食品中化学性有害物的质谱软电离裂解规律及筛查技术研究进展

doi:10.3724/SP.J.1123.2020.03002

摘要/Abstract

摘要：

食品中化学性有害物是导致食品安全问题的重要原因，质谱是对食品中化学性有害物进行定性定量分析的有效方法。该文按照化合物结构类别，综述了食品中重要化学性有害物的质谱软电离裂解机理，包括农药、兽药、真菌毒素，以及其他化学污染物。对于每类化合物，重点综述化合物质谱裂解产生的特征碎片、中性丢失等，以及这些质谱软电离裂解机理在食品中化学性有害物筛查及发现中的应用。研究化合物的质谱裂解机理可以帮助研究者对化合物进行结构解析和结构确证，为食品中同类结构新型化学性有害物的发掘提供理论依据。

关键词: 裂解规律, 软电离, 质谱, 特征碎片, 非定向筛查, 未知化合物, 综述

Abstract:

Hazardous chemicals in food are an important cause of food safety problems. Mass spectrometry is an effective tool for the qualitative and quantitative analysis of these substances. In this paper, the fragmentation mechanisms for several chemical hazardous substances, including pesticides, veterinary drugs, mycotoxins, and other chemical pollutants classified by structural analogs, are reviewed. For each class of compounds, we summarize the characteristic fragments and neutral loss generated by cleavage in the mass spectrometry analysis. We also summarize the mechanisms applied to screen and discover new structural analogs in food. This review can help researchers analyze and confirm the structure of compounds and provide a theoretical basis for the discovery of new structural analogs in food.

Key words: fragmentation mechanisms, soft ionization technique, mass spectrometry, characteristic fragments, untargeted screening, unknown compounds, review

刘晓敏, 许秀丽, 聂雪梅, 国伟, 张峰. 食品中化学性有害物的质谱软电离裂解规律及筛查技术研究进展[J]. 色谱, 2020, 38(7): 750-758.

LIU Xiaomin, XU Xiuli, NIE Xuemei, GUO Wei, ZHANG Feng. Research progress on the fragmentation mechanisms of mass spectrometry soft ionization and screening of chemical hazardous substances in food[J]. Chinese Journal of Chromatography, 2020, 38(7): 750-758.

图/表 4

图1 典型农药的质谱软电离裂解规律

Fig. 1 Fragmentation mechanisms of mass spectrometry soft ionization of the typical pesticides -----: main bond cleavage of compounds.

图2 典型兽药的质谱软电离裂解规律

Fig. 2 Fragmentation mechanisms of mass spectrometry soft ionization of typical veterinary drugs

图3 典型真菌毒素的质谱软电离裂解规律

Fig. 3 Fragmentation mechanisms of mass spectrometry soft ionization of typical mycotoxins

图4 其他化学污染物的质谱软电离裂解规律

Fig. 4 Fragmentation mechanisms of mass spectrometry soft ionization of other chemical pollutants

