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首页> 外文期刊>Journal of mass spectrometry: JMS >Evaluation of glycosylation and malonylation patterns in flavonoid glycosides during LC/MS/MS metabolite profiling
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Evaluation of glycosylation and malonylation patterns in flavonoid glycosides during LC/MS/MS metabolite profiling

机译：LC / MS / MS代谢物分析过程中类黄酮苷中糖基化和丙二酸化模式的评估

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摘要

Flavonoid conjugates constitute several classes of plant phenolic secondary metabolites including many isomeric compounds differing in the hydroxylation pattern and substitution of their rings with different groups such as alkyls, acyls or sugars. These compounds occur in plant tissues mainly as glycosides and in many cases it is necessary to have reliable and detailed information concerning the structure of these natural products. Our results were obtained using leaf extracts of Arabidopsis thaliana and Lupinus angustifolius in which different glycosides of flavones, flavonols and isoflavones are present. Analysis of collision-induced dissociation (CID)/MS/MS spectra of protonated [M + H](+), sodiated [M + Na](+) or deprotonated [M - H](-) molecules recorded during HPLC runs may bring needed information in this respect. However, registration of mass spectra of [M + Na](+) ions with a good efficiency is possible only after post-column addition of a sodium acetate solution to the LC column eluate. The retention of sodium cation on the saccharidic parts of the molecule is observed after the CID fragmentation. In many cases, the location of this cation on the glycan attached to C-3 hydroxyl group of flavonol led to assignment of its structure. Additionally, the determination of the structure of the aglycone and of the sequence of the glycan part was made possible through the CID data obtained from the [M + H](+) and [M - H](-) ions. CID spectra show a different order of sugar elimination from hydroxyl groups at C-3 and C-7 in flavonol glycosides isolated from A. thaliana leaves and give sufficient information to discriminate flavonoid O-diglycosides from flavonoid di-O-glycosides.
机译：类黄酮缀合物构成几类植物酚类次级代谢产物，包括许多异构化化合物，它们的羟基化方式不同，并且其环被不同的基团（例如烷基，酰基或糖）取代。这些化合物主要以糖苷形式存在于植物组织中，在许多情况下，必须具有有关这些天然产物结构的可靠且详细的信息。我们的结果是使用拟南芥和羽扇豆叶提取物获得的，其中存在黄酮，黄酮醇和异黄酮的不同糖苷。 HPLC运行中记录的质子化[M + H]（+），质子化[M + Na]（+）或去质子化[M-H]（-）分子的碰撞诱导解离（CID）/ MS / MS谱图可能在这方面带来所需的信息。但是，只有在柱后向液晶柱洗脱液中添加乙酸钠溶液后，才能高效地记录[M + Na]（+）离子的质谱图。 CID断裂后，观察到钠阳离子在分子的糖基部分上的保留。在许多情况下，该阳离子在与黄酮醇C-3羟基相连的聚糖上的位置导致其结构分配。另外，通过从[M + H]（+）和[M-H]（-）离子获得的CID数据，可以确定糖苷配基的结构和聚糖部分的序列。 CID光谱显示了从拟南芥叶中分离出的黄酮糖苷中C-3和C-7处羟基清除糖的顺序不同，并提供了足够的信息来区分类黄酮O-二糖苷和类黄酮二-O-糖苷。

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