Characterization by LC-MS(n) of four new classes of chlorogenic acids in green coffee beans: dimethoxycinnamoylquinic acids, diferuloylquinic acids, caffeoyl-dimethoxycinnamoylquinic acids, and feruloyl-dimethoxycinnamoylquinic acids

Journal of Agricultural and Food Chemistry
Michael N CliffordNikolai Kuhnert

Abstract

LC-MS4 has been used to detect and characterize in green coffee beans 12 chlorogenic acids not previously reported in nature. These comprise three isomeric dimethoxycinnamoylquinic acids (7-9) (Mr 382), three caffeoyl-dimethoxycinnamoylquinic acids (22, 24, and 26) (Mr 544), three diferuloylquinic acids (13-15) (Mr 544), and three feruloyl-dimethoxycinnamoylquinic acids (28, 30, and 32) (Mr 558). Structures have been assigned on the basis of LC-MS4 patterns of fragmentation and relative hydrophobicity and, in the case of the dimethoxycinnamoylquinic acids, by comparison with authentic standards. Several new structure-diagnostic fragmentations have been identified for use with diacyl-chlorogenic acids, for example, m/z 299 and 255 for C4 caffeoyl, m/z 313 and 269 for C4 feruloyl, nearly equal elimination of both cinnamoyl residues for vic-3,4-diacyl, and an increasing ratio of "dehydrated" ions to "non-dehydrated" ions at MS2 with increasing methylation of those cinnamoyl residues. Possible mechanisms have been proposed to account for the fragmentations observed. The mass spectrometric resolution of six isomeric chlorogenic acids (Mr 544) in a crude plant extract by fragment-targeted LC-MS2 and LC-MS3 experiments illustrates the...Continue Reading

References

May 12, 2005·Journal of Agricultural and Food Chemistry·Michael N CliffordNikolai Kuhnert

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Citations

Jan 10, 2012·Journal of Agricultural and Food Chemistry·Feifei WeiMasaru Tanokura
May 9, 2013·Journal of Agricultural and Food Chemistry·W MullenE Combet
Aug 22, 2012·Journal of Proteome Research·Sofia MocoSerge Rezzi
Jun 19, 2013·Critical Reviews in Food Science and Nutrition·Jianbo XiaoXiaoqing Chen
Jun 19, 2013·Critical Reviews in Food Science and Nutrition·Rohit Upadhyay, L Jagan Mohan Rao
Feb 9, 2013·Critical Reviews in Food Science and Nutrition·Jianbo XiaoXiaoqing Chen
Mar 8, 2014·Journal of Pharmaceutical and Biomedical Analysis·Federico FerreresPaula B Andrade
Apr 2, 2011·Phytochemistry·Rakesh JaiswalNikolai Kuhnert
Oct 22, 2008·Survey of Ophthalmology·M MozaffariehJ Flammer
Apr 25, 2015·Journal of Agricultural and Food Chemistry·Naira Poerner RodriguesNeura Bragagnolo
Sep 3, 2013·Food Chemistry·Charlotte E MillsJeremy P E Spencer
Aug 31, 2014·Food Chemistry·Valentina SinisiFederico Berti
Aug 16, 2014·Bioscience, Biotechnology, and Biochemistry·Sari HondaToshiya Masuda
Jun 18, 2014·Natural Product Research·Mohamed A FaragLudger A Wessjohann
Aug 12, 2014·Critical Reviews in Food Science and Nutrition·Jianbo XiaoXiaoqing Chen
Oct 1, 2016·International Journal of Molecular Sciences·Yoshinori MikamiToshiko Yamazawa
Jan 29, 2017·Chemistry & Biodiversity·Hu ZhangHong-Hua Wu
Sep 13, 2013·Journal of Food Science·Mohamed A Farag, Paul W Paré
Dec 6, 2006·Phytochemical Analysis : PCA·Michael N CliffordNikolai Kuhnert
Dec 1, 2006·Journal of Mass Spectrometry : JMS
Feb 25, 2010·Natural Product Reports·James Warren DrynanNikolai Kuhnert
Oct 14, 2010·Rapid Communications in Mass Spectrometry : RCM·Michael N CliffordNikolai Kuhnert
Jul 29, 2009·Natural Product Reports·Alan CrozierMichael N Clifford
Jun 9, 2012·Organic & Biomolecular Chemistry·Rakesh JaiswalNikolai Kuhnert
Sep 14, 2012·Journal of Clinical Gastroenterology·Luca CalaniDaniele Del Rio

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