Contribution of mozambioside roasting products to coffee's bitter taste.

Roasting degrades the coffee compound mozambioside (1) into several products, including 17-O-β-D-glucosyl-11-hydroxycafestol-2-one (2), 11-O-β-D-glucosyl-16-desoxycafestol-2-one (3), 11-O-β-D-glucosyl-(S)-16-desoxy-17-oxocafestol-2-one (4), 11-O-β-D-glucosyl-15,16-dehydrocafestol-2-one (5), 11-O-β-D-glucosyl-(R)-16-desoxy-17-oxocafestol-2-one (6), bengalensol (7), and 11-hydroxycafestol-2-one (8). A UHPLC-MS/MS method was established to quantify 1-8 and monitor their formation during authentic coffee roasting. Concentrations of 1 and the dominant roasting products 4, 5, and 7 ranged from 21.

Curry-Odorants and Their Metabolites Transfer into Human Milk and Urine.

Scope: The excretion of dietary odorants into urine and milk is evaluated and the impact of possible influencing factors determined. Furthermore, the metabolic relevance of conjugates for the excretion into milk is investigated.

Methods And Results: Lactating mothers (n = 20) are given a standardized curry dish and donated one milk and urine sample each before and 1, 2, 3, 4.

Identification of mozambioside roasting products and their bitter taste receptor activation.

Arabica coffee contains the bitter-tasting diterpene glycoside mozambioside, which degrades during coffee roasting, leading to yet unknown structurally related degradation products with possibly similar bitter-receptor-activating properties. The study aimed at the generation, isolation, and structure elucidation of individual pyrolysis products of mozambioside and characterization of bitter receptor activation by in vitro analysis in HEK 293T-Gα16gust44 cells. The new compounds 17-O-β-d-glucosyl-11-hydroxycafestol-2-on, 11-O-β-d-glucosyl-16-desoxycafestol-2-on, 11-O-β-d-glucosyl-(S)-16-desoxy-17-oxocafestol-2-on, 11-O-β-d-glucosyl-15,16-dehydrocafestol-2-on, and 11-O-β-d-glucosyl-(R)-16-desoxy-17-oxocafestol-2-on were isolated from pyrolyzed mozambioside by HPLC and identified by NMR and UHPLC-ToF-MS.

Consumption of Roasted Coffee Leads to Conjugated Metabolites of Atractyligenin in Human Plasma.

Roasted coffee contains atractyligenin-2--β-d-glucoside and 3'--β-d-glucosyl-2'--isovaleryl-2--β-d-glucosylatractyligenin, which are ingested with the brew. Known metabolites are atractyligenin, atractyligenin-19--β-d-glucuronide (), 2β-hydroxy-15-oxoatractylan-4α-carboxy-19--β-d-glucuronide (), and 2β-hydroxy-15-oxoatractylan-4α-carboxylic acid-2--β-d-glucuronide (), but the appearance and pharmacokinetic properties are unknown. Therefore, first time-resolved quantitative data of atractyligenin glycosides and their metabolites in plasma samples from a pilot human intervention study ( = 10) were acquired.

Linalool, 1,8-Cineole, and Eugenol Transfer from a Curry Dish into Human Urine.

Scope: For most substances, there are several routes of excretion from the human body. This study focuses on urinary excretion of dietary odorants and compares the results with previously obtained results on excretion into milk.

Methods And Results: Lactating mothers (n = 18) are given a standardized curry dish and donate urine samples before and after the intervention.

Structure-Based Discovery of Mouse Trace Amine-Associated Receptor 5 Antagonists.

Trace amine-associated receptors (TAARs) were discovered in 2001 as new members of class A G protein-coupled receptors (GPCRs). With the only exception of TAAR1, TAAR members (TAAR2-9, also known as noncanonical olfactory receptors) were originally described exclusively in the olfactory epithelium and believed to mediate the innate perception of volatile amines. However, most noncanonical olfactory receptors are still orphan receptors.

Sweetener System Intervention Shifted Neutrophils from Homeostasis to Priming.

Background: Non-nutritive sweeteners (NNS) are part of personalized nutrition strategies supporting healthy glycemic control. In contrast, the consumption of non-nutritive sweeteners has been related to person-specific and microbiome-dependent glycemic impairments. Reports on the effects of NNS on our highly individual cellular immune system are sparse.

Overlapping activation pattern of bitter taste receptors affect sensory adaptation and food perception.

The composition of menus and the sequence of foodstuffs consumed during a meal underlies elaborate rules. However, the molecular foundations for the observed taste- and pleasure-raising effects of complex menus are obscure. The molecular identification and characterization of taste receptors can help to gain insight into the complex interrelationships of food items and beverages during meals.

