Structural Elucidation of cis/trans Dicaffeoylquinic Acid Photoisomerization Using Ion Mobility Spectrometry-Mass Spectrometry
| Autor: | Yehia M. Ibrahim, Dennis G. Thomas, Mwadham M. Kabanda, Mpho M. Makola, Richard D. Smith, Xueyun Zheng, Heino M. Heyman, Niranjan Govind, Ntakadzeni E. Madala, Erin S. Baker, Ryan S. Renslow, Ian K. Webb, Liulin Deng, Ian A. Dubery |
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| Rok vydání: | 2017 |
| Předmět: |
Photoisomerization
010405 organic chemistry Chemistry Ion-mobility spectrometry Stereochemistry 010401 analytical chemistry Dicaffeoylquinic acid Health benefits Mass spectrometry 01 natural sciences Article 0104 chemical sciences Ion-mobility spectrometry–mass spectrometry General Materials Science Physical and Theoretical Chemistry Cis–trans isomerism |
| Zdroj: | The Journal of Physical Chemistry Letters. 8:1381-1388 |
| ISSN: | 1948-7185 |
| Popis: | Due to the recently uncovered health benefits and anti-HIV activities of dicaffeoylquinic acids (diCQAs), understanding their structures and functions is of great interest for drug discovery efforts. DiCQAs are analytically challenging to identify and quantify since they commonly exist as a diverse mixture of positional and geometric (cis/trans) isomers. In this work, we utilized ion mobility spectrometry coupled with mass spectrometry to separate the various isomers before and after UV irradiation. The experimental collision cross sections were then compared with theoretical structures to differentiate and identify the diCQA isomers. Our analyses found that naturally the diCQAs existed predominantly as trans/trans isomers, but after 3 h of UV irradiation, cis/cis, cis/trans, trans/cis, and trans/trans isomers were all present in the mixture. This is the first report of successful differentiation of cis/trans diCQA isomers individually, which shows the great promise of IMS coupled with theoretical calculations for determining the structure and activity relationships of different isomers in drug discovery studies. |
| Databáze: | OpenAIRE |
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