| Investigation of Isomeric Transformations of Chlorogenic Acid in Buffers and Biological Matrices by Ultra Performance Liquid Chromatography Coupled with Hybrid Quadrupole/Ion Mobility/Orthogonal Acceleration Time-of-flight Mass Spectrometry. | |
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MedLine Citation:
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PMID: 21942218 Owner: NLM Status: Publisher |
Abstract/OtherAbstract:
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Ultra performance liquid chromatography coupled with hybrid quadrupole/ion mobility/orthogonal acceleration time-of-flight (<i>oa</i>-TOF) mass spectrometry (UPLC-IM-MS) was used to study the isomeric transformations of <i>trans</i>-5-caffeoylquinic acid, an extremely active compound present in multiple vegetables, fruits, and beverages. The UPLC/<i>oa</i>-TOF MS results proved that in phosphate buffer (pH 7.4), plasma or urine sample, <i>trans</i>-5-caffeoylquinic acid first isomerizes to <i>trans</i>-4-caffeoylquinic acid, and then to <i>trans</i>-3-caffeoylquinic acid by intramolecular acyl migration. When exposed to UV light, <i>trans</i>-3-, -4-, and -5-caffeoylquinic acids undergo <i>cis/trans</i> isomerization to form <i>cis</i> 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 <i>cis/trans</i> 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. |
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Authors:
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Cen Xie; Kate Yu; Dafang Zhong; Tao Yuan; Fei Ye; Joseph Andy Jarrell; Alan Millar; Xiaoyan Chen |
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Publication Detail:
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Type: JOURNAL ARTICLE Date: 2011-9-25 |
Journal Detail:
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Title: Journal of agricultural and food chemistry Volume: - ISSN: 1520-5118 ISO Abbreviation: - Publication Date: 2011 Sep |
Date Detail:
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Created Date: 2011-9-27 Completed Date: - Revised Date: - |
Medline Journal Info:
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Nlm Unique ID: 0374755 Medline TA: J Agric Food Chem Country: - |
Other Details:
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Languages: ENG Pagination: - Citation Subset: - |
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From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
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