2026-06-28T16:28:09Zhttps://www.radar-service.eu/oai/OAIHandler

10.22000/3812023-11-15T14:40:20Z

10.22000/381 Schnabel, Arianne Arianne Schnabel 0000-0002-2172-2905 Leibniz Institute of Plant Biochemistry, Department of Cell and Metabolic Biology Cotinguiba, Fernando Fernando Cotinguiba 0000-0002-7006-0768 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 Benedikt Athmer 0000-0002-0234-4398 Leibniz Institute of Plant Biochemistry, Department of Cell and Metabolic Biology Vogt, Thomas Thomas Vogt 0000-0001-6155-3360 Leibniz Institute of Plant Biochemistry, Department of Cell and Metabolic Biology Thomas Vogt 2019-2020 2021 Biochemistry black pepper, cytochrome P450, enzyme activity, methylenedioxy bridge, piperine, Piper nigrum, yeast expression, raw data chromatograms, Excel data, sequence data chromatograms, raw data, excel files (zipped) Open Access Creative Commons Attribution 4.0 International Leibniz Institute of Plant Biochemistry 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. Waters e2695 chromatography workstation with photodiode array detector (PDA) and a QDA mass detector (Waters) BioRad CFX ConnectTM Real-Time System 10.3390/plants10010128 Deutsche Forschungsgemeinschaft (DFG) grid.424150.6 VO719/15-1 Deutsche Forschungsgemeinschaft (DFG) grid.424150.6 VO719/15-2 application/x-tar