Rubemamine and Rubescenamine, Two Naturally Occurring <i>N</i>‑Cinnamoyl Phenethylamines with Umami-Taste-Modulating
Properties
Michael Backes
Katja Obst
Juliane Bojahr
Anika Thorhauer
Natacha Roudnitzky
Susanne Paetz
Katharina
V. Reichelt
Gerhard E. Krammer
Wolfgang Meyerhof
Jakob P. Ley
10.1021/acs.jafc.5b04402.s001
https://acs.figshare.com/articles/journal_contribution/Rubemamine_and_Rubescenamine_Two_Naturally_Occurring_i_N_i_Cinnamoyl_Phenethylamines_with_Umami_Taste_Modulating_Properties/2124880
Sensory
screening of a series of naturally occurring <i>N</i>-cinnamoyl
derivatives of substituted phenethylamines revealed that
rubemamine (<b>9</b>, from Chenopodium album) and rubescenamine (<b>10</b>, from Zanthoxylum
rubsecens) elicit strong intrinsic umami taste in
water at 50 and 10 ppm, respectively. Sensory tests in glutamate-
and nucleotide-containing bases showed that the compounds influence
the whole flavor profile of savory formulations. Both rubemamine (<b>9</b>) and rubescenamine (<b>10</b>) at 10–100 ppm
dose-dependently positively modulated the umami taste of MSG (0.17–0.22%)
up to threefold. Among the investigated amides, only rubemamine (<b>9</b>) and rubescenamine (<b>10</b>) are able to directly
activate the TAS1R1-TAS1R3 umami taste receptor. Moreover, both compounds
also synergistically modulated the activation of TAS1R1-TAS1R3 by
MSG. Most remarkably, rubemamine (<b>9</b>) was able to further
positively modulate the IMP-enhanced TAS1R1-TAS1R3 response to MSG
∼1.8-fold. Finally, armatamide (<b>11</b>), zanthosinamide
(<b>13</b>), and dioxamine (<b>14</b>), which lack intrinsic
umami taste in vivo and direct receptor response in vitro, also positively
modulated receptor activation by MSG about twofold and the IMP-enhanced
MSG-induced TAS1R1-TAS1R3 responses approximately by 50%. In sensory
experiments, dioxamine (<b>14</b>) at 25 ppm in combination
with 0.17% MSG exhibited a sensory equivalent to 0.37% MSG.
2015-10-07 00:00:00
umami taste
ppm
TAS 1R umami taste receptor
MSG
rubemamine
rubescenamine
response