Conjugation of the mycotoxins alternariol and alternariol monomethyl ether in tobacco suspension cells.
The mycotoxins alternariol (AOH) and alternariol-9-O-methyl ether (AME) carry three and two phenolic hydroxyl groups, respectively, which makes them candidates for the formation of conjugated metabolites in plants. Such conjugates may escape routine methods of analysis and have therefore been termed masked or, more recently, modified mycotoxins. We report now that AOH and AME are extensively conjugated in suspension cultures of tobacco BY-2 cells. Five conjugates of AOH were identified by MS and NMR spectroscopy as β-D-glucopyranosides (attached in AOH 3- or 9-position) as well as their 6'-malonyl derivatives, and as a gentiobiose conjugate. For AME, conjugation resulted in the d-glucopyranoside (mostly attached in the AME 3-position) and its 6'- and 4'-malonyl derivatives. Pronounced differences were noted for the quantitative pattern of AOH and AME conjugates as well as for their phytotoxicity. Our in vitro study demonstrates for the first time that masked mycotoxins of AOH and AME can be formed in plant cells.
Institute of Applied Biosciences, Department of Food Chemistry and Phytochemistry, Karlsruhe Institute of Technology (KIT), Adenauerring 20a, 76131 Karlsruhe, Germany.
Andreas A
AA
Hildebrand
Institute of Applied Biosciences, Department of Food Chemistry and Phytochemistry, Karlsruhe Institute of Technology (KIT), Adenauerring 20a, 76131 Karlsruhe, Germany.
Beate N
BN
Kohn
Institute of Applied Biosciences, Department of Food Chemistry and Phytochemistry, Karlsruhe Institute of Technology (KIT), Adenauerring 20a, 76131 Karlsruhe, Germany.
Erika
E
Pfeiffer
Institute of Applied Biosciences, Department of Food Chemistry and Phytochemistry, Karlsruhe Institute of Technology (KIT), Adenauerring 20a, 76131 Karlsruhe, Germany.
Daniel
D
Wefers
Institute of Applied Biosciences, Department of Food Chemistry and Phytochemistry, Karlsruhe Institute of Technology (KIT), Adenauerring 20a, 76131 Karlsruhe, Germany.
Manfred
M
Metzler
Institute of Applied Biosciences, Department of Food Chemistry and Phytochemistry, Karlsruhe Institute of Technology (KIT), Adenauerring 20a, 76131 Karlsruhe, Germany.
Mirko
M
Bunzel
D000528:Alternaria / Q000737:chemistry / Q000378:metabolism*; D002478:Cells, Cultured; D007783:Lactones / Q000737:chemistry* / Q000378:metabolism; D009183:Mycotoxins / Q000737:chemistry* / Q000378:metabolism; D014026:Nicotiana / Q000737:chemistry* / Q000254:growth & development* / Q000378:metabolism / Q000382:microbiology
D007783:Lactones; D009183:Mycotoxins; C005197:alternariol; C018206:alternariol monomethyl ether
Alternaria toxins; malonyl glucosides; masked mycotoxins; modified mycotoxins; plant cell culture