Co-Oxidative Transformation of Piperine to Piperonal and 3,4-Methylenedioxycinnamaldehyde by a Lipoxygenase from Pleurotus sapidus |
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| Authors: | Nina-Katharina Krahe Prof. Dr. Dr. Ralf G. Berger Lukas Kahlert Dr. Franziska Ersoy |
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| Affiliation: | 1. Institut für Lebensmittelchemie, Gottfried Wilhelm Leibniz Universität Hannover, Callinstr. 5, 30167 Hannover, Germany;2. Institut für Lebensmittelchemie, Gottfried Wilhelm Leibniz Universität Hannover, Callinstr. 5, 30167 Hannover, Germany Present address: Institut für Organische Chemie und, Biomolekulares Wirkstoffzentrum, Gottfried Wilhelm Leibniz Universität Hannover, Schneiderberg 38, 30167 Hannover, Germany |
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| Abstract: | The valuable aroma compound piperonal with its vanilla-like olfactory properties is of high interest for the fragrance and flavor industry. A lipoxygenase (LOXPsa1) of the basidiomycete Pleurotus sapidus was identified to convert piperine, the abundant pungent principle of black pepper (Piper nigrum), to piperonal and a second volatile product, 3,4-methylenedioxycinnamaldehyde, with a vanilla-like odor through an alkene cleavage. The reaction principle was co-oxidation, as proven by its dependence on the presence of linoleic or α-linolenic acid, common substrates of lipoxygenases. Optimization of the reaction conditions (substrate concentrations, reaction temperature and time) led to a 24-fold and 15-fold increase of the piperonal and 3,4-methylenedioxycinnamaldehyde concentration using the recombinant enzyme. Monokaryotic strains showed different concentrations of and ratios between the two reaction products. |
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| Keywords: | biotransformations cleavage reactions co-oxidation lipoxygenase piperonal |
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