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首页> 外文期刊>Journal of mass spectrometry: JMS >Dereplication of known pregnane glycosides and structural characterization of novel pregnanes in Marsdenia tenacissima by high-performance liquid chromatography and electrospray ionization-tandem mass spectrometry
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Dereplication of known pregnane glycosides and structural characterization of novel pregnanes in Marsdenia tenacissima by high-performance liquid chromatography and electrospray ionization-tandem mass spectrometry

机译：高效液相色谱和电喷雾电离串联质谱法对马氏小球藻中已知孕烷糖苷的去复制和新型孕烷的结构表征

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摘要

In the search for novel natural products in plants, particularly those with potential bioactivity, it is important to efficiently distinguish novel compounds from previously isolated, known compounds, a process known as dereplication. In this study, electrospray ionization-multiple stage tandem mass spectrometry (ESI-MS~n) was used to study the behaviour of 12 pregnane glycosides and genins previously isolated from Marsdenia tenacissima, a traditional Chinese medicinal plant, as a basis for dereplication of compounds in a plant extract. In addition to [M?+?Na]~+ and [M?+?NH_4]~+ ions, a characteristic [M-glycosyl?+?H]~+ ion was observed in full-scan mode with in-source fragmentation. Sequential in-trap collision-induced dissociation of [M?+?Na]~+ ions from 11, 12-diesters revealed consistent preferred losses of substituents first from C-12, then from C-11, followed by losses of monosaccharide fragments from the C-3 tri-and tetrasaccharide substituents. A crude methanol extract of M. tenacissima stems was analysed using high-performance liquid chromatography coupled to ESI-MS. Several previously isolated pregnane glycosides were dereplicated, and the presence of an additional nine novel pregnane glycosides is predicted on the basis of the primary and fragment ions observed, including two with a previously unreported C_4H_7O C-11/C-12 substituent of pregnane glycosides. This study is the first report of prediction of the structures of novel pregnane glycosides in a crude plant extract by a combination of in-source fragmentation and in-trap collision-induced dissociation and supports the usefulness of LC-ESI-MS~n not only for dereplication of active compounds in extracts of medicinal plants but also for detecting the presence of novel related compounds.
机译：在寻找植物中的新型天然产物，特别是具有潜在生物活性的天然产物时，重要的是要有效地将新型化合物与先前分离的已知化合物区分开，这一过程称为重复复制。在这项研究中，使用电喷雾电离多级串联质谱（ESI-MS〜n）来研究先前从传统中草药马氏den（Marsdenia tenacissima）中分离的12种孕烷苷和异基因苷的行为，以此作为重复复制化合物的基础在植物提取物中。除了[M + + Na] +和[M + NH_4] +离子外，在全扫描模式下还观察到了特征性的[M-糖基+ + H]-+离子，且具有源内裂解。 。阱内碰撞诱导的11、12个二酯的[Mα+ΔNa]〜+离子的顺序解离显示，首先从C-12，然​​后从C-11，一致的优选取代基丢失，随后是从C-11丢失单糖片段C-3三和四糖取代基。使用与ESI-MS联用的高效液相色谱分析了tenacissima茎粗甲醇提取物。重复复制了几个先前分离的孕烷糖苷，并根据观察到的初级离子和碎片离子预测了另外九个新的孕烷糖苷的存在，包括两个未报告的孕烷糖苷C_4H_7O C-11 / C-12取代基。这项研究是通过源内裂解和陷阱内碰撞诱导的解离相结合预测粗植物提取物中新孕烷糖苷结构的首次报道，不仅支持LC-ESI-MS〜n的有用性用于药用植物提取物中活性化合物的去复制，也用于检测新型相关化合物的存在。

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