RESUMO
Myocardial ischemia (MI) is a significant contributor to ischemic heart diseases like angina pectoris and myocardial infarction. Reactive oxygen species produced during MI can trigger lipid peroxidation, damaging cell structure and function. Salvia miltiorrhiza (SM) has been widely used clinically in the treatment of cardiovascular diseases. However, in the process of rooting, the aboveground parts of this plant are usually discarded by tons. To make better use of these plant resources, the phenolic acids extracted and purified from the aerial part of SM were studied and chemically transformed, and the potential protective effect and possible mechanism of salvianolic acids containing a higher content of salvianolic acid A on MI were obtained. The transformed products of SM stem-leaves total phenolic acids with 8.16â¯% salvianolic acid A showed a better protective effect on the isoproterenol (ISO)-induced acute MI injury rat model. It can improve ST segment changes and has good antioxidant, anti-inflammatory and anticoagulant effects. In addition, the dysbiosis of gut microbiota and the related metabolic levels of short chain fatty acids (SCFAs), phenylalanine and glycerophospholipids were improved. This was achieved by reducing the abundance of Bacteroides, Faecalibaculum, and L-phenylalanine levels. In addition, the abundance of probiotics in Butyricoccus, Roseburia, and norank_f_Eubacterium_coprostanoligenes_group, as well as the contents of propionic acid and isobutyric acid, LPCs and PCs were increased. In conclusion, total phenolic acids of SM stem-leaves showed protective effects against ISO-induced rats, especially the strongest effect after conversion, which is a new option for the prevention and treatment of MI.
Assuntos
Microbioma Gastrointestinal , Hidroxibenzoatos , Isquemia Miocárdica , Caules de Planta , Ratos Sprague-Dawley , Salvia miltiorrhiza , Salvia miltiorrhiza/química , Animais , Microbioma Gastrointestinal/efeitos dos fármacos , Hidroxibenzoatos/farmacologia , Hidroxibenzoatos/isolamento & purificação , Masculino , Caules de Planta/química , Isquemia Miocárdica/metabolismo , Isquemia Miocárdica/tratamento farmacológico , Ratos , Folhas de Planta , Metaboloma/efeitos dos fármacos , Antioxidantes/farmacologia , DisbioseRESUMO
A magnetic MXene aerogel (Fe3O4@MXene@PEI) was prepared by crosslinking amino modified MXene with polyethyleneimine using epichlorohydrin as a cross-linker. Adsorption properties of Fe3O4@MXene@PEI aerogel for phenolic acids were evaluated by adsorption kinetics and isotherms experiments, showing that the high adsorption affinity was governed by multilayer chemisorption process. An efficient MSPE/HPLC method was developed for the determination of phenolic acids with excellent selectivity, good linearity (0.025-5.0 µg mL-1), low LODs (0.007-0.017 µg mL-1), and satisfactory recoveries (80.0-120.0 %). Moreover, the antioxidant activity of the Fe3O4@MXene@PEI purified compounds was superior to that of the conventional method as demonstrated by the results of scavenging experiments on 2,2 -diphenyl-1-picrylhydrazyl radical scavenging assay. Finally, 65 organic acids were identified in the Fe3O4@MXene@PEI treated honeysuckle extracts by UHPLC-Q-Exactive Orbitrap MS/MS analysis. The proposed sorbent exhibits remarkable promise for the selective separation and purification of organic acids from herbal products.
