Caffeic Research Articles

Development and characterisation of buccal dispersible film, syrup and effervescent granules of extemporaneous antigout remedy.

Homemade medicinal remedies used to treat both acute and chronic ailments for centuries need to be transformed into modern evidence-based dosage forms. Therefore, the present study aimed to develop buccal dispersible film, syrup and effervescent granules of an extemporaneous antigout homemade remedy. The dosage forms were prepared using holistic remedy (HR) as an active entity and excipients masking disagreeable features. The dosage forms and HR were subjected to physicochemical evaluation, and standardised by a reversed-phase HPLC method using chlorogenic acid, caffeic acid, vanillin, and ferulic acid as analytical standards. The standardised dosage forms were investigated for antigout activity using an appropriate model. The dosage forms were found to be physically elegant and phytochemically aligned with HR. The developed dosage forms contained the selected markers and possessed antigout activity. Hence, these standardised and evidence-based dosage forms may have wider acceptance in the market compared to HR.

Phenolic compound profiling and antioxidant potential of different types of Schisandra henryi in vitro cultures.

Schisandra henryi is an endemic species of medicinal potential known from traditional Chinese medicine. As part of this study, a complex biotechnological and phytochemical assessment was conducted on S. henryi with a focus on phenolic compounds and antioxidant profiling. The following in vitro cultures were tested: microshoot agar and callus, microshoot agitated, and suspension, along with the microshoot culture in PlantForm bioreactors. Qualitative profiling was performed by ultra-high-performance liquid chromatography with a photodiode array detector coupled with ion-trap mass spectrophotometry with electrospray ionization and then quantitative analysis by high-performance liquid chromatography with a diode array detector using standards. In the extracts, mainly the compounds from procyanidins were identified as well as phenolic acids (neochlorogenic acid, caffeic acid, protocatechuic acid) and catechin. The highest content of phenolic compounds was found for in vitro agar microshoot culture (max. total content 229.87mg/100g DW) and agitated culture (max. total content 22.82mg/100g DW). The max. TPC measured using the Folin-Ciocalteu assay was equal to 1240.51mg GAE/100g DW (agar microshoot culture). The extracts were evaluated for their antioxidant potential by the DPPH, FRAP, and chelate iron ion assays. The highest potential was indicated for agar microshoot culture (90% of inhibition and 59.31nM/L TEAC, respectively). The research conducted on the polyphenol profiling and antioxidant potential of S. henryi in vitro culture extracts indicates the high therapeutic potential of this species. KEY POINTS: • Different types of S. henryi in vitro cultures were compared for the first time. • The S. henryi in vitro culture strong antioxidant potential was determined for the first time. • The polyphenol profiling of different types of S. henryi in vitro cultures was shown.

Stability of dentin matrix treated with caffeic acid phenethyl ester at different concentrations

Stability of dentin matrix treated with caffeic acid phenethyl ester at different concentrations

Characterization and molecular docking of sustainable wine lees and gelatin-based emulsions: innovative fat substitution.

The present study aimed to determine how various amounts (0.00, 0.58, 1.52 and 4.50 g 100 g-1) of wine lees (WL), which contains numerous essential components, impact the emulsifying properties of fish gelatin (FG) at a low concentration (0.5 g 100 g-1) in the high-fat phase (65 g 100 g-1). This study conducted rheology, physicochemical technical and characterization analyses on the emulsions to provide sustainable and innovative approaches for spreadable oils. The addition of WL to FG emulsions improved oxidative stability, emulsion stability and bioactive compounds. The zeta potential (-101 ± 5.62 mV) of 0.58 g 100 g-1 WL-containing emulsion (PE1) was found to be high, whereas particle size (347.6 ± 5.25 nm) and polydispersity index (0.50) were statistically low. It was also found that the addition of WL improved the intermolecular interactions, crystallinity and microstructural properties of the emulsions. All these results were supported by simulating the molecular configuration between FG and WL. The compounds gallic acid, caffeic acid, myricetin, quercetin and resveratrol showed a strong affinity to FG, with free binding energies of -5.50, -5.88, -6.53, -6.68 and -6.66 kcal mol-1, respectively. As a result, WL-supported FG has the potential to be used as an alternative to egg proteins to develop sustainable low-cost spreadable emulsions. © 2024 The Authors. Journal of The Science of Food and Agriculture published by John Wiley & Sons Ltd on behalf of Society of Chemical Industry.

