The time of flight mass spectrometry technology and its application in plant polyphenols identification

Authors

LI Weizhou, College of Food Science, Southwest University, Chongqing 400715, China
MING Jian, College of Food Science, Southwest University, Chongqing 400715, China; Chongqing Engineering Research Center for Special Foods, Chongqing 400715, China
XIAO Xingning, College of Food Science, Southwest University, Chongqing 400715, China
SHI Fang, College of Food Science, Southwest University, Chongqing 400715, China
LI Yao, College of Food Science, Southwest University, Chongqing 400715, China

Abstract

Time of flight mass spectrometry (TOF-MS) has been widely applied in food, biological medicine, environmental monitoring for its great precision, wide range of detection and high speed of analysis. TOF-MS with various techniques in tandem plays an important role in the structure identification of polyphenols. In this review, it was outlined the application of time of flight mass spectrometry in the structure identification of plant polyphenols to provide some references for the study of plant polyphenol.

Publication Date

4-28-2017

First Page

200

Last Page

204

DOI

10.13652/j.issn.1003-5788.2017.04.039

Recommended Citation

Weizhou, LI; Jian, MING; Xingning, XIAO; Fang, SHI; and Yao, LI (2017) "The time of flight mass spectrometry technology and its application in plant polyphenols identification," Food and Machinery: Vol. 33: Iss. 4, Article 39.
DOI: 10.13652/j.issn.1003-5788.2017.04.039
Available at: https://www.ifoodmm.cn/journal/vol33/iss4/39