Metabolites of dietary atractyligenin glucoside in coffee drinkers' urine.

Arabica roast coffee contains a substantial amount of water soluble atractyligenin-2-O-β-d-glucoside, which is ingested by consumption of coffee brew. Metabolomics data suggest this coffee compound is excreted as glucuronides, but the structures of conjugates have not been elucidated so far. We collected coffee drinkers' urine and isolated four metabolites by MS-guided liquid chromatographic fractionation.

Metabolites of Key Flavor Compound 2,3,5-Trimethylpyrazine in Human Urine.

Pyrazines are among the most important compound class conveying the odor impressions "roasty", "nutty", and "earthy". They are formed by the Maillard reaction and occur ubiquitously in heated foods. The excretion of metabolites of the key flavor odorant 2,3,5-trimethylpyrazine, abundant in the volatile fraction of roasted coffee, was investigated.

An aqueous extract of the brown alga extends lifespan in a sex-specific manner by interfering with the Tor-FoxO axis.

Food has a decisive influence on our health, to the extent where even lifespan can be directly affected by it. In the present work, we have examined the effects of an aqueous extract of the marine brown alga Eisenia bicyclis in terms of its potential to extend lifespan. For this purpose, we used the fruit fly melanogaster as a model.

Activation Spectra of Human Bitter Taste Receptors Stimulated with Cyclolinopeptides Corresponding to Fresh and Aged Linseed Oil.

Linseed oil is rich in unsaturated fatty acids, and its increased consumption could aid in health-promoting nutrition. However, rapid oxidation of linseed oil and concomitant development of bitterness impair consumers' acceptance. Previous research revealed that cyclolinopeptides, a group of cyclic peptides inherent to linseed oil, dominantly contribute to the observed bitterness.

Dietary Linalool is Transferred into the Milk of Nursing Mothers.

Scope: Breast milk is repeatedly postulated to shape the first aroma and taste impressions of infants and thus impact their flavor learning. The objective of this study is to assess the transition of aroma compounds from a customary curry dish into milk.

Methods And Results: The article prepares a standardized curry dish and administers the dish to nursing mothers (n = 18) in an intervention study.

Dietary Piperine is Transferred into the Milk of Nursing Mothers.

Introduction: The diet of breastfeeding mothers could bring nurslings into contact with flavor compounds putatively contributing to early sensory programming of the infant. The study investigates whether tastants from a customary curry dish consumed by mothers are detectable in their milk afterwards and can be perceived by the infant.

Methods And Results: Sensory evaluation identifies pungency as the dominating taste impression of the curry dish.

Comparative assessment of purified saponins as permeabilization agents during respirometry.

Saponins are a diverse group of secondary plant metabolites, some of which display hemolytic toxicity due to plasma membrane permeabilization. This feature is employed in biological applications for transferring hydrophilic molecules through cell membranes. Widely used commercial saponins include digitonin and saponins from soap tree bark, both of which constitute complex mixtures of little definition.

Numerous Compounds Orchestrate Coffee's Bitterness.

Coffee is one of the most consumed hot beverages worldwide and is highly regarded because of its stimulating effect despite having a pronounced bitterness. Even though numerous bitter ingredients have been identified, the detailed molecular basis for coffee's bitterness is not well understood except for caffeine, which activates five human bitter taste receptors. We elucidated the contribution of other bitter coffee constituents in addition to caffeine with functional calcium imaging experiments using mammalian cells expressing the cDNAs of human bitter taste receptors, sensory experiments, and in silico modeling approaches.

Targeted metabolomics of pellicle and saliva in children with different caries activity.

Pellicle is the initial proteinaceous layer that is formed almost instantaneously on all solid surfaces in the oral cavity. It is of essential relevance for any interactions and metabolism on the tooth surface. Up to now, there is no information on the metabolome of this structure.

Activity and distribution pattern of enzymes in the in-situ pellicle of children.

Objective: This study investigated, for the first time, pellicle enzymes with respect to their activity, distribution and fluorescence pattern in children with different caries experience.

Design: In-situ pellicles were collected from 41 children (aged 4-6 years) with different caries status; 17 of them were caries-free (dmf = 0), 12 had dental restorations but no current caries (dmf ≥ 2) and 12 had at least two carious lesions (dmf ≥ 2). Bovine enamel samples were fixed on individual upper jaw braces for pellicle formation.

Bioavailability and Biological Effects of 2- O-β-d-Glucopyranosyl-carboxyatractyligenin from Green Coffee in Caenorhabditis elegans.

Targeted analysis of Coffea arabica and Coffea canephora green coffees (total sample size n = 57) confirmed 2- O-β-d-glucopyranosyl-carboxyatractyligenin (6) as the quantitatively dominating carboxyatractyligenin derivative. Its abundance in Arabicas (2425 ± 549 nmol/g, n = 48) exceeded that in Robustas (34 ± 12 nmol/g, n = 9) roughly by a factor of 70. Coffee processing involving heat (e.

