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首页> 外文期刊>Journal of mass spectrometry: JMS >Combined use of tandem mass spectrometry and computational chemistry to study 2H-chromenes from Piper aduncum
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Combined use of tandem mass spectrometry and computational chemistry to study 2H-chromenes from Piper aduncum

机译：结合串联质谱和计算化学的使用来研究吹笛子Aduncum的2H-铬

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摘要

Natural 2H-chromenes were isolated from the crude extract of Piper aduncum (Piperaceae) and analyzed by electrospray ionization tandem mass spectrometry (ESI-MS/MS) applying collision-induced dissociation. Density functional theory (DFT) calculations were used to explain the preferred protonation sites of the 2H-chromenes based on thermochemical parameters, including atomic charges, proton affinity, and gas-phase basicity. After identifying the nucleophilic sites, the pathways were proposed to justify the formation of the diagnostic ions under ESI-MS/MS conditions. The calculated relative energy for each pathway was in good agreement with the energy-resolved plot obtained from ESI-MS/MS data. Moreover, the 2H-chromene underwent proton attachment on the prenyl moiety via a six-membered transition state. This behavior resulted in the formation of a diagnostic ion due to 2-methylpropene loss. These studies provide novel insights into gas-phase dissociation for natural benzopyran compounds, indicating how reactivity is correlated to the intrinsic acid-base equilibrium and structural aspects, including the substitution pattern on the aromatic moiety. Therefore, these results can be applied in the identification of benzopyran derivatives in a variety of biological samples.
机译：从吹笛子（Piperaceae）的粗提物中分离天然2H-铬，并通过电喷雾电离串联质谱（ESI-MS / MS）分析施加碰撞诱导的解离。密度函数理论（DFT）计算用于基于热化学参数来解释2H-色敏的优选质子化位点，包括原子电荷，质子亲和力和气相碱度。在识别亲核位置后，提出了途径，以证明在ESI-MS / MS条件下形成诊断离子。每个途径的计算相对能量与从ESI-MS / MS数据获得的能量分辨曲线吻合良好。此外，通过六元的过渡状态在戊烯部分上接受质子附着的2H-铬烯。这种行为导致由于2-甲基丙烯损失导致诊断离子。这些研究提供了对天然苯并吡喃化合物的气相解离的新颖见解，表明反应性如何与本征酸基平衡和结构方面相关，包括芳族部分上的替代图案。因此，这些结果可以应用于各种生物样品中的苯并吡喃衍生物的鉴定。

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