References

[1] 付真烈, 刘胜利, 王敏. 氧自由基造成肝细胞损害的机理[J]. 临床肝胆病杂志, 1996(4): 181-183.
[2] OKARTER N, LIU Rui-hai. Health benefits of whole grain phytochemicals[J]. Critical Reviews in Food Science and Nutrition, 2010, 50(3): 193-208.
[3] LIU Rui-hai. Whole grain phytochemicals and health[J]. Journal of Cereal Science, 2007, 46(3): 207-219.
[4] PREZ-JIMNEZ J, TORRES J L. Analysis of non-extractable phenolic compounds in foods: the corrent state of the art[J]. Journal of Agricultural and Food Chemistry, 2011, 59(24): 12 713-12 724.
[5] MEZUCA M, MALATO O, GARCA-REYES J F, et al. Accurate-mass databases for comprehensive screening of pesticide residues in food by fast liquid chromatography time-of-flight mass spectrometry[J]. Analytical Chemistry, 2009, 81(3): 913-929.
[6] 李晓颍, 张红医, 范春林, 等. 气相色谱-飞行时间质谱在化合物鉴定方面的应用进展[J]. 化学通报, 2014, 77(2): 123-130.
[7] 汪聪慧. 有机质谱技术与方法[M]. 北京: 中国轻工业出版社, 2011: 56-58.
[8] 韩瑶. 寡糖的基质辅助激光解吸电离飞行时间质谱分析方法研究[D]. 青岛: 中国海洋大学, 2006: 10-12.
[9] 徐国宾. 飞行时间质谱及串联质谱关键技术的系统研究[D]. 上海: 复旦大学, 2010.
[10] PASCH H, ALPHEUS MAUTJANA N. Matrix-assisted laser desorption/ionization mass spectrometry of polymers[M]// ROBERT A M. Encyclopedia of Analytical Chemistry. New Jersey: Wiley-Blackwell, 2011: 3 126-3 131.
[11] 侯可勇, 董璨, 王俊德, 等. 飞行时间质谱仪新技术的进展及应用[J]. 化学进展, 2007, 19(1): 385-392.
[12] BEHRENS A, MAIE N, KNICKER H, et al. MALDI-TOF mass spectrometry and PSD fragmentation as means for the analysis of condensed tannins in plant leaves and needles[J]. Phytochemistry, 2003, 62(7): 1 159-1 170.
[13] VELOO A C M, ERHARD M, WELKER M, et al. Identification of gram-positive anaerobic cocci by MALDI-TOF mass spectrometry[J]. Systematic and Applied Microbiology, 2011, 34(1): 58-62.
[14] 陈秀金, 尹红红, 匡华, 等. 沙门氏菌MALDI-TOF-MS蛋白质指纹图谱分析方法的研究[J]. 食品与生物技术学报, 2012, 31(11): 1 189-1 197.
[15] GRIMM B, KRGER R P, SCHRADER S, et al. Molecular structure investigations on fluorine containing polyazomethines by means of the MALDI-TOF-MS technique[J]. Journal of Fluorine Chemistry, 2002, 113(1): 85-91.
[16] BOZZINI C, CAMPOSTRINI N, TROMBINI P, et al. Measurement of urinary hepcidin levels by SELDI-TOF-MS in HFE-hemochromatosis[J]. Blood Cells Molecules and Diseases, 2008, 40(3): 347-352.
[17] MOON Y S, PARK E S, KIM T O, et al. SELDI-TOF-MS based discovery of a biomarker in cucumis sativus seeds exposed to CuO nanoparticles[J]. Environmental Toxicology and Pharmacology, 2014, 38(3): 922-931.
[18] SCHIPPER R, LOOF A, GROOT J D, et al. Salivary Protein/Peptide Profiling with SELDI-TOF-MS[J]. Annals of the New York Academy of Sciences, 2007, 1 098(1): 498-503.
[19] 李晓颖, 张红医, 常巧英, 等. 气相色谱—四极杆飞行时间质谱准确鉴定常见水果蔬菜中的农药残留[J]. 色谱, 2014, 32(3): 268-277.
[20] DALSGAARD P W, RASMUSSEN B S, MLLER I B, et al. Toxicological screening of basic drugs in whole blood using UPLC-TOF-MS[J]. Drug Testing and Analysis, 2012, 4(5): 313-319.
[21] GRATA E, BOCCARD J, GUILLARME D, et al. UPLC-TOF-MS for plant metabolomics: a sequential approach for wound marker analysis in Arabidopsis thaliana[J]. Journal of Chromatography B, 2008, 871(2): 261-270.
[22] 钱疆, 陈方, 陈驰, 等. 超高效液相色谱飞行时间质谱测定食品中36种合成色素[J]. 食品科学, 2013, 34(6): 215-218.
[23] 杜志峰, 冼燕萍, 刘付健, 等. 液相色谱-高分辨率飞行时间质谱法测定食品接触纸包装材料中的7种荧光增白剂[J]. 分析化学, 2014, 42(5): 636-642.
[24] SHI Qi-yuan, JIALIE C, ZHOU Qin-fen, et al. Indirect identification of antioxidants in polygalae radix through their reaction with 2,2-diphenyl-1-picrylhydrazyl and subsequent HPLC-ESI-Q-TOF-MS/MS[J]. Talanta, 2015, 144: 830-835.
[25] 杨英, 饶春明, 王威, 等. HPLC-ESI-Q-TOF-MS鉴定重组人白细胞介素II的一级结构[J]. 质谱学报, 2006, 27(2): 117-121.
[26] DINELLI G, SEGURA-CARRETERO A, DI SILVESTRO R, et al. Profiles of phenolic compounds in modern and old common wheat varieties determined by liquid chromatography coupled with time-of-flight mass spectrometry[J]. Journal of Chromatography A, 2011, 1 218(42): 7 670-7 681.
[27] 范金波, 蔡茜彤, 郑立红, 等. 果蔬中多酚成分及其分析方法的研究进展[J]. 食品工业科技, 2014, 35(4): 374-379.
[28] WOLFENDER J L, WARIDEL P, NDJOKO K, et al. Evaluation of Q-TOF-MS/MS and multiple stage IT-MSⁿ for the dereplication of flavonoids and related compounds in crude plant extracts[J]. Analysis, 2000, 28(10): 895-906.
[29] ARREZ-ROMN D, FU Shao-ping, SAWALHA S, et al. HPLC/CE-ESI-TOF-MS methods for the characterization of polyphenols in almond-skin extracts[J]. Electrophoresis, 2010, 31(13): 2 289-2 296.
