Theanine Capture of Reactive Carbonyl Species in Humans after Consuming Theanine Capsules or Green Tea.

Acrolein (ACR), methylglyoxal (MGO), and glyoxal (GO) are a class of reactive carbonyl species (RCS), which play a crucial role in the pathogenesis of chronic and age-related diseases. Here, we explored a new RCS inhibitor (theanine, THE) and investigated its capture capacity on RCS in vivo by human experiments. After proving that theanine could efficiently capture ACR instead of MGO/GO by forming adducts under simulated physiological conditions, we further detected the ACR/MGO/GO adducts of theanine in the human urine samples after consumption of theanine capsules (200 and 400 mg) or green tea (4 cups, containing 200 mg of theanine) by using ultraperformance liquid chromatography-time-of-flight-high-resolution mass spectrometry. Quantitative assays revealed that THE-ACR, THE-2ACR-1, THE-MGO, and THE-GO were formed in a dose-dependent manner in the theanine capsule groups; the maximum value of the adducts of theanine was also tested. Furthermore, besides the RCS adducts of theanine, the RCS adducts of catechins could also be detected in the drinking tea group. Whereas, metabolite profile analysis showed that theanine could better capture RCS produced in the renal metabolic pathway than catechins. Our findings indicated that theanine could reduce RCS in the body in two ways: as a pure component or contained in tea leaves.

Scavenging Glyoxal and Methylglyoxal by Synephrine Alone or in Combination with Neohesperidin at High Temperatures.

α-Dicarbonyl compounds, such as glyoxal (GO) and methylglyoxal (MGO), are a series of chemical hazards that exist in vivo and in vitro, posing a threat to human health. We aimed to explore the scavenging effects on GO/MGO by synephrine (SYN) alone or in combination with neohesperidin (NEO). First, through LC-MS/MS, we confirmed that both SYN and NEO could effectively remove GO and form GO adducts, while NEO could also clear MGO by forming MGO adducts, and its ability to clear MGO was stronger than that of GO. Second, a synergistic inhibitory effect on GO was found when SYN and NEO were used in combination by using the Chou-Talalay method; on the other hand, SYN could promote NEO to clear more MGO, although SYN could not capture MGO. Third, after synthesizing four GO/MGO-adducts (SYN-GO-1, SYN-GO-3, NEO-GO-7, and NEO-MGO-2) and identifying their structure through NMR, strict correlations between the GO/MGO-adducts and the GO/MGO-clearance rate were found when using SYN and NEO alone or in combination. Furthermore, it was inferred that the synergistic effect between SYN and NEO stems from their mutual promotion in capturing more GO by the quantitative analysis of the adducts in the combined model. Finally, a study was conducted on flowers of Citrus aurantium L. var. amara Engl. (FCAVA, an edible tea) rich in SYN and NEO, which could serve as an effective GO and MGO scavenger in the presence of both GO and MGO. Therefore, our study provided well-defined evidence that SYN and NEO, alone or in combination, could efficiently scavenge GO/MGO at high temperatures, whether in the pure form or located in FCAVA.

Scavenging Glyoxal and Methylglyoxal by Synephrine and Neohesperidin from Flowers of Citrus aurantium L. var. amara Engl. in Mice and Humans.

There is considerable research evidence that α-dicarbonyl compounds, including glyoxal (GO) and methylglyoxal (MGO), are closely related to many chronic diseases. In this work, after comparison of the capture capacity, reaction pathway, and reaction rate of synephrine (SYN) and neohesperidin (NEO) on GO/MGO in vitro, experimental mice were administrated with SYN and NEO alone and in combination. Quantitative data from UHPLC-QQQ-MS/MS revealed that SYN/NEO/HES (hesperetin, the metabolite of NEO) could form the GO/MGO-adducts in mice (except SYN-MGO), and the levels of GO/MGO-adducts in mouse urine and fecal samples were dose-dependent. Moreover, SYN and NEO had a synergistic scavenging effect on GO in vivo by promoting each other to form more GO adducts, while SYN could promote NEO to form more MGO-adducts, although it could not form MGO-adducts. Additionally, human experiments showed that the GO/MGO-adducts of SYN/NEO/HES found in mice were also detected in human urine and fecal samples after drinking flowers of Citrus aurantium L. var. amara Engl. (FCAVA) tea using UHPLC-QTOF-MS/MS. These findings provide a novel strategy to reduce endogenous GO/MGO via the consumption of dietary FCAVA rich in SYN and NEO.

