Detection of Bitterness in Vitamins Is Mediated by the Activation of Bitter Taste Receptors.

Vitamins are known to generate bitterness, which may contribute to an off-taste or aftertaste for some nutritional supplements. This negative sensation can lead to a reduction in their consumption. Little is known about the bitter taste threshold and taste sensing system for the bitter taste detection of vitamins. To better understand the mechanisms involved in bitterness perception, we combined taste receptor functional assays and sensory analysis. In humans, bitter taste detection is mediated by 25 G-protein-coupled receptors belonging to the TAS2R family. First, we studied the bitterness of thirteen vitamins using a cellular-based functional taste receptor assay. We found four vitamins that can stimulate one or more TAS2Rs. For each positive molecule-receptor combination, we tested seven increasing concentrations to determine the half-maximal effective concentration (EC50) and the cellular bitter taste threshold. Second, we measured the bitter taste detection threshold for four vitamins that exhibit a strong bitter taste using a combination of ascending series and sensory difference tests. A combination of sensory and biological data can provide useful results that explain the perception of vitamin bitterness and its real contribution to the off-taste of nutritional supplements.

Perceived Intensity and Palatability of Fatty Culinary Preparations is Associated with Individual Fatty Acid Detection Threshold and the Fatty Acid Profile of Oils Used as Ingredients.

The term oleogustus was recently proposed to describe a sixth basic taste that could guide preference for fatty foods and dishes to an extent. However, experimental data on food preference based on fatty acid (FA) content is scarce. Our aim was to examine the role of FA profile of oils and preparations as well as FA sensory thresholds on the palatability of salty and sweet culinary preparations representative of traditional Spanish Mediterranean cooking. In this study, we used three oils with similar texture and odor profile but different in their FA composition (saturated, monounsaturated, and polyunsaturated) and compared subjects in regard to their FA detection threshold and perceived pleasantness and intensity. Our results indicate that whereas saturated FAs cannot be detected at physiological concentrations, individuals can be categorized as tasters and nontasters, according to their sensory threshold to linoleic acid, which is negatively associated with perceived intensity (r = -0.393, P < 0.001) but positively with palatability (r = 0.246, P = 0.018). These differences may be due to a possible response to a fat taste. This sixth taste, or oleogustus. would allow establishing differences in taste intensity/palatability considering the FA profile of the culinary preparations. Given that tasters can detect linoleic and oleic acid at lower concentrations than nontasters, a greater amount of unsaturated FAs in culinary preparations could provoke an unpleasant experience. This finding could be relevant in the context of the culinary sector and to further our understanding of food preference and eating behavior.

Characterization of the Aroma of an Instant White Tea Dried by Freeze Drying.

The aroma of an instant white tea (IWT) was extracted through simultaneous distillation-extraction (SDE) and analyzed by sensory evaluation, gas chromatography-mass spectrometry-olfactometry (GC-MS-O), aroma reconstruction, omission test and synergistic interaction analysis. Sensory evaluation showed the IWT was dominated with floral and sweet notes. The SDE extract had the aroma similar to the IWT. The main volatile components in the SDE extract were benzyl alcohol, linalool, hotrienol, geraniol, α-terpineol, coumarin, camphene, benzeneacetaldehyde, 2-hexanone, cis-jasmin lactone and phenylethyl alcohol. GC-MS-O and aroma reconstruction experiments showed 16 aroma-active compounds. Linalool, trans-ß-damascenone and camphene were the major contributors to floral, sweet and green notes based on flavor dilution analysis and omission test. Linalool and trans-ß-damascenone had synergistic effect to promote floral and sweet notes. Camphene and trans-ß-damascenone had synergistic effect to reduce green and sweet notes. The study helps to understand the aroma of IWT and antagonism interactions among aroma-active volatiles.

Remote psychophysical evaluation of olfactory and gustatory functions in early-stage coronavirus disease 2019 patients: the Bologna experience of 300 cases.

