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Journal of Analytical Methods in Chemistry · 2020 · IF 1.878

Quantitative Analysis of Six Phenolic Acids in Artemisia capillaris (Yinchen) by HPLC-DAD and Their Transformation Pathways in Decoction Preparation Process

Fang Tian,Qun-Jia Ruan,Ying Zhang,Hui Cao,Zhi-Guo Ma,Gai-Lian Zhou,Meng-Hua Wu

We aimed to establish a quantitative analysis method of six constituents (5-caffeoylquinic acid, 3-caffeoylquinic acid, 4-caffeoylquinic acid, 1,3-dicaffeoylquinic acid, 3,4-dicaffeoylquinic acid, and 4,5-dicaffeoylquinic acid) in Artemisia capillaris (Yinchen) and its decoction by using HPLC coupled with DAD. Besides, the transformation paths of the six constituents were analyzed in decoction preparation processing. The analytical method was fully validated in terms of linearity, sensitivity, precision, repeatability, and recovery and applied to assess the transformation trend and quantitative analysis of the six constituents in Yinchen decoction. The contents of six constituents varied greatly in Yinchen herb and Yinchen decoction, and there were inextricable internal relationships between them. Presumably 3-caffeoylquinic acid was isomerized to generate 5-caffeoylquinic acid and 4-caffeoylquinic acid. Similarly, 1,3-dicaffeoylquinic acid and 3,4-dicaffeoylquinic acid were produced by isomerization of 4,5-dicaffeoylquinic acid. In conclusion, this study provides a chemical basis for quality control of Yinchen decoction, and the changes of selected markers in decoction could give us some novel perspectives to study the relationship between substances and drug efficacy.

CAS / MDL: 75-05-8 64-18-6
研究领域: 中药化学 · 分析化学 · 药效物质基础研究
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JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY · 2016 · IF 2.857

Hydrolysis of Dicaffeoylquinic Acids from Ilex kudingcha Happens in the Colon by Intestinal Microbiota

Minhao Xie,Guijie Chen,Bing Hu,Li Zhou,Shiyi Ou,Xiaoxiong Zeng,Yi Sun

Monocaffeoylquinic acids (mono-CQAs) can be hydrolyzed or metabolized by pancreatin, intestinal brush border esterase, and microbiota in the colon. Data about the conversion of dicaffeoylquinic acids (diCQAs) in digestion are scarce. The diCQA-rich fraction including 3,4-, 3,5-, and 4,5-diCQAs was prepared from Ilex kudingcha, and the conversion in simulated gastricintestine was investigated. Artificial saliva, gastric and pancreatic fluids, Caco-2 monolayer cells, and anaerobic fermentation model were utilized to mimic digestions of the oral cavity, stomach, small intestine, and colon in vitro. The results revealed that diCQAs remained intact in simulated saliva, gastric, and pancreatic fluids and within Caco-2 cells. In anaerobic fermentation with human fecal slurry, diCQAs were hydrolyzed to mono-CQAs and caffeic acid, which were further metabolized to caffeic acid and dihydrocaffeic acid, respectively. The hydrolysis of diCQAs depended on the chemical structures, carbohydrates in the culture medium, and microbial compositions. Our research demonstrated that hydrolysis of diCQAs happened in the colon by intestinal microbiota.

CAS / MDL: 64-18-6
研究领域: 食品科学 · 微生物学 · 植物化学
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Food Chemistry-X · 2025 · IF 8.2

Identification of key anti-glycation polyphenols in Sakura through metabolic profiling and in vitro assessments

Yuhang Zhu,Zhangtie Wang,Xiang Li,Siyu Chen,Daoxin Dai,Weihu Li,Binhai Shi,Baolong Wang,Guoliang Jie,Baiyi Lu

Sakura, a traditional edible flower, has been investigated for its anti-glycation potential; however, the bioactive components remain unclear. Polyphenols are recognized for their exceptional anti-glycation properties. In this study, main polyphenols were identified from seven varieties through metabolomics. 5-O-caffeoylquinic acid (5-OCA), 3-O-caffeoylquinic acid (3-OCA), and caffeic acid were confirmed as key agents through multivariate analysis, which was further validated by anti-glycation assessments. The concentrations of these polyphenols in Cerasus serrulata ‘Kanzan’ (CK) were 2.52 ± 0.08, 3.31 ± 0.18 and 2.38 ± 0.15 mg/g, respectively, contributing to its superior AGEs inhibition ratio (100 μg/mL) of 76.11 ± 0.40 %. Simulated digestion revealed that isomerization between 5-OCA and 3-OCA occurred during the gastric phase. Both compounds were metabolized to caffeic acid in the intestinal phase, contributing to a sustained anti-glycation activity of 64.74 ± 1.11 %. Overall, our study provides a theoretical basis for the development of Sakura-based functional foods targeting anti-glycation.