Synephrine as a Specific Marker for Orange Consumption.

To validate the suitability of synephrine, known to be a highly abundant alkaloid in oranges, as a dietary biomarker for orange consumption, a highly sensitive and robust stable isotope dilution analysis (SIDA) as well as an ECHO method, using the analyte itself as a pseudointernal standard injected into the analysis run to provide an "echo peak" of the analyte, was developed to quantitate synephrine by liquid chromatography-tandem mass spectrometry (LC-MS/MS) in citrus juices and human urine before and after the ingestion of orange juice. A citrus juice screening revealed high synephrine concentrations of 150-420 nmol/mL in orange (n = 11) and tangerine (n = 2) juices, whereas 20-100 times lower levels were found in juice from grapefruit (n = 14), lemon (n = 5), pomelo (n = 2), and lime (n = 4). Application of the SIDA to quantitate synephrine in sulfatase/glucuronidase-treated urine samples (n = 10) after orange juice consumption showed an increase of synephrine from trace levels (0.

High-Throughput Quantitation of Proline Betaine in Foods and Suitability as a Valid Biomarker for Citrus Consumption.

Proline betaine has been proposed as a candidate dietary biomarker for citrus intake. To validate its suitability as a dietary biomarker and to gain insight into the range of this per-methylated amino acid in foods and beverages, a quick and accurate stable isotope dilution assay was developed for quantitative high-throughput HILIC-MS/MS screening of proline betaine in foods and urine after solvent-mediated matrix precipitation. Quantitative analysis of a variety of foods confirmed substantial amounts of proline betaine in citrus juices (140-1100 mg/L) and revealed high abundance in tubers of the vegetable Stachys affinis, also known as Chinese artichocke (∼700 mg/kg).

Coffee consumption rapidly reduces background DNA strand breaks in healthy humans: Results of a short-term repeated uptake intervention study.

Scope: Intervention studies provide evidence that long-term coffee consumption correlates with reduced DNA background damage in healthy volunteers. Here, we report on short-term kinetics of this effect, showing a rapid onset after normal coffee intake.

Methods And Results: In a short-term human intervention study, we determined the effects of coffee intake on DNA integrity during 8 h.

Mozambioside Is an Arabica-Specific Bitter-Tasting Furokaurane Glucoside in Coffee Beans.

Sensory-guided fractionation of a roasted coffee beverage revealed a highly polar, bitter-tasting subfraction, from which the furokaurane glucoside mozambioside was isolated and identified in its chemical structure by means of HDMS and NMR spectra. Sensory evaluation revealed a bitter taste recognition threshold of 60 (± 10) μmol/L. UPLC-HDMS quantitation of raw coffee beans showed that Arabica coffees contained 396-1188 nmol/g mozambioside, whereas only traces (<5 nmol/g) were detected in Robusta coffees, thus suggesting that mozambioside can be used as an analytical marker for Arabica coffee.

Cardiometabolic effects of two coffee blends differing in content for major constituents in overweight adults: a randomized controlled trial.

Purpose: The hypothesis was tested that coffee types differing in content of major constituents also differ with regard to cardiometabolic effects.

Methods: Overweight persons (n = 118) were randomized to consume a dark roast [rich in N-methylpyridinium (NMP)] or medium roast (rich in caffeoylquinic acids, trigonelline) coffee blend for 3 months, after a washout period of 4 weeks. Before and after the intervention period, body weight and 15 further general and biochemical parameters were determined.

Raw coffee based dietary supplements contain carboxyatractyligenin derivatives inhibiting mitochondrial adenine-nucleotide-translocase.

Capsules, powders and tablets containing raw coffee extract are advertised to the consumer as antioxidant rich dietary supplements as part of a healthy diet. We isolated carboxyatractyligenin (4), 2-O-β-d-glucopyranosyl carboxyatractyligenin (6) and 3'-O-β-d-glucopyranosyl-2'-O-isovaleryl-2β-(2-desoxy-carboxyatractyligenin)-β-d-glucopyranoside (8) from green coffee and found strong inhibitory effects on phosphorylating respiration in isolated mitochondria similar to the effects of the known phytotoxin carboxyatractyloside. LC-MS/MS analysis of commercial green coffee based dietary supplements revealed the occurrence of carboxyatractyligenin, 3'-O-β-d-glucopyranosyl-2'-O-isovaleryl-2β-(2-desoxy-carboxyatractyligenin)-β-d-glucopyranoside, and 2-O-β-d-glucopyranosyl carboxyatractyligenin in concentrations up to 4.