Elimination of Acrolein by Disodium 5'-Guanylate or Disodium 5'-Inosinate at High Temperature and Its Application in Roasted Pork Patty.

Acrolein (ACR) is a highly active, simple unsaturated aldehyde found in various high-temperature processed foods. Its long-term accumulation in the human body increases the risk of chronic diseases. Animal and plant foodstuffs are rich in disodium 5'-guanylate (GMP) and disodium 5'-inosinate (IMP), which are authorized flavor enhancers. Herein, we used liquid chromatography with tandem mass spectrometry to explore the reaction-active kinetics and pathway of the interaction between GMP/IMP and ACR and validated it in roasted pork patties. Our results suggested that GMP and IMP could efficiently eliminate ACR by forming ACR adducts (GMP-ACR, IMP-ACR). In addition, IMP exhibited a higher reaction rate, whereas GMP had a good trapping capacity at a later stage. As carriers of GMP and IMP, dried mushrooms and shrimp exhibited an effective ACR-trapping ability in the ACR model and roasted pork patty individually and in combination. Adding 10% of dried mushroom or shrimp alone or 5% of dried mushroom and shrimp in combination eliminated up to 53.9%, 55.8%, and 55.2% ACR in a roasted pork patty, respectively. This study proposed a novel strategy to eliminate the generation of ACR in roasted pork patties by adding foodstuffs rich in GMP and IMP.

Theanine in Tea: An Effective Scavenger of Single or Multiple Reactive Carbonyl Species at the Same Time.

Reactive carbonyl species (RCS) are generated during thermal food processing, and their accumulation in the body increases the risk of various chronic diseases. Herein, the RCS-scavenging ability of theanine, a unique nonproteinogenic amino acid, was evaluated in terms of the scavenging rate, reaction kinetics, and reaction pathway using LC-MS/MS. Three major products of theanine conjugated with acrolein (ACR) and glyoxal (GO) were prepared and identified using nuclear magnetic resonance. Thereafter, the simultaneous reactions of four types of RCS (namely, ACR, crotonaldehyde, methylglyoxal, and GO) with theanine were discussed in RCS-theanine and RCS-tea models. Under different reaction ratios, theanine could nonspecifically scavenge the four coexisting RCS by forming adducts with them. The amount of theanine-RCS adducts in green and black tea was more than that of catechin (epigallocatechin gallate, epigallocatechin, epicatechin gallate, and epicatechin)-RCS adducts despite the lower content of theanine than catechins. Thus, theanine, as a food additive and dietary supplement, could demonstrate new bioactivity as a promising RCS scavenger in food processing.

Synergistic Inhibitory Effect of Multiple Polyphenols from Spice on Acrolein during High-Temperature Processing.

Acrolein (ACR) is a toxic unsaturated aldehyde that is produced during food thermal processing. Here, we investigated the synergistic effect of polyphenols in binary, ternary, and quaternary combinations on ACR by the Chou-Talalay method, and then explored the synergistic effect of cardamonin (CAR), alpinetin (ALP), and pinocembrin (PIN) in fixed proportion from Alpinia katsumadai Hayata (AKH) combined with curcumin (CUR) in the model, and roasted pork using LC-MS/MS. Our results showed that their synergistic effect depended on the intensification of their individual trapping ACR activities, which resulted in the formation of more ACR adducts. In addition, by adding 1% AKH (as the carrier of CAR, ALP, and PIN) and 0.01% CUR (vs. 6% AKH single) as spices, more than 71.5% (vs. 54.0%) of ACR was eliminated in roast pork. Our results suggested that selective complex polyphenols can synergistically remove the toxic ACR that is produced in food processing.

