Structural and sensory characterization of key pungent and tingling compounds from black pepper (Piper nigrum L.)

Corinna Dawid, Andrea Henze, Oliver Frank, Anneke Glabasnia, Mathias Rupp, Kirsten Büning, Diana Orlikowski, Matthias Bader, Thomas Hofmann

Publikation: Beitrag in FachzeitschriftArtikelBegutachtung

63 Zitate (Scopus)

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/cm 2 for pungency and from 520.6 to 2162.1 nmol/cm 2 for the tingling orosensation depending on their chemical structure.

OriginalspracheEnglisch
Seiten (von - bis)2884-2895
Seitenumfang12
FachzeitschriftJournal of agricultural and food chemistry
Jahrgang60
Ausgabenummer11
DOIs
PublikationsstatusVeröffentlicht - 21 März 2012

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