Abstract
Black pepper (Piper nigrum L.) is the world’s most popular spice and is also used as an ingredient in traditional medicine. Its pungent perception is due to the interaction of its major compound, piperine (1-piperoyl-piperidine) with the human TRPV-1 or vanilloid receptor. We now identify the hitherto concealed enzymatic formation of piperine from piperoyl coenzyme A and piperidine based on a differential RNA-Seq approach from developing black pepper fruits. This enzyme is described as piperine synthase (piperoyl-CoA:piperidine piperoyl transferase) and is a member of the BAHD-type of acyltransferases encoded by a gene that is preferentially expressed in immature fruits. A second BAHD-type enzyme, also highly expressed in immature black pepper fruits, has a rather promiscuous substrate specificity, combining diverse CoA-esters with aliphatic and aromatic amines with similar efficiencies, and was termed piperamide synthase. Recombinant piperine and piperamide synthases are members of a small gene family in black pepper. They can be used to facilitate the microbial production of a broad range of medicinally relevant aliphatic and aromatic piperamides based on a wide array of CoA-donors and amine-derived acceptors, offering widespread applications.
Highlights
Black pepper (Piper nigrum L.) is the world’s most popular spice and is used as an ingredient in traditional medicine
By a differential RNA-Seq approach we demonstrate that a specific acyltransferase, termed piperine synthase, isolated from immature black pepper fruits catalyzes the decisive step in the formation of piperine from piperoyl-CoA and piperidine
The identification of the two major biosynthetic branches of piperine biosynthetic genes remained enigmatic for several decades, with the exception of scattered labeling studies performed to unravel piperidine heterocycle biosynthesis in Crassulaceae and a single report on the identification of a piperine synthase activity in shoots of black pepper, which was unstable and could not be further characterized[12,17]
Summary
Black pepper (Piper nigrum L.) is the world’s most popular spice and is used as an ingredient in traditional medicine. We identify the hitherto concealed enzymatic formation of piperine from piperoyl coenzyme A and piperidine based on a differential RNA-Seq approach from developing black pepper fruits. This enzyme is described as piperine synthase (piperoyl-CoA:piperidine piperoyl transferase) and is a member of the BAHD-type of acyltransferases encoded by a gene that is preferentially expressed in immature fruits. Recombinant piperine and piperamide synthases are members of a small gene family in black pepper They can be used to facilitate the microbial production of a broad range of medicinally relevant aliphatic and aromatic piperamides based on a wide array of CoA-donors and amine-derived acceptors, offering widespread applications. The enzyme catalyzes methylenedioxy bridge formation, from feruperic acid to piperic acid, and not from ferulic acid or from feruperine (Fig. 1)
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