Effects of hesperidin combined with synephrine on the capture of acrolein in a mouse model, or in humans by citrus consumption.

Acrolein (ACR) is a highly reactive α,ß-unsaturated aldehyde that plays a key role in the pathogenesis of human diseases, such as atherosclerosis and pulmonary, cardiovascular, and neurodegenerative disorders. We investigated the capture capacity of hesperidin (HES) and synephrine (SYN) on ACR by individual and combined means in vitro, in vivo (utilizing a mouse model), and via a human study. After proving that HES and SYN could efficiently capture ACR by generating ACR adducts in vitro, we further detected the adducts of SYN-2ACR, HES-ACR-1, and hesperetin (HESP)-ACR in mouse urine by ultraperformance liquid chromatography-tandem mass spectrometry. Quantitative assays revealed that adduct formation occurred in a dose-dependent manner, and that there was a synergistic effect of HES and SYN on capturing ACR in vivo. Moreover, quantitative analysis suggested that SYN-2ACR, HES-ACR-1, and HESP-ACR were formed and excreted through the urine of healthy volunteers consuming citrus. The maximum excretions of SYN-2ACR, HES-ACR-1, and HESP-ACR were at 2-4, 8-10, and 10-12 h, respectively, after dosing. Our findings propose a novel strategy for eliminating ACR from the human body via the simultaneous consumption of a flavonoid and an alkaloid.

Food additive octyl gallate eliminates acrolein and inhibits bacterial growth in oil-rich food.

Acrolein (ACR) is predominantly generated from oil-rich food during thermos- processing. Accumulation of ACR in vivo through food consumption has been associated with an increased risk of developing chronic diseases. Here, we investigated the inhibitory effect of octyl gallate (OG), a new food additive tolerant to high-temperature, alkaline and fat-soluble saturations, on the generation of ACR in OG-ACR, oil-Rancimat models, and real-world frying. Our results demonstrate that approximately 80% and 60% of ACR was eliminated by OG in the two models, respectively, and OG-ACR was detected in the deep-frying process using LC-MS/MS. The reaction pathways were clarified by synthesis and OG-ACR and OG-2ACR adduct structural elucidation. Our work reveals that the antibacterial activity of OG-ACR against Escherichia coli (gram-negative) was four times higher than that of OG. Thus, OG can be developed as a promising novel ACR scavenger for high-temperature food processing and an antibacterial agent in food storage.

Dual effects of cardamonin/alpinetin and their acrolein adducts on scavenging acrolein and the anti-bacterial activity from Alpinia katsumadai Hayata as a spice in roasted meat.

Acrolein (ACR) is frequently produced by the thermal degradation of carbohydrates and amino acids and lipid peroxidation in the thermal processing of food. Long-term exposure to ACR can cause various chronic diseases. Here, we screened two high-temperature-resistant ACR inhibitors, cardamonin (CAR) and alpinetin (ALP), which can interconvert without any loss at 100 °C, and were obtained from Alpinia katsumadai Hayata (AKH). They demonstrated the best activity among the six spices investigated and could scavenge ACR generated in roasted pork by forming adducts. After three ACR adducts were prepared, namely CAR-ACR-1, CAR-ACR-2 and ALP-ACR, quantitative analysis showed that the amount of CAR-ACR-1 generated in lean roasted pork with 2% AKH addition reached the minimal inhibitory concentration against Escherichia coli and Staphylococcus aureus, which was 20 times lower than that of CAR, and the higher the generation of ACR, the stronger its antibacterial activity. These results provided well-defined evidence to promote the application of AKH to ACR inhibitors in food processing.

Inhibitory Effect on Acrolein by Cyanidin-3-O-glucoside and Its Acrolein Adducts from the Pigment of Mynica Red.