参考文献

1	Cissé G . Acta Trop, 2019, 194: 181
2	Qiao G H , Guo T , Klein K K . Food Control, 2012, 26 (2): 378
3	Chang L , Bi P Y , Li X C , et al. Food Chem, 2015, 177: 127
4	Masiá A , Suarez-Varela M M , Llopis-Gonzalez A , et al. Anal Chim Acta, 2016, 936: 40
5	Delatour T , Racault L , Bessaire T , et al. Food Addit Contam A, 2018, 35 (4): 633
6	Wittenberg J B , Simon K A , Wong J W . J Agric Food Chem, 2017, 65 (34): 7288
7	Chang G R , Chen H S , Lin F Y . Mar Pollut Bull, 2016, 113 (1/2): 579
8	Han R W , Zheng N , Yu Z N , et al. Food Chem, 2015, 181: 119
9	Fussell R J , Garcia Lopez M , Mortimer D N , et al. J Agric Food Chem, 2014, 62 (17): 3651
10	Dubreil E , Gautier S , Fourmond M P , et al. Food Addit Contam A, 2017, 34 (4): 453
11	Bignardi C , Cavazza A , Corradini C , et al. J Chromatogr A, 2014, 1372: 133
12	Niessen W M A . Mass Spectrom Rev, 2011, 30 (4): 626
13	Penkert M , Yates L M , Schümann M , et al. Anal Chem, 2017, 89 (6): 3672
14	Ge Y W , Zhu S , Yoshimatsu K , et al. Food Chem, 2017, 227: 444
15	Bi Q R , Hou J J , Yang M , et al. J Am Soc Mass Spectrom, 2017, 28 (3): 443
16	Shi X J , Yang W Z , Qiu S , et al. Anal Chim Acta, 2017, 952: 59
17	Arena S , Renzone G , D'Ambrosio C , et al. Food Chem, 2017, 219: 477
18	Hernández F , Grimalt S , Pozo ó J , et al. J Sep Sci, 2009, 32 (13): 2245
19	Wang J , Chow W , Chang J , et al. J Agric Food Chem, 2014, 62 (42): 10375
20	Zhong Y M , Cong M M , Mu S T , et al. Journal of Food Safety and Quality, 2019, 10 (10): 3132
20	钟韵梅, 丛梅梅, 牟善婷, et al. 食品安全质量检测学报, 2019, 10 (10): 3132
21	Schwarzenberg A , Ichou F , Cole R B , et al. J Mass Spectrom, 2013, 48 (5): 576
22	Guo T Y , Li Y , Dong Y Y , et al. Journal of Chinese Mass Spectrometry Society, 2019, 40 (1): 21
22	郭天洋, 李杨, 董益阳, et al. 质谱学报, 2019, 40 (1): 21
23	Niessen W M A . J Chromatogr A, 2010, 1217 (25): 4061
24	Jansomboon W , Boontanon S K , Boontanon N , et al. Food Chem, 2016, 212: 635
25	Huang C , Guo B , Wang X , et al. Anal Chim Acta, 2012, 737: 83
26	Dubreil-Chéneau E , Pirotais Y , Verdon E , et al. J Chromatogr A, 2014, 1339: 128
27	Ki N Y , Hur J , Kim B H , et al. Journal of Food and Drug Analysis, 2019, 27 (1): 164
28	Wang C , Liang R Q , Qiu Z R , et al. Chinese Journal of Pharmaceutical Analysis, 2018, 38 (8): 141
28	王聪, 梁瑞强, 钮正睿, et al. 药物分析杂志, 2018, 38 (8): 141
29	Nie X M , Dong X Y , Zhang F , et al. Chinese Journal of Chromatography, 2019 (9): 1011
29	聂雪梅, 董旭阳, 张峰, et al. 色谱, 2019 (9): 1011
30	Li T T , Cao J J , Li Z , et al. Food Chem, 2016, 192: 188
31	Domínguez-Romero J C , García-Reyes J F , Martínez-Romero R , et al. J Chromatogr B, 2013, 923/924: 128
32	Cheng J Q , Liu T , Zhang F , et al. Molecules, 2019, 24 (4): 820
