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FOOD CHEMISTRY · 2020 · IF 6.306

Rapid and simultaneous quality analysis of the three active components in Lonicerae Japonicae Flos by near-infrared spectroscopy

Xue Jintao,Yang Quanwei,Li Chunyan,Liu Xiaolong,Niu Bingxuan

Lonicerae Japonicae Flos (LJF) has historically been widely utilized as a tea and health food. To better understand and evaluate its quality evaluate its quality, a near-infrared spectroscopy (NIRS) method was developed for the rapid and simultaneous analysis of the 3 main active components (chlorogenic acid, isochlorogenic acid A and isochlorogenic acid C). The NIRS model was built using 2 different strategies: partial least squares (PLS) as a linear regression method and artificial neural networks (ANN) as a nonlinear regression method. Furthermore, the NIRS method was applied to analyze the 4 main quality factors, which included 5 processing methods (shade drying, sun drying, vacuum drying, freeze drying and hot-air drying), 2 kinds of harvest time (flower bud stage and florescence stage), 2 species and 8 geographical origins. Collectively, NIRS is a promising method for the quality analysis of LJF.

研究领域: 中药学 · 分析化学
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MOLECULES · 2023 ·Vol. 28 ·期 9 ·3948 · IF 4.6

Highly Efficient Synthesis of Chlorogenic Acid Oleyl Alcohol Ester under Non-Catalytic and Solvent-Free Conditions

Cong Sun,Hui Liu,Yanran Chen,Xianzhi Wei,Shaohua Liang

As a natural polyphenolic compound, chlorogenic acid (CGA) has attracted increasing attention for its various biological activities, such as antioxidant, liver protection, intestinal barrier protection, and effective treatment of obesity and type II diabetes. However, the poor solubility of CGA in hydrophobic media limits its application in the food, drug and cosmetic industries. In order to obtain new hydrophobic derivatives, a highly efficient synthesis approach of CGA oleyl alcohol ester (CGOA) under non-catalytic and solvent-free conditions was developed in this study. The influences of reaction temperature, reaction time, substrate molar ratio, and stirring rate on the CGA conversion were investigated. The results showed that the optimal conditions were as follows: reaction temperature 200 °C, reaction time 3 h, molar ratio of CGA to oleyl alcohol 1:20, and stirring rate 200 rpm. Under these conditions, the CGA conversion could reach 93.59%. Then, the obtained crude product was purified by solvent extraction and column chromatography, and the purify of CGOA was improved to 98.72%. Finally, the structure of CGOA was identified by FT-IR, HPLC-MS and NMR. This study provides a simple and efficient strategy for the preparation of CGOA with the avoidance of catalysts and solvents.Keywords:chlorogenic acid;chlorogenic acid oleyl alcohol ester;esterification;non-catalytic synthesis

CAS / MDL: 7553-56-2 143-28-2
研究领域: 食品科学 · 药物化学 · 天然产物化学
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MOLECULES · 2025 ·Vol. 30 ·期 3 ·481 · IF 4.6

Extraction of Chlorogenic Acid Using Single and Mixed Solvents

Hyeon Ji Jeon,Bong-Seop Lee,Changhyup Park

Chlorogenic acid, which is extracted from a wide range of natural sources, is attracting the attention of many researchers in the pharmaceutical and biomedical fields due to its various positive effects, such as such as anti-inflammatory and antibacterial properties. Considering the effects of economics and solvent toxicity, water, ethanol, and their mixtures were selected as the solvents for extracting chlorogenic acid at various temperatures (298~318 K) and over a whole range of concentrations. The solubility of chlorogenic acid increased with temperature regardless of the solvents, and the solubility was higher in pure ethanol than in pure water. The solubility of chlorogenic acid in mixed solvents exhibited a gradual rise as the water content increased, reaching a maximum at a specific water weight fraction. These trends were well predicted by the COSMO-SAC model and Hansen solubility parameter method. By comparing the σ-profile, it was confirmed that the maximum solubility in mixed solvent comes from the similarity of σ-profiles between chlorogenic acid and mixed solvent which represents the surface charge density of the molecule.