Acrolein (ACR), the simplest α,ß-unsaturated aldehyde, possesses high reactivity and toxicity both in vitro and in vivo and results in various chronic diseases. This has attracted increasing interest from researchers to screen various bioactive compounds to control it. In this article, we attempted to discover a new attribute of cyanidin-3-O-glucoside (C3G), including its ACR-scavenging capacity, reaction pathway, and possible application. Our findings revealed that C3G could capture ACR to form mono- and diadducts at room temperature by using liquid chromatography-mass spectrometry, and we further synthesized and elucidated the structures of C3G-ACR and C3G-2ACR using HRMS and 2D NMR. The structural data validated that there were two active sites of C3G for trapping ACR: at C-6 in the A-ring and C-5' in the B-ring. In addition, we found that C3G-ACR exhibited a more remarkable clearing ability than C3G within a short time. More than 65.9% of ACR was eliminated by C3G-ACR within 5 min via further formation of C3G-2ACR, but there was no obvious effect of C3G on ACR. When the incubation time was extended to 120 min, C3G could remove up to 83.2% of ACR. Subsequently, we also observed that mynica red (>5% C3G), as a pigmented food additive, could efficiently eliminate ACR generated in the Chinese liquor model and real red bayberry wine products to form C3G-ACR and C3G-2ACR. Both adducts increased significantly, by 10 times to a 100 times, after adding mynica red to red bayberry wine products for 24 h; they also increased rapidly with prolonged incubation time in the liquor-mynica red model system. Therefore, our findings suggest that C3G or mynica red may be developed as a promising novel ACR inhibitor in fruit wine and assembled alcoholic drinks or as a health food.

Adduct Formation of Acrolein with Cyanidin-3-O-glucoside and Its Degradants/Metabolites during Thermal Processing or In Vivo after Consumption of Red Bayberry.

Acrolein (ACR) derives from the external environment and the endogenous metabolism of organisms. It has super-reactivity and can induce various diseases. We investigated the capacity of cyanidin-3-O-glucoside (C3G) and its degradants/metabolites to capture ACR during thermal processing or in vivo. Our results indicated that both C3G and its degradants, including phloroglucinaldehyde (PGA) and protocatechuic acid (PCA), could efficiently trap ACR to form adducts, such as C3G-ACR, C3G-2ACR, PGA-ACR, PGA-2ACR, PCA-ACR, and PCA-2ACR. Additionally, these adducts were detected in commercial canned red bayberry products. The adducts of C3G and its metabolites conjugated with ACR, such as C3G-ACR, C3G-2ACR, PGA-ACR, and 4-hydroxybenzoic-acid-ACR (4-HBA-ACR), were also detected in mice feces treated with C3G by oral gavage, where the adduct level was dose-dependent. A similar pattern was observed in tests on human consumption of red bayberry. In human urine, only PGA-2ACR and 4-HBA-ACR, were found, whereas C3G-ACR, C3G-2ACR, myricetin-3-O-rhamnoside-ACR (M3R-ACR), PGA-2ACR, 4-HBA-ACR and ferulic acid-ACR (FA-ACR) were detected in human feces following administration of red bayberry. Our results are the first demonstration that C3G and its metabolites can capture ACR in vitro and in vivo (mice and humans) and present a novel strategy, the development of C3G as a promising ACR inhibitor.

The Role of Ultrasound in the Preparation of Zein Nanoparticles/Flaxseed Gum Complexes for the Stabilization of Pickering Emulsion.

