Details
| Original language | English |
|---|---|
| Pages (from-to) | 2857-2861 |
| Number of pages | 5 |
| Journal | CHEMBIOCHEM |
| Volume | 22 |
| Issue number | 19 |
| Early online date | 25 May 2021 |
| Publication status | Published - 3 Oct 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.
Keywords
- biotransformations, cleavage reactions, co-oxidation, lipoxygenase, piperonal
ASJC Scopus subject areas
- Biochemistry, Genetics and Molecular Biology(all)
- Molecular Medicine
- Biochemistry, Genetics and Molecular Biology(all)
- Molecular Biology
- Biochemistry, Genetics and Molecular Biology(all)
- Biochemistry
- Chemistry(all)
- Organic Chemistry
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In: CHEMBIOCHEM, Vol. 22, No. 19, 03.10.2021, p. 2857-2861.
Research output: Contribution to journal › Article › Research › peer review
}
TY - JOUR
T1 - Co‐Oxidative Transformation of Piperine to Piperonal and 3,4‐Methylenedioxycinnamaldehyde by a Lipoxygenase from Pleurotus sapidus
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
Y1 - 2021/10/3
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.
KW - biotransformations
KW - cleavage reactions
KW - co-oxidation
KW - lipoxygenase
KW - piperonal
UR - http://www.scopus.com/inward/record.url?scp=85107399487&partnerID=8YFLogxK
U2 - 10.1002/cbic.202100183
DO - 10.1002/cbic.202100183
M3 - Article
VL - 22
SP - 2857
EP - 2861
JO - CHEMBIOCHEM
JF - CHEMBIOCHEM
SN - 1439-4227
IS - 19
ER -