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新型N-苯甲酰基-脱氢枞胺衍生物的电喷雾离子阱质谱行为研究
Analysis of Novel N-benzoyl Dehydroabietylamine Derivatives through Electrospray Ionization Tandem Mass Spectrometry
【摘要】 利用电喷雾离子阱质谱(ESI-IT-MS)技术,对8个具有潜在杀菌、抗癌生物活性的三类新型N-苯甲酰基-脱氢枞胺衍生物进行了ESI质谱行为研究。结果表明,由于7位、12位及苯甲酰基上取代基的不同,三类衍生物呈现出一定的电离及碎裂特性。在(±)-ESI-MS过程中,7-肟基类衍生物(A)和12-硝基类衍生物(C)比7-羟基类衍生物(B)更易产生二聚体;A易产生[M-H2O+H]+,C则更易负离子化。在(+)-ESIMS/MS过程中,A中7-肟基的存在使其易产生特征离子碎裂峰[M-35+H]+和[M-H2O+H]+;A的18位酰基脱水离子峰[M-H2O+H]+失去一分子取代苯甲腈产生系列偶数碎裂离子峰;A的7-肟基脱水离子峰[M-H2O+H]+失去一分子取代苯甲醛产生系列奇数碎裂离子峰。在(-)-ESI-MS/MS过程中,B比C更稳定,在较高的碰撞能作用下获得的碎裂片段较少;均可通过丢失中性分子N-取代苯甲酰基亚甲胺、取代苯甲醛或取代苯产生系列碎裂离子片段;C的强吸电子基团12-硝基及4’-硝基的存在使其丢失的中性分子易捕获电子而离子化。
【Abstract】 Eight novel N-benzoyl dehydroabietylamine derivatives with potential sterilization and anticancer biological activities were analyzed through electrospray ionization tandem mass spectrometry(ESI-ITMS).The results indicated that three types of derivatives exhibited their own typical ionization and fragmentation process,due to their different 7-and 12-substituents on the dehydroabietylamine ring and different substituents on the benzoyl ring.In(±)-ESI-MS,the dimer ions of 7-oxime derivatives(A) and12-nitro derivatives(C) could be more readily formed than that of 7-hydroxy derivatives(B).[M-H2O+ H]+ of A was observed in the positive-ion mode.C were prone to be ionized in the negative-ion mode.Two typical fragmentation peaks of[M-35+H]+ and[M-H2O + H]+ were observed in(+)-ESIMS/MS spectra of 7-oxime dehydroabietylamine derivatives.The ion of[M- H2O + H]+ formed from18-acyl of(A) could induce some even fragmentation ion peaks by loss of substituted benzonitrile.The ion of[M-H2O + H]+ formed from 7-oxime of(A) can induce some odd fragmentation ion peaks by loss of substituted benzaldehyde.(B) showed more stability than(C) in(-)-ESI-MS/MS process.Fewer fragmentation ions of(B) were obtained even though(B) derivatives were collided with higher energy.Ion fragmentation of(B) and(C) derivatives were induced by loss of neutral molecules of N-substituted benzoyl methylene amine,substituted benzaldehyde or substituted benzene.Due to the strong electron-withdrawing ability of 12-and 4’-nitro of(C) derivatives,the neutral molecules lost from(C) derivatives can be ionized by capturing one electron.
【Key words】 electrospray mass spectrometry; ionization tandem; N-benzoyl dehydroabietylamine derivative;
- 【文献出处】 中山大学学报(自然科学版) ,Acta Scientiarum Naturalium Universitatis Sunyatseni , 编辑部邮箱 ,2014年04期
- 【分类号】O657.63
- 【下载频次】40