Bifonazole caffeate: The first molecular salt of bifonazole with enhanced biopharmaceutical property based on experiments and quantum chemistry research

In order to make novel breakthroughs in molecular salt studies of BCS class-IV antifungal medication bifonazole (BIF), a salification-driven strategy towards ameliorating attributes and aiding augment efficiency is raised. This strategy fully harnesses structural characters together attributes and benefits of caffeic acid (CAF) to concurrently enhance dissolvability and permeability of BIF by introducing the two ingredients into the identical molecular salt lattice through the salification reaction, which, coupled with the aroused potential activity of CAF significantly amplifies the antifungal efficacy of BIF. Guided by this route, the first BIF-organic molecular salt, BIF-CAF, is directionally designed and synthesized with satisfactorily structural characterizations and integrated theoretical and experimental explorations on the pharmaceutical properties. Single-crystal X-ray diffraction resolving confirms that there is a lipid-water amphiphilic sandwich structure constructed by robust charge-assistant hydrogen bonds in the salt crystal, endowing the molecular salt with the potential to enhance both dissolvability and permeability relative to the parent drug, which is validated by experimental evaluations. Remarkably, the comprehensive DFT-based theoretical investigations covering frontier molecular orbital, molecular electrostatic potential, Hirshfeld surface analysis, reduced density gradient, topology, sphericity and planarity analysis strongly support these observations, thereby allowing some positive relationships between macroscopic properties and microstructures of the molecular salt can be made. Intriguingly, the optimal properties, together with the stimulated activity of CAF markedly augment in vitro antifungal ability of the molecular salt, with magnifying inhibition zones and reducing minimum inhibitory concentrations. These findings fill in the gaps on researches of BIF-organic molecular salt, and adequately exemplify the feasibility and validity by integrating theoretical and experimental approaches to resolve BIF’s problems via the salification-driven tactic.

Unveiling allelopathic dynamics and impacts of invasive Erigeron bonariensis and Bidens pilosa on plant communities and soil parameters

Invasive alien species are becoming more and more prevalent worldwide, Erigeron bonariensis and Bidens pilosa are two invasive species of Asteraceae in Egypt. To mitigate their detrimental effects and understand their differences in invasiveness, we compared the allelopathic potentials of E. bonariensis and B. pilosa using leachates, decaying residues, and volatilization processes. Notably, the allelopathic variances in leachates were significant, influenced by plant types, concentrations, and response patterns of target plant traits, as indicated by EC50. The relative phytotoxicity of the invasive species decayed residues peaked between 20 and 25 days in the soil, with a positive correlation with concentrations and soil properties. The highest quantities of phenolic acids were chlorogenic acid and caffeic acid reaching (5.41 and 4.39 µg g−1) E. bonariensis and (4.53 and 4.46 µg g−1) B. pilosa, in leachates extracts respectively, while in the soil extract of decayed residues were coumaric acid and ferulic acid measuring (1.66 and 1.67 µg g−1) E. bonariensis and (1.47 and 1.57 µg g−1) B. pilosa, respectively. Using GC/MS analysis, the main volatile components in E. bonariensis were 1, 8 cineole (5.62%), and α-terpinene (5.43%) and iso-Caryophyllene (5.2%) which showed the greatest inhibitory effects. While B. pilosa main constituents were trans-sabinene (5.39%) and Camphene (5.11%), respectively. Finally, the high invasion level displayed from E. bonariensis (0.221) compared with B. pilosa (0.094) which correlated with the stronger allelopathic activities against plant species, and soil properties. Therefore, the allelopathic potentialities of these species are critically relevant to their invasion success.

