Identification of 4'-Demethyl-3,9-dihydroeucomin as a Bitter-Masking Compound from the Resin of .

Masking the bitter taste of foods is one of the key strategies to improve their taste and palatability, particularly in the context of clean labeling, where natural compounds are preferred. Despite the demand, the availability of natural bitter-masking compounds remains limited. Here, we identified the bitter-masking compound 4'-demethyl-3,9-dihydroeucomin () isolated from the resin of by means of an activity-guided in vivo (sensory bitterness rating of quinine) and in vitro (cell-based bitter response assays) approach.

Comprehensive metabolome characterization of leaves, internodes, and aerial roots of Vanilla planifolia by untargeted LC-MS and GC × GC-MS.

Introduction: Untargeted metabolomics is a powerful tool that provides strategies for gaining a systematic understanding of quantitative changes in the levels of metabolites, especially when combining different metabolomic platforms. Vanilla is one of the world's most popular flavors originating from cured pods of the orchid Vanilla planifolia. However, only a few studies have investigated the metabolome of V.

Novel Catechol -methyltransferases from Catalyze the Generation of Taste-Active Flavonoids.

Due to the increasing demand for natural food ingredients, including taste-active compounds, enzyme-catalyzed conversions of natural substrates, such as flavonoids, are promising tools to align with the principles of Green Chemistry. In this study, a novel -methyltransferase activity was identified in the mycelium of , which was successfully applied to generate the taste-active flavonoids hesperetin, hesperetin dihydrochalcone, homoeriodictyol, and homoeriodictyol dihydrochalcone. Furthermore, the mycelium-mediated OMT activity allowed for the conversion of various catecholic substrates, yielding their respective (iso-)vanilloids, while monohydroxylated compounds were not converted.

Human Gingival Fibroblasts as a Novel Cell Model Describing the Association between Bitter Taste Thresholds and Interleukin-6 Release.

Human gingival fibroblast cells (HGF-1 cells) present an important cell model to investigate the gingiva's response to inflammatory stimuli such as lipopolysaccharides from (LPS). Recently, we demonstrated -resveratrol to repress the -LPS evoked release of the pro-inflammatory cytokine interleukin-6 (IL-6) via involvement of bitter taste sensing receptor TAS2R50 in HGF-1 cells. Since HGF-1 cells express most of the known 25 TAS2Rs, we hypothesized an association between a compound's bitter taste threshold and its repressing effect on the -LPS evoked IL-6 release by HGF-1 cells.

Impact of lactisole on the time-intensity profile of selected sweeteners in dependence of the binding site.

Currently, there is limited insight into the influence of the different binding sites of agonists and antagonists of the sweet taste receptor TAS1R2/TAS1R3 on temporal sensory properties of sweet tasting compounds. We investigated whether the binding site and a competitive or allosteric inhibition of TAS1R2/TAS1R3 influence the time-dependent sensory perception and in vitro TAS1R2/TAS1R3-activation profiles. We compared time-intensity ratings of cyclamate, NHDC, acesulfame K, and aspartame with and without lactisole with the corresponding TAS1R2/TAS1R3-activation in transfected HEK293 cells.

Comprehensive Metabolite Profiling of ssp. Extracts Using Liquid Chromatography Coupled with Electrospray Ionization Ion Mobility Quadrupole Time-of-Flight Mass Spectrometry.

A wide range of secondary metabolites has been described for various species, including the sweet-tasting phenyldihydroisocoumarin phyllodulcin, which is found in the leaves of ssp. . This work aims at the development and validation of an analytical workflow for comprehensive semi-polar metabolite profiling using liquid chromatography coupled with electrospray ionization ion mobility quadrupole time-of-flight mass spectrometry (UPLC-ESI-IMS-QToF-MS) to complement existing analytical studies.

An enzymatic tandem reaction to produce odor-active fatty aldehydes.

Aldehydes represent a versatile and favored class of flavoring substances. A biocatalytic access to odor-active aldehydes was developed by conversion of fatty acids with two enzymes of the α-dioxygenase pathway. The recombinant enzymes α-dioxygenase (α-DOX) originating from Crocosphaera subtropica and fatty aldehyde dehydrogenase (FALDH) from Vibrio harveyi were heterologously expressed in E.

Individual Sweet Taste Perception Influences Salivary Characteristics After Orosensory Stimulation With Sucrose and Noncaloric Sweeteners.

Emerging evidence points to a major role of salivary flow and viscoelastic properties in taste perception and mouthfeel. It has been proposed that sweet-tasting compounds influence salivary characteristics. However, whether perceived differences in the sensory properties of structurally diverse sweet-tasting compounds contribute to salivary flow and saliva viscoelasticity as part of mouthfeel and overall sweet taste perception remains to be clarified.

