Journal of Analytical Methods in Chemistry
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2020
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IF 1.878
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.
研究领域:
中药化学
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分析化学
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药效物质基础研究
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DOI
PubMed
高影响因子
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY
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2016
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IF 2.857
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.
研究领域:
食品科学
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微生物学
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植物化学
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DOI
PubMed
高影响因子
Food Chemistry-X
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2025
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IF 8.2
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
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食品科学
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代谢组学
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DOI
PubMed
高影响因子
INTERNATIONAL JOURNAL OF MASS SPECTROMETRY
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2018
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IF 1.826
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
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分析化学
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神经科学
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药理学
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DOI
高影响因子
INDUSTRIAL CROPS AND PRODUCTS
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2018
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IF 3.849
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.
研究领域:
植物化学
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药理学
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DOI
高影响因子
ULTRASONICS SONOCHEMISTRY
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2023
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IF 8.4
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.
研究领域:
食品科学
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植物化学
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DOI
PubMed
高影响因子
INTERNATIONAL JOURNAL OF FOOD SCIENCE AND TECHNOLOGY
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2020
·Vol. 55
·期 9
·3082-3090
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IF 2.773
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.
研究领域:
植物化学
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药理学
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食品科学
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DOI
高影响因子
INTERNATIONAL JOURNAL OF BIOLOGICAL MACROMOLECULES
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2021
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IF 6.953
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 .
研究领域:
生物化学
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药理学
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产品关联
DOI
PubMed
高影响因子
FOOD CHEMISTRY
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2024
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IF 8.5
Yi-Long Ma,Zhi Li,Zheng-Fang Wu,Qian-Lan Wu,Xin Guo,Ya-Fang Shang,Kiran Thakur,Zhao-Jun Wei
The main bioavailable phenolics from of Gongju (GJ) and their mechanism for hepato-protection remain unclear. To select the GJ phenolics with high bioavailability, chrysanthemum digestion and Caco-2 cells were used and their hepato-protective potential were examined by using AML-12 cells. The digestive recovery and small intestinal transit rate of the main phenolic compounds ranged from 28.52 to 69.53% and 6.57% ∼ 15.50%, respectively. Among them, chlorogenic acid , 3,5-dicaffeoylquinic acid, and 1,5-dicaffeoylquinic acid, showed higher small intestinal transit rates and digestive recoveries. Furthermore, we found that by increasing intracellular Catalase (CAT) and Superoxide dismutase (SOD) viability and lowering Malondialdehyde (MDA) level ( P < 0.05 ), 3,5-dicaffeoylquinic acid significantly mitigated the oxidative damage of AML-12 liver cells more than the other two phenolics. Our results demonstrated that 3,5-dicaffeoylquninic acid was the primary phenolic compounds in GJ that effectively reduced liver damage, providing a theoretical basis for the development of GJ as a potentially useful resource for hepatoprotective diet.
研究领域:
营养学
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药理学
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食品科学
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产品关联
DOI
PubMed
高影响因子
INTERNATIONAL JOURNAL OF FOOD PROPERTIES
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2024
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IF 3.1
Qi-Ju Shao,Yan Wang,Xi-Jin Yang,Ke Su,Jin-Fen Zheng,Li Yang,En-Die Zhou,Xiao-Yan Yuan,Rong-Xiang Chen
Gnaphalium affine is a plant with various active properties and has been approved for use as a traditional medicine and food ingredient. In this study, liquid chromatography with electrochemical detection was utilized to separate the antioxidant compounds of G. affine, in conjunction with liquid chromatography-triple quadrupole mass spectrometry for identification. The in vitro antioxidant activity of G. affine was evaluated using DPPH and ABTS radical scavenging capacity assays, as well as the ferric reducing antioxidant power assay. The results showed that a total of 25 antioxidant compounds were screened and identified, among which 14 compounds were quantitatively analyzed. G. affine was found to be rich in phenolic substances, with the total phenolic content ranging from 14.62 to 59.30 mg GAE/g DW, which exhibited high antioxidant potential. The antioxidant activities showed a strong positive correlation with the total phenolic content (r > 0.9). The predominant phenolic compounds in G. affine were 5-O-caffeoylquinic acid, 3-O-caffeoylquinic acid, ferulic acid, luteolin-7-O-glucoside, 3,5-O-dicaffeoylquinic acid, 1,5-O-dicaffeoylquinic acid, and luteolin, with 3,5-O-dicaffeoylquinic acid and 1,5-O-dicaffeoylquinic acid exhibiting the highest levels. Statistical analysis indicated that monosubstituted caffeoylquinic acids, disubstituted caffeoylquinic acids, and luteolin derivatives strongly correlated with the antioxidant potential. This study identified and quantified the major chemical constituents responsible for the antioxidant properties of G. affine, demonstrating its potential as a natural source of antioxidants for the use in foods, pharmaceuticals, and health products.
