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npj Science of Food · 2022 ·Vol. 6 ·期 1 ·1-8 · IF 7

Effects of phenolic acids and quercetin-3-O-rutinoside on the bitterness and astringency of green tea infusion

Chen Yu-Hong,Zhang Yan-Hong,Chen Gen-Sheng,Yin Jun-Feng,Chen Jian-Xin,Wang Fang,Xu Yong-Quan

Phenolic acids are important taste components in green tea. The aim of this study was to analyze the taste characteristics of phenolic acids and their influence on the bitterness and astringency of green tea by sensory evaluation and chemical determination. The major tea phenolic acids and quercetin-3- O -rutinoside (Que-rut) were significantly positively correlated with the bitterness ( r  = 0.757, p  < 0.01; r  = 0.605, p  < 0.05) and astringency ( r  = 0.870, p  < 0.01; r  = 0.576, p  < 0.05) of green tea infusion. The phenolic acids have a sour and astringent taste, whereas Que-rut has a mild astringent taste. Phenolic acids and Que-rut can increase the bitterness of epigallocatechin gallate (EGCG). However, these components behaved differently for astringency on EGCG. Gallic acid (GA) enhances the astringency throughout all the concentrations in this study. While it seemed to be double effects of caffeic acid (CA), chlorogenic acid (CGA), and Que-rut on that, i.e., the inhibition at lower concentrations (CA: 0–0.2 mM; CGA: 0–0.2 mM; Que-rut: 0–0.05 mM) but enhancement at higher ones. The phenolic acids and Que-rut interacted synergistically with tea infusion and as their concentration increased, the synergistic enhancement of the bitterness and astringency of tea infusion increased. These findings help provide a theoretical basis for improving the taste of middle and green tea.

CAS / MDL: 75-05-8 64-18-6 67-56-1
研究领域: 食品科学 · 茶叶研究
✓ 已验证 产品关联 DOI PubMed 高影响因子
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RSC Advances · 2018 ·Vol. 8 ·期 68 ·38715-38720 · IF 2.936

A novel analytical method based on HPLC-PDA coupled post-column derivatization to evaluate the ability to inhibit tyrosine nitration in lotus leaf extracts

Yin Qian,Xi Chen,Jin Qi,Xuming Liu

Protein tyrosine nitration plays a key role in many inflammatory and cardiovascular diseases and diabetes. Many natural products are used to treat these diseases through their ability to potentially interfere this reaction. Here, we describe a novel method to provide active fingerprinting of inhibition of tyrosine nitration by natural products based on post-column tyrosine nitration reaction analysis using high-performance liquid chromatography coupled to a photometric diode array. Results indicated that lotus leaf extracts exhibited obvious inhibitory activity against tyrosine nitration by peroxynitrite, and that chemical and active fingerprints were simultaneously established, with the active fingerprints indicating the active compounds of the lotus leaves. Additionally, flavonoids were screened as the principal active compounds involved in inhibiting tyrosine nitration in the lotus leaf extracts, with quercetin-3-O-glucuronide and quercetin-3-O-glucoside exhibiting the greatest contributions. Moreover, our results suggested that lotus leaves from three regions (Nanjing, Suzhou, and Hangzhou) exhibited the best inhibitory activity. These findings indicated the usefulness of this method for screening active compounds involved in inhibiting protein tyrosine nitration, and that similar strategies can likely be applied to evaluate the inhibitory activity against tyrosine nitration of other natural products.

CAS / MDL: 64-18-6
研究领域: 分析化学 · 药理学 · 天然产物 · 生物化学
✓ 已验证 产品关联 DOI PubMed 高影响因子
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FOOD CHEMISTRY · 2021 · IF 7.514

Binding mechanism and functional evaluation of quercetin 3-rhamnoside on lipase

Di Wu,Ran Duan,Lan Tang,Xia Hu,Fang Geng,Qiaomei Sun,Yin Zhang,Hui Li

The interaction between lipase and quercetin 3-rhamnoside was studied by fluorescence spectroscopy, enzyme kinetics, and molecular dynamics simulation. The results showed that quercetin 3-rhamnoside had a strong quenching effect on the intrinsic fluorescence of lipase. The binding constant decreased with increasing temperature, and the number of binding sites approached 1. Thermodynamic parameters indicated that hydrogen bonding and van der Waals forces are the dominant forces when the interaction occurs. Circular dichroism spectroscopy and infrared spectroscopy proved that the ligand perturbed the structure of lipase. Enzyme kinetics results showed that quercetin 3-rhamnoside inhibited lipase, and the inhibitory effect was dose-dependent. Molecular dynamics simulation further explained the interaction mechanism and inhibitory effect. This study confirmed the inhibitory effect of quercetin 3-rhamnoside on lipase explained their binding mechanism, which will contribute to guiding the development of fat-reducing functional foods.

