Water-in-oil Pickering emulsion using ergosterol as an emulsifier solely.

As a crucial component of the fungal cell membranes, ergosterol has been demonstrated to possess surface activity attributed to its hydrophobic region and polar group. However, further investigation is required to explore its emulsification behavior upon migration to the oil-water interface. Therefore, this study was conducted to analyze the interface properties of ergosterol as a stabilizer for water in oil (W/O) emulsion. Moreover, the emulsion prepared under the optimal conditions was utilized to load the water-soluble bioactive substance with the chlorogenic acid as the model molecules. Our results showed that the contact angle of ergosterol was 117.017°, and its dynamic interfacial tension was obviously lower than that of a pure water-oil system. When the ratio of water to oil was 4: 6, and the content of ergosterol was 3.5 % (ergosterol/oil phase, w/w), the W/O emulsion had smaller particle size (438 nm), higher apparent viscosity, and better stability. Meanwhile, the stability of loaded chlorogenic acid was improved under unfavorable conditions (pH 1.2, 90 °C, ultraviolet irradiation, and oxidation), which were 73.87 %, 59.53 %, 62.53 %, and 69.73 %, respectively. Additionally, the bioaccessibility of chlorogenic acid (38.75 %) and ergosterol (33.69 %), and the scavenging rates of the emulsion on DPPH radicals (81.00 %) and hydroxyl radicals (82.30 %) were also enhanced. Therefore, a novel W/O Pickering emulsion was prepared in this work using ergosterol as an emulsifier solely, which has great potential for application in oil-based food and nutraceutical formulations.

Unleashing the power of chlorogenic acid: exploring its potential in nutrition delivery and the food industry.

In the contemporary era, heightened emphasis on health and safety has emerged as a paramount concern among individuals with food. The concepts of "natural" and "green" have progressively asserted dominance in the food consumption market. Consequently, through continuous exploration and development, an escalating array of natural bioactive ingredients is finding application in both nutrition delivery and the broader food industry. Chlorogenic acid (CGA), a polyphenolic compound widely distributed in various plants in nature, has garnered significant attention. Abundant research underscores CGA's robust biological activity, showcasing notable preventive and therapeutic efficacy across diverse diseases. This article commences with a comprehensive overview, summarizing the dietary sources and primary biological activities of CGA. These encompass antioxidant, anti-inflammatory, antibacterial, anti-cancer, and neuroprotective activities. Next, a comprehensive overview of the current research on nutrient delivery systems incorporating CGA is provided. This exploration encompasses nanoparticle, liposome, hydrogel, and emulsion delivery systems. Additionally, the article explores the latest applications of CGA in the food industry. Serving as a cutting-edge theoretical foundation, this paper contributes to the design and development of CGA in the realms of nutrition delivery and the food industry. Finally, the article presents informed speculations and considerations for the future development of CGA.

Bone-Targeted Supramolecular Nanoagonist Assembled by Accurate Ratiometric Herbal-Derived Therapeutics for Osteoporosis Reversal.

Developing novel strategies for defeating osteoporosis has become a world-wide challenge with the aging of the population. In this work, novel supramolecular nanoagonists (NAs), constructed from alkaloids and phenolic acids, emerge as a carrier-free nanotherapy for efficacious osteoporosis treatment. These precision nanoagonists are formed through the self-assembly of berberine (BER) and chlorogenic acid (CGA), utilizing noncovalent electrostatic, π-π, and hydrophobic interactions. This assembly results in a 100% drug loading capacity and stable nanostructure. Furthermore, the resulting weights and proportions of CGA and BER within the NAs are meticulously controlled with strong consistency when the CGA/BER assembly feed ratio is altered from 1:1 to 1:4. As anticipated, our NAs themselves could passively target osteoporotic bone tissues following prolonged blood circulation, modulate Wnt signaling, regulate osteogenic differentiation, and ameliorate bone loss in ovariectomy-induced osteoporotic mice. We hope this work will open a new strategy to design efficient herbal-derived Wnt NAs for dealing with intractable osteoporosis.

