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Flavin-induced photodecomposition of sulfur-containing amino acids is decisive in the formation of beer lightstruck flavor

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Abstract

Photooxidation of sulfur-containing amino acids and derivatives readily occurs upon visible-light irradiation in the presence of flavins. The sulfur moiety seems pivotal for interaction, as was determined from kinetic analyses using laser flash photolysis spectroscopy. After photooxidation, the resulting radical intermediates were characterized by addition to a spin trap, followed by electron paramagnetic resonance spectroscopy and evaluation of the coupling constants. The presence of the proposed radical intermediates was strongly supported by the identification of the reaction products using mass spectrometry. Accordingly, feasible degradation pathways for various sulfur-containing amino acids and derivatives were proposed. It was finally proven that flavin-induced photoproduction of sulfhydryl radicals and recombination with a 3-methylbut-2-enyl radical, derived from the photodegradation of hop-derived isohumulones, are decisive in the formation of beer lightstruck flavor.

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Authors and Affiliations

  1. Ghent University, Faculty of Pharmaceutical Sciences, Laboratory of Pharmacognosy and Phytochemistry, Harelbekestraat 72, B-9000, Ghent, Belgium

    Kevin Huvaere & Denis De Keukeleire

  2. Royal Veterinary and Agricultural University, Department of Food Science, Food Chemistry, Rolighedsvej 30, DK-1958, Frederiksberg C, Denmark

    Mogens L. Andersen & Leif H. Skibsted

  3. Ghent University, Faculty of Pharmaceutical Sciences, Laboratory of Medical Biochemistry and Clinical Analysis, Harelbekestraat 72, B-9000, Ghent, Belgium

    Michael Storme & Jan Van Bocxlaer

Authors
  1. Kevin Huvaere
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  2. Mogens L. Andersen
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  3. Michael Storme
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  4. Jan Van Bocxlaer
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  5. Leif H. Skibsted
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  6. Denis De Keukeleire
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Correspondence to Denis De Keukeleire.

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This paper was published as part of the special issue in honour of the late Professor George S. Hammond.

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Huvaere, K., Andersen, M.L., Storme, M. et al. Flavin-induced photodecomposition of sulfur-containing amino acids is decisive in the formation of beer lightstruck flavor. Photochem Photobiol Sci 5, 961–969 (2006). https://doi.org/10.1039/b609337j

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