BACKGROUND: An objective evaluation of coronavirus disease 2019 in the first days of infection is almost impossible, as affected individuals are generally in home quarantine, and there is limited accessibility for the operator who should perform the test. To overcome this limitation, a recently validated psychophysical self-administered test was used, which can be performed remotely in the assessment of early-stage coronavirus disease 2019 patients. METHODS: Olfactory and gustatory functions were objectively assessed in 300 patients in the first 7 days from coronavirus disease 2019 symptom onset. RESULTS: Seventy per cent of the patients presented olfactory and/or gustatory disorders. The dysfunctions detected were mainly complete anosmia (47 per cent) or ageusia (38 per cent). A significant correlation was found between taste dysfunction and female gender (odds ratio = 1.936, p = 0.014) and fever (odds ratio = 2.132, p = 0.003). CONCLUSION: The psychophysical evaluation protocol proposed is an effective tool for the fast and objective evaluation of patients in the early stages of coronavirus disease 2019. Chemosensitive disorders have been confirmed to be frequent and early symptoms of the coronavirus infection, and, in a significant number of cases, they are the first or only manifestation of coronavirus disease 2019.

Detection thresholds for four different fatty stimuli are associated with increased dietary intake of processed high-caloric food.

BMI-specific differences in food choice and energy intake have been suggested to modulate taste perception. However, associations between body composition and fat taste sensitivity are controversial. The objective of this study was to examine the association between body composition, dietary intake and detection thresholds of four fatty stimuli (oleic acid, paraffin oil, canola oil, and canola oil spiked with oleic acid) that could be perceived via gustatory and/or textural cues. In 30 participants, fat detection thresholds were determined in a repeated measurements design over twelve days. Weight status was examined by measuring the participants' BMI, waist circumference and waist-to-hip ratio. The habitual food intake was assessed via several questionnaires and twelve, non-consecutive 24-hour food diaries. In this study, a negative correlation was found between fat detection thresholds and the intake of food rich in vitamins and fibre. Moreover, a positive correlation was identified between the intake of high-fat food and fat detection thresholds. No differences in fat detection thresholds were observed due to variations in BMI or waist-to-hip ratio. These findings indicate that a regular intake of fatty foods might decrease an individuals' perceptual response to fats which might lead to excess fat intake on the long term.

Change in oral health status associated with menopause in Japanese dental hygienists.

OBJECTIVES: Oral symptoms such as xerostomia and burning mouth syndrome have been recognized to increase associated with menopause. The purpose of this study was to clarify the changes in oral health as well as systemic health due to menopause and their relations with hormonal change and mental status. METHODS: Ninety-seven female dental hygienists aged 40-59 years were assigned to premenopausal, menopausal and post-menopausal groups based on self-reported menstrual condition. Subjective health statuses were evaluated by questionnaire, and objective holistic and oral statuses were evaluated by measuring serum 17ß-estradiol (E2), salivary flow rate, α-amylase and secretory IgA (SIgA) and taste sensitivity. RESULTS: A significant difference among the three groups was observed in the self-rating questionnaire of depression (SRQ-D) score and serum E2 level as well as unstimulated salivary flow rate, whereas no significant difference was observed in Simplified menopausal index, Short-Form 36-Item Health Survey, General Oral Health Assessment Index, salivary α-amylase activity, salivary SIgA concentration and taste threshold. Serum E2 levels positively correlated with unstimulated salivary flow rates and negatively correlated with SRQ-D scores and α-amylase activities. CONCLUSIONS: The results demonstrated a negative correlation between E2 levels and SRQ-D scores as well as salivary α-amylase activities, suggesting an influence of E2 on mental condition. Furthermore, E2 decrease may result in reduction of salivary flow which in turn causes various problems of oral health. Since the participants were graduates from several dental hygienist schools and working at various places, these results can be generalized to Japanese dental hygienists to some extent.

Oil Perception-Detection Thresholds for Varying Fatty Stimuli and Inter-individual Differences.

