compared with the corresponding chemical modifications. The growing mycelia of Fusarium spp. did not convert 4beta-acetoxy-3alpha,7alpha, 15-trihydroxy-12, 13-epoxytrichothec-9-en-8-one (fusarenon) into 3alpha,4beta, 7alpha,15-tetrahydroxy-12,13-epoxy-trichothec-9-en-8-one (nivalenol), whereas 3alpha,4beta,7alpha,15-tetracetoxy-12,13-epoxytrichothec-9-en-8-one (tetraacetylnivalenol) was deacetylated to yield 3alpha-hydroxy-4beta,7alpha,15-triacetoxy-12,13-epoxytrichothec-9-en-8-one (4,7,15-triae-tylnivalenol), which was resistant to further deacetylation. T-2 toxin was transformed intoHT-2 toxin, and 8alpha-(3-methylbutyryloxy)-3alpha,4beta,-15-triacetoxy-12,13-epoxytrichothec-9-en-8-one (T-2 acetate) was transformed into HT-2 toxin via T-2 toxin. Chemical modification with ammonium hydroxide converted tetraacetylnivalenol into fusarenon via 4,7,15-triacetylnivalenol. 3alpha-7alpha,15-Triacetoxy-12,13-epoxytrichothec-9-en-8-one (triacetyldeoxynivalenol) gave deacetylation products lacking the C-7 or c-15 acetyl group in addition to 7alpha,15- diacetoxy-3alpha-hydroxy-12, 13-epoxytrichothec-9-en-8-one (7,15-diacetyldeoxynivalenol). These results demonstrate the regio-selectivity in microbial modification of trichothecenes. Based on the results and available knowledge concerning the transformation of trichothecenes, mechanisms for biological modifications of these mycotoxins are postulated.
D055598:Chemical Phenomena; D002621:Chemistry; D002849:Chromatography, Gas; D002855:Chromatography, Thin Layer; D005670:Fusarium / Q000254:growth & development / Q000378:metabolism*; D006868:Hydrolysis; D006878:Hydroxides; D000644:Quaternary Ammonium Compounds; D012717:Sesquiterpenes / Q000378:metabolism*; D014255:Trichothecenes / Q000096:biosynthesis / Q000378:metabolism*
D006878:Hydroxides; D000644:Quaternary Ammonium Compounds; D012717:Sesquiterpenes; D014255:Trichothecenes