Assuntos
Hidroxibenzoatos , Polietilenoimina , Hidroxibenzoatos/química , Hidroxibenzoatos/análise , Hidroxibenzoatos/isolamento & purificação , Polietilenoimina/química , Adsorção , Cromatografia Líquida de Alta Pressão/métodos , Géis/química , Plantas Medicinais/química , Extração em Fase Sólida/métodos , Antioxidantes/química , Antioxidantes/análise , Antioxidantes/isolamento & purificação , Espectrometria de Massas em Tandem/métodosRESUMO
The supramolecular solvent (SUPRAS) has garnered significant attention as an innovative, efficient, and environmentally friendly solvent for the effective extraction and separation of bioactive compounds from natural resources. However, research on the use of a SUPRAS for the extraction of phenolic compounds from plants, which are highly valued in food products due to their exceptional antioxidant properties, remains scarce. The present study developed a green, ultra-sound-assisted SUPRAS method for the simultaneous determination of three phenolic acids in Prunella vulgaris using high-performance liquid chromatography (HPLC). The experimental parameters were meticulously optimized. The efficiency and antioxidant properties of the phenolic compounds obtained using different extraction methods were also compared. Under optimal conditions, the extraction efficiency of the SUPRAS, prepared with octanoic acid reverse micelles dispersed in ethanol-water, significantly exceeded that of conventional organic solvents. Moreover, the SUPRAS method demonstrated greater antioxidant capacity. Confocal laser scanning microscopy (CLSM) images revealed the spherical droplet structure of the SUPRAS, characterized by a well-defined circular fluorescence position, which coincided with the position of the phenolic acids. The phenolic acids were encapsulated within the SUPRAS droplets, indicating their efficient extraction capacity. Furthermore, molecular dynamics simulations combined with CLSM supported the proposed method's mechanism and theoretically demonstrated the superior extraction performance of the SUPRAS. In contrast to conventional methods, the higher extraction efficiency of the SUPRAS can be attributed to the larger solvent contact surface area, the formation of more types of hydrogen bonds between the extractants and the supramolecular solvents, and stronger, more stable interaction forces. The results of the theoretical studies corroborate the experimental outcomes.
Assuntos
Antioxidantes , Fenóis , Extratos Vegetais , Solventes , Solventes/química , Fenóis/química , Fenóis/isolamento & purificação , Antioxidantes/química , Antioxidantes/isolamento & purificação , Extratos Vegetais/química , Cromatografia Líquida de Alta Pressão/métodos , Química Verde , Simulação de Dinâmica Molecular , Hidroxibenzoatos/química , Hidroxibenzoatos/isolamento & purificaçãoRESUMO
Alpinia officinarum is a commonly used spice with proven folk uses in various traditional medicines. In the current study, six compounds were isolated from its rhizomes, compounds 1-3 were identified as diarylheptanoids, while 4-6 were identified as flavonoids and phenolic acids. The isolated compounds were subjected to virtual screening against α-glucosidase, butyrylcholinesterase (BChE), and acetylcholinesterase (AChE) enzymes to evaluate their potential antidiabetic and anti-Alzheimer's activities. Molecular docking and dynamics studies revealed that 3 exhibited a strong binding affinity to human a α- glucosidase crystal structure compared to acarbose. Furthermore, 2 and 5 demonstrated high potency against AChE. The virtual screening results were further supported by in vitro assays, which assessed the compounds' effects on α-glucosidase, cholinesterases, and their antioxidant activities. 5-Hydroxy-7-(4-hydroxy-3-methoxyphenyl)-1-phenylheptan-3-one (2) showed potent antioxidant effect in both ABTs and ORAC assays, while p-hydroxy cinnamic acid (6) was the most potent in the ORAC assay. In contrary, kaempferide (4) and galangin (5) showed the most potent effect in metal chelation assay. 5-Hydroxy-1,7-diphenylhepta-4,6-dien-3-one (3) and 6 revealed the most potent effect as α-glucosidase inhibitors where compound 3 showed more potent effect compared to acarbose. Galangin (5) revealed a higher selectivity to BChE, while 2 showed the most potent activity to (AChE).