Reducing the Bitter Taste of Pharmaceuticals Using Cell-Based Identification of Bitter-Masking Compounds.

The palatability of a pharmaceutical preparation is a significant obstacle in developing a patient-friendly dosage form. Bitter taste is an important factor for patients in (i) selecting a certain drug from generic products available in the market and (ii) adhering to a therapeutic regimen. The various methods developed for identification of bitter tasting and bitter-taste modulating compounds present a number of limitations, ranging from limited sensitivity to lack of close correlations with sensory data.

Astringent Gallic Acid in Red Wine Regulates Mechanisms of Gastric Acid Secretion via Activation of Bitter Taste Sensing Receptor TAS2R4.

Red wine is rich in phenolic compounds, which chiefly determine its characteristic taste. One of its major phenolic acid constituents for which an astringency, yet no clear contribution to bitter taste has been reported, is gallic acid (GA). In previous studies, we have demonstrated bitter-tasting constituents to regulate cellular proton secretion (PS) as a key mechanism of gastric acid secretion via activation of bitter taste sensing receptors (TAS2Rs).

Discovery of Novel Bacterial Chalcone Isomerases by a Sequence-Structure-Function-Evolution Strategy for Enzymatic Synthesis of (S)-Flavanones.

Chalcone isomerase (CHI) is a key enzyme in the biosynthesis of flavonoids in plants. The first bacterial CHI (CHI ) was identified from Eubacterium ramulus, but its distribution, evolutionary source, substrate scope, and stereoselectivity are still unclear. Here, we describe the identification of 66 novel bacterial CHIs from Genbank using a novel Sequence-Structure-Function-Evolution (SSFE) strategy.

Bitter Sensing Mediates the -Resveratrol-Induced Anti-inflammatory Effect on Interleukin 6 Release in HGF-1 Cells in Culture.

Recent data have shown anti-inflammatory effects for -resveratrol (RSV) and rosmarinic acid (RA) in various immune-competent cell models through reduction of lipopolysaccharide (LPS)-induced interleukin 6 (IL-6) release. Because both compounds have been reported to taste bitter, we hypothesized an involvement of human bitter taste sensing receptors (TAS2Rs) on IL-6 release in LPS-treated human gingival fibroblasts (HGF-1). First, the bitter taste intensity of RSV and RA was compared in a sensory trial with 10 untrained panelists, of whom 90% rated a 50 ppm of RSV in water solution more bitter than 50 ppm of RA.

TRPA1 Agonist Cinnamaldehyde Decreases Adipogenesis in 3T3-L1 Cells More Potently than the Non-agonist Structural Analog Cinnamyl Isobutyrate.

The cinnamon-derived bioactive aroma compound cinnamaldehyde (CAL) has been identified as a promising antiobesity agent, inhibiting adipogenesis and decreasing lipid accumulation in vitro as well as in animal models. Here, we investigated the antiadipogenic effect of cinnamyl isobutyrate (CIB), another cinnamon-derived aroma compound, in comparison to CAL in 3T3-L1 adipocyte cells. In a concentration of 30 μM, CIB reduced triglyceride (TG) and phospholipid (PL) accumulation in 3T3-L1 pre-adipocytes by 21.

Biotechnological Production and Sensory Evaluation of ω1-Unsaturated Aldehydes.

Lipid extracts of the fungus were found to contain various scarce fatty acids including dodec-11-enoic acid and di- and tri-unsaturated C isomers. A biotechnological approach using a heterologously expressed carboxylic acid reductase was developed to transform the fatty acids into the respective aldehydes, yielding dodec-11-enal. Supplementation studies gave insights into the fungal biosynthesis of this rarely occurring acid and suggested a terminal desaturation of lauric acid being responsible for its formation.

Sweetness Perception is not Involved in the Regulation of Blood Glucose after Oral Application of Sucrose and Glucose Solutions in Healthy Male Subjects.

Scope: This study investigates the effect of the sweetness of a sucrose versus an isocaloric glucose solution in dietary concentrations on blood glucose regulation by adjusting the sweetness level using the sweet taste inhibitor lactisole.

Methods And Results: A total of 27 healthy males participated in this randomized, crossover study with four treatments: 10% glucose, 10% sucrose, 10% sucrose + 60 ppm lactisole, and 10% glucose + 60 ppm lactisole. Plasma glucose, insulin, glucagon-like peptide 1, and glucagon levels are measured at baseline and 15, 30, 60, 90, and 120 min after beverage consumption.

Sweet Taste Antagonist Lactisole Administered in Combination with Sucrose, But Not Glucose, Increases Energy Intake and Decreases Peripheral Serotonin in Male Subjects.

