Bitter compounds: Occurrence and structure‐activity relationships

Belitz, Hans‐Dieter; Wieser, Herbert

doi:10.1080/87559128509540773

Cited by 91 publications

(56 citation statements)

References 224 publications

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“…Numerous potentially noxious chemicals, synthetic, natural, or generated during food processing and aging, evoke bitter taste (Belitz and Wieser, 1985;Schieberle and Hofmann, 2003;DuBois et al, 2008). Given the rich presence of bitter substances in edible plants and other foodstuff, several of them are usually present in the mouth simultaneously when we eat (Belitz and Wieser, 1985;Stewart et al, 1996;Hofmann, 2009).…”

Section: Introductionmentioning

confidence: 99%

“…Given the rich presence of bitter substances in edible plants and other foodstuff, several of them are usually present in the mouth simultaneously when we eat (Belitz and Wieser, 1985;Stewart et al, 1996;Hofmann, 2009). Moreover, the bitter blends can combine with stimuli of other taste qualities to evoke complex flavor perceptions, including mixture suppression and synergistic effects (Bartoshuk, 1975;Drewnowski, 2001).…”

Section: Introductionmentioning

confidence: 99%

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Receptor Agonism and Antagonism of Dietary Bitter Compounds

Brockhoff¹,

Behrens²,

Roudnitzky³

et al. 2011

J. Neurosci.

105

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Food contains complex blends of structurally diverse bitter compounds that trigger bitterness through activation of one or more of the ϳ25 human TAS2 bitter taste receptors. It remains unsolved, however, whether the perceived bitterness of binary bitter-compound mixtures can be considered an additive function of all bitter-inducing chemicals in the mouth, suggesting that little mutual interaction takes place among bitter substances or if mixture suppression and synergism occurs. Here we report on two natural sesquiterpene lactones from edible plants, which stimulate distinct sets of hTAS2Rs in transfected cells. Both chemicals also robustly inhibit different but overlapping subsets of agonist-activated hTAS2Rs. These findings demonstrate that mixtures of bitter compounds, because they normally occur in human foodstuff, likely elicit bitter perception in a complex and not in a merely additive manner. An unexpected implication of this discovery is that, during evolution, the naturally occurring bitter taste receptor antagonists have shaped some of the pharmacological properties of the receptors, such as overlapping recognition profiles and breadth of tuning.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Receptor Agonism and Antagonism of Dietary Bitter Compounds

Brockhoff¹,

Behrens²,

Roudnitzky³

et al. 2011

J. Neurosci.

105

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show abstract

“…Mainly in the tyrosinase incubations the formation of theatridimensins was clearly visible, even in higher amounts than theanaphtoquinones. Besides T3D (TF-EC), the theatridimensins TF-C (stereo isomer of T3D) and tentatively T3Dg (TFg-EC) (38) were formed during incubations of C+EGC and EC+EGCg, respectively. The formation of T3Dg (m/z 1003) has not been reported before.…”

Section: Theaflavin Formation With Combinations Of Tea Catechinsmentioning

confidence: 99%

“…Several hypotheses about the formation of all these different compounds have been put forward throughout the years, [35][36][37][38] with the 'oxidative cascade hypothesis' 1 as the last and most complete description. The word 'cascade' in the name refers mainly to the hydroxylation level (level 2), where every hydroxylation will increase the probability of a next hydroxylation.…”

mentioning

confidence: 99%

“…Also, it was suggested that steric hindrance was of influence for the binding of bitter compounds to the bitter receptors. 38 Hence, oligomerization of catechins might reduce bitterness, as the molecules might become too large to fit the tastant-binding pockets of T2Rs. The dimeric TFs do not comply with this idea, as they had a lower EC 50 value, thus are more bitter, than monomeric catechins.…”

mentioning

confidence: 99%

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Oligomerization and hydroxylation of green tea catechins by oxidative enzymes

Verloop¹

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Black teas are known for their characteristic brown colour, bitter taste and astringent mouth feel. These sensory characteristics are mainly influenced by the phenolic oxidation products present in black tea. The oxidation of phenolics from green tea leaves during black tea manufacturing is an uncontrolled process. With the objective to make tea oxidation a more controlled process, the aim of this thesis was to understand the enzymatic oxidation reactions occurring during tea oxidation, and to enable more rapid analysis of complex mixtures of phenolics. By incubating green tea catechins with an exogenous tyrosinase, a black tea-like phenolic profile was obtained, enriched in theaflavins, which are important for quality of tea. Further oxidation of theaflavins yielded theatridimensins, in which an epicatechin is coupled to the benzotropolone ring of theaflavin. By using MS/MS on selected ions these theatridimensins were shown to occur in black tea. This MS method could also be used to distinguish isomeric procyanidins and dehydrocatechins based on MS 2 fragments, as well as the different interflavanic configurations occurring in dehydrodicatechins. The dehydrocatechins were shown to occur in black tea as well. Besides these oligomerization reactions mediated by tyrosinase, oxidation of tea phenolics also comprised hydroxylation. The enzymatic activity from tea leaves responsible for this hydroxylation reaction, was found to be peroxidase. All findings were condensed into a new version of the 'oxidative cascade hypothesis', describing the oxidation reactions towards formation of a black tea.

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Taste

Halpern¹

2002

Stevens' Handbook of Experimental Psychology

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Mammalian taste systems are complex. Taste buds, the taste receptor organs, are composed of many gustatory receptor cells that are themselves transient structures, and contain a wide variety of transduction mechanisms. Some details of these transduction mechanisms are now known, and candidate receptor molecules for initial interactions with tastants have been identified. Often, the degree to which these observations can be generalized to humans is unresolved. For humans, tasting requires the presence of taste buds. Initial processing of taste responses may occur in taste buds before any neural output to the central nervous system (CNS). The CNS gustatory anatomy of humans and other higher primates is fundamentally different from that of most mammals, further limiting facile generalizations. Imaging techniques such as fMRI and PET, as well as recording approaches such as MEG, are revealing the complex CNS functional anatomy and processing of the human taste system. A fundamental theoretical issue, the organizational and informational characteristics of the human taste systems, remains debatable, with both the Basic Tastes model and the Pattern model receiving empirical support. Although some differences between these models may be only semantic or illusory, other differences generate opposite testable predictions and lead to divergent research programs.

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Bitter compounds: Occurrence and structure‐activity relationships

Cited by 91 publications

References 224 publications

Receptor Agonism and Antagonism of Dietary Bitter Compounds

Receptor Agonism and Antagonism of Dietary Bitter Compounds

Oligomerization and hydroxylation of green tea catechins by oxidative enzymes

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