Long-lasting insecticidal activity in plants driven by chlorogenic acid-loaded metal-organic frameworks.

Metal-organic frameworks (MOFs) possess a variety of interesting features related to their composition and structure that make them excellent candidates to be used in agriculture. However, few studies have reported their use as delivery agents of agrochemicals. In this work, the natural polyphenol chlorogenic acid (CGA) was entrapped via simple impregnation in the titanium aminoterephthalate MOF, MIL-125-NH2. A combination of experimental and computational techniques was used to understand and quantify the encapsulated CGA in MIL-125-NH2. Subsequently, CGA delivery studies were carried out in water at different pHs, showing a fast release of CGA during the first 2 h (17.3 ± 0.3% at pH = 6.5). In vivo studies were also performed against larvae of mealworm (Tenebrio molitor), evidencing the long-lasting insecticidal activity of CGA@MIL-125-NH2. This report demonstrates the potential of MOFs in the efficient release of agrochemicals, and paves the way to their study against in vivo models.

Anti-Atherosclerotic Properties of Aronia melanocarpa Extracts Influenced by Their Chemical Composition Associated with the Ripening Stage of the Berries.

The high content of bioactive compounds in Aronia melanocarpa fruit offers health benefits. In this study, the anti-atherosclerotic effect of Aronia extracts was assessed. The impact on the level of adhesion molecules and the inflammatory response of human umbilical vein endothelial cells (HUVECs) was shown in relation to the chemical composition and the stage of ripening of the fruits. Samples were collected between May (green, unripe) and October (red, overripe) on two farms in Poland, which differed in climate. The content of chlorogenic acids, anthocyanins, and carbohydrates in the extracts was determined using HPLC-DAD/RI. The surface expression of ICAM-1 and VCAM-1 in HUVECs was determined by flow cytometry. The mRNA levels of VCAM-1, ICAM-1, IL-6, and MCP-1 were assessed using the quantitative real-time PCR method. The farms' geographical location was associated with the quantity of active compounds in berries and their anti-atherosclerotic properties. Confirmed activity for green fruits was linked to their high chlorogenic acid content.

Reducing the allergenicity of tropomyosin in shrimp by covalent conjugation with quercetin and chlorogenic acid.

The study aimed to assay the allergenicity of shrimp tropomyosin (TM) following covalent conjugation with quercetin (QR) and chlorogenic acid (CA). The structure of the TM-polyphenol covalent conjugates was examined by sodium dodecyl sulfate polyacrylamide gel electrophoresis (SDS-PAGE), circular dichroism (CD), fluorescence, differential scanning calorimetry (DSC), and Fourier Transform infrared spectroscopy (FTIR). Potential allergenicity was evaluated using in vitro and in vivo methods. The results showed that QR and CA induced structural changes in TM through aggregation. RBL-2H3 cell results showed that TM-QR and TM-CA covalent conjugates reduced the release of ß-hexosaminidase and histamine, respectively. In the mice model, TM-QR and TM-CA covalent conjugates reduced the level of IgE, IgG, IgG1, histamine, and mMCP-1 in sera. Furthermore, the allergenicity was reduced by suppressing Th2-related cytokines (IL-4, IL-5, IL-13) and promoting Th1-related cytokines (IFN-γ). These research findings demonstrate that the covalent binding of TM with QR and CA, modifies the allergenic epitopes of shrimp TM, thereby reducing its potential allergenicity. This approach holds practical applications in the production of low-allergenicity food within the food industry.

Antioxidant, antimicrobial and healing properties of an extract from coffee pulp for the development of a phytocosmetic.