Analysis of Salt Stress on Soil Microbial Community Composition and Its Correlation with Active Components in the Rhizosphere of Acanthopanax senticosus.

Salt stress can adversely affect plant seed germination, growth and development, and eventually lead to slow growth and even death of plants. The purpose of this study was to investigate the effects of different concentrations of NaCl and Na2SO4 stress on the physicochemical properties, enzyme activities, rhizosphere microbial community and seven active components (L-phenylalanine, Protocatechuic acid, Eleutheroside B, Chlorogenic acid, Caffeic acid, Eleutheroside E, Isofraxidin) of Acanthopanax senticosus rhizosphere soil. Statistical analysis was used to explore the correlation between the rhizosphere ecological factors of Acanthopanax senticosus and its active components. Compared with Acanthopanax senticosus under NaCl stress, Na2SO4 generally had a greater effect on Acanthopanax senticosus, which reduced the richness of fungi in rhizosphere soil and adversely affected the content of multiple active components. Pearson analysis showed that pH, organic matter, ammonium nitrogen, available phosphorus, available potassium, catalase and urease were significantly correlated with active components such as Caffeic acid and Isofraxidin. There were 11 known bacterial genera, 12 unknown bacterial genera, 9 known fungal genera and 1 unknown fungal genus significantly associated with the active ingredient. Salt stress had great changes in the physicochemical properties, enzyme activities and microorganisms of the rhizosphere soil of Acanthopanax senticosus. In conclusion, different types and concentrations of salts had different effects on Acanthopanax senticosus, and the active components of Acanthopanax senticosus were regulated by rhizosphere soil ecological factors.

Review of the pharmacokinetics of French maritime pine bark extract (Pycnogenol®) in humans

The French maritime pine bark extract Pycnogenol® is a proprietary product from Pinus pinaster Aiton. It complies with the quality specifications in the United States Pharmacopeia monograph “Pine extract” in the section of dietary supplements. Pycnogenol® is standardized to contain 65–75% procyanidins which are a variety of biopolymers consisting of catechin and epicatechin monomeric units. The effects of Pycnogenol® have been researched in a multitude of human studies. The basis for any in vivo activity is the bioavailability of constituents and metabolites of the extract. General principles of compound absorption, distribution, metabolism and elimination as well as specific data from studies with Pycnogenol® are summarized and discussed in this review. Based on plasma concentration profiles it can be concluded that low molecular weight constituents of the extract, such as catechin, caffeic and ferulic acid, taxifolin are readily absorbed from the small intestine into systemic circulation. Procyanidin oligomers and polymers are subjected to gut microbial degradation in the large intestine yielding small bioavailable metabolites such as 5-(3′,4′-dihydroxyphenyl)-γ-valerolactone. After intake of Pycnogenol®, constituents and metabolites have been also detected in blood cells, synovial fluid and saliva indicating a substantial distribution in compartments other than serum. In studies simultaneously investigating concentrations in different specimen, a preferential distribution of individual compounds has been observed, e.g., of ferulic acid and 5-(3′,4′-dihydroxyphenyl)-γ-valerolactone into synovial fluid compared to serum. The main route of elimination of constituents and metabolites of the French pine bark extract is the renal excretion. The broad knowledge accumulated regarding the pharmacokinetics of compounds and metabolites of Pycnogenol® constitute a rational basis for effects characterized on a cellular level and observed in human clinical studies.