研究领域: 植物化学 · 食品科学 · 代谢组学
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JOURNAL OF FOOD BIOCHEMISTRY · 2016 ·Vol. 40 ·期 4 ·603-612 · IF 0.832

Antioxidant Activity and Phenolic Acids Profiles of Artemisia Selengensis Turcz Extracted with Various Methods by HPLC-QTOF-MS/MS

Lu Zhang,Zong-Cai Tu,Hui Wang,Qing-Hui Wen,Zhi-Feng Fu,Xing Xie

Effects of dynamic high pressure microfluidization (DHPM), microwave, ultrasound, maceration and high temperature, on the phenolic acids and antioxidant activity of Artemisia selengensis Turcz (AST) were investigated. Microwave exhibited the best extraction efficacy on phenolic compounds and flavonoids with the content of 40.30 μg GAE/mg Extract, and 37.75 μg RTE/mg Extract, respectively. Microwave extract (MWE) also showed the strongest DPPH· and HO· scavenging ability (IC 50 value of 0.23 and 0.50 mg/mL, respectively), and reducing power (Ab 0.3 value of 0.23 mg/mL). Quinic acid, 3 caffeoylquinic acids (CQAs), 2 coumaroylquinic acids, 4 dicaffeoylquinic acids (diCQAs) were identified as the major phenolic acids in AST using HPLC-QTOF-MS/MS, and 3-CQA (63.71 μg/mL) showed the highest content followed by 1,5-diCQA (17.91 μg/mL) and 3,5-diCQA (13.50 μg/mL). MWE had the highest 3-CQA and diCQAs. While, high temperature could promote the degradation of diCQAs, 3- and 4-caffeoyl are more liable to decompose as compared with 1- and 5-caffeoyl. Practical Application Over production of reactive oxygen species (ROS) in body will induce various chronic diseases. AST is an underutilized vegetable with many health benefits. This research indicates that AST possessed appreciating antioxidant activities and abundant phenolic acids, it is could be a potentail antioxidants resource and for prevention of chronic diseases associated with ROS. It also suggested that microwave could be a promising method for extracting the antioxidants in AST. Therefore, this research could lay a foundation for the high-value application of AST in food, health care and natural therapy industry, and provide some methodological references for the development of antioxidants in AST.

研究领域: 药理学 · 食品科学 · 分析化学
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INTERNATIONAL JOURNAL OF MASS SPECTROMETRY · 2018 · IF 1.826

Investigation of the interaction between superoxide dismutase and caffeoylquinic acids by alkali metal assisted cationization-ion mobility mass spectrometry

Bing Zhao,Xiaoyu Zhuang,Shu Liu,Zhiqiang Liu,Fengrui Song,Shuying Liu

Misfolding and dissociation of Cu, Zn-superoxide dismutase (SOD1) is closely related to the pathogenesis of Amyotrophic Lateral Sclerosis (ALS), so that, it is important to discover the compounds which can stabilize the structure of SOD1 for the prevention and treatment of ALS disease. Caffeoylquinic acids (CQAs), as potential antioxidants, are important bioactive components in multiple vegetables and fruits. In this research, we studied the interactions between the CQAs and SOD1, and explored their effects on stabilizing the SOD1 structure and inhibiting the misfolding of SOD1. Because metal-free SOD1 (apo-SOD1) may be one of the precursor compounds of SOD1 dissociation and aggregation, we investigated the non-covalent complex between CQAs and apo-SOD1 by the electrospray ionization mass spectrometry (ESI-MS) and tandem mass spectrometry (MS/MS). Among the CQAs observed in this research, dicaffeoylquinic acids (di-CQAs) have the stronger binding affinity to apo-SOD1 than monocaffeoylquinic acids (mo-CQAs). In order to study the interactions of di-CQA isomers with apo-SOD1, a novel method based on alkali metal assisted cationization-ion mobility mass spectrometry was established and used to investigate the binding affinity between the di-CQA isomers and apo-SOD1 by distinguishing and quantifying the unbound di-CQA. Collision induced unfolding (CIU), as a new methodology, was further used to assess the stabilities of di-CQAs and apo-SOD1 complexes. The results show that there were no distinct differences in the binding affinity between different di-CQA isomers and apo-SOD1. Furthermore, CIU data obtained in this work reveal that di-CQAs can stabilize apo-SOD1 dimer and retard the unfolding of apo-SOD1 dimer. The strategy developed by us can be also used to study the interactions between other isomeric compounds and target protein in order to discover more potential drug-like small molecules.