Consumer demand for natural, chemical-free products has grown. Food industry residues, like coffee pulp, rich in caffeine, chlorogenic acid and phenolic compounds, offer potential for pharmaceutical and cosmetic applications due to their antioxidant, anti-inflammatory, and antibacterial properties. Therefore, the objective of this work was to develop a phytocosmetic only with natural products containing coffee pulp extract as active pharmaceutical ingredient with antioxidant, antimicrobial and healing activity. Eight samples from Coffea arabica and Coffea canephora Pierre were analyzed for caffeine, chlorogenic acid, phenolic compounds, tannins, flavonoids, cytotoxicity, antibacterial activity, and healing potential. The Robusta IAC-extract had the greatest prominence with 192.92 µg/mL of chlorogenic acid, 58.98 ± 2.88 mg GAE/g sample in the FRAP test, 79.53 ± 5.61 mg GAE/g sample in the test of total phenolics, was not cytotoxic, and MIC 3 mg/mL against Staphylococcus aureus. This extract was incorporated into a stable formulation and preferred by 88% of volunteers. At last, a scratch assay exhibited the formulation promoted cell migration after 24 h, therefore, increased scratch retraction. In this way, it was possible to develop a phytocosmetic with the coffee pulp that showed desirable antioxidant, antimicrobial and healing properties.

Recent Updates on the Therapeutics Benefits, Clinical Trials, and Novel Delivery Systems of Chlorogenic Acid for the Management of Diseases with a Special Emphasis on Ulcerative Colitis.

Ulcerative colitis (UC) is a multifactorial disorder of the large intestine, especially the colon, and has become a challenge globally. Allopathic medicines are primarily available for the treatment and prevention of UC. However, their uses are limited due to several side effects. Hence, an alternative therapy is of utmost importance in this regard. Herbal medicines are considered safe and effective for managing human health problems. Chlorogenic acid (CGA), the herbal-derived bioactive, has been reported for pharmacological effects like antiinflammatory, immunomodulatory, antimicrobial, hepatoprotective, antioxidant, anticancer, etc. This review aims to understand the antiinflammatory and chemopreventive potential of CGA against UC. Apart from its excellent therapeutic potential, it has been associated with low absorption and poor oral bioavailability. In this context, colon-specific novel drug delivery systems (NDDS)are pioneering to overcome these problems. The pertinent literature was compiled from a thorough search on various databases such as ScienceDirect, PubMed, Google Scholar, etc., utilizing numerous keywords, including ulcerative colitis, herbal drugs, CGA, pharmacological activities, mechanism of actions, nanoformulations, clinical updates, and many others. Relevant publications accessed till now were chosen, whereas non-relevant papers, unpublished data, and non-original articles were excluded. The present review comprises recent studies on pharmacological activities and novel drug delivery systems of CGA for managing UC. In addition, the clinical trials of CGA against UC have been discussed.

Combination of a Deep Eutectic Solvent and Macroporous Resin for Green Recovery of Iridoids, Chlorogenic Acid, and Flavonoids from Eucommia ulmoides Leaves.

To increase the effectiveness of using typical biomass waste as a resource, iridoids, chlorogenic acid, and flavonoids from the waste biomass of Eucommia ulmoides leaves (EULs) were extracted by deep eutectic solvents (DESs) in conjunction with macroporous resin. To optimize the extract conditions, the experiment of response surface was employed with the single-factor of DES composition molar ratio, liquid-solid ratio, water percentage, extraction temperature, and extraction time. The findings demonstrated that the theoretical simulated extraction yield of chlorogenic acid (CGA), geniposidic acid (GPA), aucubin (AU), geniposide (GP), rutin (RU), and isoquercetin (IQU) were 42.8, 137.2, 156.7, 5.4, 13.5, and 12.8 mg/g, respectively, under optimal conditions (hydrogen bond donor-hydrogen bond acceptor molar ratio of 1.96, liquid-solid ratio of 28.89 mL/g, water percentage of 38.44%, temperature of 317.36 K, and time of 55.59 min). Then, 12 resins were evaluated for their adsorption and desorption capabilities for the target components, and the HPD950 resin was found to operate at its optimum. Additionally, the HPD950 resin demonstrated significant sustainability and considerable potential in the recyclability test. Finally, the hypoglycemic in vitro, hypolipidemic in vitro, immunomodulatory, and anti-inflammatory effects of EUL extract were evaluated, and the correlation analysis of six active components with biological activity and physicochemical characteristics of DESs by heatmap were discussed. The findings of this study can offer a theoretical foundation for the extraction of valuable components by DESs from waste biomass, as well as specific utility benefits for the creation and development of natural products.

