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
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
Food Chemistry-X
·
2025
·
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
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY
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2020
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IF 4.192
Xiaoyun Jiang,Yongling Lu,Lishuang Lv
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.
研究领域:
药理学
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毒理学
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营养学
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生物化学
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产品关联
DOI
PubMed
高影响因子
INDUSTRIAL CROPS AND PRODUCTS
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2020
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IF 4.244
Qiyu Chen,Wenjiang Dong,Changqing Wei,Rongsuo Hu,Yuzhou Long
This study was designed to integrate ultrasonic-microwave assisted extraction (UMAE) with ethanol, a green solvent, to extract green coffee oil (GCO) from green coffee beans. Response surface methodology was utilised to maximise the efficiency of GCO extraction. Structural changes occurring in the coffee residue were explored using scanning electron microscopy , and extraction kinetics was established. Results indicated that the yield of GCO obtained by UMAE under optimum conditions (microwave power 350 W; extraction time 10 min; and liquid-solid ratio 28:1 mL/g) was 10.58 ± 0.34%. Extraction kinetics revealed that UMAE exhibited higher efficiency and took less time (10 min vs 5 h with solvent extraction) compared with conventional process. The highest contents of kahweol and cafestol found in the UMAE extract were 12.00 and 22.28 mg/g oil, respectively. This study demonstrated that UMAE with ethanol is a rapid, efficient, and environmentally friendly green technique for the extraction of green coffee oil.
研究领域:
食品科学
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植物化学
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产品关联
DOI
高影响因子
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY
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2011
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IF 2.816
Biao Cheng,Xinran Liu,Hao Gong,Lianqi Huang,Hong Chen,Xin Zhang,Chuanzhou Li,Muyang Yang,Bingjun Ma,Lihua Jiao,Ling Zheng,Kun Huang
Global epidemic studies have suggested that coffee consumption is reversely correlated with the incidence of type 2 diabetes mellitus (T2DM), a metabolic disease. The misfolding of human islet amyloid polypeptide (hIAPP) is regarded as one of the causative factors of T2DM. Coffee extracts have three major active components: caffeine, caffeic acid (CA), and chlorogenic acid (CGA). In this study, the effects of these major coffee components, as well as dihydrocaffeic acid (DHCA) (a major metabolite of CGA and CA), on the amyloidogenicity of hIAPP were investigated by thioflavin-T based fluorescence emission, transmission electronic microscopy, circular dichroism, light-induced cross-linking, dynamic light scattering, and MTT-based cell viability assays. The results suggest that all components show varied inhibitory effects on the formation of toxic hIAPP amyloids, in which CA shows the highest potency in delaying the conformational transition of the hIAPP molecule with the most prolonged lag time, whereas caffeine shows the lowest potency. At a 5-fold excess molar ratio of compound to hIAPP, all coffee-derived compounds affect the secondary structures of incubated hIAPP as suggested by the circular dichroism spectra and CDPro deconvolution analysis. Further photoinduced cross-linking based oligomerization and dynamic light scattering studies suggested CA and CGA significantly suppressed the formation of hIAPP oligomers, whereas caffeine showed no significant effect on oligomerization. Cell protection effects were also observed for all three compounds, with the protection efficiency being greatest for CA and least for CGA. These findings suggest that the beneficial effects of coffee consumption on T2DM may be partly due to the ability of the major coffee components and metabolites to inhibit the toxic aggregation of hIAPP.
研究领域:
生物化学
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分子生物学
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糖尿病研究
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DOI
PubMed
高影响因子
JOURNAL OF INDUSTRIAL MICROBIOLOGY & BIOTECHNOLOGY
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2024
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IF 3.2
Wysocki Łukasz,Adamczuk Patrycja,Bardadyn Paula,Gabor Anna,Jelonek Karolina,Kudelska Monika,Kukuć Maksymilian,Piasek Adrianna,Pietras Marta,Słomka Monika,Trojan Zoja,Tybulczuk Wiktoria,Sobiepanek Anna,Żylińska-Urban Joanna,Cieśla Joanna
Spent coffee grounds (SCG) are commercial waste that are still rich in numerous valuable ingredients and can be further processed into useful products such as coffee oil, antioxidant extract, lactic acid, and lignin. The challenge and innovation is to develop the SCG processing technology, maximizing the use of raw material and minimizing the use of other resources within the sequential process. The presented research is focused on the aspect of biotechnological production of lactic acid from SCG by using the Lacticaseibacillus rhamnosus strain isolated from the environment. Thanks to the optimization of the processes of acid hydrolysis, neutralization, enzymatic hydrolysis of SCG, and fermentation, the obtained concentration of lactic acid was increased after 72 hr of culture from the initial 4.60 g/l to 48.6 g/l. In addition, the whole process has been improved, taking into account the dependence on other processes within the complete SCG biorefinery, economy, energy, and waste aspects. Costly enzymatic hydrolysis was completely eliminated, and it was proven that supplementation of SCG hydrolysate with expensive yeast extract can be replaced by cheap waste from the agri-food industry.One-Sentence SummaryA process for efficient lactic acid production from spent coffee grounds using the Lacticaseibacillus rhamnosus strain was developed and optimized, including nutrient solution preparation, supplementation and fermentation.