Assuntos
Acetilcolinesterase , Alpinia , Antioxidantes , Butirilcolinesterase , Inibidores da Colinesterase , Inibidores de Glicosídeo Hidrolases , Simulação de Acoplamento Molecular , Rizoma , Alpinia/química , Inibidores da Colinesterase/farmacologia , Inibidores da Colinesterase/química , Inibidores da Colinesterase/isolamento & purificação , Inibidores de Glicosídeo Hidrolases/farmacologia , Inibidores de Glicosídeo Hidrolases/química , Inibidores de Glicosídeo Hidrolases/isolamento & purificação , Antioxidantes/farmacologia , Antioxidantes/química , Antioxidantes/isolamento & purificação , Rizoma/química , Butirilcolinesterase/metabolismo , Acetilcolinesterase/metabolismo , alfa-Glucosidases/metabolismo , Relação Quantitativa Estrutura-Atividade , Flavonoides/química , Flavonoides/farmacologia , Flavonoides/isolamento & purificação , Hidroxibenzoatos/farmacologia , Hidroxibenzoatos/química , Hidroxibenzoatos/isolamento & purificação , HumanosRESUMO
ATP citrate lyase (ACLY) is a key enzyme in glucolipid metabolism, and abnormally high expression of ACLY occurs in many diseases, including cancers, dyslipidemia and cardiovascular diseases. ACLY inhibitors are prospective treatments for these diseases. However, the scaffolds of ACLY inhibitors are insufficient with weak activity. The discovery of inhibitors with structural novelty and high activity continues to be a research hotpot. Acanthopanax senticosus (Rupr. & Maxim.) Harms is used for cardiovascular disease treatment, from which no ACLY inhibitors have ever been found. In this work, we discovered three novel ACLY inhibitors, and the most potent one was isochlorogenic acid C (ICC) with an IC50 value of 0.14 ± 0.04 µM. We found dicaffeoylquinic acids with ortho-dihydroxyphenyl groups were important features for inhibition by studying ten phenolic acids. We further investigated interactions between the highly active compound ICC and ACLY. Thermal shift assay revealed that ICC could directly bind to ACLY and improve its stability in the heating process. Enzymatic kinetic studies indicated ICC was a noncompetitive inhibitor of ACLY. Our work discovered novel ACLY inhibitors, provided valuable structure-activity patterns and deepened knowledge on the interactions between this targe tand its inhibitors.
Assuntos
ATP Citrato (pro-S)-Liase , Eleutherococcus , Eleutherococcus/química , Estrutura Molecular , ATP Citrato (pro-S)-Liase/antagonistas & inibidores , Inibidores Enzimáticos/farmacologia , Inibidores Enzimáticos/isolamento & purificação , Inibidores Enzimáticos/química , Ácido Clorogênico/farmacologia , Ácido Clorogênico/isolamento & purificação , Ácido Clorogênico/química , Compostos Fitoquímicos/farmacologia , Compostos Fitoquímicos/isolamento & purificação , Compostos Fitoquímicos/química , Ácido Quínico/análogos & derivados , Ácido Quínico/farmacologia , Ácido Quínico/isolamento & purificação , Ácido Quínico/química , Hidroxibenzoatos/farmacologia , Hidroxibenzoatos/isolamento & purificação , Hidroxibenzoatos/química , Relação Estrutura-AtividadeRESUMO
Hyperuricemia (HUA) is a metabolic disease characterized by the increase of serum uric acid (UA) level. Sargentodoxae Caulis (SC) is a commonly used herbal medicine for the treatment of gouty arthritis, traumatic swelling, and rheumatic arthritis in clinic. In this study, a total of fifteen compounds were identified in SC water extract using UHPLC-Q-TOF-MS/MS, including three phenolic acids, seven phenolic glycosides, four organic acids, and one lignan. Then, to study the hypouricemia effect of SC, a HUA mouse model was induced using a combination of PO, HX, and 20% yeast feed. After 14 days of treatment with the SC water extract, the levels of serum UA, creatinine (CRE), blood urea nitrogen (BUN) were reduced significantly, and the organ indexes were restored, the xanthine oxidase (XOD) activity were inhibited as well. Meanwhile, SC water extract could ameliorate the pathological status of kidneys and intestine of HUA mice. Additionally, quantitative real-time PCR (qRT-PCR) and western blotting results showed that SC water extract could increase the expression of ATP binding cassette subfamily G member 2 (ABCG2), organic cation transporter 1 (OCT1), organic anion transporter 1 (OAT1) and organic anion transporter 3 (OAT3), whereas decrease the expression of glucose transporter 9 (GLUT9). This study provided a data support for the clinical application of SC in the treatment of HUA.
