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Identification and Quantitation of Reaction Products from Quinic Acid, Quinic Acid Lactone, and Chlorogenic Acid with Strecker Aldehydes in Roasted Coffee.
J Agric Food Chem. 2021 Jan 27; 69(3):1027-1038.JA

Abstract

To gain comprehensive insight into the interactions of key coffee odorants, like the Strecker aldehydes, acetaldehyde, propanal, methylpropanal, 2- and 3-methylbutanal, and methional, and the nonvolatile fraction of coffee, an untargeted metabolomics approach was applied. Ultra performance liquid chromatography (UPLC)-time of flight (TOF)-mass spectrometry (ESI-) profiling followed by statistical data analysis revealed a marker substance for a coffee beverage spiked with acetaldehyde with an accurate mass of 217.0703 [M - H]-. This compound could be identified as a reaction product of quinic acid (QA) and acetaldehyde linked by acetalization at the cis-diol function of QA. Consequently, the acetalization of aldehydes, QA, 5-O-caffeoyl quinic acid (CQA), and quinic acid γ-lactone (QAL) was investigated by means of model reactions, followed by synthesis, isolation, and structure elucidation via UPLC-TOF-MS and 1D and 2D NMR techniques. UHPLC-MS/MSMRM screening and the quantification of aldehyde adducts in coffee beverages revealed the presence of QA/acetaldehyde, -/propanal, -/methylpropanal, and -/methional reaction products and CQA/acetaldehyde, -/propanal, -/methylpropanal, -/2- and 3-methylbutanal, and -/methional and QAL/acetaldehyde adducts for the first time, in concentrations of 12-270 μg/L for QA/aldehydes, 5-225 μg/L for CQA/aldehydes, and 62-173 μg/L for QAL/acetaldehyde. The sensory characterization of the identified compounds showed bitter taste recognition thresholds of 48-297 μmol/L for CQA adducts and 658 μmol/L for QAL/acetaldehyde, while the QA adducts showed no bitter taste (<2000 μmol/L).

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Publisher Full Text (DOI)

Authors+Show Affiliations

Chair of Food Chemistry and Molecular and Sensory Science, Technische Universität München, Lise-Meitner-Str. 34, D-85354 Freising, Germany.

Chair of Food Chemistry and Molecular and Sensory Science, Technische Universität München, Lise-Meitner-Str. 34, D-85354 Freising, Germany.

Chair of Food Chemistry and Molecular and Sensory Science, Technische Universität München, Lise-Meitner-Str. 34, D-85354 Freising, Germany.

Chair of Food Chemistry and Molecular and Sensory Science, Technische Universität München, Lise-Meitner-Str. 34, D-85354 Freising, Germany.

Chair of Food Chemistry and Molecular and Sensory Science, Technische Universität München, Lise-Meitner-Str. 34, D-85354 Freising, Germany.

Chair of Food Chemistry and Molecular and Sensory Science, Technische Universität München, Lise-Meitner-Str. 34, D-85354 Freising, Germany.

MeSH

AdultAldehydesChlorogenic AcidChromatography, High Pressure LiquidCoffeaCoffeeCookingFemaleHot TemperatureHumansLactonesMaleMolecular StructureQuinic AcidSeedsTandem Mass SpectrometryTasteYoung Adult

Pub Type(s)

Journal Article

Language

eng

PubMed ID

33433215

Citation

Gigl, Michael, et al. "Identification and Quantitation of Reaction Products From Quinic Acid, Quinic Acid Lactone, and Chlorogenic Acid With Strecker Aldehydes in Roasted Coffee." Journal of Agricultural and Food Chemistry, vol. 69, no. 3, 2021, pp. 1027-1038.

Gigl M, Frank O, Barz J, et al. Identification and Quantitation of Reaction Products from Quinic Acid, Quinic Acid Lactone, and Chlorogenic Acid with Strecker Aldehydes in Roasted Coffee. J Agric Food Chem. 2021;69(3):1027-1038.

