A piperic acid CoA ligase produces a putative precursor of piperine, the pungent principle from black pepper fruits

Abstract

SummaryBlack pepper (Piper nigrum L.) is known for its high content of piperine, a cinnamoyl amide derivative regarded as largely responsible for the pungent taste of this widely used spice. Despite its long history and worldwide use, the biosynthesis of piperine and related amides has been enigmatic up to now. In this report we describe a specific piperic acid CoA ligase from immature green fruits of P. nigrum. The corresponding enzyme was cloned and functionally expressed in E. coli. The recombinant enzyme displays a high specificity for piperic acid and does not accept the structurally related feruperic acid characterized by a similar C‐2 extension of the general C6–C3 phenylpropanoid structure. The enzyme is also inactive with the standard set of hydroxycinnamic acids tested including caffeic acid, 4‐coumaric acid, ferulic acid, and sinapic acid. Substrate specificity is corroborated by in silico modelling that suggests a perfect fit for the substrate piperic acid to the active site of the piperic acid CoA ligase. The CoA ligase gene shows its highest expression levels in immature green fruits, is also expressed in leaves and flowers, but not in roots. Virus‐induced gene silencing provided some preliminary indications that the production of piperoyl‐CoA is required for the biosynthesis of piperine in black pepper fruits.

Construction of an Artificial Biosynthetic Pathway for the Styrylpyrone Compound 11-Methoxy-Bisnoryangonin Produced in Engineered Escherichia coli

“…Piper nigrum (black pepper) produces an alkaloid compound, piperine, which is derived from the polyketide pathway ( Geisler and Gross, 1990 ; Srinivasan, 2007 ). The corresponding PKS that provides the piperine polyketide chain has not been identified, but it is estimated that the CHS-like type III PKS can produce it ( Jin et al, 2020 ; Schnabel et al, 2020 ). In our investigation of piperine biosynthesis, we identified one CHS-like gene, pnpks , in the P. nigrum transcriptome data.…”

Target screening of plant secondary metabolites in river waters by liquid chromatography coupled to high-resolution mass spectrometry (LC–HRMS)

“…Nicotine is highly addictive and acts as a receptor agonist at most nicotinic acetylcholine receptors (nAChRs) [12]. Piperine is a major component of Piper species (e.g., Piper nigrum, Piper longum, Piper officinarum and Piper retrofractum), which are globally marketed as flavoring agent and cooking spice with a long history of human health benefits and a wide consumption [44,46]. Piperine has been found to have numerous medicinal applications such as antioxidant, antiplatelet, anti-inflammatory, antihypertensive, hepatoprotective, antithyroid, antitumor, antiasthmatic activity and has also been used as fertility enhancer [8].…”

Target screening of plant secondary metabolites in river waters by liquid chromatography coupled to high resolution mass spectrometry (LC-HRMS)

“…Nicotine is highly addictive and acts as a receptor agonist at most nicotinic acetylcholine receptors (nAChRs) (Godin et al 2019). Piperine is a major component of Piper species (e.g Piper nigrum, Piper longum, Piper o cinarum and Piper retrofractum), which are globally marketed as avoring agent and cooking spice with a long history of human health bene ts and a wide consumption (Shoba et al 1998;Schnabel et al 2020). Piperine has been found to have numerous medicinal applications such as antioxidant, antiplatelet, anti-in ammatory, antihypertensive, hepatoprotective, antithyroid, antitumor, antiasthmatic activity and has also been used as fertility enhance (Derosa et al…”