Journal
FOOD CHEMISTRY
Volume 185, Issue -, Pages 135-144Publisher
ELSEVIER SCI LTD
DOI: 10.1016/j.foodchem.2015.03.086
Keywords
Roasting; Polysaccharides; Arabinogalactans; Caffeoylquinic acid; Transglycosylation; Mass spectrometry
Funding
- Fundacao para a Ciencia e a Tecnologia (FCT, Portugal) [PEst-C/QUI/UI0062/2013, FCOMP-01-0124-FEDER-037296, Pest-C/CTM/LA0011/2013, FCOMP-01-0124-FEDER-037271, NORTE-07-0162-FEDER-000048, NORTE-07-0124-FEDER-000066/67, PEst-C/EQB/LA0006/2011, REDE/1504/REM/2005]
- European Union [PEst-C/QUI/UI0062/2013, FCOMP-01-0124-FEDER-037296, Pest-C/CTM/LA0011/2013, FCOMP-01-0124-FEDER-037271, NORTE-07-0162-FEDER-000048, NORTE-07-0124-FEDER-000066/67, PEst-C/EQB/LA0006/2011, REDE/1504/REM/2005]
- QREN [PEst-C/QUI/UI0062/2013, FCOMP-01-0124-FEDER-037296, Pest-C/CTM/LA0011/2013, FCOMP-01-0124-FEDER-037271, NORTE-07-0162-FEDER-000048, NORTE-07-0124-FEDER-000066/67, PEst-C/EQB/LA0006/2011, REDE/1504/REM/2005]
- FEDER [PEst-C/QUI/UI0062/2013, FCOMP-01-0124-FEDER-037296, Pest-C/CTM/LA0011/2013, FCOMP-01-0124-FEDER-037271, NORTE-07-0162-FEDER-000048, NORTE-07-0124-FEDER-000066/67, PEst-C/EQB/LA0006/2011, REDE/1504/REM/2005]
- COMPETE [PEst-C/QUI/UI0062/2013, FCOMP-01-0124-FEDER-037296, Pest-C/CTM/LA0011/2013, FCOMP-01-0124-FEDER-037271, NORTE-07-0162-FEDER-000048, NORTE-07-0124-FEDER-000066/67, PEst-C/EQB/LA0006/2011, REDE/1504/REM/2005]
- FCT [SFRH/BD/80553/2011, SFRH/BDP/65718/2009]
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Arabinose from arabinogalactan side chains was hypothesized as a possible binding site for chlorogenic acids in coffee melanoidins. To investigate this hypothesis, a mixture of 5-O-caffeoylquinic acid (5-CQA), the most abundant chlorogenic acid in green coffee beans, and (alpha 1 -> 5)-L-arabinotriose, structurally related to arabinogalactan side chains, was submitted to dry thermal treatments. The compounds formed during thermal processing were identified by electrospray ionization mass spectrometry (ESI-MS) and characterized by tandem MS (ESI-MSn). Compounds composed by one or two CQAs covalently linked with pentose (Pent) residues (1-12) were identified, along with compounds bearing a sugar moiety but composed exclusively by the quinic or caffeic acid moiety of CQAs. The presence of isomers was demonstrated by liquid chromatography online coupled to ESI-MS and ESI-MSn. Pent(1-2)CQA were identified in coffee samples. These results give evidence for a diversity of chlorogenic acid arabinose hybrids formed during roasting, opening new perspectives for their identification in melanoidin structures. (C) 2015 Elsevier Ltd. All rights reserved.
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