Bioactive functions of chlorogenic acid and its research progress in pig industry.

Chlorogenic acid (CGA), also known as 3-caffeioylquinic acid or coffee tannin, is a water-soluble polyphenol phenylacrylate compound produced through the shikimate pathway by plants during aerobic respiration. CGA widely exists in higher dicotyledons, ferns and many Chinese medicinal materials, and enjoys the reputation of 'plant gold'. Here, we summarized the source, chemical structure, biological activity functions of CGA and its research progress in pigs, aiming to provide a more comprehensive understanding and theoretical basis for the prospect of CGA replacing antibiotics as a pig feed additive.

Chlorogenic acid-chitosan copolymers: Synthesis, characterization and application in O/W emulsions for enhanced ß-carotene stability.

In this study, chlorogenic acid-chitosan (CA-CS) copolymers were prepared with varying Chitosan (CS): chlorogenic acid (CA)ratios and characterized for their water solubility, antioxidant capacity, and emulsions stability. Results showed that CA-CS samples exhibited up to 90.5 % increase in DPPH scavenging efficiency and 20 % increase in hydroxyl radical scavenging efficiency compared to CS alone. CA-CS copolymers used to stabilize oil in water (O/W) emulsions, which were evaluated for their potential in encapsulating and protecting ß-carotene. Microscopic observations revealed homogeneous spherical droplets in stable emulsions, suggesting effective interfacial structures. The selected CA-CS-stabilized O/W emulsions demonstrated encapsulation efficiencies of 74.8 % and 75.26 % for ß-carotene. The CA-CS stabilized O/W emulsions provided the most effective protection against ß-carotene degradation under UV exposure, retaining over 80 % of ß-carotene content after 12 h of testing. These findings indicate that CA-CS-based O/W emulsions show promise as carriers and protectors for bioactive compounds, due to their improved antioxidant capacity, emulsions stability, and protection against degradation.

Synergistic interaction of Cu(II) with caffeic acid and chlorogenic acid in α-glucosidase inhibition.

BACKGROUND: Phenolic acids are widespread in foods and are beneficial to human health. However, the role of metal ions in influencing the binding of proteins with phenolic acids that contain the same parent nucleus structure remains unclear. This study investigated the inhibitory effect of caffeic acid (CA) and chlorogenic acid (CHA) on α-glucosidase and the biological effect of copper on this process. RESULTS: It was found that the esterification of CA with quinic acid could increase the fluorescence quenching, conformational change, and inhibitory effect of CHA on α-glucosidase. Copper ions reduced their fluorescence quenching and conformation-changing ability by binding to the neighboring phenolic hydroxyl group but also increased their ability to alter secondary structure and to inhibit α-glucosidase and in vitro anti-glycation. CONCLUSION: Overall, this study shows that the binding of copper ions to the phenolic hydroxyl group adjacent to CA and CHA synergistically inhibited α-glucosidase. The findings will offer a theoretical basis for investigating the properties of metal ions and phenolic acid in food chemistry and their potential applications in the prevention and treatment of diabetes mellitus. © 2023 Society of Chemical Industry.

Synergistic improvement of antioxidant and antibacterial properties of carbon quantum complexes with zinc doping and chlorogenic acid for longan preservation.