33	SalutiaI G , Diamanti I , Giusepponi D , et al. Food Chem, 2018, 266: 9
34	Savoy M C , Woo P M , Ulrich P , et al. Food Addit Contam A, 2018, 35 (4): 675
35	Farouk F , Azzazy H M E , Niessen W M A . Anal Chim Acta, 2015, 890: 21
36	Rao Y K , Li Z , Zhang D Y , et al. Chinese Journal of Chromatography, 2019, 37 (6): 626
36	饶雅琨, 李卓, 张荻悦, et al. 色谱, 2019, 37 (6): 626
37	Chen J Y , Chen W Q , Liu Z , et al. Journal of Chinese Mass Spectrometry Society, 2019, 40 (2): 123
37	陈晶燕, 陈万勤, 刘柱, et al. 质谱学报, 2019, 40 (2): 123
38	Zheng Y , Zhao H , Zhu L , et al. Anal Chim Acta, 2019, 1089: 100
39	Palermo A , Botrè F , de la Torre X , et al. Anal Chim Acta, 2017, 964: 112
40	Zhang T L , Shi M Y , Di X , et al. Acta Pharmaceutica Sinica, 2014, 49: 507
40	张婷岚, 史美云, 邸欣, et al. 药学学报, 2014, 49: 507
41	Kova?evi? B , Schorr P , Qi Y , et al. J Am Soc Mass Spectrom, 2014, 25 (11): 1974
42	Dorival-García N , Zafra-Gómez A , Camino-Sánchez F J , et al. Talanta, 2013, 106: 104
43	Dorival-García N , Zafra-Gómez A , Cantarero S , et al. Microchem J, 2013, 106: 323
44	Chen Q , Pan X D , Huang B F , et al. J Pharmaceut Biomed, 2017, 145: 525
45	Hong Y H , Xu X L , Zhang F , et al. Anal Methods, 2017, 9 (46): 6534
46	Xu Y , Wang J . Chinese Journal of Pharmaceutical Analysis, 2019, 39 (6): 1019
46	徐雨, 王建. 药物分析杂志, 2019, 39 (6): 1019
47	Beltrán E , Ibá?ez M , Sancho J V , et al. Food Chem, 2011, 126 (2): 737
48	Hu Q R , Cao P , Cong Z X , et al. Chinese Journal of Chromatography, 2019, 37 (11): 1241
48	胡巧茹, 曹鹏, 丛中笑, et al. 色谱, 2019, 37 (11): 1241
49	Wu H Q , Xu X L , Zhang F , et al. Chinese Journal of Analysis Laboratory, 2017, 36: 235
49	吴寒秋, 许秀丽, 张峰, et al. 分析试验室, 2017, 36: 135
50	Arroyo-Manzanares N , Malysheva S V , Bussche J V , et al. Talanta, 2014, 118: 359
51	Liu Z Y , Yu C H , Wan L , et al. Int J Mass Spectrom, 2012, 309: 133
52	Cheng Y , Nie X M , Zhang F , et al. Anal Chim Acta, 2017, 950: 98
53	Zhao H , Xiang L , Li J , et al. Rapid Commun Mass Spectrom, 2016, 30 (16): 1901
54	Heffernan A L , Thompson K , Eaglesham G , et al. Talanta, 2016, 151: 224
55	Vi?as P , Campillo N , Pastor-Belda M , et al. J Chromatogr A, 2015, 1376: 18
56	Sun L , Zhang F , Yong W , et al. Food Chem, 2010, 123 (3): 647
57	Xian Y P , Wu Y L , Dong H , et al. Food Chem, 2019, 285: 77
58	Tan H J , Guo C C , Xing S , et al. Chinese Journal of Chromatography, 2019, 37 (9): 969
58	谭会洁, 郭常川, 邢晟, et al. 色谱, 2019, 37 (9): 969
59	He Z , Xu Y , Zhang Y , et al. J Agric Food Chem, 2019, 67 (38): 10800
60	Jia W , Zhang R , Shi L , et al. Chinese Journal of Analytical Chemistry, 2019, 47: 1098
60	贾玮, 张荣, 石琳, et al. 分析化学, 2019, 47: 1098
61	Zhang F , Chu X G , Sun L , et al. J Chromatogr A, 2008, 1209: 220
62	Sun Y , Feng F , Zhang F , et al. Talanta, 2019, 205: 120011