CAS / MDL: 327-97-9
研究领域: 药学 · 生物化学
✓ 已验证 产品关联 DOI PubMed 高影响因子
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JOURNAL OF SEPARATION SCIENCE · 2019 ·Vol. 42 ·期 6 ·1289-1298 · IF 2.516

Ligand fishing of anti-neurodegenerative components from Lonicera japonica using magnetic nanoparticles immobilised with monoamine oxidase B

Gui-Fang Wu,Xiao-Lan Jiang,Yu-Zhou Gong,Ya-Dong Hu,Xiao-Lin Bai,Xun Liao

In this work, monoamine oxidase B was immobilised onto magnetic nanoparticles to prepare a new type of affinity solid-phase extraction adsorbent, which was used to extract the possible anti-neurodegenerative components from the Lonicera japonica flower extracts. Coupled with high-performance liquid chromatography with mass spectrometry, two monoamine oxidase B ligands were fished-out and identified as isochlorogenic acid A and isochlorogenic acid C, which were found to be inhibitors of the enzyme for the first time, with similar half maximal inhibitory concentration values of 29.05 ± 0.49 and 29.77 ± 1.03 μM, respectively. Furthermore, equilibrium-dialysis dissociation assay of enzyme-inhibitor complex showed that both compounds have reversible binding patterns to monoamine oxidase B, and kinetic analysis demonstrated that they were mixed-type inhibitors for monoamine oxidase B, with K i and K is values of 9.55 and 37.24 μM for isochlorogenic acid A, 9.53 and 35.50 μM for isochlorogenic acid C, respectively. The results indicated that isochlorogenic acid A and isochlorogenic acid C were the major active components responsible for the anti-degenerative activity of the flowers of L. japonica , while magnetic nanoparticles immobilised monoamine oxidase B could serve as an efficient solid-phase extraction adsorbent to specifically extract monoamine oxidase B inhibitors from complex herbal extracts.

研究领域: 药理学 · 生物化学
✓ 已验证 产品关联 DOI PubMed 高影响因子
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FOOD CHEMISTRY · 2025 · IF 9.8

Revealing the non-enzymatic covalent interaction between neo−/crypto-chlorogenic acid and beta-lactoglobulin under nonthermal process and potential delivery capability

Fang Li,Haina Hou,Tian Zhao,Gongshuai Song,Danli Wang,Tinglan Yuan,Ling Li,Jinyan Gong

Several studies have shown that the protein-chlorogenic acid covalent complex has better function and stability than the non-covalent. The degree of binding between the proteins and chlorogenic acids (CQA) can be enhanced by the ultrasound process. Herein, the effects of ultrasound-assisted non-enzymatic covalent binding (the free radical induction (Vc)-ultrasound combination and the alkali treatment (Alkali)-ultrasound combination) of two chlorogenic acids (neochlorogenic acid (3-CQA), cryptochlorogenic acid (4-CQA)) and β-lactoglobulin (β-LG) on proteins structure and properties were investigated. Results showed that ULG-Alkali-4CQA exhibited a 5.1 % reduction in α-helices, a 6.8 % increase in random curl and proteins structures becoming loose and disordered. The hydrophilicity and thermal stability of β-LG were effectively enhanced by the addition of 4-CQA and the effect of alkali treatment-ultrasound combination. Curcumin (CUR) and lycopene (LYC) were successfully delivered by the covalent complexes as delivery vehicles. The encapsulation efficiencies of the ULG-Vc/Alkali-4CQA + CUR and ULG-Vc/Alkali-4CQA + LYC complexes were 82.81 %, 84.16 %, 89.56 % and 90.51 %, respectively. The stabilities of CUR and LYC in the ULG-Vc/Alkali-4CQA + CUR/LYC ternary complexes were superior to those of all the measured complexes delivery systems. The study hopes to establish a theoretical foundation and serve as a reference for the advancement of a highly stable food-grade delivery system.