研究领域:
生物技术
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环境科学
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食品科学
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DOI
PubMed
高影响因子
JOURNAL OF MOLECULAR LIQUIDS
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2024
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IF 5.3
Kexin Yang,Yanyan Huang,Huan Lin,Yiming Zhao,Yushan Hou,Jie Zhou,Chenxi Zhao,Chenyu Qi,Yaowei Zhang,Lingyun Li,Chen Yin,Gaofeng Cao,Guangyang Liu,Miaomiao Liu,Donghui Xu
Inspired by the surface structure of mussel, a novel bionic adsorbent (MPN@COFs) was prepared using an in situ synthetic strategy for the selective adsorption of caffeine and the physicochemical structure, surface morphology and composition of were characterized by scanning electron microscopy, Fourier-transform infrared spectrometry, X-ray photoelectron spectroscopy. The analytical data showed that the specific surface area of MPN @ COF was as high as 133.62 m 2 /g, which was stable and adaptable to acid and alkaline environments, with a adsorption rate of 78 %, and still maintained a high adsorption rate after reuse for three times. The adsorption isotherms and adsorption kinetics fit the Langmuir model and the quasi-secondary kinetic model better, respectively. Compared with single COFs and MPN, the adsorption efficiency of MPN@COFs increased by 40.54 % and 57.65 %, respectively. Moreover, the composite material could be reused three times, the HPLC-MS/MS method established in this study has high sensitivity, and this rapid detection technique can provide strong support for the detection of caffeine in beverages and the removal of caffeine from tea and its products.
研究领域:
食品科学
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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 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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产品关联
DOI
高影响因子
ACS Sustainable Chemistry & Engineering
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2024
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IF 7.1
Chang Liu,Yinuo Wu,Huizhe Zhao,Xiangyu Gu,Jinyang Gu,Mengmeng Zhao,Shangci Zuo,Pengchao Wang
7-Methylxanthine (7-MX), a caffeine (1,3,7-trimethylxanthine) derivative, has gained significant attention as a potential drug for myopia treatment. However, the efficient production of this valuable compound poses challenges: Isolation and chemical synthesis of 7-MX are both difficult to realize due to their poor yields and high costs. Therefore, developing efficient biosynthetic pathways has emerged as a promising alternative strategy. This study aimed to establish an efficient, low-cost, and pollutant-free biosynthetic process for producing 7-MX from caffeine, in which the biosynthetic process is achieved by utilization of ndmA, ndmB, and modified ndmD genes. Moreover, the rich caffeine in coffee waste can be used as an ideal substrate for this reaction, which can reduce the production cost and treat the caffeine in coffee waste residue to promote secondary utilization. By optimizing the gene expression, constructing cofactor regeneration system composed of frmA, frmB, and FDH to regenerate NADH to remove the bottleneck, and engineering Escherichia coli for high-density fermentation, we increased the production of 7-MX to an unprecedented 8.37 g/L. This approach represents the most efficient method thus far for producing 7-MX from caffeine and provides insights into synthesizing other valuable methylxanthines.
研究领域:
生物技术
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药学
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代谢工程
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产品关联
DOI
高影响因子
JOURNAL OF MOLECULAR LIQUIDS
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2019
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IF 4.561
Shangde Sun,Xuebei Hou
Glycerol caffeates (GC) is one kind of hydrophilic caffeoyl derivatives, which can be synthesized by the reaction of solid caffeic acid (CA) with different caffeoyl acceptors. The poor solubility of solid CA in the reaction resulted in great mass transfer limitation, low yield and time-consuming. In the work, in order to improve reaction efficiency, a novel liquid CA-based deep eutectic solvent (DES) was prepared and firstly used as caffeoyl donor for GC synthesis. Several solid acids were used as catalysts and the maximum GC yield (~55%) was achieved using NKC-9 as catalyst. Compared with solid CA as caffeoyl donor, CA conversion and initial reaction rate can be enhanced using liquid CA-based DES as caffeoyl donor. Especially at low temperature, initial CA conversion rate of liquid CA-based DES at 70 °C was 7 times that of solid CA. And the maximum CA conversion (~91%) was 2 times that of CA (44.6 ± 3.0%). When liquid CA-based DES was used as caffeoyl donor, the effect of external mass transfer limitation can also be neglected, and the activation energies of CA conversion and glyceryl monocaffeate formation (70.66 and 65.38 kJ/mol) were lower than those (83.31 and 80.41 kJ/mol) of solid CA. These indicated that liquid CA-based DES was favorable for hydrophilic GMC and GDC selective formations.
研究领域:
化学工程
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有机化学
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催化
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产品关联
DOI
高影响因子
RSC Advances
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2022
·Vol. 12
·期 16
·9744-9754
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IF 4.036
Xuejing Liu,Xiaowei Chen,Hao Zhang,Shangde Sun
Caffeic acid (CA) is widely found in nature, and has a broad spectrum of biological activities. However, the low hydrophilicity and lipophilicity of CA limited its application. Dodecyl caffeate (DC) is the lipophilic ester of caffeic acid (CA), and also has high antioxidant activity. In this work, CA, used as a substrate, and three ionic liquids with different acidities and H2SO4 were used as economic catalysts for DC preparation. The effects of variables on DC yield were investigated and optimized by response surface methodology (RSM). And the kinetic and thermodynamic parameters of the esterification of CA and dodecanol were evaluated. Results showed that lipophilic DC was successfully synthesized using ionic liquid ([Hnmp]HSO4) as a catalyst. And the optimal conditions by RSM were substrate ratio of 10.2 : 1, IL dosage of 9.8% at 87 °C for 118 min. Under the optional conditions, the maximum DC yield was 94.67 ± 1.32%. The k0, Ea, ΔH, ΔS, and ΔG were 7.18 × 107 mol (L min)−1, 65.77 kJ mol−1, 63.10 kJ (mol K)−1, −103.80 J (mol K)−1, and 99.78 kJ mol−1 at 363 K, respectively. DC prepared in this work showed a good DPPH radical scavenging activity, which indicated that DC can be used as a potential antioxidant in food and cosmetics.
研究领域:
化学
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材料科学
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食品科学
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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）