Conjugation of the Mycotoxins Alternariol and Alternariol Monomethyl Ether in Tobacco Suspension Cells
Conjugation of the Mycotoxins Alternariol and Alternariol Monomethyl Ether in Tobacco Suspension Cells
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DOI：
10.1021/acs.jafc.5b00806
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发表时间：
2015-05-20
影响因子：
6.1
通讯作者：
Bunzel, Mirko
中科院分区：
文献类型：
--
作者：
Hildebrand, Andreas A.;Kohn, Beate N.;Bunzel, Mirko
真菌毒素交链孢醇(AOH)和交链孢酚-9-O-甲醚(AME)分别含有三个和两个酚羟基，这使它们成为植物体内形成共轭代谢产物的候选物质。这样的结合物可能逃脱了常规的分析方法，因此被称为掩蔽的或最近被修饰的霉菌毒素。我们现在报告AOH和AME在烟草BY-2细胞悬浮培养中广泛结合。通过MS和核磁共振波谱鉴定了5个AOH的结合物为β-D-吡喃葡萄糖苷(连接在AOH3-或9-位)及其6‘-丙二酰衍生物，以及龙胆二糖结合物。对于AME，接合得到了D-吡喃葡萄糖苷(主要连接在AME 3-位)及其6‘-和4’-丙二酸基衍生物。在AOH和AME偶联物的数量模式以及它们的植物毒性方面注意到了显著的差异。我们的体外研究首次证明了AOH和AME的掩蔽真菌毒素可以在植物细胞中形成。
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 beta-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.