Ultrasound is one of the most commonly used methods to prepare Pickering emulsions. In the study, zein nanoparticles-flaxseed gum (ZNP-FSG) complexes were fabricated through various preparation routes. Firstly, the ZNP-FSG complexes were prepared either through direct homogenization/ultrasonication of the zein and flaxseed gum mixture or through pretreatment of zein and/or flaxseed gum solutions by ultrasonication before homogenization. The Pickering emulsions were then produced with the various ZNP-FSG complexes prepared. ZNP-FSG complexes and the final emulsions were then characterized. We found that the complex prepared by ultrasonication of zein as pretreatment followed by homogenization of the ZNP with FSG ((ZNPU-FSG)H) exhibited the smallest turbidity, highest absolute potential value, relatively small particle size, and formed the most stable complex particles. Meanwhile, complex prepared through direct ultrasonication plus homogenization on the mixture ((ZNP-FSG)HU) showed significantly decreased emulsifying properties and stability. Compared with the complex without ultrasonic treatment, the complex and emulsion, which prepared by ultrasonicated FSG were extremely unstable, and the phase separation phenomenon of the emulsion was observed 30 min after preparation. The above conclusions are also in line with the findings obtained from the properties of the corresponding emulsions, such as the droplets size, microstructure, freeze-thaw stability, and storage stability. It is, therefore, clear that to produce stable Pickering emulsion, ultrasonication should be avoided to apply together at the end of ZNP-FGS complex preparation. It is worth noticing that the emulsions prepared by complex with ultrasonicated zein (ZNPU-FSG)H are smaller, distributed more uniformly, and are able to encapsulate oil droplets well. It was found that the emulsions prepared with ZNPU-FSG remained stable without serum phase for 14 days and exhibited improved stability at low-temperature storage. The current study will provide guidance for the preparation of protein-polysaccharide complexes and Pickering emulsions for future work.

Interconversion and Acrolein-Trapping Capacity of Cardamonin/Alpinetin and Their Metabolites In Vitro and In Vivo.

People are at high risk of exposure to endogenous and exogenous acrolein (ACR). ACR can cause a multitude of illnesses, including cardiovascular disease, Alzheimer's disease, and diabetes. In this study, we investigated the reaction pathway of cardamonin (CAR) or alpinetin (ALP) with ACR and the interconversion of CAR and ALP in vitro at 37 °C in phosphate-buffered saline using liquid chromatography-tandem mass spectrometry (LC-MS/MS). Subsequently, ACR adducts of CAR, ALP, and their metabolites, for example, CAR-ACR-1, ALP-ACR, mono-ACR-pinocembrin chalcone (PIN-ACR), and mono- and di-ACR-naringenin (NAR-ACR and NAR-2ACR), were detected in urine samples, but only CAR-ACR-1 and ALP-ACR were detected in fecal samples from the CAR- and ALP-treated mouse groups using ultraperformance liquid chromatography-MS/MS, respectively. Quantitative analyses showed that CAR, ALP, and their metabolites markedly scavenged ACR in a dose-dependent manner in vivo. Furthermore, we also found that the metabolites of CAR or ALP remained and promoted the ACR-trapping ability.

Inhibitory Activity on the Formation of Reactive Carbonyl Species in Edible Oil by Synthetic Polyphenol Antioxidants.

Food lipids play an important role in food quality, and their attributes contribute to texture, flavor, and nutrition. However, high-temperature processing leads to lipid peroxidation, degradation, and the formation of reactive carbonyl species (RCS), such as acrolein (ACR), glyoxal (GO), and methylglyoxal (MGO). We investigated the changes in the peroxidation value (POV), Rancimat induction time, formation and total amount of RCS, and inhibitory effects of synthetic polyphenol antioxidants on ACR/GO/MGO in plant oils during heating processing through an accelerated oxidation test using Rancimat. With increasing temperature and heating time, the amounts of ACR, GO, and MGO in oil increased and the level of ACR was about several times higher than that of GO and MGO. We also found that some amounts of ACR, GO, and MGO were produced at the initial stage before reaching the peak value of POV, even before oil oxidative rancidity, and the common antioxidant butyl hydroxyanisole (BHA)/butylated hydroxytoluene (BHT) could not remove them once they were generated. This is first time to purify PG-ACR-MGO and elucidate the structure based on analysis of their high resolution mass spectrometry and 1H, 13C, and two-dimensional nuclear magnetic resonance. We further found that PG rather than BHT and BHA efficiently trapped ACR, OG, and MGO to form adducts in oil and roasted beef burgers with corn oil. Additionally, after incubation at 80 °C, the trapping order of PG was as follows: ACR, MGO, and GO, and the adduct of PG-ACR was formed within 1 min; after 10 min, PG-MGO was generated; and three adducts formed at 15 min. However, PG could not trap ACR, GO, or MGO to form adducts at room temperature. This study provided novel knowledge to advance our understanding of the ability of synthetic polyphenol antioxidants to scavenge RCS simultaneously, such as ACR, MGO, and GO. Our findings demonstrated that PG, as an inhibitor of RCS, is suitable for medium- and high-temperature food processing but not for normal-temperature storage.

