Investigation of Isomeric Transformations of Chlorogenic Acid in Buffers and Biological Matrixes by Ultraperformance Liquid Chromatography Coupled with Hybrid Quadrupole/Ion Mobility/Orthogonal Acceleration Time-of-Flight Mass Spectrometry

doi:10.1021/jf203104k

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	Investigation of Isomeric Transformations of Chlorogenic Acid in Buffers and Biological Matrixes by Ultraperformance Liquid Chromatography Coupled with Hybrid Quadrupole/Ion Mobility/Orthogonal Acceleration Time-of-Flight Mass Spectrometry
	Xie, Cen1 ; Yu, Kate 2; Zhong, Dafang1 ; Yuan, Tao 1; Ye, Fei 1; Jarrell, Joseph Andy 2; Millar, Alan 2; Chen, Xiaoyan1
刊名	JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY
	2011-10-26
卷号	59 期号:20 页码:11078-11087
关键词	chlorogenic acid acyl migration cis/trans isomerization ultraperformance liquid chromatography coupled with hybrid quadrupole/time-of-flight mass spectrometry ion mobility
ISSN号	0021-8561
DOI	10.1021/jf203104k
文献子类	Article
英文摘要	Ultraperformance liquid chromatography coupled with hybrid quadrupole/ion mobility/orthogonal acceleration time-of-flight (oa-TOF) mass spectrometry (UPLC-IM-MS) was used to study the isomeric transformations of trans-5-caffeoylquinic acid, an extremely active compound present in multiple vegetables, fruits, and beverages. The UPLC/oa-TOF MS results proved that in phosphate buffer (pH 7.4), plasma, or urine sample, trans-5-caffeoylquinic acid first isomerizes to trans-4-caffeoylquinic acid and then to trans-3-caffeoylquinic acid by intramolecular acyl migration. When exposed to UV light, trans-3-, -4-, and -5-caffeoylquinic acids undergo cis/trans isomerization to form cis isomers. The isomerization was solely dependent on the pH of the matrix, as well as the incubation temperature, and was independent of metabolic enzymes. UPLC-IM-MS results revealed that a reversible cis/trans isomerization of caffeoylquinic acids could also be induced by the electric field in an electrospray source. Thus, understanding the possible role of electric field-induced isomerization of caffeoylquinic acids may help lessen the confusion between gas phase phenomena and liquid state chemistry when applying IM-MS analysis. The comprehensive understanding of caffeoylquinic acid isomerization transformations is crucial for the appropriate handling of samples and interpretation of experimental data.
资助项目	National Natural Science Foundation of China[81173115] ; National Basic Research Program of China[2009CB930300]
WOS关键词	ION MOBILITY SPECTROMETRY ; LC-MSN ; RAT PLASMA ; POLYPHENOL ; AZOBENZENE ; TOFMS
WOS研究方向	Agriculture ; Chemistry ; Food Science & Technology
语种	英语
出版者	AMER CHEMICAL SOC
WOS记录号	WOS:000295915000040
内容类型	期刊论文
源URL	[http://119.78.100.183/handle/2S10ELR8/278366]
专题	上海药物代谢研究中心
通讯作者	Chen, Xiaoyan
作者单位	1.Chinese Acad Sci, Shanghai Inst Mat Med, Shanghai 201203, Peoples R China; 2.Waters Corp, Milford, MA 01757 USA
推荐引用方式 GB/T 7714	Xie, Cen,Yu, Kate,Zhong, Dafang,et al. Investigation of Isomeric Transformations of Chlorogenic Acid in Buffers and Biological Matrixes by Ultraperformance Liquid Chromatography Coupled with Hybrid Quadrupole/Ion Mobility/Orthogonal Acceleration Time-of-Flight Mass Spectrometry[J]. JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY,2011,59(20):11078-11087.
APA	Xie, Cen.,Yu, Kate.,Zhong, Dafang.,Yuan, Tao.,Ye, Fei.,...&Chen, Xiaoyan.(2011).Investigation of Isomeric Transformations of Chlorogenic Acid in Buffers and Biological Matrixes by Ultraperformance Liquid Chromatography Coupled with Hybrid Quadrupole/Ion Mobility/Orthogonal Acceleration Time-of-Flight Mass Spectrometry.JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY,59(20),11078-11087.
MLA	Xie, Cen,et al."Investigation of Isomeric Transformations of Chlorogenic Acid in Buffers and Biological Matrixes by Ultraperformance Liquid Chromatography Coupled with Hybrid Quadrupole/Ion Mobility/Orthogonal Acceleration Time-of-Flight Mass Spectrometry".JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY 59.20(2011):11078-11087.