Assuntos
Membro 2 da Subfamília G de Transportadores de Cassetes de Ligação de ATP , Hiperuricemia , Ácido Úrico , Xantina Oxidase , Animais , Camundongos , Hiperuricemia/tratamento farmacológico , Masculino , Membro 2 da Subfamília G de Transportadores de Cassetes de Ligação de ATP/metabolismo , Ácido Úrico/sangue , Xantina Oxidase/metabolismo , Modelos Animais de Doenças , Proteínas Facilitadoras de Transporte de Glucose/metabolismo , Rim/efeitos dos fármacos , Nitrogênio da Ureia Sanguínea , Creatinina/sangue , Extratos Vegetais/farmacologia , Extratos Vegetais/química , Transportadores de Ânions Orgânicos/metabolismo , Compostos Fitoquímicos/farmacologia , Compostos Fitoquímicos/isolamento & purificação , Proteína 1 Transportadora de Ânions Orgânicos/metabolismo , Hidroxibenzoatos/isolamento & purificação , Hidroxibenzoatos/farmacologiaRESUMO
Stingless bees belong to the Meliponini tribe and are widely distributed in the tropics and subtropics, where they perform important ecological services. Among the best distributed groups of stingless bees is the genus Scaptotrigona, which includes 22 species distributed throughout the neotropical region, including the area from Mexico to Argentina. Bees of this genus are responsible for the production of products such as honey, propolis, geopropolis and fermented pollen ("saburá"). This review aimed to provide an overview of the chemical composition and biological activities associated with derived products from stingless bees of the genus Scaptotrigona. The bibliographic review was carried out through searches in the Scopus, Web of Science, ScienceDirect and PubMed databases, including publications from 2003 to January 2023. The study of the chemodiversity of products derived from Scaptotrigona demonstrated the mainly presence of flavonoids, phenolic acids, terpenoids and alkaloids. It was also demonstrated that products derived from bees of the genus Scaptotrigona exhibit a wide range of biological effects, such as antibacterial, antioxidant, anti-inflammatory and antifungal activities, among other bioactivities. This review provides an overview of phytochemical and pharmacological investigations of the genus Scaptotrigona. However, it is essential to clarify the toxicity and food safety of these products.
Assuntos
Mel , Himenópteros , Própole , Animais , Antibacterianos/farmacologia , Abelhas , México , Própole/farmacologia , Flavonoides/química , Flavonoides/isolamento & purificação , Flavonoides/farmacologia , Hidroxibenzoatos/química , Hidroxibenzoatos/isolamento & purificação , Hidroxibenzoatos/farmacologia , Terpenos/química , Terpenos/isolamento & purificação , Terpenos/farmacologia , Anti-Inflamatórios/química , Anti-Inflamatórios/isolamento & purificação , Anti-Inflamatórios/farmacologiaRESUMO
Six new ß-resorcylic acid derivatives (1-5 and 7) were isolated from a halophyte-associated fungus, Colletotrichum gloeosporioides JS0419, together with four previously reported ß-resorcylic acid lactones (RALs). The relative and absolute stereochemistry of 1 was completely established by a combination of spectroscopic data and chemical reactions. The structures of the isolated compounds were elucidated by analysis of HRMS and NMR data. Notably, compounds 1-3 had a ß-resorcylic acid harboring a long unesterified aliphatic side chain, whereas the long aliphatic chains were esterified to form macrolactones in 4-9. Among the isolated compounds, monocillin I and radicicol showed potent antifungal activities against Cryptococcus neoformans, comparable to clinically available antifungal agents and radicicol showed weak antifungal activity against Candida albicans. These findings provide insight into the chemical diversity of fungal RAL-type compounds and their pharmacological potential.