CAS / MDL: 50-81-7
研究领域: 食品科学 · 生物化学
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JOURNAL OF CHEMICAL ECOLOGY · 2015 ·Vol. 41 ·期 11 ·1028-1036 · IF 2.747

Nectar Attracts Foraging Honey Bees with Components of Their Queen Pheromones

Liu Fanglin,Gao Jie,Di Nayan,Adler Lynn S.

Floral nectar often contains chemicals that are deterrent to pollinators, presenting potential challenges to outcrossing plant species. Plants may be able to co-opt pollinator chemical signals to mitigate the negative effects of nectar deterrent compounds on pollination services. We found that buckwheat ( Fagopyrum esculentum ) and Mexican sunflower ( Tithonia diversifolia ) produce nectar with abundant phenolics, including three components of the Apis honeybee queen mandibular pheromone (QMP). In addition, these nectars contain a non-pheromonal phenolic, chlorogenic acid (CA), which was toxic to honeybees, and T. diversifolia nectar also contained isochlorogenic acid (IA). Fresh nectar or solutions containing nectar phenolics reduced Apis individual feeding compared to sucrose solutions. However, freely foraging bees preferred solutions with QMP components to control solutions, and QMP components over-rode or reversed avoidance of CA and IA. Furthermore, prior exposure to the presence or just the odor of QMP components removed the deterrent effects of CA and IA. By mimicking the honey bee pheromone blend, nectar may maintain pollinator attraction in spite of deterrent nectar compounds.

研究领域: 植物学 · 昆虫学 · 生态学
✓ 已验证 DOI PubMed 高影响因子
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INTERNATIONAL JOURNAL OF FOOD SCIENCE AND TECHNOLOGY · 2018 ·Vol. 54 ·期 5 ·1697-1705 · IF 2.383

Antibacterial activity and mechanism of cinnamic acid and chlorogenic acid against Alicyclobacillus acidoterrestris vegetative cells in apple juice

Rui Cai,Miao Miao,Tianli Yue,Yijun Zhang,Lu Cui,Zhouli Wang,Yahong Yuan

Summary The aim of this study was to investigate the antibacterial activity and mechanism of cinnamic acid and chlorogenic acid against Alicyclobacillus acidoterrestris . Minimum inhibitory concentrations of cinnamic acid and chlorogenic acid were 0.375 and 2.0 mg mL −1 , and the minimum bactericidal concentrations were 0.50 and 4.0 mg mL −1 , respectively. The apple juice ingredients had little influence on the inactivation of A. acidoterrestris . After treatment with cinnamic acid and chlorogenic acid, the morphology of A. acidoterrestris cells were severely destroyed; the leakage of nucleic acids and proteins increased significantly. SDS-PAGE investigation of bacterial proteins proved that the loss of soluble proteins was obvious as well. These results demonstrated that cinnamic acid and chlorogenic acid exerted their antibacterial activity mainly by an action mode of membrane disruption. This study provides an alternative method for the control of A. acidoterrestris -related spoilage in the fruit juice/beverage industry.

研究领域: 食品科学 · 微生物学
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MICROCHEMICAL JOURNAL · 2025 · IF 5.1

Extraction of chlorogenic acid from Lonicera japonica Thunb. using deep eutectic solvents: Process optimization and mechanism exploration by the combination of experiment and molecular simulation

