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Article

Piper nigrum CYP719A37 Catalyzes the Decisive Methylenedioxy Bridge Formation in Piperine Biosynthesis

1
Leibniz Institute of Plant Biochemistry, Department Cell and Metabolic Biology, Weinberg 3, D-06120 Halle (Saale), Germany
2
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, Brazil
*
Author to whom correspondence should be addressed.
Plants 2021, 10(1), 128; https://doi.org/10.3390/plants10010128
Received: 7 December 2020 / Revised: 5 January 2021 / Accepted: 6 January 2021 / Published: 9 January 2021
(This article belongs to the Special Issue Plant Phenolics: Occurrence, Biosynthesis, and Biological Roles)
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 specificity, storage, and phylogenetic origin of CYP719 catalyzed reactions in magnoliids and eudicots. View Full-Text
Keywords: black pepper; cytochrome P450; enzyme activity; methylenedioxy bridge; piperine; Piper nigrum; yeast expression black pepper; cytochrome P450; enzyme activity; methylenedioxy bridge; piperine; Piper nigrum; yeast expression
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MDPI and ACS Style

Schnabel, A.; Cotinguiba, F.; Athmer, B.; Vogt, T. Piper nigrum CYP719A37 Catalyzes the Decisive Methylenedioxy Bridge Formation in Piperine Biosynthesis. Plants 2021, 10, 128. https://doi.org/10.3390/plants10010128

AMA Style

Schnabel A, Cotinguiba F, Athmer B, Vogt T. Piper nigrum CYP719A37 Catalyzes the Decisive Methylenedioxy Bridge Formation in Piperine Biosynthesis. Plants. 2021; 10(1):128. https://doi.org/10.3390/plants10010128

Chicago/Turabian Style

Schnabel, Arianne, Fernando Cotinguiba, Benedikt Athmer, and Thomas Vogt. 2021. "Piper nigrum CYP719A37 Catalyzes the Decisive Methylenedioxy Bridge Formation in Piperine Biosynthesis" Plants 10, no. 1: 128. https://doi.org/10.3390/plants10010128

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