Multiple lines of research have demonstrated that humans can perceive fat in the form of free fatty acids (FFAs). However, the dietary concentration of FFAs is generally very low and fat is mainly consumed as triacylglycerol (TAG). The aim of this study was to examine the perception of different fatty stimuli and possible associations between them. Therefore, detection thresholds for 4 fatty stimuli (oleic acid [FFA], paraffin oil [mixture of hydrocarbon molecules], canola oil [TAG-rich], and canola oil spiked with oleic acid [rich in TAGs and FFAs]) were determined in 30 healthy participants. Additionally, inter-individual differences in fat perception were examined. It was observed that oleic acid was perceivable at significantly lower concentrations than all other stimuli (P < 0.001). Similarly, canola oil with oleic acid was detectable at lower concentrations than canola oil alone (P < 0.001). Moreover, canola oil detection thresholds were significantly lower than paraffin oil detection thresholds (P = 0.017). Participants who were sensitive for low concentrations for oleic acid showed lower detection thresholds for canola oil with and without oleic acid, compared with participants that were less sensitive for oleic acid. The results of this study demonstrate that the higher the concentrations of FFAs in the stimuli, the lower the individual fat detection threshold. Moreover, participants being sensitive for lower concentrations of FFAs are also more likely to detect low concentrations of TAG-rich fats as it is found in the human diet.

Fat Taste Sensitivity Is Associated with Short-Term and Habitual Fat Intake.

Evidence suggests individuals less sensitive to fat taste (high fat taste thresholds (FTT)) may be overweight or obese and consume greater amounts of dietary fat than more sensitive individuals. The aims of this study were to assess associations between FTT, anthropometric measurements, fat intake, and liking of fatty foods. FTT was assessed in 69 Australian females (mean age 41.3 (15.6) (SD) years and mean body mass index 26.3 (5.7) kg/m²) by a 3-alternate forced choice methodology and transformed to an ordinal scale (FT rank). Food liking was assessed by hedonic ratings of high-fat and reduced-fat foods, and a 24-h food recall and food frequency questionnaire was completed. Linear mixed regression models were fitted. FT rank was associated with dietary % energy from fat ( ß ^ = 0.110 [95% CI: 0.003, 0.216]), % energy from carbohydrate ( ß ^ = -0.112 [-0.188, -0.035]), and frequency of consumption of foods per day from food groups: high-fat dairy ( ß ^ = 1.091 [0.106, 2.242]), meat & meat alternatives ( ß ^ = 0.669 [0.168, 1.170]), and grain & cereals ( ß ^ = 0.771 [0.212, 1.329]) (adjusted for energy and age). There were no associations between FT rank and anthropometric measurements or hedonic ratings. Therefore, fat taste sensitivity appears to be associated with short-term fat intake, but not body size in this group of females.

Sensory Threshold Studies of Picrocrocin, the Major Bitter Compound of Saffron.

This study is part of a wider project on the bitter taste of saffron and its preparations. A deeper knowledge on the taste perception of picrocrocin is necessary in order to develop products that satisfy consumer senses and provide them with adequate amounts of saffron major constituents, also appreciated for bioactivity. A systematic approach on the bitterness of picrocrocin, the major responsible compound, was conducted. A panel was trained specifically for the determination of taste detection and recognition thresholds of picrocrocin, which were found to be 5.34 and 7.26 mg/L, respectively, using the Ascending Forced Choice of Limits methodology. The threshold values were examined in water in absence and presence of other saffron constituents and ethanol and were found to decrease when served hot (61 ± 4 °C). Bitterness was enhanced in 40% (v/v) aqueous ethanol. In both aqueous and ethanol extracts, the presence of saffron volatiles improved bitterness perception. The usefulness of the study was tested in the case of commercial saffron based infusions.

The impact of individual variations in taste sensitivity on coffee perceptions and preferences.

