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Activity-Guided Identification of (S)-Malic Acid 1-O-d-Glucopyranoside (Morelid) and γ-Aminobutyric Acid as Contributors to Umami Taste and Mouth-Drying Oral Sensation of Morel Mushrooms (Morchella deliciosa Fr.)

Nina Rotzoll,^† Andreas Dunkel,^# and Thomas Hofmann*^#

Deutsche Forschungsanstalt fr Lebensmittelchemie, Lichtenbergstrasse 4, D-85748 Garching, Germany, and Institut fr Lebensmittelchemie, Universitt Mnster, Corrensstrasse 45, D-48149 Mnster, Germany

J. Agric. Food Chem., 2005, 53 (10), pp 4149–4156

DOI: 10.1021/jf050056i

Publication Date (Web): April 21, 2005

†

Deutsche Forschungsanstalt für Lebensmittelchemie.

Institut für Lebensmittelchemie.

Author to whom correspondence should be addressed (telephone +49-251-83-33-391; fax +49-251-83-33-396; e-mail thomas.hofmann@uni-muenster.de).

Abstract

Although morel mushrooms are widely used as tasty ingredients in savory dishes, knowledge of the key compounds evoking their attractive taste is still very fragmentary. In the present study, taste activity-guided fractionation of an aqueous morel extract by means of the recently developed taste dilution analysis (TDA) enabled the localization of several umami-like-tasting fractions as well as a fraction imparting an intense mouth-drying sensation to the oral cavity. Hydrophilic interaction liquid chromatography (HILIC), LC-MS, and amino acid analysis led to the successful identification of γ-aminobutyric acid as the chemical inducer of the mouth-drying and mouth-coating oral sensations imparted by the morel extract. Besides the well-known umami-like taste contributors l-glutamic acid, l-aspartic acid, and succinic acid, an additional HILIC fraction was isolated and evaluated as tasting umami-like. LC-MS and NMR studies revealed that this fraction consisted of a mixture of (S)-malic acid 1-O-α-d-glucopyranoside and (S)-malic acid 1-O-β-d-glucopyranoside, the structure of which could be successfully confirmed by independent synthesis. To the best of our knowledge, this morel-derived glycoside, which we named (S)-morelid, has previously not been reported in any food products. Sensory analysis of aqueous solutions of the compounds identified revealed threshold concentrations of 0.02 mmol/L for the mouth-drying effect of γ-aminobutyric acid and 6.0 mmol/L for the umami-like, slightly sour taste of (S)-morelid.

Keywords: Umami; mouth-drying; mushrooms; taste dilution analysis; morelid; (S)-malic acid 1-O-β-d-glucopyranoside; γ-aminobutyric acid

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