In vitro Antioxidant Activity of 5-caffeoylquinic Acid and Ester Analogues

Background: Chlorogenic acid, an ester of caffeic acid with quinic acid, also known as 5- O-caffeoylquinic acid (5-CQA), is a ubiquitous plant constituent that is an important intermediate in lignin biosynthesis. In some cases, it occurs at surprisingly high levels in the leaves and fruits of certain higher plants, such as coffee beans. Due to its catechol moiety and an extended side chain conjugation, it easily forms a resonance-stabilised phenoxy radical, accounting for its powerful antioxidant potential. Objective: The objective of this work was to determine if the esterification and methylation of 5- CQA would enhance its antioxidant activity. Methods: Two 5-CQA derivatives were prepared for this study. Chlorogenic acid was esterified with methanol over Amberlite IR120-H to obtain methyl chlorogenate, while methyl 3',4´-dimethyl chlorogenate was prepared from 5-CQA by treatment with diazomethane. Spectroscopic methods confirmed the structure of these derivatives. Their antioxidant properties were tested to establish a relationship between structure and antioxidant activity. Results: Antioxidant activity results were generated for 5-CQA and its ester analogues using eight different methods. Depending on the method applied, results were expressed as IC50/MCE50 values or as equivalents of the applied standard (ascorbic acid and Trolox). Conclusion: In most of these tests, 5-CQA showed the highest antioxidant activity compared to its derivatives. Nevertheless, due to their hydrophobic characteristics, their ester analogues remain promising antioxidant candidates in emulsifying systems.

Effects of synergistic action on rheological and thermal properties of potato starch complexes co-gelatinized with caffeic acid and squash polysaccharides extracted with water and subcritical water

In order to broaden the application range of squash polysaccharide (WESP/SWESP) and caffeic acid (CAA) and improve the quality of potato starch (PS) products, the effects of WESP/SWESP and CAA on the gelatinization, rheology, thermodynamics, microstructure and in vitro digestion of PS were investigated. Meanwhile, the synergistic effect of WESP/SWESP and CAA on PS was further analyzed. Differently, due to WESP and SWESP had different monosaccharide composition and structure, they had different effects on the system. Pasting properties results showed that the presence of WESP/SWESP and CAA significantly reduced the peak viscosity, trough viscosity, breakdown viscosity and final viscosity of PS, especially under the combined action. In rheological tests, all sample gels belonged to the pseudoplastic fluids and weak gel system (tan δ < 1). Besides, thermodynamic properties revealed that WESP/SWESP and CAA synergistic effect had better retrogradation delay effect. In the ternary system, WESP/SWESP, CAA and PS can form a new network structure and improve the stability of the gel system. In addition, the results of infrared spectroscopy, Raman spectroscopy, x-ray diffraction and scanning electron microscopy exhibited that the ternary system can promote the accumulation and winding of the spiral structure of PS chain, and make the structure of PS gel network more orderly and stable. Furthermore, compared with PS gel, the ternary system had lower RDS and higher SDS and RS content, suggesting that the addition of WESP/SWESP and CAA at the same time was more conducive to reducing the hydrolysis rate of PS. This work revealed the interaction between WESP/SWESP, CAA and PS, which improved the physicochemical and digestive properties of PS. It will provide a theoretical basis for improving the quality of potato starch-related products and developing functional foods.

Metabolomics Analysis Reveals the Effects of Salvia Miltiorrhiza Bunge Extract on Ameliorating Acute Myocardial Ischemia in Rats Induced by Isoproterenol

Salvia MiltiorrhizaBunge (SM) is a widespread herbal therapy for myocardial ischemia (MI). Nevertheless, the therapeutic signaling networks of SM extract on MI is yet unknown. Emerging evidences suggested that alterations in cardiac metabolite influences host metabolism and accelerates MI progression. Herein, we employed an isoproterenol (ISO)-induced acute myocardial ischemia (AMI) rat model to confirm the pharmacological effects of SM extract (0.8, 0.9, 1.8 g/kg/day) via assessment of the histopathological alterations that occur within the heart tissue and associated cytokines; we also examined the underlying SM extract-mediated signaling networks using untargeted metabolomics. The results indicated that 25 compounds with a relative content higher than 1% in SM aqueous extract were identified using LC-MS/MS analysis, which included salvianolic acid B, lithospermic acid, salvianolic acid A, and caffeic acid as main components. An in vivo experiment showed that pretreatment with SM extract attenuated ISO-induced myocardial injury, shown as decreased myocardial ischemic size, transformed electrocardiographic, histopathological, and serum biochemical aberrations, reduced levels of proinflammatory cytokines, inhibited oxidative stress (OS), and reversed the trepidations of the cardiac tissue metabolic profiles. Metabolomics analysis shows that the levels of 24 differential metabolites (DMs) approached the same value as controls after SM extract therapy, which were primarily involved in histidine; alanine, aspartate, and glutamate; glycerophospholipid; and glycine, serine, and threonine metabolisms through metabolic pathway analysis. Correlation analysis demonstrated that the levels of modulatory effects of SM extract on the inflammation and OS were related to alterations in endogenous metabolites. Overall, SM extract demonstrated significant cardioprotective effects in an ISO-induced AMI rat model, alleviating myocardial injury, inflammation and oxidative stress, with metabolomics analysis indicating potential therapeutic pathways for myocardial ischemia.