Knowledge regarding the involvement of sweetness perception on energy intake is scarce. Here, the impact of glucose and sucrose sweetness, beyond their caloric load, on subsequent food intake and biomarkers of satiation was evaluated by co-administration of the sweet taste receptor inhibitor lactisole. A total of 27 healthy, male subjects received solutions of either 10% glucose / 60 ppm lactisole or 10% sucrose / 60 ppm lactisole.

Structure-dependent effects of sweet and sweet taste affecting compounds on their sensorial properties.

A reduction in sugar consumption is desirable from a health point of view. However, the sensory profiles of alternative sweet tasting compounds differ from sucrose regarding their temporal profile and undesired side tastes, reducing consumers' acceptance. The present study describes a sensory characterization of a variety of sweet and sweet taste affecting compounds followed by a comparison of similarity to sucrose and a multivariate regression analysis to investigate structural determinants and possible interactions for the temporal profile of the sweetness and side-tastes.

Structure-Dependent Effects of Cinnamaldehyde Derivatives on TRPA1-Induced Serotonin Release in Human Intestinal Cell Models.

Activation of the transient receptor potential (TRP) channel TRPA1 by cinnamaldehyde has been shown to stimulate serotonin release in enterochromaffin QGP-1 cells. However, the impact of cinnamaldehyde on serotonin release in enterocytes is less well understood. In addition, since the neurotransmitter serotonin plays a regulatory role in a large variety of gastrointestinal and metabolic functions, it is of interest to study which structural characteristics determine cinnamaldehyde-induced serotonin release by enterocytes.

Bitter-Tasting Amino Acids l-Arginine and l-Isoleucine Differentially Regulate Proton Secretion via T2R1 Signaling in Human Parietal Cells in Culture.

This study aimed at identifying whether the bitter-tasting amino acids l-arginine (l-ARG) and l-isoleucine (l-ILE) differentially regulate mechanisms of gastric acid secretion in human parietal cells (HGT-1 cells) via activation of bitter taste sensing receptors (T2Rs). In a first set of experiments, involvement of T2Rs in l-ARG and l-ILE-modulated proton secretion was demonstrated by co-treatment of HGT-1 cells with T2R antagonists. Subsequent whole genome screenings by means of cDNA arrays revealed T2R1 as a prominent target for both amino acids.

Wheat Protein Hydrolysate Fortified With l-Arginine Enhances Satiation Induced by the Capsaicinoid Nonivamide in Moderately Overweight Male Subjects.

Scope: Increasing the intake of satiety-enhancing food compounds represents a promising strategy for maintaining a healthy body weight. Recently, satiating effects for the capsaicinoid nonivamide have been demonstrated. As various proteins and amino acids have also been demonstrated to decrease energy intake, oral glucose tolerance test (oGTT)-based bolus interventions of 75 g glucose + 0.

Identification of Cinnamaldehyde as Most Effective Fatty Acid Uptake Reducing Cinnamon-Derived Compound in Differentiated Caco-2 Cells Compared to Its Structural Analogues Cinnamyl Alcohol, Cinnamic Acid, and Cinnamyl Isobutyrate.

Naturally occurring cinnamon compounds such as cinnamaldehyde (CAL) and structurally related constituents have been associated with antiobesity activities, although studies regarding the impact on intestinal fatty acid uptake are scarce. Here, we demonstrate the effects of CAL and structural analogues cinnamyl alcohol (CALC), cinnamic acid (CAC), and cinnamyl isobutyrate on mechanisms regulating intestinal fatty acid uptake in differentiated Caco-2 cells. CAL, CALC, and CAC (3000 μM) were found to decrease fatty acid uptake by 58.

Cinnamyl Isobutyrate Decreases Plasma Glucose Levels and Total Energy Intake from a Standardized Breakfast: A Randomized, Crossover Intervention.

Scope: Cinnamon is associated with anti-obesity effects, regulating food intake, improving plasma glucose levels and lipid profiles in vivo. In the present study, the impact of cinnamyl isobutyrate (CIB), one constituent of cinnamon, on ad libitum food intake from a standardized breakfast and outcome measures of hormonal regulation of appetite were investigated.

Methods And Results: In this randomized, short-term crossover intervention study, a 75 g per 300 mL glucose solution solely (control) or supplemented with 0.

Identification of Bitter-Taste Intensity and Molecular Weight as Amino Acid Determinants for the Stimulating Mechanisms of Gastric Acid Secretion in Human Parietal Cells in Culture.

Secretion of gastric acid, aimed at preventing bacterial growth and aiding the digestion of foods in the stomach, is chiefly stimulated by dietary intake of protein and amino acids (AAs). However, AAs' key structural determinants responsible for their effects on mechanisms regulating gastric acid secretion (GAS) have not been identified yet. In this study, AAs have been tested in the parietal cell model HGT-1 on GAS and on mRNA expression of genes regulating GAS.