The deterioration of fruit could reduce the shelf life, decreased marketability and substantial economic value. Thus, a safe, simple, economical and environmentally friendly preservation technology for fruit is of great significance. Here, the postharvest preservation technology was investigated with zinc-doped carbon quantum dots and chlorogenic acid (Zn-CQDs/CGA) composite. Zn-CQDs/CGA composite were synthesized, which exhibits superior antioxidant and antibacterial activities. The binding mechanism of the Zn-CQDs/CGA composite was investigated, which revealed that the bindings of two components were mainly driven by hydrogen bonding and van der Waals forces to create a novel composite. The Zn-CQDs/CGA composite was applied to longan preservation and was found to significantly reduce the incidence of mildew spot, browning of fruit endocarp and pulp, as well as the degree of degradation of quality indexes. These results suggest that the Zn-CQDs/CGA composite has the potential for inhibiting browning and preserving the quality of longan during storage.

Non-covalent binding of chlorogenic acid to myofibrillar protein improved its bio-functionality properties and metabolic fate.

As natural antioxidants added to meat products, polyphenols can interact with proteins, and the acid-base environment influenced the extent of non-covalent and covalent interactions between them. This study compared the bio-functional characteristics and metabolic outcomes of the myofibrillar protein-chlorogenic acid (MP-CGA) complexes binding in different environments (pH 6.0 and 8.5). The results showed that CGA bound with MP significantly enhanced its antioxidant activity and inhibitory effect on metabolism enzymes. CGA bound deeply into the MP structure hydrophobic cavity at pH 6.0, which reduced its degradation by digestive enzymes, thus increasing its bio-accessibility from 59.5% to 71.6%. The digestion products of the two complexes exhibited significant differences, with the non-covalent MP-CGA complexes formed at pH 6.0 showing significantly higher concentrations of rhetsinine and piplartine, two well-known compounds to modulate diabetes. This study demonstrated that non-covalent binding between protein and polyphenol in the acidic environment held greater promising prospects for improving health.

Effects of Covalent or Noncovalent Binding of Different Polyphenols to Acid-Soluble Collagen on Protein Structure, Functionality, and Digestibility.

In this study, the structure, function, and digestibility of noncovalent complexes and covalent conjugates formed by acid-soluble collagen with polyphenols of different structures (quercetin, epicatechin, gallic acid, chlorogenic acid, procyanidin, and tannic acid) were investigated. Sodium dodecyl sulfate-polyacrylamide gel electrophoresis (SDS-PAGE) showed that polyphenols were covalently bound to collagen by laccase catalytic oxidation. Biolayer interferometry revealed that the noncovalent binding strength of polyphenols to collagen from high to low was quercetin > gallic acid > chlorogenic acid > epicatechin, which was consistent with the trend of covalent polyphenol binding. Procyanidin and tannic acid had strong noncovalent binding, but their covalent binding ability was weak. Compared with the pure collagen, the complexes improved emulsification and antioxidant properties (more than 2.5 times), and the conjugates exhibited better thermal stability (99.4-106.8 °C) and antidigestion ability (reduced by more than 37%). The finding sheds new light on the use of collagen as a functional food ingredient in the food industry.

An optimized 3D-printed capsule scaffold utilizing artificial neural network for the targeted delivery of chlorogenic acid to the colon.

Chlorogenic acid (CGA) is an important bioactive polyphenol with extensive biological properties. This study aimed to fabricate an optimized three-dimensional (3D)-printed capsule scaffold and CGA capsules for targeted delivery of hydrophobic CGA to the colon. The optimized printing parameters identified using the neural network model were a temperature of 170 °C, a printing speed of 20 mm/s, and a nozzle diameter of 0.3 mm. The capsules exhibited slow releasing properties of CGA, and the releasing rates of Eudragit®FS 30D-sealed capsules (due to more cracks and voids) were faster than those of Eudragit®S100-sealed capsules. The Ritger-peppas model was the best fitting model to describe the releasing process of CGA from 8 CGA capsules (R2 ≥ 0.98). All CGA capsules exhibited shear-thinning properties with stable sol-gel viscosity at low shear rates. FTIR spectra confirmed the formation of non-covalent bonds between CGA and the sol. Overall, the obtained 3D-printed capsules provided a promising carrier for the targeted delivery of CGA in the development of personalized dietary supplements.