Polyphenolic dendrimers as carriers of anticancer siRNA.

Dendrimers have emerged as an important group of nanoparticles to transport drugs, DNA, or RNA into target cells in cancer and other diseases. Various functional modifications can be imposed on dendrimers to increase the efficacy and specificity in delivering their cargo to the target cells and decrease their toxicity. In the present work, we evaluated the potential of carbosilane polyphenolic dendrimers modified with caffeic acid (CA) and polyethylene glycol (PEG) to deliver proapoptotic Mcl-1 and Bcl-2 siRNAs to A549 cancer cells. Dendrimers formed stable complexes with siRNAs as assessed by transmission electron microscopy and gel electrophoresis. Modification of dendrimers with PEG reduced the size and the zeta potential of dendrimer/siRNA complexes. The presence of PEG caused a red shift of the CD spectrum, and this effect was the more pronounced, the higher the dendrimer/siRNA ratio was. The nanocomplexes were internalized by A549. All studied dendrimer/siRNA formulations inhibited tumor cell migration and adhesion and caused an increase in the population of early apoptotic cells. Among four tested dendrimers, the polyphenolic compound containing two caffeic acid moieties complexed with siRNA demonstrated the lowest polydispersity index and showed an excellent transfection profile. In conclusion, this dendrimer are a promising candidate for the delivery of siRNA into cancer cells in further in vivo studies.

Synthesis and dopaminergic neuroprotective activity of the proposed structure of bassiamide A, a caffeamide alkaloid derived from Bassia indica Wight.

Herein, we describe the synthesis of the proposed structure of the caffeamide alkaloid bassiamide A. The amide moiety of bassiamide A was readily formed via an amide coupling reaction between caffeic acid and the known N-(3-aminopropyl)-3-methylbutanamide. However, the spectral data of the synthesized bassiamide A did not agree with that of a previous study. The structure of the synthesized bassiamide A was confirmed using combined two-dimensional NMR analysis. Extended analyses of the bioactivity of the synthesized bassiamide A revealed its efficacy in protecting dopaminergic neurons from MPP+-induced neurotoxicity in C. elegans. Additionally, treatment with bassiamide A notably ameliorated the impaired food-sensing ability and locomotion of C. elegans, suggesting a protective effect on the functionality of dopaminergic neurons.

Integrated HS-GC–IMS and UPLC-Q-Orbitrap HRMS-based metabolomics revealed the characteristics and differential volatile and nonvolatile metabolites of different citrus peels