Comparison of functional and structural properties of ginkgo seed protein dried by spray and freeze process.

The influences of spray-drying and freeze-drying processes on functional properties of ginkgo seed proteins (GSP) were systematically investigated. It was revealed that GSP dried by spray (SGSP) displays an significantly improved water holding capacity and superior emulsifying properties than the freezing-drying GSP (FGSP), whereas, the oil binding capacity is higher in FGSP. The difference in properties of SGSP and FGSP can be attributed to their different structural characteristics. Comparing with FGSP, SGSP was demonstrated having more disulfide bonds, more amorphous and less ordered structure, accounted for big differences in functional properties. With the outstanding functional characteristics, GSP could be potentially applied in oil-in-water type food system, such as milk and mayonnaise. Finally, it is important to choose the suitable drying method according to the requirements of the specific food system.

Trapping of Acrolein by Curcumin and the Synergistic Inhibition Effect of Curcumin Combined with Quercetin.

Acrolein (ACR) is a toxic unsaturated aldehyde that is formed during different steps of thermal food processing. Here, we explored the kinetics of curcumin and ACR and elucidated the pathway of curcumin trapping ACR by preparing a mono-adduct of ACR (CMA-1) conjugated with curcumin. The synergistic scavenging effect and mechanism of curcumin combined with quercetin on ACR was analyzed by liquid chromatography-tandem mass spectrometry (LC-MS/MS). Comparing the uses of curcumin and quercetin both individually and in combination, we found that quercetin in combination resulted in more curcumin being transformed into CMA-2, while curcumin in combination made the amount of di-ACR conjugated to quercetin (QDA) increase. We also added combined curcumin and quercetin into grilled chicken wings to demonstrate that curcumin and quercetin could scavenge ACR by forming their own ACR adducts and antioxidant activity during the process. Our results have noted a new strategy, in which some combinations of dietary polyphenols might contribute to the removal of toxic ACR produced during thermal food processing.

Trapping Acrolein by Theophylline/Caffeine and Their Metabolites from Green Tea and Coffee in Mice and Humans.

Acrolein (ACR) is found exogenously as a widespread environmental pollutant and endogenously, where it is thought to be involved as a pathogenic factor in the progression of many pathological conditions. Eliminating ACR by dietary-active substances has been found to be one potential strategy to prevent ACR-associated chronic diseases. This study first compared the scavenging ACR efficacy of four purine alkaloids, theophylline (TP), paraxanthine (PXT), theobromine (TB), and caffeine (CAF), and then, TP, CAF, and their metabolites were investigated for their ability to trap ACR in vivo. Our results indicated that TP, which possesses an -NH moiety at the N-7 position, exhibits the best ACR-trapping capacity in vitro, while CAF has a slight ability to trap ACR due to the substitutions by -CH3 at the N-1, N-3, and N-7 positions. After oral administration of TP or CAF, the ACR adducts of TP and the metabolites of TP or CAF (e.g., mono- and di-ACR-TP, mono-ACR-1,3-DMU, and mono-ACR-1-MU) were detected in urinary samples obtained from both TP- and CAF-treated mouse groups by using ultra-performance liquid chromatography-tandem mass spectrometry. The quantification studies demonstrated that TP and its metabolites significantly trapped ACR in a dose-dependent manner in vivo. Furthermore, we also detected those ACR adducts of TP and TP/CAF's metabolites in human urine after four cups of green tea (2 g tea leaf/cup) or two cups of coffee (4 g coffee/cup) were consumed per day. Those results indicated that dietary TP or CAF has the potential capacity to scavenge ACR in vivo.

