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(Is Supplement To) 10.3390/plants10010128 - DOI
Schnabel, Arianne [Leibniz Institute of Plant Biochemistry, Department of Cell and Metabolic Biology]
Cotinguiba, Fernando [Instituto de Pesquisas de Produtos Naturais (IPPN), Universidade Federal do Rio de Janeiro (UFRJ), Avenida Carlos Chagas Filho, 373, 21941-902, Rio de Janeiro/RJ, Brasil]
Athmer, Benedikt [Leibniz Institute of Plant Biochemistry, Department of Cell and Metabolic Biology]
Vogt, Thomas [Leibniz Institute of Plant Biochemistry, Department of Cell and Metabolic Biology]
Additional titles:
(Alternative Title) Piper nigrum CYP719A37 catalyses the decisive methylenedioxy bridge formation in piperine biosynthesis
(Abstract) Black pepper (Piper nigrum) is among the world’s most popular spices. Its pungent principle, piperine, has already been identified 200 years ago, yet the biosynthesis of piperine in black pepper remains largely enigmatic. In this report we analyzed the characteristic methylenedioxy bridge formation of the aromatic part of piperine by a combination of RNA-sequencing, functional expression in yeast, and LC-MS based analysis of substrate and product profiles. We identified a single cytochrome P450 transcript, specifically expressed in black pepper immature fruits. The corresponding gene was functionally expressed in yeast (Saccharomyces cerevisiae) and characterized for substrate specificity with a series of putative aromatic precursors with an aromatic vanilloid structure. Methylenedioxy bridge formation was only detected when feruperic acid (5-(4-hydroxy-3-methoxyphenyl)-2,4-pentadienoic acid) was used as a substrate, and the corresponding product was identified as piperic acid. Two alternative precursors, ferulic acid and feruperine, were not accepted. Our data provide experimental evidence that formation of the piperine methylenedioxy bridge takes place in young black pepper fruits after a currently hypothetical chain elongation of ferulic acid and before the formation of the amide bond. The partially characterized enzyme was classified as CYP719A37 and is discussed in terms of the phylogenetic origin of CYP719 catalysed reactions in magnoliids and eudicots.
black pepper, cytochrome P450, enzyme activity, methylenedioxy bridge, piperine, Piper nigrum, yeast expression, raw data chromatograms, Excel data, sequence data
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Thomas Vogt
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Resource type:
(Dataset) chromatograms, raw data, excel files (zipped)
Data source:
(Instrument) Waters e2695 chromatography workstation with photodiode array detector (PDA) and a QDA mass detector (Waters)
(Instrument) BioRad CFX ConnectTM Real-Time System
Software used:
Resource Processing
Microsoft Office - 2013
Systat SigmaPlot - 14.0
Serif Affinity Graphics - unknown
Biomatters Geneious - 11.0
DNAStar Lasergene Package incl. EditSeq, Protean, Megalign - 11
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Software used:
Resource Production
Waters Empower - 3
BioRad CFX (qPCR) - 2.1
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Leibniz Institute of Plant Biochemistry
Deutsche Forschungsgemeinschaft (DFG) - (VO719/15-1)
Deutsche Forschungsgemeinschaft (DFG) - (VO719/15-2)
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