Despite a few relationships between fungiform papillae (FP) density and 6-n-propylthiouracil (PROP) taster status have been reported for sensory qualities within foods, the impact on preferences remains relatively unclear. The present study investigated responses of FP number and PROP taster groups to different bitter compounds and how these affect coffee perception, consumption and liking. Subjects (Ss) with higher FP numbers (HFP) gave higher liking ratings to coffee samples than those with lower FP numbers (LFP), but only for sweetened coffee. Moreover, HFP Ss added more sugar to the samples than LFP Ss. Significant differences between FP groups were also found for the sourness of the coffee samples, but not for bitterness and astringency. However, HFP Ss rated bitter taste stimuli as stronger than did LFP Ss. While coffee liking was unrelated to PROP status, PROP non-tasters (NTs) added more sugar to the coffee samples than did super-tasters (STs). In addition, STs rated sourness, bitterness and astringency as stronger than NTs, both in coffee and standard solutions. These results confirm that FP density and PROP status play a significant role in taste sensitivity for bitter compounds in general and also demonstrate that sugar use is partly a function of fundamental individual differences in physiology.

Effectiveness of an oral health educational program on community-dwelling older people with xerostomia.

AIM: The purpose of the present study was to evaluate the changes in oral health and function through an oral health educational program for the independent older people with xerostomia. METHODS: Community-dwelling older people with xerostomia aged over 65 years who participated in a preliminary comprehensive health survey in 2011 were recruited for the educational program. A total of 47 participants were randomly assigned into two groups, the intervention group (n = 26) and the control group (n = 21). The intervention group attended a 90-min oral health education program every 2 weeks for 3 months. The program consisted of oral hygiene instruction, facial and tongue muscle exercise, and salivary gland massage. The control group was provided only general information about oral health. The assessments of oral function, such as oral diadochokinesis of articulation, swallowing, taste threshold and salivary flow rate, were carried out before and after 3 months with or without intervention. RESULTS: A total of 38 participants (21 of intervention group and 17 of control group) completed the study protocol. In the intervention group, resting salivation significantly improved after the program. The second and third cumulated Repetitive Saliva Swallowing Test times significantly improved in the intervention group. The threshold for bitterness significantly lowered in the intervention group, whereas the sour threshold significantly heightened in the control group after 3 months (P < 0.05). CONCLUSIONS: The present study suggests that the educational program targeting oral function improvement is effective among the independent older population.

Marked increase in PROP taste responsiveness following oral supplementation with selected salivary proteins or their related free amino acids.

The genetic predisposition to taste 6-n-propylthiouracil (PROP) varies among individuals and is associated with salivary levels of Ps-1 and II-2 peptides, belonging to the basic proline-rich protein family (bPRP). We evaluated the role of these proteins and free amino acids that selectively interact with the PROP molecule, in modulating bitter taste responsiveness. Subjects were classified by their PROP taster status based on ratings of perceived taste intensity for PROP and NaCl solutions. Quantitative and qualitative determinations of Ps-1 and II-2 proteins in unstimulated saliva were performed by HPLC-ESI-MS analysis. Subjects rated PROP bitterness after supplementation with Ps-1 and II-2, and two amino acids (L-Arg and L-Lys) whose interaction with PROP was demonstrated by (1)H-NMR spectroscopy. ANOVA showed that salivary levels of II-2 and Ps-1 proteins were higher in unstimulated saliva of PROP super-tasters and medium tasters than in non-tasters. Supplementation of Ps-1 protein in individuals lacking it in saliva enhanced their PROP bitter taste responsiveness, and this effect was specific to the non-taster group.(1)H-NMR results showed that the interaction between PROP and L-Arg is stronger than that involving L-Lys, and taste experiments confirmed that oral supplementation with these two amino acids increased PROP bitterness intensity, more for L-Arg than for L-Lys. These data suggest that Ps-1 protein facilitates PROP bitter taste perception and identifies a role for free L-Arg and L-Lys in PROP tasting.

