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Structure determination of 3-O-caffeoyl-epi-gamma-quinide, an orphan bitter lactone in roasted coffee.
J Agric Food Chem. 2008 Oct 22; 56(20):9581-5.JA

Abstract

Recent investigations on the bitterness of coffee as well as 5- O-caffeoyl quinic acid roasting mixtures indicated the existence of another, yet unknown, bitter lactone besides the previously identified bitter compounds 5- O-caffeoyl- muco-gamma-quinide, 3- O-caffeoyl-gamma-quinide, 4- O-caffeoyl- muco-gamma-quinide, 5- O-caffeoyl- epi-delta-quinide, and 4- O-caffeoyl-gamma-quinide. In the present study, this orphan bitter lactone was isolated from the reaction products generated by dry heating of 5- O-caffeoylquinic acid model, and its structure was determined as the previously unreported 3- O-caffeoyl- epi-gamma-quinide by means of liquid chromatography-mass spectrometry (LC-MS) and one-/two-dimensional NMR experiments. The occurrence of this bitter lactone, exhibiting a low bitter recognition threshold of 58 micromol/L, in coffee beverages could be confirmed by LC-MS/MS (negative electrospray ionization) operating in the multiple reaction monitoring mode.

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Publisher Full Text (DOI)

Authors+Show Affiliations

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

MeSH

Chromatography, High Pressure LiquidCoffeeHumansLactonesMagnetic Resonance SpectroscopyQuinic AcidTasteTaste Threshold

Pub Type(s)

Journal Article

Language

eng

PubMed ID

18817412

Citation

Frank, Oliver, et al. "Structure Determination of 3-O-caffeoyl-epi-gamma-quinide, an Orphan Bitter Lactone in Roasted Coffee." Journal of Agricultural and Food Chemistry, vol. 56, no. 20, 2008, pp. 9581-5.
Frank O, Blumberg S, Krümpel G, et al. Structure determination of 3-O-caffeoyl-epi-gamma-quinide, an orphan bitter lactone in roasted coffee. J Agric Food Chem. 2008;56(20):9581-5.
Frank, O., Blumberg, S., Krümpel, G., & Hofmann, T. (2008). Structure determination of 3-O-caffeoyl-epi-gamma-quinide, an orphan bitter lactone in roasted coffee. Journal of Agricultural and Food Chemistry, 56(20), 9581-5. https://doi.org/10.1021/jf802210a
Frank O, et al. Structure Determination of 3-O-caffeoyl-epi-gamma-quinide, an Orphan Bitter Lactone in Roasted Coffee. J Agric Food Chem. 2008 Oct 22;56(20):9581-5. PubMed PMID: 18817412.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Structure determination of 3-O-caffeoyl-epi-gamma-quinide, an orphan bitter lactone in roasted coffee. AU - Frank,Oliver, AU - Blumberg,Simone, AU - Krümpel,Gudrun, AU - Hofmann,Thomas, Y1 - 2008/09/26/ PY - 2008/9/27/pubmed PY - 2008/12/25/medline PY - 2008/9/27/entrez SP - 9581 EP - 5 JF - Journal of agricultural and food chemistry JO - J Agric Food Chem VL - 56 IS - 20 N2 - Recent investigations on the bitterness of coffee as well as 5- O-caffeoyl quinic acid roasting mixtures indicated the existence of another, yet unknown, bitter lactone besides the previously identified bitter compounds 5- O-caffeoyl- muco-gamma-quinide, 3- O-caffeoyl-gamma-quinide, 4- O-caffeoyl- muco-gamma-quinide, 5- O-caffeoyl- epi-delta-quinide, and 4- O-caffeoyl-gamma-quinide. In the present study, this orphan bitter lactone was isolated from the reaction products generated by dry heating of 5- O-caffeoylquinic acid model, and its structure was determined as the previously unreported 3- O-caffeoyl- epi-gamma-quinide by means of liquid chromatography-mass spectrometry (LC-MS) and one-/two-dimensional NMR experiments. The occurrence of this bitter lactone, exhibiting a low bitter recognition threshold of 58 micromol/L, in coffee beverages could be confirmed by LC-MS/MS (negative electrospray ionization) operating in the multiple reaction monitoring mode. SN - 1520-5118 UR - https://www.unboundmedicine.com/medline/citation/18817412/Structure_determination_of_3_O_caffeoyl_epi_gamma_quinide_an_orphan_bitter_lactone_in_roasted_coffee_ L2 - https://doi.org/10.1021/jf802210a DB - PRIME DP - Unbound Medicine ER -