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Structure determination and sensory analysis of bitter-tasting 4-vinylcatechol oligomers and their identification in roasted coffee by means of LC-MS/MS.
J Agric Food Chem. 2007 Mar 07; 55(5):1945-54.JA

Abstract

Aimed at elucidating intense bitter-tasting molecules in coffee, various bean ingredients were thermally treated in model experiments and evaluated for their potential to produce bitter compounds. As caffeic acid was found to generate intense bitterness reminiscent of the bitter taste of a strongly roasted espresso-type coffee, the reaction products formed were screened for bitter compounds by means of taste dilution analysis, and the most bitter tastants were isolated and purified. LC-MS/MS as well as 1-D/2-D NMR experiments enabled the identification of 10 bitter compounds with rather low recognition threshold concentrations ranging between 23 and 178 micromol/L. These bitter compounds are the previously unreported 1,3-bis(3',4'-dihydroxyphenyl) butane, trans-1,3-bis(3',4'-dihydroxyphenyl)-1-butene, and eight multiply hydroxylated phenylindanes, among which five derivatives are reported for the first time. In addition, the occurrence of each of these bitter compounds in a coffee brew was verified by means of LC-MS/MS (ESI-) operating in the multiple reaction monitoring (MRM) mode. The structures of these bitter compounds show strong evidence that they are generated by oligomerization of 4-vinylcatechol released from caffeic acid moieties upon roasting.

Authors+Show Affiliations

Frank O
Lehrstuhl für Lebensmittelchemie und Molekulare Sensorik, Technische Universität München, Lise-Meitner-Strasse 34, D-85350 Freising-Weihenstephan, Germany.
Blumberg S
No affiliation info available
Kunert C
No affiliation info available
Zehentbauer G
No affiliation info available
Hofmann T
No affiliation info available

MeSH

Caffeic AcidsCatecholsChromatography, LiquidCoffeaCoffeeHot TemperatureMagnetic Resonance SpectroscopyMass SpectrometryMolecular StructureSeedsTaste

Pub Type(s)

Journal Article

Language

eng

PubMed ID

17269788

Citation

Frank, Oliver, et al. "Structure Determination and Sensory Analysis of Bitter-tasting 4-vinylcatechol Oligomers and Their Identification in Roasted Coffee By Means of LC-MS/MS." Journal of Agricultural and Food Chemistry, vol. 55, no. 5, 2007, pp. 1945-54.
Frank O, Blumberg S, Kunert C, et al. Structure determination and sensory analysis of bitter-tasting 4-vinylcatechol oligomers and their identification in roasted coffee by means of LC-MS/MS. J Agric Food Chem. 2007;55(5):1945-54.
Frank, O., Blumberg, S., Kunert, C., Zehentbauer, G., & Hofmann, T. (2007). Structure determination and sensory analysis of bitter-tasting 4-vinylcatechol oligomers and their identification in roasted coffee by means of LC-MS/MS. Journal of Agricultural and Food Chemistry, 55(5), 1945-54.
Frank O, et al. Structure Determination and Sensory Analysis of Bitter-tasting 4-vinylcatechol Oligomers and Their Identification in Roasted Coffee By Means of LC-MS/MS. J Agric Food Chem. 2007 Mar 7;55(5):1945-54. PubMed PMID: 17269788.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Structure determination and sensory analysis of bitter-tasting 4-vinylcatechol oligomers and their identification in roasted coffee by means of LC-MS/MS. AU - Frank,Oliver, AU - Blumberg,Simone, AU - Kunert,Christof, AU - Zehentbauer,Gerhard, AU - Hofmann,Thomas, Y1 - 2007/02/02/ PY - 2007/2/3/pubmed PY - 2007/6/21/medline PY - 2007/2/3/entrez SP - 1945 EP - 54 JF - Journal of agricultural and food chemistry JO - J Agric Food Chem VL - 55 IS - 5 N2 - Aimed at elucidating intense bitter-tasting molecules in coffee, various bean ingredients were thermally treated in model experiments and evaluated for their potential to produce bitter compounds. As caffeic acid was found to generate intense bitterness reminiscent of the bitter taste of a strongly roasted espresso-type coffee, the reaction products formed were screened for bitter compounds by means of taste dilution analysis, and the most bitter tastants were isolated and purified. LC-MS/MS as well as 1-D/2-D NMR experiments enabled the identification of 10 bitter compounds with rather low recognition threshold concentrations ranging between 23 and 178 micromol/L. These bitter compounds are the previously unreported 1,3-bis(3',4'-dihydroxyphenyl) butane, trans-1,3-bis(3',4'-dihydroxyphenyl)-1-butene, and eight multiply hydroxylated phenylindanes, among which five derivatives are reported for the first time. In addition, the occurrence of each of these bitter compounds in a coffee brew was verified by means of LC-MS/MS (ESI-) operating in the multiple reaction monitoring (MRM) mode. The structures of these bitter compounds show strong evidence that they are generated by oligomerization of 4-vinylcatechol released from caffeic acid moieties upon roasting. SN - 0021-8561 UR - https://www.unboundmedicine.com/medline/citation/17269788/Structure_determination_and_sensory_analysis_of_bitter_tasting_4_vinylcatechol_oligomers_and_their_identification_in_roasted_coffee_by_means_of_LC_MS/MS_ DB - PRIME DP - Unbound Medicine ER -