Unité de Biologie des Plantes et Insectes ravageurs, Université de Picardie Jules Verne, 33 rue Saint Leu, F-80039 Amiens Cedex, France.
Phytochemistry. 2012 Feb;74:105-14. doi: 10.1016/j.phytochem.2011.10.010. Epub 2011 Nov 13.
The presence of two compounds, norlittorine and norhyoscyamine, has been reported in leaves and roots of Datura innoxia; however their metabolic origin in the tropane alkaloid pathway has remained unknown. Precise knowledge of this pathway is a necessary pre-requisite to optimize the production of hyoscyamine and scopolamine in D. innoxia hairy root cultures. The exact structure of norlittorine and norhyoscyamine was confirmed by LC-MS/MS and NMR analyses. Isotopic labeling experiments, using [1-(13)C]-phenylalanine, [1'-(13)C]-littorine and [1'-(13)C]-hyoscyamine, combined with elicitor treatments, using methyl jasmonate, coronalon and 1-aminocyclopropane-1-carboxylic acid, were used to investigate the metabolic origin of the N-demethylated tropane alkaloids. The results suggest that norlittorine and norhyoscyamine are induced under stress conditions by conversion of littorine and hyoscyamine. We propose the N-demethylation of tropane alkaloids as a mechanism to detoxify cells in overproducing conditions.
在龙葵的叶子和根中已经报道了两种化合物，即去甲乌药碱和去甲莨菪碱的存在；然而，它们在托烷生物碱途径中的代谢来源仍然未知。精确了解这条途径是优化龙葵毛状根培养物中天仙子胺和东莨菪碱产量的必要前提。通过 LC-MS/MS 和 NMR 分析证实了去甲乌药碱和去甲莨菪碱的确切结构。使用 [1-(13)C]-苯丙氨酸、[1'-(13)C]-乌头碱和[1'-(13)C]-天仙子胺进行同位素标记实验，并结合茉莉酸甲酯、冠状菌素和 1-氨基环丙烷-1-羧酸等诱导剂处理，用于研究 N-去甲基托烷生物碱的代谢来源。结果表明，去甲乌药碱和去甲莨菪碱是在应激条件下通过乌头碱和天仙子碱的转化诱导产生的。我们提出托烷生物碱的 N-去甲基化是在过度产生条件下解毒细胞的一种机制。