Evaluation of taste acuity by the filter-paper disc in Japanese young women: the relationship with micronutrients status.

The aim of the present study is to investigate the taste acuity in Japanese young women in relation to their micronutrient status. Thirty-eight healthy young women (mean age; 21.3, range; 19-27 years) were enrolled. Gustatory thresholds were estimated for four basic tastes: sweet (sucrose), salty (sodium chloride), sour (tartaric acid), and bitter (quinine hydrochloride) by a filter-paper disk method. Various concentrations at each taste were serially scored from disc number 1 (lowest) to number 5 (highest). The lowest concentration at which the quality of the taste was correctly identified was defined as the recognition threshold. The mean of three measurements for each test on three different days was calculated. We divided our participants into normal taste and hypogeusia groups based on the mean threshold disc numbers, <=3.5 and >3.5, respectively, according to previous literature using the same method. We also measured serum concentrations and dietary intakes of micronutrients including zinc, iron, copper, and selenium. The numbers of participants belonging to the hypogeusia group were 24 (63.2%) for sweet, 19 (50.0%) for sour, 17 (44.7%) for bitter, and 16 (42.1%) for salty taste. Although the hypogeusia group exhibited significantly lower serum iron concentrations, except for the salty taste, the other three micronutrients concentrations did not show any association with the four taste acuities. Dietary micronutrient intake did not show any association with the four taste acuities. This study indicates that in addition to zinc status, iron status should be considered in the study of taste acuity.

The influence of sodium on liking and consumption of salty food.

Excessive sodium (Na) intake has been linked to development of hypertension and related pathologies. In this study, we assessed if the sodium chloride (NaCl) concentration in a prototypical food influences the liking and intake of that food. In study 1, detection and recognition thresholds for NaCl were assessed, and perceived salt intensity and liking for hash browns of varying sodium concentrations (40 mg, 120 mg, 170 mg, and 220 mg Na/100 g) were compared in a lab setting. In study 2, detection and recognition thresholds for NaCl were assessed in a lab setting, and lunches consisting of hash browns, basic salad, and beverages were consumed freely in a dining setting on 4 separate occasions. Intake and liking ratings for hash browns were recorded after the lunch. In both studies, detection and recognition thresholds for NaCl were not associated with perceived saltiness, liking, or intake of hash browns. Liking and perceived salt taste intensity of hash browns were correlated (r = 0.547 P < 0.01), and in study 1 the 220 mg sodium hash brown was most liked (P < 0.05). In study 2, there was no association between Na concentration and liking or consumption of hash browns. In summary, liking of hash browns were influenced by whether testing was in a lab or dining room environment. In a dining room environment, large decreases (>50%) of sodium content of food were achievable with only minor decrease in liking and no effect on consumption of the food.

Investigating age-related changes in taste and affects on sensory perceptions of oral nutritional supplements.

BACKGROUND: sip feeds are oral nutritional supplements (ONSs) that are commonly prescribed to malnourished patients to improve their nutritional and clinical status. However, ONSs are poorly consumed and frequently wasted, with sweetness being identified as one of the factors leading to patients' dislike of ONSs. OBJECTIVES: to investigate if age affects sweetness thresholds and if this impacts upon perceived sweetness intensity, hedonic (sweetness and overall) and ranked preference of ONS products. DESIGN: prospective, observational. SUBJECTS: thirty-six young adults (18-33 years) and 48 healthy older adults (63-85 years). SETTING: Department of Food and Nutritional Sciences and the Clinical Health Sciences at the University of Reading. METHODS: detection and recognition threshold levels, basic taste identification and 'just about right' level of sweetness were examined. Three ONSs (chocolate, vanilla, strawberry) and sucrose solutions were evaluated for hedonic sweetness, overall hedonic liking, sweetness intensity and rank preference. RESULTS: significant differences were found in both sweetness detection and recognition thresholds (P = 0.0001) between young and older adults, with older adults more likely to incorrectly identify the taste (P = 0.0001). Despite the deterioration in sweetness sensitivity among the older adults, there were no significant differences found in sweetness intensity perceived for the ONS products presented (P > 0.05) when compared with the young adults. However, across both groups sweetness intensity was found to be correlated with overall product dislike across all flavour variants tested (R = 0.398, P = 0.0001). CONCLUSIONS: sweetness appears to be one of many factors contributing to the dislike of ONSs. Manufacturers are encouraged to reconsider the formulations of these products so that beneficial effects of ONSs can be delivered in a more palatable and acceptable form and wastage reduced.

