PLANTS CYP719 RADAR

DOI

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

Identifier
DOI https://doi.org/10.22000/381
Related Identifier https://doi.org/10.3390/plants10010128
Metadata Access https://www.radar-service.eu/oai/OAIHandler?verb=GetRecord&metadataPrefix=datacite&identifier=10.22000/381
Provenance
Creator Schnabel, Arianne ORCID logo; Cotinguiba, Fernando ORCID logo; Athmer, Benedikt ORCID logo; Vogt, Thomas ORCID logo
Publisher Thomas Vogt
Contributor RADAR
Publication Year 2021
Funding Reference Deutsche Forschungsgemeinschaft (DFG) grid.424150.6 GRID VO719/15-1 ; Deutsche Forschungsgemeinschaft (DFG) grid.424150.6 GRID VO719/15-2
Rights Open Access; Creative Commons Attribution 4.0 International; info:eu-repo/semantics/openAccess; https://creativecommons.org/licenses/by/4.0/legalcode
OpenAccess true
Representation
Resource Type chromatograms, raw data, excel files (zipped); Dataset
Format application/x-tar
Discipline Basic Biological and Medical Research; Biochemistry; Biology; Life Sciences
Temporal Coverage 2019-2020