Citrus is an important genus in the Rutaceae family, and citrus peels can be used in both food and herbal medicine. However, the bulk of citrus peels are discarded as waste by the fruit processing industry, causing environmental pollution. This study aimed to provide guidelines for the rational and effective use of citrus peels by elucidating the volatile and nonvolatile metabolites within them using metabolomics based on headspace-gas chromatography–ion mobility spectrometry and ultra-high-performance liquid chromatography–Q-Orbitrap high-resolution mass spectrometry. In addition, the antioxidant activities of the citrus peels were evaluated using DPPH radical scavenging, ABTS radical scavenging, and ferric reducing antioxidant power. In total, 103 volatile and 53 nonvolatile metabolites were identified and characterized. Alcohols, aldehydes, and terpenes constituted 87.36% of the volatile metabolites, while flavonoids and carboxylic acids accounted for 85.46% of the nonvolatile metabolites. Furthermore, (Z)-2-penten-1-ol, L-pipecolinic acid, and limonin were identified as characteristic components of Citrus reticulata Blanco cv. Ponkan (PK), C. reticulata ‘Unshiu’ (CLU), and C. reticulata 'Wo Gan' (WG), respectively. Principal component analysis and partial least squares discriminant analysis indicated that C. reticulata Blanco 'Chun Jian' (CJ), PK, CLU, and C. reticulata ‘Dahongpao’ (DHP) were clustered together. DHP is a traditional Chinese medicine documented in the Chinese Pharmacopoeia, suggesting that the chemical compositions of CJ, PK, and CLU may also have medicinal values similar to those of DHP. Moreover, DHP, PK, C. reticulata 'Ai Yuan 38’(AY38), CJ, C. reticulata 'Gan Ping’(GP), and C. reticulata 'Qing Jian’(QJ) displayed better antioxidant activities, recommending their use as additives in cosmetics and food. Correlation analysis suggested that some polyphenols including tangeritin, nobiletin, skullcapflavone II, genistein, caffeic acid, and isokaempferide were potential antioxidant compounds in citrus peel. The results of this study deepen our understanding of the differences in metabolites and antioxidant activities of different citrus peel varieties and ultimately provide guidance for the full and rational use of citrus peels.

Xuebijing injection and its bioactive components alleviate nephrotic syndrome by inhibiting podocyte inflammatory injury

Xuebijing injection (XBJ) is widely used to treat nephrotic syndrome (NS) in clinic, but its bioactive components and therapeutic mechanism are still unclear. In this study, the bioactive components of XBJ were determined by ultra-performance liquid chromatography quadrupole time-of-flight tandem mass spectrometry (UPLC-Q-TOF/MS). The therapeutic effect of XBJ on NS was evaluated in BALB/c mice induced by adriamycin (ADR, 10 mg/kg) via a single tail vein. The protective effect of XBJ and its bioactive components on podocytes was demonstrated using mouse podocytes (MPC-5) induced by lipopolysaccharide (LPS, 4 μg/mL). The results show that 33 components of XBJ were identified. Furthermore, 12 bioactive components were detected in blood, including protocatechuic acid, salvianolic acid C, benzoyloxypaeoniflorin, danshensu, salvianolic acid A, salvianolic acid B, catechin, caffeic acid, galloylpaeoniflorin, oxypaeoniflorin, hydroxysafflor yellow A, rosmarinic acid. The relative content (%) of the bioactive components were 59.32, 16.01, 9.97, 9.73, 8.72, 8.31, 7.92, 6.54, 1.54, 1.30, 0.68 and 0.59 in this order. After XBJ treatment, the renal function, hyperlipidemia and renal pathological damage were improved in NS model mice. Moreover, the levels of nephrin and desmin which are functional proteins in podocytes were reversed, and the levels of pro-inflammatory factors were reduced by XBJ. Interestingly, protocatechuic acid and salvianolic acid C also showed good protective effects on podocyte function and reduced the level of inflammation in LPS-induced MPC-5. The study is the first time to elucidate the bioactive components of XBJ and its potential therapeutic mechanism for treating NS by protecting podocyte function.

Influence of soaking Malus domeri (Bois) Chev. leaves on gut microbiota and metabolites of long-living elderly individuals in Hezhou city, Guangxi, China