Assuntos
Antifúngicos/farmacologia , Candida albicans/efeitos dos fármacos , Chenopodiaceae/microbiologia , Colletotrichum/química , Cryptococcus neoformans/efeitos dos fármacos , Hidroxibenzoatos/farmacologia , Plantas Tolerantes a Sal/microbiologia , Antifúngicos/química , Antifúngicos/isolamento & purificação , Candida albicans/crescimento & desenvolvimento , Cryptococcus neoformans/crescimento & desenvolvimento , Hidroxibenzoatos/química , Hidroxibenzoatos/isolamento & purificação , Estrutura Molecular , EstereoisomerismoRESUMO
The chemical composition of extractives in the sapwood (SW), heartwood (HW), knotwood (KW), and branchwood (BW of silver fir (Abies alba Mill.) was analyzed, and their antifungal and antioxidant properties were studied. In addition, the variability of extractives content in a centripetal direction, i.e., from the periphery of the stem towards the pith, was investigated. The extracts were analyzed chemically with gravimetry, spectrophotometry, and chromatography. The antifungal and antioxidative properties of the extracts were evaluated by the agar well diffusion method and the diphenyl picrylhydrazyl radical scavenging method. Average amounts of hydrophilic extractives were higher in KW (up to 210.4 mg/g) and BW (148.6 mg/g) than in HW (34.1 mg/g) and SW (14.8 mg/g). Extractives identified included lignans (isolariciresinol, lariciresinol, secoisolariciresinol, pinoresinol, matairesinol) phenolic acids (homovanillic acid, coumaric acid, ferulic acid), and flavonoids epicatechin, taxifolin, quercetin). Secoisolariciresinol was confirmed to be the predominant compound in the KW (29.8 mg/g) and BW (37.6 mg/g) extracts. The largest amount of phenolic compounds was extracted from parts of knots (281.7 mg/g) embedded in the sapwood and from parts of branches (258.9 mg/g) adjacent to the stem. HW contained more lignans in its older sections. Hydrophilic extracts from knots and branches inhibited the growth of wood-decaying fungi and molds. KW and BW extracts were better free radical scavengers than HW extracts. The results of the biological activity tests suggest that the protective function of phenolic extracts in silver fir wood can also be explained by their antioxidative properties. The results of this study describe BW as a potential source of phenolic extractives in silver fir.
Assuntos
Antifúngicos/farmacologia , Antioxidantes/farmacologia , Hidroxibenzoatos/farmacologia , Lignanas/farmacologia , Extratos Vegetais/farmacologia , Madeira/química , Antifúngicos/química , Antifúngicos/isolamento & purificação , Antioxidantes/química , Antioxidantes/isolamento & purificação , Basidiomycota/efeitos dos fármacos , Compostos de Bifenilo/antagonistas & inibidores , Relação Dose-Resposta a Droga , Fusarium/efeitos dos fármacos , Hidroxibenzoatos/química , Hidroxibenzoatos/isolamento & purificação , Lignanas/química , Lignanas/isolamento & purificação , Testes de Sensibilidade Microbiana , Penicillium/efeitos dos fármacos , Picratos/antagonistas & inibidores , Extratos Vegetais/química , Extratos Vegetais/isolamento & purificação , Polyporaceae/efeitos dos fármacos , Schizophyllum/efeitos dos fármacosRESUMO
Alpinia officinarum (AO) has been traditionally used in Asia as an herbal medicine to treat inflammatory and internal diseases. However, the therapeutic effect of AO on atopic dermatitis (AD) is unclear. Therefore, we examined whether Alpinia officinarum water extract (AOWex) affects AD in vivo and in vitro. Oral administration of AOWex to NC/Nga mice with Dermatophagoies farina extract (DfE)-induced AD-like symptoms significantly reduced the severity of clinical dermatitis, epidermal thickness, and mast cell infiltration into the skin and ear tissue. Decreased total serum IgE, macrophage-derived chemokine (MDC), and regulated on activation, normal T-cell expressed and secreted (RANTES) levels were observed in DfE-induced NC/Nga mice in the AOWex-treated group. These effects were confirmed in vitro using HaCaT cells. Treatment with AOWex inhibited the expression of proinflammatory chemokines such as MDC, RANTES, IP-10 and I-TAC in interferon-γ and tumor necrosis factor-α-stimulated HaCaT cells. The anti-inflammatory effects of AOWex were due to its inhibitory action on MAPK phosphorylation (ERK and JNK), NF-κB, and STAT1. Furthermore, galangin, protocatechuic acid, and epicatechin from AOWex were identified as candidate anti-AD compounds. These results suggest that AOWex exerts therapeutic effects against AD by alleviating AD-like skin lesions, suppressing inflammatory mediators, and inhibiting major signaling molecules.