Zhenyan Fan,Jingyu Li,Junyu Zhou,Yueyuan Chen,Zhifang Cui

The green extraction of chlorogenic acid (CGA) from Lonicera japonica Thunb. using deep eutectic solvents (DESs) was systematically investigated in the study. Quantum chemical calculations (QC) were adopted to evaluate the σ -profiles of CGA and DESs. Subsequent extraction experiments revealed that amongst the 15 DESs studied, those showing better complementarity in polar regions of σ -profile with that of CGA exhibited higher CGA yield, accompanied by lower infinite dilution activity coefficient ( γ ∞ ) of CGA in these solvents. Betaine/glycerol (BET/GLY) demonstrated superior extraction performance and was selected for process optimization via Box-Behnken Design. The established model, validated by ANOVA analysis, indicated that the optimized conditions resulted in a CGA yield 1.9 times higher than that with ethanol extraction. To elucidate the mechanistic basis for performance differences among betaine-based DESs, molecular simulations were conducted, revealing that higher CGA yields correlated with increased interaction energies and greater numbers of hydrogen bonds within the system. Notably, among the six active hydrogen atoms in CGA, three participated in intramolecular H-bonding, while the phenolic hydroxyl group of CGA primarily interacted with the carboxyl group of BET, serving as the dominant contributor during extraction. Furthermore, the highest CGA yield from BET/GLY was likely due to synergistic cooperation between BET, GLY, and H 2 O to interact with CGA. These findings highlight the importance of identifying key interaction sites in both target molecules and extractants to rationally design tailored solvents for enhanced extraction performance. This work provides a strategy integrating computational insights and experimental optimization to advance sustainable extraction of bioproducts.

CAS / MDL: 327-97-9
研究领域: 植物化学 · 绿色化学 · 药用植物学
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INTERNATIONAL JOURNAL OF FOOD SCIENCES AND NUTRITION · 2017 · IF 1.444

Dietary chlorogenic acid regulates gut microbiota, serum-free amino acids and colonic serotonin levels in growing pigs

Yi Wu,Wenhui Liu,Qi Li,Yafei Li,Yali Yan,Fang Huang,Xin Wu,Quancheng Zhou,Xugang Shu,Zheng Ruan

Chlorogenic acid (CGA) has many biological properties, including antibacterial, antioxidant and anti‐inflammatory properties, and is one of the most abundant phenolic acids available in the human diet. The aim of this study was to investigate the effects of CGA on regulation of the gut microbiota, and on the levels of free amino acids and 5-hydroxytryptamine (5-HT, serotonin). Ninety-six healthy growing pigs were randomly assigned to two treatment groups: the Ctrl group (control group, standard feed) and the CGA group [standard feed plus 0.05% 3-caffeoylquinic acid (3-CQA)] for 60 days. The diversity of the gut microbiota was increased after CGA supplementation. Changes in these microbes were significantly associated with the serum free amino acid levels and colonic 5-HT level. Compared with the Ctrl group, the levels of serum aspartic acid, threonine, alanine, arginine, and colonic 5-HT were significantly increased (p < .05). These data suggest important roles for CGA in regulating the gut microbiota and increasing the serum free amino acid levels.

CAS / MDL: 327-97-9
研究领域: 营养学 · 微生物学 · 动物科学
✓ 已验证 产品关联 DOI PubMed 高影响因子
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MOLECULES · 2025 ·Vol. 30 ·期 5 ·1055 · IF 4.6

Identification of Acanthopanax trifoliatus (L.) Merr as a Novel Potential Therapeutic Agent Against COVID-19 and Pharyngitis

Qi Chen,Hui He,Yanghong Zhu,Xiang Li,Junhao Fang,Zhexi Li,Panghui Liu,Lin Zhou,Yufang Pan,Guoyu Wu

Individuals infected with COVID-19 often experience the distressing discomfort of pharyngitis. Thus, it is crucial to develop novel drugs to improve therapeutic options. In this study, we investigated the interaction between bioactive compounds isolated from Acanthopanax trifoliatus (L.) Merr and proteins associated with COVID-19 and pharyngitis through in silico analysis. Several molecules demonstrated high affinities to multiple targets, indicating significant potential for alleviating pharyngitis and other COVID-19-related symptoms. Among them, rutin and isochlorogenic acid C, two major components in Acanthopanax trifoliatus (L.) Merr ethanol extracts, were further experimentally demonstrated to exhibit strong inhibitory effects against SARS-CoV-2 and to possess significant anti-inflammatory activities. Inhibition of over 50% in several key genes was observed, demonstrating the efficacy of in silico methods in identifying high-affinity target binders. Our findings provide a theoretical foundation for the development of Acanthopanax trifoliatus (L.) Merr as a novel multi-target therapeutic agent for both COVID-19 and pharyngitis.