Sustained release of chlorogenic acid by co-encapsulation of sodium alginate binding to the Northern pike (Esox Lucius) liver ferritin.

Ferritin has a unique hollow spherical structure, which makes it a promising nanocarrier for food functional substances. In this study, a new ferritin was successfully extracted from the liver of Northern pike, purified, and identified. We used the reversible self-assembly characteristics of ferritin to fabricate chlorogenic acid (CA)-loaded apoferritin (Apo) complex (Apo-CA) and sodium alginate (SA)-apoferritin (Apo) co-encapsulate system. Apo-CA was encapsulated into the SA system to form SA-Apo-CA. The fabricated composites were analyzed using particle size, UV-Vis absorption spectroscopy, fluorescence spectroscopy, flourier transform infrared spectroscopy and transmission electron microscope. Physicochemical property of analysis confirmed th successful preparation of Apo-CA/SA-Apo-CA and improved thermal and UV radiation stability. The effect of sustained-release of CA were tested in vitro of simulated gastrointestinal tract digestion. SA-Apo-CA exhibited greater release ability than unencapsulated CA and Apo-CA. This study provides a new strategy for designing a multilayer delivery system with improved stability and sustained-release property.

Full-length transcriptome sequencing and transgenic tobacco revealed the key genes in the chlorogenic acid synthesis pathway of Sambucus chinensis L.

Chlorogenic acid is a key chemical in antioxidation and antisepsis. Sambucus chinensis L. is an herbaceous plant rich in chlorogenic acid and a potential genetic resource for breeding high-chlorogenic acid plants. However, there are few studies on the synthesis pathway of chlorogenic acid in S. chinensis. Our study found chlorogenic acid accumulation in S. chinensis to be organ-specific, higher in leaves and buds but lower in roots, stems and fruits. A total number of 546,844 CCS (circular consensus sequence), including 402,767 full-length nonchimeric (FLNC) and 39 annotated sequences related to the synthesis of chlorogenic acid, was obtained by single-molecule real-time sequencing technology (SMRT). qRT-PCR showed that a number of key genes involved in chlorogenic acid synthesis were differentially expressed in various tissues of S. chinensis. Transgenic tobacco revealed that ectopic expression of the HCT homologous gene HCT-45178 increased the content of chlorogenic acid. Our results should be the first report of full-length transcriptome data of S. chinensis, which help to understand the basis of chlorogenic acid synthesis and provide a novel strategy for breeding tobacco cultivars with higher levels of chlorogenic acid.

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

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.

Identification of alkaline-induced thiolyl-chlorogenic acid conjugates with cysteine and glutathione.

Alkaline reactions of chlorogenic acid (CGA) yield undesirable development of brown or green pigments, limiting the utilization of alkalized CGA-rich foods. Thiols such as cysteine and glutathione mitigate pigment formation through several mechanisms, including redox coupling to reduce CGA quinones, and thiol conjugation, which forms colorless thiolyl-CGA compounds that do not readily participate in color-generating reactions. This work provided evidence of the formation of both aromatic and benzylic thiolyl-CGA conjugate species formed with cysteine and glutathione under alkaline conditions in addition to hydroxylated conjugate species hypothesized to arise from reactions with hydroxyl radicals. Formation of these conjugates proceeds more quickly than CGA dimerization and amine addition reactions mitigating pigment development. Differentiation between aromatic and benzylic conjugates is enabled by characteristic fragmentation of CS bonds. Acyl migration and hydrolysis of the quinic acid moiety of thiolyl-CGA conjugates yielded a variety of isomeric species also identified through untargeted LC-MS methods.