Fu Zhiwen, Xue Rui, Li Zhixiong, Chen Mingcang, Sun Zhaolin, Hu Yiyang, Huang Chenggang
Shanghai Institute of Materia Medica, Chinese Academy of Sciences, 501 Haike Rd., Shanghai, 201203, People's Republic of China; Department of Clinical Pharmacology, Shuguang hospital affiliated to Shanghai University of Traditional Chinese Medicine, 1200 Cailun Rd, Shanghai, 201203, People's Republic of China.
Biomed Chromatogr. 2014 Dec;28(12):1795-807. doi: 10.1002/bmc.3223. Epub 2014 Apr 30.
Iridoid glycosides (IGs), the major constituents in Fructus Gardeniae, have demonstrated various pharmacological activities, but there is no systematic chemical profile of IGs in Fructus Gardeniae in the published literature until now. Therefore, it is imperative that a rapid and sensitive high-performance liquid chromatography coupled with quadrupole time-of-flight tandem mass spectrometry (HPLC-Q/TOF-MS/MS) method is established for comprehensive characterization of IGs in Fructus Gardeniae. Firstly, the fragmentation patterns of six known IGs were investigated and proposed and further concluded the diagnostic fragment ions and characteristic fragmentation pathways. Then, based on the summarized fragmentation patterns and the known compounds in the literatures, the other IGs in Fructus Gardeniae were identified successively. As a result, a total of 20 IGs were identified, of which three pairs of epimers were structurally characterized and differentiated. More importantly, one compound, the isoshanzhiside methyl ester, was tentatively identified as a new compound. The results of this study demonstrate the superiority of HPLC-MS with a high-resolution mass spectrometer for the rapid and sensitive structural elucidation of the multiple groups of constituents in Fructus Gardeniae.
环烯醚萜苷(IGs)是栀子中的主要成分,已显示出多种药理活性,但迄今为止,公开文献中尚无栀子中环烯醚萜苷的系统化学图谱。因此,必须建立一种快速灵敏的高效液相色谱-四极杆飞行时间串联质谱(HPLC-Q/TOF-MS/MS)方法,以全面表征栀子中的环烯醚萜苷。首先,研究并提出了六种已知环烯醚萜苷的裂解模式,进一步总结了诊断性碎片离子和特征裂解途径。然后,根据总结的裂解模式和文献中的已知化合物,依次鉴定了栀子中的其他环烯醚萜苷。结果,共鉴定出20种环烯醚萜苷,其中三对差向异构体的结构得到了表征和区分。更重要的是,一种化合物异山栀苷甲酯被初步鉴定为新化合物。本研究结果证明了HPLC-MS联用高分辨率质谱仪在快速灵敏地阐明栀子中多组成分结构方面的优越性。