研究领域:
植物化学
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药理学
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分析化学
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产品关联
DOI
高影响因子
INTERNATIONAL JOURNAL OF BIOLOGICAL MACROMOLECULES
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2024
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IF 7.7
Yingzhu Lian,Guiming Fu,Xinmei Liang,Xinchao He,Jin Xu,Haowei Fan,Yin Wan
Caffeioyl quinic acids and polysaccharides from Artemisia selengensis Turcz are considered potential bioactive substances for hyperuricemia (HUA) treatment. While the mechanism of multi-component combined intervention of polysaccharides and dicaffeoylquinic acids (diCQAs) is not yet clear. In this study, we investigated the effect of A. selengensis Turcz leaves polysaccharides (APS) on the HUA treatment with diCQAs in vitro by direct inhibition of XOD activities and in vivo by using animal model. The results showed that APS had almost no inhibitory effect on XOD activities in vitro , but the inhibitory activity of diCQAs on XOD was affected by changes in inhibition type and inhibition constant. Compared to APS and diCQAs alone, high-dose APS and diCQAs in combination (ADPSh) could significantly reduce the production of uric acid (16.38 % reduction compared to diCQAs group) and oxidative stress damage. Additionally, this combined therapy showed promise in restoring the gut microbiota balance and increasing the short-chain fatty acids levels. The results suggested that APS and diCQAs in combination could be a potential inhibitor for HUA treatment.
研究领域:
药理学
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生物化学
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营养学
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产品关联
DOI
PubMed
高影响因子
JOURNAL OF CHROMATOGRAPHY B-ANALYTICAL TECHNOLOGIES IN THE BIOMEDICAL AND LIFE SCIENCES
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2023
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IF 3
Yue-Hua Chen,Si-Yu Li,Dan Wang,Wei Yuan,Kun Xu,Jia-Wei Wang,Ting-Guo Kang,Hui Zhang
Marsdenia tenacissima is a traditional Chinese medicinal plant used for treating cancer, and its main medicinal part is the stem. Considering the resource shortage of M. tenacissima , it is of great significance to improve its utilization efficiency. Steroids and caffeoylquinic acids, the two main components of M. tenacissima , are composed of several basic structures. Based on this rule, a novel strategy of combinatorics-based chemical characterization was proposed to analyze the constituents of roots, stems and leaves of M. tenacissima . Combinatorics was used to generate a compound library for structure alignment, which has the advantages of wide coverage and high specificity. Steroids are composed of four basic parts: core skeleton (C), substituent at position 11 (A), substituent at position 12 (B) and sugar moiety (S). Based on combinatorics, a compound library consisting of 1080 steroids was generated. Diagnostic neutral loss has been used to effectively predict the substituents at position 11 and 12 of steroids, including acetyl, 2-methylpropionyl, tigloyl, 2-methylbutyryl and benzoyl. As a result, 131, 131 and 99 components were detected from the roots, stems and leaves of M. tenacissima , respectively. Principal component analysis (PCA) was used to analyze the differences of roots, stems and leaves, and orthogonal partial least squares-discriminant analysis (OPLS-DA) was further applied to find differential components. Tenacissoside H, a critical indicator component for quality evaluation of the stem, has been proved to be a differential component between roots and stems. Notably, the relative content of tenacissoside H in the roots was significantly higher than that in the stems. The bioactivity comparison showed that roots, stems and leaves of M. tenacissima had similar scavenging activity on 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical. However, their α-glucosidase inhibitory activity was ranked as leaves > stems > roots. Therefore, besides stems, the other parts of M. tenacissima have potential medicinal value. This study not only helps to develop the resource of M. tenacissima , but also provides a paradigm for the research of other similar medicinal plants.
研究领域:
药用植物学
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分析化学
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中药学
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产品关联
DOI
PubMed
高影响因子
危险品化学品经营许可证（带存储）