Assuntos
Alpinia , Anti-Inflamatórios/farmacologia , Quimiocinas/metabolismo , Dermatite Atópica/prevenção & controle , Queratinócitos/efeitos dos fármacos , Extratos Vegetais/farmacologia , Pele/efeitos dos fármacos , Alpinia/química , Animais , Anti-Inflamatórios/isolamento & purificação , Antígenos de Dermatophagoides/imunologia , Proteínas de Artrópodes/imunologia , Catequina/isolamento & purificação , Catequina/farmacologia , Dermatite Atópica/imunologia , Dermatite Atópica/metabolismo , Dermatite Atópica/patologia , Dermatophagoides farinae/imunologia , Modelos Animais de Doenças , Flavonoides/isolamento & purificação , Flavonoides/farmacologia , Células HaCaT , Humanos , Hidroxibenzoatos/isolamento & purificação , Hidroxibenzoatos/farmacologia , Queratinócitos/imunologia , Queratinócitos/metabolismo , Queratinócitos/patologia , Masculino , Camundongos , Extratos Vegetais/isolamento & purificação , Transdução de Sinais , Pele/imunologia , Pele/metabolismo , Pele/patologia , Solventes/química , Água/químicaRESUMO
Staphylococcus aureus and Methicillin-resistant S. aureus (MRSA) remains one of the major concerns of healthcare associated and community-onset infections worldwide. The number of cases of treatment failure for infections associated with resistant bacteria is on the rise, due to the decreasing efficacy of current antibiotics. Notably, Acrophialophora levis, a thermophilous fungus species, showed antibacterial activity, namely against S. aureus and clinical MRSA strains. The ethyl acetate extract of culture filtrate was found to display significant activity against S. aureus and MRSA with a minimum inhibitory concentration (MIC) of 1 µg/mL and 4 µg/mL, respectively. Scanning electron micrographs demonstrated drastic changes in the cellular architecture of metabolite treated cells of S. aureus and an MRSA clinical isolate. Cell wall disruption, membrane lysis and probable leakage of cytoplasmic are hallmarks of the antibacterial effect of fungal metabolites against MRSA. The ethyl acetate extract also showed strong antioxidant activity using two different complementary free radicals scavenging methods, DPPH and ABTS with efficiency of 55% and 47% at 1 mg/mL, respectively. The total phenolic and flavonoid content was found to be 50 mg/GAE and 20 mg/CAE, respectively. More than ten metabolites from different classes were identified: phenolic acids, phenylpropanoids, sesquiterpenes, tannins, lignans and flavonoids. In conclusion, the significant antibacterial activity renders this fungal strain as a bioresource for natural compounds an interesting alternative against resistant bacteria.
Assuntos
Antibacterianos/farmacologia , Antioxidantes/farmacologia , Fatores Biológicos/farmacologia , Staphylococcus aureus Resistente à Meticilina/ultraestrutura , Sordariales/química , Acetatos/química , Antibacterianos/química , Antioxidantes/química , Fatores Biológicos/química , Flavonoides/isolamento & purificação , Hidroxibenzoatos/isolamento & purificação , Índia , Lignanas/isolamento & purificação , Staphylococcus aureus Resistente à Meticilina/efeitos dos fármacos , Testes de Sensibilidade Microbiana , Microscopia Eletrônica de Varredura , Sesquiterpenos/isolamento & purificação , Taninos/isolamento & purificaçãoRESUMO
Although Australia is the largest exporter of faba bean globally, there is limited information available on the levels of bioactive compounds found in current commercial faba bean varieties grown in this country. This study profiled the phenolic acid and flavonoid composition of 10 Australian faba bean varieties, grown at two different locations. Phenolic profiling by HPLC-DAD revealed the most abundant flavonoid to be catechin, followed by rutin. For the phenolic acids, syringic acid was found in high concentrations (72.4-122.5 mg/kg), while protocatechuic, vanillic, p-hydroxybenzoic, chlorogenic, p-coumaric, and trans-ferulic acid were all found in low concentrations. The content of most individual phenolics varied significantly with the variety, while some effect of the growing location was also observed. This information could be used by food processors and plant breeders to maximise the potential health benefits of Australian-grown faba bean.