研究领域: 生物化学 · 分析化学 · 神经科学 · 药理学
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INDUSTRIAL CROPS AND PRODUCTS · 2018 · IF 3.849

Solvent extraction of caffeoylquinic acids from Artemisia selengensis Turcz leaves and their in vitro inhibitory activities on xanthine oxidase

Yizhen Li,Yin Wan,Ruyi Li,Laojiu Xu,Mingyong Xie,Guiming Fu

In this study, the caffeoylquinic acid (CQA) extract solution of the Artemisia selengensis Turcz (AST) leaves prepared by 70% ethanol reflux method was separated with petroleum ether, ethyl acetate, and water-saturated n -butanol to obtain the proper solvent to purify CQAs. Results showed that the ethyl acetate fraction (EAF) exhibited the highest total chlorogenic acid content (TCC) (241.46 ± 0.00 mg/g dry fraction), followed by the water-saturated n -butanol fraction ( n BuF) (TCC = 62.30 ± 0.82 mg/g dry fraction). Ultra-high performance liquid chromatography-quadrupole time-of-flight mass spectrometry and high-performance liquid chromatography photodiode array were used to qualitatively and quantitatively determine the CQAs in these two fractions. In EAF, four CQAs, namely, 3-CQA, 3,5-diCQA, 3,4-diCQA, and 4,5-diCQA, were identified with the contents of 5.69 ± 0.03, 106.65 ± 0.83, 15.65 ± 0.24, and 28.08 ± 0.82 mg/g, respectively. Six CQAs, namely, 3-CQA, 4-CQA, 1,3-diCQA, 3,5-diCQA, 3,4-diCQA, and 4,5-diCQA, with contents of 16.57 ± 0.23, 3.22 ± 0.55, 4.49 ± 0.01, 16.86 ± 0.24, 7.35 ± 0.11, and 6.41 ± 0.13 mg/g, respectively, were identified in n BuF. Quantitative analysis of the six CQAs in AST leaves have not been reported, and 1,3-diCQA has been found in AST leaves for the first time. Moreover, either EAF or n BuF and the six CQA reference compounds showed certain inhibitory activity on xanthine oxidase (XOD) in vitro . EAF demonstrated a stronger XOD inhibitory effect (IC 50  = 1.67 mg/mL) than n BuF. Among the six CQA compounds, 3,4-diCQA had the lowest IC 50 of 12.80 μM, whereas 1,3-diCQA and 3-CQA had IC 50 values of 23.69 and 28.29 μM, respectively. The inhibitory activity of 4-CQA was weak. These findings indicated that CQAs are the major components inhibiting the XOD activity in vitro in AST leaves.

CAS / MDL: 69-89-6
研究领域: 植物化学 · 药理学
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RSC Advances · 2019 ·Vol. 9 ·期 7 ·3938-3945 · IF 3.049

Insight into the effect of quinic acid on biofilm formed by Staphylococcus aureus

Jin-Rong Bai,Yan-Ping Wu,Grosu Elena,Kai Zhong,Hong Gao

The biofilm formation of Staphylococcus aureus on food contact surfaces is the main risk of food contamination. In the present study, we firstly investigated the inhibitory effect of quinic acid (QA) on biofilm formed by S. aureus. Crystal violet staining assay and microscopy analysis clearly showed that QA at sub-MIC concentrations was able to significantly reduce the biofilm biomass and cause a collapse on biofilm architecture. Meanwhile, fibrinogen binding assay showed that QA had obviously effect on the S. aureus bacteria adhesion. XTT reduction assay and confocal laser scanning microscopic images revealed that QA significantly decreased metabolic activity and viability of biofilm cells. In addition, qRT-PCR analysis explored the potential inhibitory mechanism of QA against biofilm formation, which indicated that QA significantly repressed the gene sarA and activated the gene agrA. Moreover, QA exhibited a highly ability to reduce the number of sessile S. aureus cells adhered on the stainless steel. So, it was suggested that QA could be used as a promising antibiofilm agent to control biofilm formation of S. aureus.

