Chlorogenic acid-arabinose hybrid domains in coffee melanoidins: Evidences from a model system
authors Moreira, ASP; Coimbra, MA; Nunes, FM; Passos, CP; Santos, SAO; Silvestre, AJD; Silva, AMN; Rangel, M; Domingues, MRM
nationality International
journal FOOD CHEMISTRY
author keywords Roasting; Polysaccharides; Arabinogalactans; Caffeoylquinic acid; Transglycosylation; Mass spectrometry
keywords SUPERHEATED WATER EXTRACTION; MASS-SPECTROMETRY; BREW MELANOIDINS; CINNAMOYLSHIKIMATE ESTERS; PHENOLIC-COMPOUNDS; MOLECULAR-WEIGHT; LACTONES; POLYSACCHARIDES; MECHANISMS; BEANS
abstract 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.
publisher ELSEVIER SCI LTD
issn 0308-8146
year published 2015
volume 185
beginning page 135
ending page 144
digital object identifier (doi) 10.1016/j.foodchem.2015.03.086
web of science category Chemistry, Applied; Food Science & Technology; Nutrition & Dietetics
subject category Chemistry; Food Science & Technology; Nutrition & Dietetics
unique article identifier WOS:000355027100018
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journal impact factor 6.306
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