Co‐Oxidative Transformation of Piperine to Piperonal and 3,4‐Methylenedioxycinnamaldehyde by a Lipoxygenase from Pleurotus sapidus

Publikation: Beitrag in FachzeitschriftArtikelForschungPeer-Review

Autoren

  • Nina‐Katharina Krahe
  • Ralf G. Berger
  • Lukas Kahlert
  • Franziska Ersoy

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OriginalspracheEnglisch
Seiten (von - bis)2857-2861
Seitenumfang5
FachzeitschriftCHEMBIOCHEM
Jahrgang22
Ausgabenummer19
Frühes Online-Datum25 Mai 2021
PublikationsstatusVeröffentlicht - 3 Okt. 2021

Abstract

The valuable aroma compound piperonal with its vanilla-like olfactory properties is of high interest for the fragrance and flavor industry. A lipoxygenase (LOX Psa1) 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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Co‐Oxidative Transformation of Piperine to Piperonal and 3,4‐Methylenedioxycinnamaldehyde by a Lipoxygenase from Pleurotus sapidus. / Krahe, Nina‐Katharina; Berger, Ralf G.; Kahlert, Lukas et al.
in: CHEMBIOCHEM, Jahrgang 22, Nr. 19, 03.10.2021, S. 2857-2861.

Publikation: Beitrag in FachzeitschriftArtikelForschungPeer-Review

Krahe NK, Berger RG, Kahlert L, Ersoy F. Co‐Oxidative Transformation of Piperine to Piperonal and 3,4‐Methylenedioxycinnamaldehyde by a Lipoxygenase from Pleurotus sapidus. CHEMBIOCHEM. 2021 Okt 3;22(19):2857-2861. Epub 2021 Mai 25. doi: 10.1002/cbic.202100183
Krahe, Nina‐Katharina ; Berger, Ralf G. ; Kahlert, Lukas et al. / Co‐Oxidative Transformation of Piperine to Piperonal and 3,4‐Methylenedioxycinnamaldehyde by a Lipoxygenase from Pleurotus sapidus. in: CHEMBIOCHEM. 2021 ; Jahrgang 22, Nr. 19. S. 2857-2861.
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title = "Co‐Oxidative Transformation of Piperine to Piperonal and 3,4‐Methylenedioxycinnamaldehyde by a Lipoxygenase from Pleurotus sapidus",
abstract = "The valuable aroma compound piperonal with its vanilla-like olfactory properties is of high interest for the fragrance and flavor industry. A lipoxygenase (LOX Psa1) 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.",
keywords = "biotransformations, cleavage reactions, co-oxidation, lipoxygenase, piperonal",
author = "Nina‐Katharina Krahe and Berger, {Ralf G.} and Lukas Kahlert and Franziska Ersoy",
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AU - Krahe, Nina‐Katharina

AU - Berger, Ralf G.

AU - Kahlert, Lukas

AU - Ersoy, Franziska

N1 - Funding Information: This research was funded by the BMBF cluster Bioeconomy International 2015, grant number 031B0307A. We thank B. Fuchs for her preparatory work for this project and C. Theobald and N. Püth for the olfactory analysis of 3,4‐methylenedioxycinnamaldehyde. Open access funding enabled and organized by Projekt DEAL.

PY - 2021/10/3

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N2 - The valuable aroma compound piperonal with its vanilla-like olfactory properties is of high interest for the fragrance and flavor industry. A lipoxygenase (LOX Psa1) 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.

AB - The valuable aroma compound piperonal with its vanilla-like olfactory properties is of high interest for the fragrance and flavor industry. A lipoxygenase (LOX Psa1) 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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