CAS / MDL: 522-12-3
研究领域: 生物化学 · 营养学 · 药理学
✓ 已验证 产品关联 DOI PubMed 高影响因子
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PeerJ · 2019 · IF 2.353

Pharmacokinetic comparison of quercetin, isoquercitrin, and quercetin-3-O-β-D-glucuronide in rats by HPLC-MS

Hongli Yin,Ji Ma,Jichun Han,Maoru Li,Jing Shang

Background Quercetin (Qr), isoquercitrin (IQ), and quercetin-3-O-β-D-glucuronide (QG) are powerful phytochemicals that have been shown to exhibit disease prevention and health promotion properties. However, there may exist transformations between Qr, IQ, and QG in vivo . And the pharmacokinetic profiles of Qr, IQ, and QG have not been systematically compared. The pharmacokinetics study would be helpful to better understand the pharmacological actions of them. Methods Herein, we developed a reliable HPLC-MS method to compare the pharmacokinetics of Qr, IQ, and QG after separate (50 mg/kg) oral administration of them in rats, using puerarin as internal standard. The detection was performed using negative selected ion monitoring. This method was validated in terms of selectivity, linearity, precision, accuracy, extraction recovery, matrix effect, and stability; and shows reliabilities in monitoring the pharmacokinetic behaviors of these three compounds. Results Our results showed that after separate oral administration of Qr, IQ, and QG, all of the compounds could be detected in plasma. In addition, QG could be detected in the Qr group; Qr and QG could be measured in the IQ group; and Qr could be found in rat plasma after 1.5 h of QG administration. Moreover, the AUC 0− t of Qr in the; Qr group (2,590.5 ± 987.9 mg/L*min), IQ group (2,212.7 ± 914.1 mg/L*min), and QG group (3,505.7 ± 1,565.0 mg/L*min) was larger than the AUC 0− t of QG in the; Qr group (1,550.0 ± 454.2 mg/L*min), IQ group (669.3 ± 188.3 mg/L*min), and QG group (962.7 ± 602.3 mg/L*min). The AUC 0− t of IQ was the lowest among all groups. Discussion Quercetin, IQ, and QG can all be absorbed into plasma. A mutual transformation exists between Qr and QG, and IQ can be metabolized into Qr and QG in SD rats. These results would provide a meaningful basis for understanding the pharmacological actions of these three compounds.

研究领域: 药理学 · 分析化学
✓ 已验证 DOI PubMed 高影响因子
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Horticulture Research · 2022 · IF 7.291

Identification of UDP-rhamnosyltransferases and UDP-galactosyltransferase involved in flavonol glycosylation in Morella rubra

Ren Chuanhong,Guo Yan,Xie Linfeng,Zhao Zhikang,Xing Mengyun,Cao Yunlin,Liu Yilong,Lin Jing,Grierson Donald,Zhang Bo,Xu Changjie,Chen Kunsong,Li Xian

Flavonol glycosides are health-promoting phytochemicals important for human nutrition and plant defense against environmental stresses. Glycosylation modification greatly enriches the diversity of flavonols. Morella rubra, a member of the Myricaceae, contains high amounts of myricetin 3-O-rhamnoside (M3Rha), quercetin 3-O-rhamnoside (Q3Rha), and quercetin 3-O-galactoside (Q3Gal). In the present study, MrUGT78R1 and MrUGT78R2 were identified as two functional UDP-rhamnosyltransferases, while MrUGT78W1 was identified as a UDP-galactosyltransferase. Site-directed mutagenesis identified Pro143 and Asn386 as important residues for rhamnosyl transfer activity of MrUGT78R1, while the two corresponding positions in MrUGT78W1 (i.e. Ser147 and Asn370) also play important roles in galactosyl transfer activity. Transient expression data for these three MrUGTs in Nicotiana benthamiana tested the function of MrUGT78R1 and MrUGT78R2 as rhamnosyltransferases and MrUGT78W1 as a galactosyltransferase in glycosylation of flavonols. This work enriches knowledge of the diversity of UDP-rhamnosyltransferase in planta and identifies two amino acid positions important for both rhamnosyltransferase and galactosyltransferase.