To investigate the effects of drinking the soaking of Malus domeri (Bois) Chev. leaves on gut microbiota and metabolites of long-living elderly individuals in Hezhou city, Guangxi, China. It has been reported that longevity is closely related to metabolism and the gut microbiota. The 16S rRNA sequencing and liquid chromatography-mass spectrometry (LC-MS) were used to analysis fecal samples and explore the factors affecting longevity in the region. Interestingly, we discovered, that elderly individuals who had been drinking the soaking of M. domeri (Bois) Chev. leaves for a long time exhibited higher diversity of the gut microbiota than without drinking the soaking, notably. The proportions of Ruminococcaceae and Prevotella were decreased in those who did not drink this soaking. In addition, a total of 106 metabolites were characterized, and the people of long-lived people (> 90 years old) and elderly people (< 90 years old) who drinking soaking of M. domeri (Bois) Chev. leaves significantly altered the gut microbiota and upregulated levels of haplopine, farnesol, genipic acid, momordicinin, 2-hydroxyestrone, hydroxyphenyllactic acid, caffeic acid, sophoraflavanone B, and soyasaponin I. We preliminarily determined that M. domeri (Bois) Chev. leaves consumption may be an important factor affecting longevity in this area.

Absolute kinetics of peroxidation and antioxidant protection of intact triglyceride vegetable oils

To verfy their difference from isolated fatty acids, the absolute kinetics of peroxidation was studied for seven triglyceride-based oils of olive (OLI-1, OLI-2), high-oleic sunflower (SUN-HO), high-oleic and high-linoleic safflower (SAF-HO, SAF-HL) grapeseed (GRA) and borage (BOR), by oxygen uptake monitoring, using 2,6-di-tert-butyl-4-methoxyphenol and 2,2,5,7,8-pentamethyl-6-chromanol as reference inhibitors. Propagation constants (kp/M−1 s−1 at 303 K in PhCl) were respectively 34.8 ± 2.3, 35.1 ± 1.8, 40.6 ± 5.5, 36.0 ± 7.7, 160.8 ± 5.1, 145.1 ± 24.5, 275.1 ± 63.8, while oxidizability responded to empirical equation kp(2kt)-½/M-½s-½ = 1.63 × 10−3[allyl >CH2/M] + 1.82 × 10−2[bisallyl >CH2/M], based on fatty acids residues assessed by GC–MS. Peroxidation kinetics was markedly different from that of isolated fatty acids. The H-bond basicity of all oils was measured by FT-IR affording Abraham's βH2 values in the range 0.55 ± 0.03. H-bonding explained the protection of oils measured for seven reference phenolic antioxidants, except for the catechols quercetin and caffeic acid phenethyl ester, which were 2-to-4-folds more effective than expected, supporting a proposed different mechanism.

Single and multiple inhibitors of the biosynthesis of 5-, 12-, 15-lipoxygenase products derived from cinnamyl-3,4-dihydroxy-α-cyanocinnamate: Synthesis and structure-activity relationship.

The involvement of lipoxygenases in various pathologies, combined with the unavailability of safe and effective inhibitors of the biosynthesis of their products, is a source of inspiration for the development of new inhibitors. Based on a structural analysis of known inhibitors of lipoxygenase products biosynthesis, a comprehensive structure-activity study was carried out, which led to the discovery of several novel compounds (16a-c, 17a) demonstrating promising potency to inhibit the biosynthesis of products of 5-, 12- and 15-LO. Compounds 16b and 16c outperformed zileuton (1), the only FDA-approved 5-LO inhibitor, as well as known inhibitors such as caffeic acid phenethyl ester (CAPE (2)) and cinnamyl-3,4-dihydroxy-α-cyanocinnamate (CDC (4)). However, the introduction of a cyano group at the α-position of the carbonyl abolished the activity. Compounds 16a and 17a also inhibited the biosynthesis of 12- and 15-LO products. Compounds 16a, 17a far surpassed baicalein, a known 12-LO inhibitor, as inhibitors of 12-LO products biosynthesis. Compound 17a and CDC (4) showed equivalent inhibition of LO products, proposing that the double bond in the ester moiety is not necessary for the inhibitory activity. The introduction of the cyano group, as in compound 17a, at the α-position of the carbonyl in compound 16a significantly reduced the inhibitory activity against the biosynthesis of 15-LO products. In addition to the interactions with residues His372 and Phe421 also found with zileuton and CAPE, compounds 16a and 16c each interact with residue His367 as shown by molecular docking. This new interaction may explain their high affinity with the 5-LO active site.