Chemical composition, structural and functional properties of soluble dietary fiber obtained from coffee peel using different extraction methods.

This study aimed to evaluate the effects of chemical, enzymatic, chemical-enzymatic, ultrasound-assisted enzymatic, and shear emulsifying-assisted enzymatic extraction methods on the physicochemical, structural, and functional properties of soluble dietary fiber from coffee peel. We found that the highest extraction yield of soluble dietary fiber was obtained using the shear emulsifying-assisted enzymatic method, and that similar protein contents were obtained from coffee peel using the enzymatic and shear emulsifying-assisted enzymatic methods. Compared with the other extraction methods, shear emulsifying-assisted enzymatic processing resulted in a higher water-holding capacity (7.05 g/g) and oil-holding capacity (3.61 g/g), but a lower emulsifying capacity (58.50%) when compared with that of chemical, enzymatic, and chemical-enzymatic processings. The soluble dietary fiber obtained from coffee peel using shear emulsifying-assisted enzymatic extraction was also characterized by the highest glucose absorption activity (228.06 mg/g), and enzymatic processing resulted in the highest nitrite ion absorption capacity (10.09 mg/g, pH = 2). These results indicated that shear emulsifying-assisted enzymatic extraction method was the most appropriate extraction method for coffee peel soluble dietary fiber.

Acrolein-Trapping Mechanism of Theophylline in Green Tea, Coffee, and Cocoa: Speedy and Successful.

Increasing evidence has identified the unsaturated aldehyde acrolein (ACR) as the potential factor that causes deoxyribonucleic acid cross-linking and the development of chronic diseases. The objective of this study was to investigate the mechanism by which theophylline (TP) scavenges ACR for the first time. TP efficiently scavenged ACR through forming adducts, which was demonstrated in a system in which TP was incubated with ACR at different ratios for different times for liquid chromatography with tandem mass spectrometry. Then, the mono- and di-ACR-TP adducts were purified, and their structures were elucidated by high-resolution mass spectrometry and nuclear magnetic resonance analysis. We found that the ACR residue on mono-ACR-TP further trapped one more ACR and formed di-ACR-TP adducts. Furthermore, mono- and di-ACR-TP had similar time-dependent ACR-scavenging activity to TP. Finally, we demonstrated that green tea, coffee, and cocoa inhibited ACR by trapping ACR to form mono- and di-ACR-TP adducts during the incubation of green tea, coffee, and cocoa with ACR.

Trapping Methylglyoxal by Myricetin and Its Metabolites in Mice.

Trapping of methylglyoxal (MGO) has been determined to be one of the potential mechanisms for dietary polyphenols to prevent chronic diseases. In this study, myricetin was demonstrated to efficiently trap MGO to generate mono- and di-MGO adducts under in vitro conditions. Furthermore, the mono- and di-MGO adducts of myricetin were detected in urine and fecal samples collected from myricetin-treated mice based on LC-MS analysis. More importantly, the mono-MGO adducts of the mono- and di-methylated myricetin were also found in these mouse samples. Further dose-dependent studies demonstrated that myricetin and its methylated metabolites significantly trapped MGO in a dose-dependent manner with the 400 mg/kg dose having the highest trapping efficacy (mono-MGO-myricetin: 272.0 ± 90.9 nM in urine and 1.05 ± 0.67 µg/g in feces; mono-MGO-mono-Me-myricetin: 135.2 ± 77.6 nM in urine and 1.16 ± 0.65 µg/g in feces; and mono-MGO-di-Me-myricetin: 17.0 ± 5.9 nM in urine and 0.19 ± 0.04 µg/g in feces) compared to the 100 and 200 mg/kg doses. In conclusion, this study demonstrates for the first time the in vivo trapping efficacy of myricetin, suggesting that intake of myricetin-containing foods has the potential to scavenge MGO in vivo and to prevent MGO-induced harmful effects to human health.