Sensory quality of functional beverages: bitterness perception and bitter masking of olive leaf extract fortified fruit smoothies.

Olive leaf extract (OLE) contains high amounts of oleuropein and hydroxytyrosol. The antioxidant capacity of these polyphenols makes OLE a promising ingredient for functional food. OLE causes very strong bitterness perception and can therefore only be formulated in low concentrations. In this research, bitter detection and recognition thresholds of OLE-fortified fruit smoothies were determined by a trained sensory panel (n = 11). Masking of the OLE's bitter taste was investigated with addition of sodium cyclamate, sodium chloride, and sucrose by means of a standardized ranking method and a scale test. Detection (5.78 mg/100 g) and recognition thresholds (8.05 mg/100 g) of OLE polyphenols confirmed the low formulation limits when bitterness was not masked by other substances. At higher polyphenol levels of 20 mg/100 g, sodium cyclamate and sucrose were able to reduce bitter taste perception by 39.9% and 24.9%, respectively, whereas sodium chloride could not effectively mask bitterness. Practical Application: Development of functional food poses new challenges for the food industry. A major problem in this field is the high bitterness of natural polyphenol-containing extracts with potential health benefits. This research was conducted to understand the sensory impact of olive leaf extract (OLE), a novel food ingredient with very bitter taste. In product development, the data of this research can be considered for formulation limits and the general sensory quality of OLE-fortified food and beverages.

Influence of an iron intervention on the zinc status of young adult New Zealand women with mild iron deficiency.

Interventions to combat mild Fe deficiency in women of childbearing age may affect Zn nutriture. We used dietary and laboratory indices to assess change in Zn status during a 4-month partially blinded placebo-controlled Fe intervention in women with low Fe stores (serum ferritin < 20 microg/l and Hb > or = 120 g/l) from Dunedin, New Zealand. Subjects aged 18-40 years were randomly assigned to three groups: dietary advice (diet group; DG; n 29), daily Fe supplement with meals (supplement group; SG; n 23; 50 mg Fe as amino acid chelate) and placebo (placebo group; PG, n 26). A validated semi-quantitative FFQ (SFFQ) was administered at baseline, and at 4, 8 and 15 weeks; fasting morning blood samples were assayed for serum Zn, alkaline phosphatase (ALP) and C-reactive protein at baseline, and at 4, 8, 12 and 16 weeks; hair Zn and taste detection thresholds by electrogustometry were measured at baseline and at 16 weeks. Intakes of flesh foods and vitamin C but not Zn or Fe increased, whereas phytate and phytate:Zn molar ratios decreased (all P < or = 0.01) in the DG compared with the PG and SG, based on three SFFQ. Serum Zn increased in both the DG and PG (adjusted, P < or = 0.002), so the between-group difference was not significant; the lack of a parallel rise in the SG was significant when compared with the PG (P = 0.02). ALP activity (but not hair Zn or taste acuity) followed a similar trend. In conclusion, Zn status was not improved compared with placebo by an Fe-based dietary intervention. However, a daily moderate-dose Fe supplement with meals appeared to lower Zn status in these young adult women.

Effects of zinc supplementation on serum zinc concentration and ratio of apo/holo-activities of angiotensin converting enzyme in patients with taste impairment.