Gigl, M., Frank, O., Barz, J., Gabler, A., Hegmanns, C., & Hofmann, T. (2021). Identification and Quantitation of Reaction Products from Quinic Acid, Quinic Acid Lactone, and Chlorogenic Acid with Strecker Aldehydes in Roasted Coffee. Journal of Agricultural and Food Chemistry, 69(3), 1027-1038. https://doi.org/10.1021/acs.jafc.0c06887

Gigl M, et al. Identification and Quantitation of Reaction Products From Quinic Acid, Quinic Acid Lactone, and Chlorogenic Acid With Strecker Aldehydes in Roasted Coffee. J Agric Food Chem. 2021 Jan 27;69(3):1027-1038. PubMed PMID: 33433215.

* Article titles in AMA citation format should be in sentence-case

TY - JOUR T1 - Identification and Quantitation of Reaction Products from Quinic Acid, Quinic Acid Lactone, and Chlorogenic Acid with Strecker Aldehydes in Roasted Coffee. AU - Gigl,Michael, AU - Frank,Oliver, AU - Barz,Johanna, AU - Gabler,Anna, AU - Hegmanns,Christian, AU - Hofmann,Thomas, Y1 - 2021/01/12/ PY - 2021/1/13/pubmed PY - 2021/4/10/medline PY - 2021/1/12/entrez KW - Strecker aldehydes KW - aroma staling KW - chlorogenic acid KW - low molecular weight fraction KW - quinic acid KW - quinic acid lactone KW - roasted coffee KW - untargeted UPLC−TOF-MS screening SP - 1027 EP - 1038 JF - Journal of agricultural and food chemistry JO - J Agric Food Chem VL - 69 IS - 3 N2 - To gain comprehensive insight into the interactions of key coffee odorants, like the Strecker aldehydes, acetaldehyde, propanal, methylpropanal, 2- and 3-methylbutanal, and methional, and the nonvolatile fraction of coffee, an untargeted metabolomics approach was applied. Ultra performance liquid chromatography (UPLC)-time of flight (TOF)-mass spectrometry (ESI-) profiling followed by statistical data analysis revealed a marker substance for a coffee beverage spiked with acetaldehyde with an accurate mass of 217.0703 [M - H]-. This compound could be identified as a reaction product of quinic acid (QA) and acetaldehyde linked by acetalization at the cis-diol function of QA. Consequently, the acetalization of aldehydes, QA, 5-O-caffeoyl quinic acid (CQA), and quinic acid γ-lactone (QAL) was investigated by means of model reactions, followed by synthesis, isolation, and structure elucidation via UPLC-TOF-MS and 1D and 2D NMR techniques. UHPLC-MS/MSMRM screening and the quantification of aldehyde adducts in coffee beverages revealed the presence of QA/acetaldehyde, -/propanal, -/methylpropanal, and -/methional reaction products and CQA/acetaldehyde, -/propanal, -/methylpropanal, -/2- and 3-methylbutanal, and -/methional and QAL/acetaldehyde adducts for the first time, in concentrations of 12-270 μg/L for QA/aldehydes, 5-225 μg/L for CQA/aldehydes, and 62-173 μg/L for QAL/acetaldehyde. The sensory characterization of the identified compounds showed bitter taste recognition thresholds of 48-297 μmol/L for CQA adducts and 658 μmol/L for QAL/acetaldehyde, while the QA adducts showed no bitter taste (<2000 μmol/L). SN - 1520-5118 UR - https://www.unboundmedicine.com/medline/citation/33433215/Identification_and_Quantitation_of_Reaction_Products_from_Quinic_Acid_Quinic_Acid_Lactone_and_Chlorogenic_Acid_with_Strecker_Aldehydes_in_Roasted_Coffee_ DB - PRIME DP - Unbound Medicine ER -