研究领域: 微生物学 · 食品安全 · 分子生物学
✓ 已验证 DOI PubMed 高影响因子
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ULTRASONICS SONOCHEMISTRY · 2023 · IF 8.4

Degradation, isomerization and stabilization of three dicaffeoylquinic acids under ultrasonic treatment at different pH

Danli Wang,Yushi Wang,Zhenlei Zhang,Shaoping Qiu,Yawen Yuan,Gongshuai Song,Ling Li,Tinglan Yuan,Jinyan Gong

Dicaffeoylquinic acids (diCQAs) are found in a variety of edible and medicinal plants with various biological activities. An important issue is the low stability of diCQAs during extraction and food processing, resulting in the degradation and transformation. This work used 3,5-diCQA as a representative to study the influence of different parameters in ultrasonic treatment on the stability of diCQAs, including solvent, temperature, treatment time, ultrasonic power, duty cycle, and probe immersion depth. The generation of free radicals and its influence were investigated during the treatment. The stability of three diCQAs (3,5-diCQA, 4,5-diCQA and 3,4-diCQA) under the certain ultrasonic condition at different pH conditions was evaluated and found to decrease with the increase of pH, further weakened by ultrasonic treatment. Ultrasound was found to accelerate the degradation and isomerization of diCQAs. Different diCQAs showed different pattern of degradation and isomerization. The stability of diCQAs could be improved by adding epigallocatechin gallate and vitamin C.

CAS / MDL: 50-81-7
研究领域: 食品科学 · 植物化学
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INTERNATIONAL JOURNAL OF FOOD SCIENCE AND TECHNOLOGY · 2020 ·Vol. 55 ·期 9 ·3082-3090 · IF 2.773

Effects of impregnate temperature on extraction of caffeoylquinic acid derivatives from Moringa oleifera leaves and evaluation of inhibitory activity on digestive enzyme, antioxidant, anti-proliferative and antibacterial activities of the extract

Yahya Saud Hamed,Mohamed Abdin,Guijie Chen,Hafiz Muhammad Saleem Akhtar,Xiaoxiong Zeng

Summary In an ultrasonic bath and for 30 min in the presence of water as extraction solvent in a ratio of 1:10 (g/mL), effect of extraction temperature on extraction of caffeoylquinic acids (CQAs) from Moringa oleifera leaves (MOL) was investigated. Gradually increasing in extraction temperature caused a growing in mono-CQA and declining in 3,5-diCQA. The extract obtained at 80 °C showed the highest antioxidant capacity, and IC 50 values for scavenging activities on DPPH radicals and ABTS radicals were 56.9 and 53.6 µg/mL, respectively. Compared with α-glucosidase and α-amylase, the extract showed the highest inhibition on pancreatic lipase (IC 50 of 0.073 mg/mL). Increasing the extraction temperature improved cytotoxicity of the extract on cancer cell lines of HeLa and HepG2. Compared with gram-negative Escherichia coli and Salmonella typhimurium , all the extracts showed higher inhibition on the growth of gram-positive Bacillus cereus and Staphylococcus aureus . Our results suggested that use of higher extraction temperature (80 °C) improved the biological activity of MOL extract.