研究领域: 植物科学 · 生物化学 · 分子生物学
✓ 已验证 产品关联 DOI PubMed 高影响因子
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FOOD CHEMISTRY · 2014 · IF 3.259

Characterisation of polyphenol constituents of Linderae aggregate leaves using HPLC fingerprint analysis and their antioxidant activities

Chanjuan Xu,Bingxian Yang,Wei Zhu,Ximin Li,Jingkui Tian,Lin Zhang

The leaves of Linderae aggregate (LAL) has been used as a type of tea in China and other Southeast Asian countries. In this study, 11 polyphenols in LAL were clarified for the first time using multiple high-performance liquid chromatographic techniques. An optimal extracting method was developed through the comparison of the amount of quercetin-3- O -α- l -rhamnoside using a uniform design method. From the fingerprint liquid chromatography data, 11 common peaks in the 8 samples collected from April to November were semi-determined. The antioxidant capacities were examined using the 2,2-diphenyl-1-picrylhydrazyl free radical scavenging assay and the ferric reducing/antioxidant power assay. All 8 samples contained the same 11 polyphenols in similar ratios. Three samples, S2, S5 and S6 contained higher amount of quercetin-3- O -α- l -rhamnoside and were demonstrated to have stronger antioxidant capacities in both antioxidant assays. These results are critical in optimising harvest time and quality control of LAL.

研究领域: 植物化学 · 药理学 · 分析化学
✓ 已验证 DOI 高影响因子
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Journal of Inflammation Research · 2021 · IF 6.922

Crm1-Dependent Nuclear Export of Bach1 is Involved in the Protective Effect of Hyperoside on Oxidative Damage in Hepatocytes and CCl4-induced Acute Liver Injury

Yongqing Cai,Bin Li,Dan Peng,Xianfeng Wang,Pan Li,Mingchun Huang,Haiyan Xing,Jianhong Chen

Background Nrf2-Bach1 antioxidant signaling pathway is considered as one of the most important mechanisms of cellular resistance to oxidative injury. The effect of hyperoside (Hyp) on the expression and distribution of Bach1, the relationship of Hyp’s antioxidative effect and the influence of Bach1 remains unclear. Purpose The aim of this study was to investigate the role and mechanisms of Bach1 in the protective effect of Hyp on oxidative liver injury. Methods The protective effect of Hyp on oxidative stress injury was observed in vivo and in vitro. Next, the influence of Hyp on Bach1 expression and distribution, and competitive combination of Nrf2-Bach1 with ARE in H 2 O 2 -induced L02 cell was studied by Western blot, RT-PCR, immunofluorescence and CHIP assay. Finally, the expressions of Crm1, ERK and p38 and their roles on Hyp mediated nuclear export of Bach1 were investigated by Western blot. Results Hyp ameliorated the pathological damage, reduced the liver index, AST, ALT and MDA activities, and increased SOD and GSH levels in the CCl 4 -induced acute liver injury mouse model. Hyp attenuated H 2 O 2 -induced oxidative stress injury in L02 cells. Hyp promoted the early rapid redistribution of Bach1 from nucleus to cytoplasm. CHIP analyses demonstrated that Hyp enhanced the levels of Nrf2-ARE complex, and weakened the levels of Bach1-ARE complex within three hours. In addition, Hyp enhanced transport protein Crm1 expression and ERK1/2 activity. And LMB, a Crm1 inhibitor, attenuated the effect of Hyp on Bach1 nuclear export and anti-oxidation. U0126, an ERK1/2 inhibitor, reduced the effect of Hyp on Crm1 expression and the Bach1 redistribution. Conclusion The hepatoprotective mechanism of Hyp was related to improve Bach1 nuclear export depending on ERK1/2-Crm1 to upregulate the level of Nrf2 binding to ARE.

