title: Structural and sensory characterization of key pungent and tingling compounds from black pepper (Piper nigrum L.).
abstract: To gain a more comprehensive knowledge on whether, besides the well-known piperine, other compounds are responsible for the pungent and tingling oral impression imparted by black pepper, an ethanol extract prepared from black pepper (Piper nigrum L.) was screened for its key sensory-active nonvolatiles by application of taste dilution analysis (TDA). Purification of the compounds perceived with the highest sensory impact, followed by LC-MS and 1D/2D NMR experiments as well as synthesis, led to the structure determination of 25 key pungent and tingling phytochemicals, among which the eight amides 1-(octadeca-2E,4E,13Z-trienyl)piperidine, 1-(octadeca-2E,4E,13Z-trienyl)pyrrolidine, (2E,4E,13Z)-N-isobutyl-octadeca-2,4,13-trienamide, 1-(octadeca-2E,4E,12Z-trienoyl)-pyrrolidine, 1-(eicosa-2E,4E,15Z-trienyl)piperidine, 1-(eicosa-2E,4E,15Z-trienyl)pyrrolidine, (2E,4E,15Z)-N-isobutyl-eicosa-2,4,15-trienamide, and 1-(eicosa-2E,4E,14Z-trienoyl)-pyrrolidine were not yet reported in literature. Sensory studies by means of a modified half-tongue test revealed recognition thresholds ranging from 3.0 to 1150.2 nmol/cm² for pungency and from 520.6 to 2162.1 nmol/cm² for the tingling orosensation depending on their chemical structure.
authors.affiliation: Chair for Food Chemistry and Molecular Sensory Science, Technische Universität München, Lise-Meitner-Strasse 34, D-85354 Freising, Germany.
authors.forename: Corinna
authors.initials: C
authors.lastname: Dawid
authors.forename: Andrea
authors.initials: A
authors.lastname: Henze
authors.forename: Oliver
authors.initials: O
authors.lastname: Frank
authors.forename: Anneke
authors.initials: A
authors.lastname: Glabasnia
authors.forename: Mathias
authors.initials: M
authors.lastname: Rupp
authors.forename: Kirsten
authors.initials: K
authors.lastname: Büning
authors.forename: Diana
authors.initials: D
authors.lastname: Orlikowski
authors.forename: Matthias
authors.initials: M
authors.lastname: Bader
authors.forename: Thomas
authors.initials: T
authors.lastname: Hofmann
mesh_terms: D000328:Adult; D000470:Alkaloids / Q000737:chemistry*; D052117:Benzodioxoles / Q000737:chemistry*; D005260:Female; D006801:Humans; D008297:Male; D015394:Molecular Structure; D029222:Piper nigrum / Q000737:chemistry*; D010880:Piperidines / Q000737:chemistry*; D010936:Plant Extracts / Q000737:chemistry*; D053284:Polyunsaturated Alkamides / Q000737:chemistry*; D013649:Taste; D055815:Young Adult
chemical_list: D000470:Alkaloids; D052117:Benzodioxoles; D010880:Piperidines; D010936:Plant Extracts; D053284:Polyunsaturated Alkamides; C008922:piperine