[1]	史洪飞, 徐伯芃, 徐成鑫, 周修齐, 许宏福. 溶剂萃取-高效液相色谱-四极杆飞行时间质谱法快速提取检测干燥恰特草中5种生物碱成分[J]. 色谱, 2023, 41(9): 771-780.
[2]	唐泽坤, 万慧慧, 李红, 陈绍云, 赵金凤, 孙玉明, 蔡蕊, 徐强, 张华. 亲水相互作用色谱-静电场轨道阱高分辨质谱法测定CO₂吸收液中9种有机胺类化合物[J]. 色谱, 2023, 41(9): 799-806.
[3]	周然锋, 张惠贤, 尹小丽, 彭西甜. 新型纳米材料在农产品安全分析中的应用进展[J]. 色谱, 2023, 41(9): 731-741.
[4]	赵芮, 黄晴雯, 余智颖, 韩铮, 范楷, 赵志辉, 聂冬霞. QuEChERS-超高效液相色谱-串联质谱法同时测定水果中36种真菌毒素[J]. 色谱, 2023, 41(9): 760-770.
[5]	岳超, 赵超群, 毛思浩, 王展华, 施贝, 徐欣丰, 梁晶晶. 通过式固相萃取净化-超高效液相色谱-串联质谱法测定液体乳中10种氨基甲酸酯类农药残留[J]. 色谱, 2023, 41(9): 807-813.
[6]	马超, 倪洪星, 戚羽霖. 超高效液相色谱-傅里叶变换离子回旋共振质谱法解析溶解性有机质的化学多样性[J]. 色谱, 2023, 41(8): 662-672.
[7]	孟二琼, 念琪循, 李峰, 张秋萍, 许茜, 王春民. 磺酸化磁性氮化碳固相萃取-超高液相色谱-串联质谱筛检淡水鱼中孔雀石绿和隐色孔雀石绿[J]. 色谱, 2023, 41(8): 673-682.
[8]	于霜, 高媛, 朱秀华, 耿柠波, 代玉冰, 洪建尧, 陈吉平. 气相色谱-电子捕获负化学源-低分辨质谱法测定人体血液不同组分中短链及中链氯化石蜡[J]. 色谱, 2023, 41(8): 698-706.
[9]	陈东洋, 张昊, 张磊, 王一红, 王小丹, 冯家力, 梁静, 钟旋. 固相萃取-超高效液相色谱-串联质谱法测定发酵食品中的曲酸[J]. 色谱, 2023, 41(7): 632-639.
[10]	王秋旭, 冯启言, 朱雪强. 加速溶剂萃取-固相萃取净化结合超高效液相色谱-串联质谱法测定沉积物中双酚类化合物[J]. 色谱, 2023, 41(7): 582-590.
[11]	李洁, 鞠香, 王艳丽, 田其燕, 梁秀清, 李海霞, 刘艳明. QuEChERS-在线凝胶渗透色谱-气相色谱-串联质谱法高通量筛查动物源性食品中的多农药残留[J]. 色谱, 2023, 41(7): 610-621.
[12]	夏宝林, 汪仕韬, 殷晶晶, 张维益, 杨娜, 刘强, 吴海晶. 自动上样固相萃取-超高效液相色谱-串联质谱法同时测定水中9类43种抗菌药物残留[J]. 色谱, 2023, 41(7): 591-601.
[13]	童学智, 陈东洋, 冯家力, 范翔, 张昊, 杨胜园. QuEChERS-超高效液相色谱-串联质谱法快速测定水产品中5种卤代苯醌[J]. 色谱, 2023, 41(6): 490-496.
[14]	王园媛, 李璐璐, 吕佳, 陈永艳, 张岚. 固相萃取-超高效液相色谱-三重四极杆质谱法测定饮用水中13种卤代苯醌类消毒副产物[J]. 色谱, 2023, 41(6): 482-489.
[15]	李鑫玉, 赵芳, 平华, 马智宏, 李冰茹, 马挺军, 李成. 稳定同位素稀释气相色谱-三重四极杆质谱法测定水产品中15种卤代多环芳烃[J]. 色谱, 2023, 41(6): 527-534.