研究领域: 药理学 · 肝病学 · 分子生物学
✓ 已验证 DOI PubMed 高影响因子
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JOURNAL OF CHROMATOGRAPHY B-ANALYTICAL TECHNOLOGIES IN THE BIOMEDICAL AND LIFE SCIENCES · 2017 · IF 2.603

Purification of quercetin-3-O-sophoroside and isoquercitrin from Poacynum hendersonii leaves using macroporous resins followed by Sephadex LH-20 column chromatography

Hongjuan Li,Ying Liu,Yuetao Yi,Qin miao,Sujing Liu,Feng Zhao,Wei Cong,Chunhua Wang,Chuanhai Xia

In China, Poacynum hendersonii is frequently used as a substitute for Apoacynum venetum L (Luobuma), which is a famous traditional Chinese medicine. Quercetin-3- O -sophoroside and isoquercitrin are two major flavonoids in Poacynum hendersonii leaves. In this work, a suitable method was established for the large-scale preparation of quercetin-3- O -sophoroside (QOS) and isoquercitrin (ISO) from Poacynum hendersonii leaves using macroporous resin combined with Sephadex LH-20 column chromatography. The adsorption/desorption capacities and desorption ratios of six macroporous resins were evaluated using static experiments. The HPD-300 resin had the best adsorption performance because it had the largest surface area, and was selected for further study. Compared with pseudo-first-order and intraparticle diffusion kinetics models, the pseudo-second-order model could better fit the adsorption kinetics of both QOS and ISO on the HPD-300 resin. In addition, the adsorption isotherms of the two compounds on the HPD-300 resin were fitted well to the Langmuir model. Under optimal conditions, the purities of QOS and ISO in the product were increased from 2.16% and 1.26% to 21.34% and 10.70% with recovery yields of 82.1% and 77.3%, respectively. Subsequently, Sephadex LH-20 column chromatography was employed for improving the purities of the two compounds. After separation by Sephadex LH-20 column chromatography, the purities of QOS and ISO achieved 93.5% and 95.6%, respectively.

研究领域: 药学 · 化学工程 · 天然产物化学 · 中药学
✓ 已验证 DOI PubMed 高影响因子
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JOURNAL OF ETHNOPHARMACOLOGY · 2022 · IF 5.195

Anti-Alzheimer's disease active components screened out and identified from Hedyotis diffusa combining bioaffinity ultrafiltration LC-MS with acetylcholinesterase

Jing Li,Guangyi Yang,Wenfeng Shi,Xiaoping Fang,Lintao Han,Yan Cao

Ethnopharmacological relevance Hedyotis diffusa is a traditional ethnomedicinal plant in local communities in northeastern Asia and used to treat inflammation, nervous breakdown, among others. In recent years, it has been applied in the treatment of Alzheimer's disease (AD), while the specific chemical components responsible for the activity remain need to be explored. Aim of the study To prepare, screen and identify the potential anti-AD active components from Hedyotis diffusa . Materials and methods The acetylcholinesterase (AChE) inhibitory activity of four different extracts of Hedyotis diffusa were initially assessed using a spectrophotometric Ellman's method. A more accurate LC-MS/MS screening method combining functional enzyme assay and affinity ultrafiltration (AU) screening assay was developed and applied for the screening of natural compound inhibitors of AChE from Hedyotis diffusa . The binding mode was further investigated between protein and ligands via molecular docking. Subsequently, CL4176, a transgenic nematode model for AD, was used for activity validation of one of these components. Results N-butanol extract of Hedyotis diffusa (NHD) appeared significant inhibitory activities on AChE, were chosen to delve deeper. Five bioactive components targeting AChE were screened out and identified using AU coupled to liquid chromatography-mass spectrometry. Molecular docking technique further confirmed the results of the screening assay. Finally, quercetin-3-O-sophoroside (QS) was confirmed as a potent anti-AD agent by in vivo experiments in C. elegans . Conclusion This study explores a new idea for screening anti-AD active components from traditional medicine. The findings provide a molecular structure and bioactivity basis for future potential applications of Hedyotis diffusa in medical industries.

CAS / MDL: 1866-15-5
研究领域: 药理学 · 神经科学 · 民族药理学 · 分子生物学
✓ 已验证 产品关联 DOI PubMed 高影响因子
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JOURNAL OF FOOD BIOCHEMISTRY · 2020 ·Vol. 44 ·期 10 ·e13420 · IF 1.662

Metabolomics analysis reveals the protective effect of quercetin-3-O-galactoside (Hyperoside) on liver injury in mice induced by acetaminophen

