Schmidt Jürgen, Boettcher Chotima, Kuhnt Christine, Kutchan Toni M, Zenk Meinhart H
Department of Bioorganic Chemistry, Leibniz Institute of Plant Biochemistry, Weinberg 3, D-06120 Halle/S., Germany.
Phytochemistry. 2007 Jan;68(2):189-202. doi: 10.1016/j.phytochem.2006.10.003. Epub 2006 Nov 20.
Papaver alkaloids play a major role in medicine and pharmacy. In this study, [ring-(13)C(6)]-tyramine as a biogenetic precursor of these alkaloids was fed to Papaver somniferum seedlings. The alkaloid pattern was elucidated both by direct infusion high-resolution ESI-FT-ICR mass spectrometry and liquid chromatography/electrospray tandem mass spectrometry. Thus, based on this procedure, the structure of about 20 alkaloids displaying an incorporation of the labeled tyramine could be elucidated. These alkaloids belong to different classes, e.g. morphinan, benzylisoquinoline, protoberberine, benzo[c]phenanthridine, phthalide isoquinoline and protopine. The valuable information gained from the alkaloid profile demonstrates that the combination of these two spectrometric methods represents a powerful tool for evaluating biochemical pathways and facilitates the study of the flux of distant precursors into these natural products.
罂粟生物碱在医学和制药领域发挥着重要作用。在本研究中,将[环-(13)C(6)]-酪胺作为这些生物碱的生物合成前体喂给罂粟幼苗。通过直接进样高分辨率电喷雾傅里叶变换离子回旋共振质谱法和液相色谱/电喷雾串联质谱法阐明了生物碱模式。因此,基于此方法,可以阐明约20种显示标记酪胺掺入的生物碱的结构。这些生物碱属于不同类别,例如吗啡喃、苄基异喹啉、原小檗碱、苯并[c]菲啶、邻苯二甲酰异喹啉和原托品。从生物碱谱中获得的有价值信息表明,这两种光谱方法的结合是评估生化途径的有力工具,并有助于研究远距离前体进入这些天然产物的通量。