title: Rubemamine and Rubescenamine, Two Naturally Occurring N-Cinnamoyl Phenethylamines with Umami-Taste-Modulating Properties.
abstract: Sensory screening of a series of naturally occurring N-cinnamoyl derivatives of substituted phenethylamines revealed that rubemamine (9, from Chenopodium album) and rubescenamine (10, 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 (9) and rubescenamine (10) 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 (9) and rubescenamine (10) 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 (9) was able to further positively modulate the IMP-enhanced TAS1R1-TAS1R3 response to MSG ∼ 1.8-fold. Finally, armatamide (11), zanthosinamide (13), and dioxamine (14), 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 (14) at 25 ppm in combination with 0.17% MSG exhibited a sensory equivalent to 0.37% MSG.
authors.affiliation: Symrise AG , Flavors Division, Research & Technology, P.O. Box 1253, 37603 Holzminden, Germany.
authors.forename: Michael
authors.initials: M
authors.lastname: Backes
authors.affiliation: Symrise AG , Flavors Division, Research & Technology, P.O. Box 1253, 37603 Holzminden, Germany.
authors.forename: Katja
authors.initials: K
authors.lastname: Obst
authors.affiliation: German Institute of Human Nutrition Potsdam-Rehbrücke , Department of Molecular Genetics, Arthur-Scheunert-Allee 114-116, 14558 Nuthetal, Germany.
authors.forename: Juliane
authors.initials: J
authors.lastname: Bojahr
authors.affiliation: German Institute of Human Nutrition Potsdam-Rehbrücke , Department of Molecular Genetics, Arthur-Scheunert-Allee 114-116, 14558 Nuthetal, Germany.
authors.forename: Anika
authors.initials: A
authors.lastname: Thorhauer
authors.affiliation: German Institute of Human Nutrition Potsdam-Rehbrücke , Department of Molecular Genetics, Arthur-Scheunert-Allee 114-116, 14558 Nuthetal, Germany.
authors.forename: Natacha
authors.initials: N
authors.lastname: Roudnitzky
authors.affiliation: Symrise AG , Flavors Division, Research & Technology, P.O. Box 1253, 37603 Holzminden, Germany.
authors.forename: Susanne
authors.initials: S
authors.lastname: Paetz
authors.affiliation: Symrise AG , Flavors Division, Research & Technology, P.O. Box 1253, 37603 Holzminden, Germany.
authors.forename: Katharina V
authors.initials: KV
authors.lastname: Reichelt
authors.affiliation: Symrise AG , Flavors Division, Research & Technology, P.O. Box 1253, 37603 Holzminden, Germany.
authors.forename: Gerhard E
authors.initials: GE
authors.lastname: Krammer
authors.affiliation: German Institute of Human Nutrition Potsdam-Rehbrücke , Department of Molecular Genetics, Arthur-Scheunert-Allee 114-116, 14558 Nuthetal, Germany.
authors.forename: Wolfgang
authors.initials: W
authors.lastname: Meyerhof
authors.affiliation: Symrise AG , Flavors Division, Research & Technology, P.O. Box 1253, 37603 Holzminden, Germany.
authors.forename: Jakob P
authors.initials: JP
authors.lastname: Ley
mesh_terms: D027463:Chenopodium album / Q000737:chemistry*; D005421:Flavoring Agents / Q000138:chemical synthesis / Q000737:chemistry* / Q000378:metabolism; D006801:Humans; D015394:Molecular Structure; D010627:Phenethylamines / Q000138:chemical synthesis / Q000737:chemistry* / Q000378:metabolism; D010936:Plant Extracts / Q000138:chemical synthesis / Q000737:chemistry* / Q000378:metabolism; D043562:Receptors, G-Protein-Coupled / Q000378:metabolism; D012970:Sodium Glutamate / Q000378:metabolism*; D013649:Taste; D032106:Zanthoxylum / Q000737:chemistry*
chemical_list: D005421:Flavoring Agents; D010627:Phenethylamines; D010936:Plant Extracts; D043562:Receptors, G-Protein-Coupled; C431926:taste receptors, type 1; D012970:Sodium Glutamate
keywords: cinnamic acid phenethylamides; flavor modulators; human sensory; umami; umami receptor