| Structure determination of 3-O-caffeoyl-epi-gamma-quinide, an orphan bitter lactone in roasted coffee. | |
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MedLine Citation:
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PMID: 18817412 Owner: NLM Status: MEDLINE |
Abstract/OtherAbstract:
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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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Authors:
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Oliver Frank; Simone Blumberg; Gudrun Krümpel; Thomas Hofmann |
Publication Detail:
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Type: Journal Article Date: 2008-09-26 |
Journal Detail:
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Title: Journal of agricultural and food chemistry Volume: 56 ISSN: 1520-5118 ISO Abbreviation: J. Agric. Food Chem. Publication Date: 2008 Oct |
Date Detail:
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Created Date: 2008-10-15 Completed Date: 2008-12-24 Revised Date: - |
Medline Journal Info:
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Nlm Unique ID: 0374755 Medline TA: J Agric Food Chem Country: United States |
Other Details:
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Languages: eng Pagination: 9581-5 Citation Subset: IM |
Affiliation:
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Lehrstuhl für Lebensmittelchemie and Molekulare Sensorik, Technische Universität München, Lise-Meitner-Strasse 34, D-85350 Freising-Weihenstephan, Germany. |
Export Citation:
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| MeSH Terms | |
Descriptor/Qualifier:
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Chromatography, High Pressure Liquid Coffee / chemistry* Humans Lactones / chemistry* Magnetic Resonance Spectroscopy Quinic Acid / chemistry Taste Taste Threshold |
| Chemical | |
Reg. No./Substance:
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0/Coffee; 0/Lactones; 77-95-2/Quinic Acid |
From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
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