Structural characterization and identification of flavonoid aglycones in three Glycyrrhiza species by liquid chromatography with photodiode array detection and quadrupole time-of-flight mass spectrometry

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• 作者：Shiqi Fang ; Qiyang Qu ; Yunfeng Zheng ; Huanhuan Zhong ; Chenxiao Shan ; Fang Wang ; Cunyu Li and Guoping Peng
• 刊名：Journal of Separation Science
• 出版年：2016
• 出版时间：June 2016
• 年：2016
• 卷：39
• 期：11
• 页码：2068-2078
• 全文大小：920K
• ISSN：1615-9314

文摘

Flavonoids, including flavones, isoflavones, flavanones, chalcones, and isoflavans, have long been recognized as the main active ingredients in licorice. A method combining liquid chromatography with photodiode array detection and quadrupole time-of-flight mass spectrometry was developed to characterize components in three Glycyrrhiza species, and to expound the characteristic fragmentation behaviors in the positive ion mode. Based on the fragmentation patterns of reference compounds, a total of 39 compounds, including 37 flavonoid aglycones and two coumestans, were identified or tentatively identified. Besides, some common features, such as H₂O, CO, and CH₂O₂ losses, together with retro-Diels–Alder fragmentation, were observed in these compounds. Furthermore, diagnostic fragmentations of C-ring cleavages and UV absorption on the skeleton groups were observed to structurally characterize flavonoid aglycones. In addition, typical losses of different substituent groups were detected: Neutral losses of 56 (C₄H₈) and 68 Da (C₅H₈) were yielded from a prenyl chain; neutral losses of 42 (C₃H₆), 54 (C₄H₆), and 70 Da (C₄H₆O) were generated by a pyran ring. Particularly, neutral losses of 18 (H₂O), 16 (CH₄), 112 (C₈H₁₆), and 98 Da (C₇H₁₄) predicted a hydroxyl, a methoxyl, double prenyl chains, and a prenyl chain with a pyran ring, respectively.