Cheng Hu,Ying Chen,Yiyuan Cao,Yiqun Jia,Jiaqi Zhang

We investigated the protective effect of Hyperoside (HPS) on liver injury induced by acetaminophen (APAP) in C57 mice. HPS was administered orally for 7 days and APAP was administered orally on the 7th day. Serum and liver samples were then collected for biochemical analyses, histopathology assessments, and metabolomics studies. Metabolites were assessed using a UHPLC-MS system. Principal component analysis (PCA) and orthogonal partial least squares discriminant analysis (OPLS-DA) were used to process the data. Pathway analyses were performed using Metaboanalyst 4.0. Western blot and qRT-PCR were used to determine the protein and mRNA levels, respectively. HPS interacted with active sites in CYP2E1 and caused protein degradation. In conclusion, our results suggested that HPS prevented the oxidative stress-induced liver injury caused by APAP. Practical applications Hyperoside was shown to have potential protective and therapeutic effects against liver diseases. Male C57 mice were used to perform pharmacodynamic, pharmacology, and metabolomics evaluations. At a dose of 60 mg/kg, HPS prevented oxidative stress-induced liver injury caused by APAP by regulating the glutathione-related metabolites and enzymes through the inhibition of CYP2E1.

CAS / MDL: 7424-00-2
研究领域: 药理学 · 代谢组学 · 毒理学 · 分子生物学
✓ 已验证 产品关联 DOI PubMed 高影响因子
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JOURNAL OF LIQUID CHROMATOGRAPHY & RELATED TECHNOLOGIES · 2022 · IF 1.467

Immobilized α-glucosidase using polydopamine-coated magnetic nanoparticles for targeted screening of an active component from Toona sinensis

Yi Zhang,Jing Meng,Shuai Wang,Dongyu Gu,Xingtao Lin,Dezhi Huang,Yi Yang

Toona sinensis is a traditional vegetable with rich nutrition and wide biological activity. In our previous study, an active composition against α-amylase was screened from T. sinensis by ligand fishing. To investigate the effect of T. sinensis on other targets of antidiabetes, in this work, α-glucosidase was immobilized on polydopamine-coated magnetic nanoparticles to further screen the compounds against α-glucosidase by ligand fishing. The enzyme activity test showed that the 70% ethanol extract of T. sinensis (crude sample) had weak α-glucosidase inhibitory activity, but after extraction with different solvents, the ethyl acetate extract showed the highest α-glucosidase inhibitory activity. After immobilization of α-glucosidase on polydopamine (PDA)-coated magnetic nanoparticles, the properties of the enzyme were characterized and determined, and then quercetin-3-O-α-L-rhamnopyranoside was screened by ligand fishing and isolated by high-speed counter-current chromatography using the two-phase solvent system composed of n-hexane-ethyl acetate-methanol-water (1:5:1:5, v/v). The results of enzymes assay showed that the screened compound (IC50 value of 374.94 ± 4.35 μg/mL) possessed moderate α-glucosidase inhibitory activity. The presented results not only proved that ligand fishing based on polydopamine-coated magnetic α-glucosidase was an effective method for the rapid discovery of natural active substances, but also further strengthened the evidence of antidiabetic effect of T. sinensis.

CAS / MDL: 6104-58-1 51-61-6
研究领域: 生物化学 · 药理学 · 纳米技术 · 植物科学
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Food & Function · 2022 ·Vol. 13 ·期 10 ·5547-5558 · IF 6.317

Protective role of bayberry extract: associations with gut microbiota modulation and key metabolites

Pengcheng Tu,Qiong Tang,Meng Wang,Wen Chen,Xiang Ye,Xiaodong Zheng

Dysbiosis of the gut microbiota is inextricably intertwined with the onset and development of metabolic diseases. Dietary modulation of the gut microbiota has received much attention in recent years; however, currently there are still few effective approaches. Polyphenols extracted from fruits protect against metabolic disorders, and this effect is associated with the gut microbiota. We aimed to investigate the metabolic impact of bayberry extract cyanidin-3-O-glucoside and its associations with changes in the gut microbiota. Based on C57BL/6 and db/db mouse models, combined with 16S rRNA high-throughput sequencing and metabolomic profiling, we found that C3G administration reduced weight gain and fasting blood glucose levels. More importantly, C3G significantly modulated the gut microbiota including its composition, diversity and functional pathways. A distinct metabolite profile in addition to alterations of key metabolites was observed probably resulting from changes in the gut bacterial composition and metabolic pathways induced by C3G administration. This study may provide evidence for the missing link in mechanisms underlying the beneficial effects of poorly absorbed dietary polyphenols.

研究领域: 营养学 · 微生物学 · 代谢组学 · 药理学
✓ 已验证 DOI PubMed 高影响因子
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