10.1021/jf300036a.s001
Corinna Dawid
Corinna
Dawid
Andrea Henze
Andrea
Henze
Oliver Frank
Oliver
Frank
Anneke Glabasnia
Anneke
Glabasnia
Mathias Rupp
Mathias
Rupp
Kirsten Büning
Kirsten
Büning
Diana Orlikowski
Diana
Orlikowski
Matthias Bader
Matthias
Bader
Thomas Hofmann
Thomas
Hofmann
Structural and Sensory
Characterization of Key Pungent and Tingling Compounds from Black
Pepper (<i>Piper nigrum</i> L.)
American Chemical Society
2016
Piper
nigrum
Tingling Compounds
eicosa
recognition thresholds
chemical structure
Sensory Characterization
taste dilution analysis
octadeca
Black Pepper
compound
Key Pungent
Sensory studies
NMR
nmol
TDA
structure determination
2016-02-21 17:02:04
Journal contribution
https://acs.figshare.com/articles/journal_contribution/Structural_and_Sensory_Characterization_of_Key_Pungent_and_Tingling_Compounds_from_Black_Pepper_i_Piper_nigrum_i_L_/2538304
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 (<i>Piper nigrum</i> 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-2<i>E</i>,4<i>E</i>,13<i>Z</i>-trienyl)piperidine, 1-(octadeca-2<i>E</i>,4<i>E</i>,13<i>Z</i>-trienyl)pyrrolidine, (2<i>E</i>,4<i>E</i>,13<i>Z</i>)-<i>N</i>-isobutyl-octadeca-2,4,13-trienamide,
1-(octadeca-2<i>E</i>,4<i>E</i>,12<i>Z</i>-trienoyl)-pyrrolidine, 1-(eicosa-2<i>E</i>,4<i>E</i>,15<i>Z</i>-trienyl)piperidine, 1-(eicosa-2<i>E</i>,4<i>E</i>,15<i>Z</i>-trienyl)pyrrolidine, (2<i>E</i>,4<i>E</i>,15<i>Z</i>)-<i>N</i>-isobutyl-eicosa-2,4,15-trienamide, and 1-(eicosa-2<i>E</i>,4<i>E</i>,14<i>Z</i>-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<sup>2</sup> for pungency and from 520.6 to 2162.1
nmol/cm<sup>2</sup> for the tingling orosensation depending on their
chemical structure.