Potentialities of Dandelion (Taraxacum Mongolicum Hand.-Mazz.) Flower Extracts on Gastric Protection against Helicobacter Pylori and Characterization of its Bioactive Constituents.

Dandelion has been shown to exert anti-inflammatory and anti-bacterial effects. Our study aimed to identify the effect and mechanism of dandelion flower extracts on H. pylori-induced gastritis and screen for novel antimicrobial substances. Anti-H. pylori activities of water extracts(WEDF) and ethanol extracts (EEDF) of dandelion flowers were performed with disk diffusion method assay, MIC, and MBC. The H. pylori-induced model was constructed to examine the gastroprotective of EEDF using RUT, pathological analysis, and ELISA. EEDF exhibited better anti- H. pylori and urease inhibition activities than WEDF. In vivo studies, EEDF can reduce the adhesion of H. pylori to the gastric mucosa, alleviate gastric damage, and concurrently reduce the levels of TNF-α and IL-6 in gastric tissues. The six phenolic compounds showed urease inhibition effect (IC50: 2.99±0.15 to 66.08±6.46 mmol/mL). Among them, chlorogenic acid, caffeic acid, and luteolin also had anti-H. pylori activity (MIC: 64-256 μg/mL). EEDF exhibited anti-H. pylori, gastroprotective and anti-inflammatory effects. Chicoric acid and luteolin may be the main active compounds of dandelion flowers to exert anti-H. pylori, and worthy of further investigation.

Chemical composition, antioxidant, cytotoxic, antiviral, and lung-protective activities of Salvia officinalis L. ethanol extract herb growing in Sinai, Egypt

BackgroundPulmonary fibrosis (PF) is a respiratory ailment that causes the substitution of healthy lung tissue with scar tissue due to collagen deposition and fibroblast proliferation. The incidence of PF increased with the successive waves of Coronaviruses and other viruses affecting the lungs. Therefore, the priority is moving toward treatment with medicinal plants for their active constituents. Salvia officinalis L. herbal drug (sage, family; Lamiaceae) is characterized by its strong antioxidative activity. This study aims to declare the effect of using sage ethanol extract (SOEE) as a protective agent from PF through an in vivo study on mercuric chloride (HgCl2)-induced lung fibrosis and in vitro evaluation of its anticancer, antiviral, and antioxidant activities concerning its phytoconstituents.ResultsTwelve compounds were isolated and identified as apigenin, luteolin, genkwanin, quercetin, hispidulin, luteolin-7-O-β- glucopyranoside, rutin, rosmarinic acid, caffeic acid, ferulic acid chlorogenic acid, and ellagic acid. The results of antioxidants indicated that SOEE exhibited the greatest efficacy as an antioxidant agent in the 1,1-Diphenyl-2-picrylhydrazyl assay with inhibitory concentration (IC50) 23.21 ± 1.17 µg/ mL followed by 1864.71 and 1793.80 µM Trolox equivalent/mg extract for ferric ion reducing antioxidant power and 3-ethylbenzothiazoline-6-sulfonic acid (ABTS), respectively. SOEE showed notable cytotoxic activity against A549. Oral administration of SOEE at 69.4 and 173.5 mg/kg.bw afforded a noteworthy protective effect against HgCl2-induced pulmonary fibrosis. Also, lung superoxide dismutase (SOD), catalase (CAT), and reduced glutathione (GSH) were increased by SOEE. That was in parallel with working to reduce the malondialdehyde (MDA), necrosis factor kappa (NF-κB), interleukin-1β (IL-1β), and cyclooxygenase-2 (COX-2) levels. The lung P53, Bcl-2, Bcl-XL, AKT, and vanin-1 gene expression was upregulated in SOEE-treated rats compared to HgCl2-treated rats.ConclusionSOEE reduces acute lung injury and can be used to inhibit the proliferation and migration of lung fibrotic cells. These activities may be related to its high antioxidant activity, which could result from the phenolic constituents. The authors recommended using sage in the treatment of lung diseases to protect from lung fibrosis. Additional animal and human experiments are needed for future research.Graphical abstract