OBJECTIVE: The aim of the present study was to evaluate the effects of zinc supplementation on hypogeusia, serum zinc concentration and the ratio of apo/holo-activities of angiotensin converting enzyme (ACE ratio) in patients with taste impairment. ACE ratio was used as an index of zinc nutritional status. METHODS: Forty patients complaining of taste impairment were divided into two groups: zinc deficiency taste impairment (n=12) and idiopathic taste impairment (n=28). Patients with zincemia values of less than 63 microg/dl with no history of other disorder or medication known to cause dysgeusia were diagnosed as zinc deficiency group, while those with the same condition and values more than 64 microg/dl were considered to belong to the idiopathic group. Patients orally received 150 mg of polaprezinc containing 33 mg of zinc every day. Subjective symptom was scored according to visual analogue scale (VAS). RESULTS: Zinc supplementation improved hypogeusia in both idiopathic and zinc deficiency groups. The mean improvements of VAS were 3.02+/-3.03 in the idiopathic group and 3.13+/-2.53 in the zinc deficiency group. Thus, there were no significant differences in idiopathic and zinc deficiency groups. Significant correlations were found between the improvement of VAS score and the ACE ratio after zinc supplementation in both idiopathic and zinc deficiency groups. On the contrary, significant correlations were not found between the improvement of VAS score and the zinc concentration in the serum after zinc supplementation in both groups. CONCLUSION: The results of the present study indicated that zinc deficiency is a predominant factor underlying taste impairment and ACE ratio may be a predictor of the prognosis for taste impairment after zinc supplementation, in addition to a more sensitive indicator of zinc nutrition than zinc concentration in the serum.

Reinvestigation of the bitter compounds in carrots (Daucus carota L.) by using a molecular sensory science approach.

In order to reinvestigate the key molecules inducing bitter off-taste of carrots ( Daucus carota L.), a sensory-guided fractionation approach was applied to bitter carrot extracts. Besides the previously reported bitter compounds, 6-methoxymellein (1), falcarindiol (2), falcarinol (3), and falcarindiol-3-acetate (4), the following compounds were identified for the first time as bitter compounds in carrots with low bitter recognition thresholds between 8 and 47 micromol/L: vaginatin (5), isovaginatin (6), 2-epilaserine oxide (7), laserine oxide (8), laserine (14), 2-epilaserine (15), 6,8-O-ditigloyl- (9), 6-O-angeloyl-, 8-O-tigloyl- (10), 6-O-tigloyl-, 8-O-angeloyl- (11), and 6-, 8-O-diangeloyl-6 ss,8alpha,11-trihydroxygermacra-1(10) E,4 E-diene (12), as well as 8-O-angeloyl-tovarol (13) and alpha-angeloyloxy-latifolone (16). Among these bitter molecules, compounds 9, 10, 13, and 16 were not previously identified in carrots and compounds 6, 11, and 12 were yet not reported in the literature.

Structure determination of 3-O-caffeoyl-epi-gamma-quinide, an orphan bitter lactone in roasted coffee.

Recent investigations on the bitterness of coffee as well as 5- O-caffeoyl quinic acid roasting mixtures indicated the existence of another, yet unknown, bitter lactone besides the previously identified bitter compounds 5- O-caffeoyl- muco-gamma-quinide, 3- O-caffeoyl-gamma-quinide, 4- O-caffeoyl- muco-gamma-quinide, 5- O-caffeoyl- epi-delta-quinide, and 4- O-caffeoyl-gamma-quinide. In the present study, this orphan bitter lactone was isolated from the reaction products generated by dry heating of 5- O-caffeoylquinic acid model, and its structure was determined as the previously unreported 3- O-caffeoyl- epi-gamma-quinide by means of liquid chromatography-mass spectrometry (LC-MS) and one-/two-dimensional NMR experiments. The occurrence of this bitter lactone, exhibiting a low bitter recognition threshold of 58 micromol/L, in coffee beverages could be confirmed by LC-MS/MS (negative electrospray ionization) operating in the multiple reaction monitoring mode.