jf300036a_si_001.pdf (100.47 kB)
Structural and Sensory Characterization of Key Pungent and Tingling Compounds from Black Pepper (Piper nigrum L.)
journal contribution
posted on 2016-02-21, 17:02 authored by Corinna Dawid, Andrea Henze, Oliver Frank, Anneke Glabasnia, Mathias Rupp, Kirsten Büning, Diana Orlikowski, Matthias Bader, Thomas HofmannTo 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.