[30] RAMESHKUMAR A, SIVASUDHA T, JEYADEVI R, et al. Profiling of phenolic compounds using UPLC-Q-TOF-MS/MS and nephroprotective activity of Indian green leafy vegetable Merremia emarginata (Burm. f.)[J]. Food Research International, 2013, 50(1): 94-101.
[31] DUGO P, DONATO P, CACCIOLA F, et al. Characterization of the polyphenolic fraction of Morusalba leaves extracts by HPLC coupled to a hybrid IT-TOF MS system[J]. Journal of Separation Science, 2009, 32(21): 3 627-3 634.
[32] 李富华, 郭晓晖, 夏春燕, 等. 全谷物酚类化合物抗氧化活性研究进展[J]. 食品科学, 2012, 33(13): 299-304.
[33] MATTILA P, PIHLAVA J, HELLSTRM J. Contents of phenolic acids, alkyl- and alkenylresorcinols, and avenanthramides in commercial grain products[J]. Journal of Agricultural and Food Chemistry, 2005, 53(21): 8 290-8 295.
[34] MOORE J, LIU Jian-guo, ZHOU Ke-quan, et al. Effects of genotype and environment on the antioxidant properties of hard winter wheat bran[J]. Journal of Agricultural and Food Chemistry, 2006, 54(15): 5 313-5 322.
[35] OKARTER N, LIU Chang-shu, SORRELLS M E, et al. Phytochemical content and antioxidant activity of six diverse varieties of whole wheat[J]. Food Chemistry, 2010, 119(1): 249-257.
[36] ABU-REIDAH I M, ARREZ-ROMN D, SEGURA-CARRETERO A, et al. Profiling of phenolic and other polar constituents from hydromethanolic extract of watermelon (Citrullus lanatus) by means of accurate-mass spectrometry (HPLC-ESI-QTOF-MS)[J]. Food Research International, 2013, 51(1): 354-362.
[37] WANG Ya-qin, GUO Zhi-mou, JIN Yu, et al. Identification of prenyl flavonoid glycosides and phenolic acids in Epimedium koreanum Nakai by Q-TOF-MS combined with selective enrichment on “click oligo (ethylene glycol)” column[J]. Journal of Pharmaceutical and Biomedical Analysis, 2010, 51(3): 606-616.
[38] 马英华, 田婷婷, 解伟伟, 等. 采用UHPLC-TRIPLE-TOF-MS法鉴定松萝主要酚酸类化学成分[J]. 中草药, 2016, 47(3): 392-400.
[39] ES-SAFI N E, GUYOT S, DUCROT P H. NMR, ESI/MS, and MALDI-TOF/MS analysis of pear juice polymeric proanthocyanidins with potent free radical scavenging activity[J]. Journal of Agricultural and Food Chemistry, 2006, 54(19): 6 969-6 977.
[40] CUYCKENS F, CLAEYS M. Mass spectrometry in the structural analysis of flavonoids[J]. Journal of Mass Spectrometry, 2004, 39(1): 1-15.
[41] VERARDO V, ARREZ-ROMN D, SEGURA-CARRETERO A, et al. Identification of buckwheat phenolic compounds by reverse phase high performance liquid chromatography-electrospray ionization- time-of-flight-mass spectrometry (RP-HPLC-ESI-TOF-MS)[J]. Journal of Cereal Science, 2010, 52(2): 170-176.
[42] KOOLEN H H F, DA SILVA F, GOZZO F C, et al. Antioxidant, antimicrobial activities and characterization of phenolic compounds from buriti (Mauritia flexuosa, L. f.) by UPLC-ESI-MS/ MS[J]. Food Research International, 2013, 51(2): 467-473.
[43] 尹亮亮, 董静, 徐英, 等. 应用负的ESI-IT-TOF/MSⁿ研究黄酮类化合物的裂解规律[C]// 第九届全国中药和天然药物学术研讨会大会报告及论文集. 北京: 中国药学会, 2007: 5.
[44] 孙冬梅, 董玉娟, 胥爱丽, 等. 葛根枳椇软胶囊中黄酮类化合物的UPLC/Q-TOF-MS快速分析[J]. 中草药, 2015, 46(7): 970-976.
[55] 温鹏飞. 葡萄多酚[M]. 北京: 中国农业科学技术出版社, 2012: 2-8.
[46] 傅瑜. 杨梅叶原花色素的结构鉴定以及对黑色素生成和细胞凋亡的作用研究[D]. 杭州: 浙江大学, 2015: 1-3.
[47] MONAGAS M, QUINTANILLA-LPEZ J E, GMEZ-CORDOVS C, et al. MALDI-TOF-MS analysis of plant proanthocyanidins[J]. Journal of Pharmaceutical and Biomedical Analysis, 2010, 51(2): 358-372.
[48] Hanton S D. Mass spectrometry of polymers and polymer surfaces[J]. Chemical Reviews, 2001, 101(2): 527-570.
[49] 王晓青, 陈栓虎. 基质辅助激光解吸电离飞行时间质谱在聚合物表征中的应用[J]. 质谱学报, 2008, 29(1): 51-59.
[50] 范铁男, 邹继宏, 卢行安, 等. MALDI—TOF质谱在细菌检测及鉴定中的研究进展[J]. 中国微生态学杂志, 2010, 22(3): 282-284.
[51] FULCRAND H, MAN C, PREYS S, et al. Direct mass spectrometry approaches to characterize polyphenol composition of complex samples[J]. Phytochemistry, 2008, 69(18): 3 131-3 138.
[52] MUELLER-HARVEY I. Analysis of hydrolysable tannins[J]. Animal Food Science and Technology, 2001, 91(1): 3-20.
[53] MAN C, SOMMERER N, YALCIN T, et al. Assessment of the molecular weight distribution of tannin fractions through MALDI-TOF-MS analysis of protein-tannin complexes[J]. Analytical Chemistry, 2007, 79(6): 2 239-2 248.
[54] TAKAHATA Y, OHNISHI-KAMEYAMA M, FURUTA S, et al. Highly polymerized procyanidins in brown soybean seed coat with a high radical-scavenging activity[J]. Journal of Agricultural and Food Chemistry, 2001, 49(12): 5 843-5 847.
[55] 陈小鑫. 抗氧化剂原花色素对蘑菇酪氨酸酶活性的影响及机理研究[D]. 厦门: 厦门大学, 2014: 34-37.
[56] 张亮亮. MALDI—TOF质谱联合NMR及HPLC分析植物单宁结构及抗氧化能力的研究[D]. 厦门: 厦门大学, 2009: 39-40.