香蕉和野蕉中苯并菲类植物抗毒素的 O-甲基化作用。
O-Methylation of phenylphenalenone phytoalexins in Musaacuminata and Wachendorfia thyrsiflora.
机构信息
Instituto de Química, Universidad de Antioquia, Calle 67# 53-108, A.A. 1226 Medellín, Colombia.
出版信息
Phytochemistry. 2010 Feb;71(2-3):206-13. doi: 10.1016/j.phytochem.2009.10.019. Epub 2009 Nov 24.
Biosynthetic O-methylation at various sites along the backbone of inducible phenylphenalenones in Musaacuminata var. "Williams" (Musaceae) and Wachendorfiathyrsiflora (Haemodoraceae) was investigated using 13C-labelled precursors. The inducibility of O-methylated metabolites was demonstrated in both species and the origin of methoxyl group from [methyl-13C]L-methionine was confirmed. In addition to known phenylphenalenones, a methoxylated metabolite, 4-(4-hydroxy-3-methoxy-phenyl)-benzo[de]isochromene-1,3-dione, was detected and its structure elucidated mainly by NMR spectroscopic techniques. The experiments were used to discriminate methionine-derived and artificial methoxy groups formed during methanolic extraction. Finally, demethylation of 4'-methoxycinnamic acid and subsequent conversion to 3',4'-methylenedioxycinnamic acid was demonstrated in M.acuminata.
利用 13C 标记前体研究了 Musa acuminata var. "Williams"（Musaceae）和 Wachendorfia thyrsiflora（Haemodoraceae）中诱导型苯并菲酮骨架上各种位置的生物合成 O-甲基化。在这两个物种中都证明了 O-甲基化代谢物的诱导性，并证实了甲氧基来自 [甲基-13C]L-蛋氨酸。除了已知的苯并菲酮外，还检测到了一种甲氧基代谢物，4-(4-羟基-3-甲氧基-苯基)-苯并[de]异色烯-1,3-二酮，并主要通过 NMR 光谱技术阐明了其结构。这些实验用于区分甲硫氨酸衍生的和在甲醇提取过程中形成的人工甲氧基。最后，在 M.acuminata 中证明了 4'-甲氧基肉桂酸的脱甲基及其随后转化为 3',4'-亚甲二氧基肉桂酸。
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