CAS / MDL: 50-02-2
研究领域: 药理学 · 生物信息学 · 病毒学
✓ 已验证 产品关联 DOI PubMed 高影响因子
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JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY · 2025 · IF 6.2

Isochlorogenic Acid A Attenuated Periodontitis by Inhibiting Inflammation via ACE/PGK1/STAT1 Signaling

Xin Huang,Hong Shen,Zirui Li,Tingting Fu,Xin Wei,Sainan Qiu

The purpose of the present study was to evaluate the effect of isochlorogenic acid A (IAA) on periodontitis and explore its potential mechanism. A ligature/LPS procedure was employed to induce periodontitis in rats. LPS-induced HPDLF was used as the in vitro model. Bioinformatic analyses indicated that angiotensin-converting enzyme (ACE) might be the target of IAA in periodontitis. PGK1/STAT1 might be the related molecules of ACE. Treatment with IAA inhibited inflammatory cytokines, inflammatory molecule transcriptions in gingival tissues and HPDLFs. MicroCT, H&E, TRAP and Runx2 staining showed that IAA relieved periodontitis. Immunofluorescence observation and WB revealed that IAA inhibited ACE/PGK1/STAT1 in dental papilla, parodontium, gingival tissues and HPDLFs. IAA suppressed glycolysis, mitochondrial fission, oxidative stress and promoted oxidative phosphorylation, mitochondrial fusion. The application of the ACE-overexpression plasmid, PGK1 SiRNA, the ACE inhibitor captopril, the PGK1 inhibitor NG52 suggested that ACE and PGK1 were involved in IAA-mediated anti-inflammatory response. Molecular docking, molecular dynamics, DARTS and CETSA indicated that IAA might combine with ACE. It was also found that MYC governed ACE transcription. The Y195 residue of PGK1 was conservative and critical for the combination between PGK1 and ACE. ACE and PGK1 were also upregulated in gingival tissues of periodontitis patients. In conclusion, IAA ameliorated periodontitis by inhibiting inflammation via ACE/PGK1/STAT1 signaling.

CAS / MDL: 62571-86-2 80731-10-8
研究领域: 药理学 · 口腔医学 · 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 · 2025 · IF 9.8

Combination of Lycium barbarum polysaccharide and chlorogenic acid: Characterization of solution property, interaction, and regulatory function on typical gut Bacteroides and pathogens

Lisi Liang,Lianzhu Lin,Mouming Zhao

Lycium barbarum polysaccharide (LBP) is a prebiotic that promotes the proliferation of beneficial bacteria, but lacks of regulatory function on harmful bacteria. In this study, chlorogenic acid (CGA) was used to achieve the functional enhancement of two LBPs (LBP-A and LBP-M). The combination of CGA resulted in changes in the solution properties of LBPs, manifested as increased pseudoplasticity, viscosity, turbidity, and decreased water mobility, absolute potential value, pH value. CGA was non-covalently bound to LBPs through hydrophobic interaction and hydrogen bond. LBP-A had strong affinity with CGA, mainly through hydrophobic interaction, while LBP-M had weak affinity with CGA, mainly through hydrogen bond. Both LBP-CGA complexes exhibited Bacteroides proliferative activity and gut pathogens inhibitory activity, among which LBP-A-CGA complex showed strong inhibitory effects on Escherichia coli and Bacillus cereus , and LBP-M-CGA complex showed strong inhibitory effect on Staphylococcus aureus . This study provided guidance for the development of LBP-CGA as novel prebiotic.

CAS / MDL: 327-97-9
研究领域: 食品科学 · 微生物学 · 营养学
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