CAS / MDL: 1898-66-4 28752-68-3
研究领域: 植物化学 · 药理学 · 食品科学
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JOURNAL OF FOOD COMPOSITION AND ANALYSIS · 2022 · IF 4.52

Simultaneously quantification of organic acids metabolites by HPLC mass spectrometry to reveal the postharvest quality change in cherry tomato

Meng Dong,Ran Xin,Zhi-Yuan Li,Yu-Lian Li,Xu-Hui Huang,Xiu-Ping Dong,Bei-Wei Zhu,Lei Qin

The organic acids in fruits have critical impacts on palatability and flavor . In this paper, we established a method to quantify 21 essential organic acids in animal and plant matrices using HPLC mass spectrometry with high sensitivity and broad applicability. The organic acids in 12 animal and plant matrices were quantified. Additionally, the profile and concentration of organic acids could achieve the classification of samples. The fruit quality traits and important organic acids content during the storage of cherry tomatoes were monitored via our method. Nine organic acids changed significantly in 16 days of storage, especially citric acid , as the most predominant organic acid, decreased from 4260 to 2290 μg/g, leading to a decline in sourness of 46.2 %. In contrast, after 16 days of storage, galacturonic, gluconic, malonic and quinic acids increased by 155 %, 88 %, 162 %, and 112 %, respectively, which had a potential effect on softening and deteriorating of cherry tomatoes.

研究领域: 食品科学 · 植物生理学
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Food Frontiers · 2024 · IF 7.4

Quinic acid as an inhibitor of α-glucosidase activity, nonenzymatic glycosylation, and glucose transport in Caco-2 cells

Ziyi Han,Leyu Wang,Panjie Sun,Mengxin Huang,Fei Yu,Junsheng Liu,Yuanyuan Wu,Puming He,Youying Tu,Bo Li

Hyperglycemia and diabetes are common metabolic disorders. It is considered a safe and effective strategy to screen active ingredients from food and herbs for controlling blood sugar levels. Quinic acid (QA) is a natural polyphenolic acid with various health-promoting properties. In this study, QA was found to exhibit a potent inhibitory effect on α-glucosidase activity, with a half maximal inhibitory concentration (IC 50 ) of 5.46 mM. This inhibitory property surpassed that of three common organic acids including gallic acid, malic acid, and citric acid. A combination of 25% acarbose (0.5 mM) and 75% QA (5 mM) (v/v) exhibited synergistic inhibition of α-glucosidase activity. Enzyme kinetics, fluorescence spectra, and molecular docking analyses indicated that QA acted as an uncompetitive inhibitor of α-glucosidase, with hydrogen bonds playing a key role in the intermolecular interactions. Moreover, QA was found to effectively inhibit three major nonenzymatic glycation products including advanced glycosylation end products (AGEs), fructosamine, and α-dicarbonyl in a dose-dependent manner, outperforming the positive control aminoguanidine (AG) within the tested concentration range. Utilizing a Caco-2 cell model, QA demonstrated the ability to inhibit the transmembrane absorption of glucose. This study highlighted QA as a promising food functional factor that had been overlooked in the past, offering potential benefits in improving hyperglycemia, diabetes, and associated complications through the inhibition of α-glucosidase, nonenzymatic glycosylation, and glucose uptake.

CAS / MDL: 149-91-7 6915-15-7
研究领域: 食品科学 · 分子生物学 · 代谢疾病研究
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INTERNATIONAL JOURNAL OF BIOLOGICAL MACROMOLECULES · 2021 · IF 6.953

Inhibitory mechanism of xanthine oxidase activity by caffeoylquinic acids in vitro

Yin Wan,Jin Qian,Yizhen Li,Yuefeng Shen,Yanru Chen,Guiming Fu,Mingyong Xie

In this study, the inhibitory activities of eight caffeoylquinic acids (CQAs) against xanthine oxidase (XOD) in vitro were investigated, and the interaction mechanisms between each compound and XOD were studied. HPLC and fluorescence spectra showed that the inhibitory activities of dicaffeoylquinic acids (diCQAs) were higher than that of monocaffeoylquinic acids (monoCQAs), due to the main roles of hydrophobic interaction and hydrogen bond between XOD and diCQAs. Both the binding constant and the lowest binding energy data indicated that the affinities of diCQAs to XOD were stronger than that of monoCQAs. Circular dichroism showed that the structure of XOD was compacted with the increased of α-helix content, resulting in decreased enzyme catalytic activity . Molecular docking revealed that CQAs preferentially bind to the flavin adenine dinucleotide region in XOD. These results provided the mechanisms of CQAs on inhibiting XOD and the further utilization of CQAs as XOD inhibitors to prevent hyperuricemia .

CAS / MDL: 315-30-0 69-93-2 69-89-6
研究领域: 生物化学 · 药理学
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