Assuntos
Antioxidantes/química , Produtos Agrícolas/química , Flavonoides/química , Vicia faba/química , Antioxidantes/classificação , Antioxidantes/isolamento & purificação , Austrália , Catequina/química , Catequina/isolamento & purificação , Ácido Clorogênico/química , Ácido Clorogênico/isolamento & purificação , Cromatografia Líquida de Alta Pressão/métodos , Ácidos Cumáricos/química , Ácidos Cumáricos/isolamento & purificação , Produtos Agrícolas/crescimento & desenvolvimento , Produtos Agrícolas/metabolismo , Flavonoides/classificação , Flavonoides/isolamento & purificação , Ácido Gálico/análogos & derivados , Ácido Gálico/química , Ácido Gálico/isolamento & purificação , Humanos , Hidroxibenzoatos/química , Hidroxibenzoatos/isolamento & purificação , Parabenos/química , Parabenos/isolamento & purificação , Rutina/química , Rutina/isolamento & purificação , Ácido Vanílico/química , Ácido Vanílico/isolamento & purificação , Vicia faba/crescimento & desenvolvimento , Vicia faba/metabolismoRESUMO
Magnetism-assisted in-tube solid phase microextraction based on porous monolith mingled with Fe3 O4 nanoparticles was developed for capture of phenolic acids in fruit juices. First, poly (1-allyl-3-methylimidazolium bis [(trifluoro methyl) sulfonyl] imide-co-ethylene dimethacrylate) monolith embedded with Fe3 O4 nanoparticles was facile fabrication in a capillary and employed as microextraction column. Subsequently, a magnetic coil adopted to produce variable magnetic fields during extraction stage was twined on the microextraction column. The analytes contents in eluant were quantified by high performance liquid chromatogram with diode array detector. Various parameters affecting the extraction performance were inspected and optimized in detail. Results revealed that the exertion of magnetic fields in adsorption and desorption steps enhanced the extraction efficiencies of analytes from 44.9-64.0% to 78.6-87.1%. Under the optimal extraction factors, the limits of detection were between 0.012 and 0.061 µg/L, relative standard deviations for precision in terms of intra- and inter-day assay variability ranged from 1.9 to 9.8%. The introduced approach was successfully applied to simultaneously quantify the contents of five analytes in real fruit juices with satisfying fortified recoveries (80.1-116%). The obtained results well demonstrate the promising potential of the developed method in the highly sensitive quantification of trace phenolic acids in complex samples.
Assuntos
Cromatografia Líquida de Alta Pressão/métodos , Sucos de Frutas e Vegetais/análise , Hidroxibenzoatos , Microextração em Fase Sólida/métodos , Adsorção , Hidroxibenzoatos/análise , Hidroxibenzoatos/química , Hidroxibenzoatos/isolamento & purificação , Limite de Detecção , Modelos Lineares , Nanopartículas de Magnetita/química , Reprodutibilidade dos TestesRESUMO
Honey consumption is attributed to potentially advantageous effects on human health due to its antioxidant capacity as well as anti-inflammatory and antimicrobial activity, which are mainly related to phenolic compound content. Phenolic compounds are secondary metabolites of plants, and their content in honey is primarily affected by the botanical and geographical origin. In this study, a high-resolution mass spectrometry (HRMS) method was applied to determine the phenolic profile of various honey matrices and investigate authenticity markers. A fruitful sample set was collected, including honey from 10 different botanical sources (n = 51) originating from Greece and Poland. Generic liquid-liquid extraction using ethyl acetate as the extractant was used to apply targeted and non-targeted workflows simultaneously. The method was fully validated according to the Eurachem guidelines, and it demonstrated high accuracy, precision, and sensitivity resulting in the detection of 11 target analytes in the samples. Suspect screening identified 16 bioactive compounds in at least one sample, with abscisic acid isomers being the most abundant in arbutus honey. Importantly, 10 markers related to honey geographical origin were revealed through non-targeted screening and the application of advanced chemometric tools. In conclusion, authenticity markers and discrimination patterns were emerged using targeted and non-targeted workflows, indicating the impact of this study on food authenticity and metabolomic fields.
Assuntos
Antioxidantes/análise , Benzaldeídos/análise , Cinamatos/análise , Flavonoides/análise , Mel/análise , Hidroxibenzoatos/análise , Espectrometria de Massas/métodos , Metaboloma , Metabolômica/métodos , Antioxidantes/isolamento & purificação , Benzaldeídos/isolamento & purificação , Cinamatos/isolamento & purificação , Confiabilidade dos Dados , Flavonoides/isolamento & purificação , Grécia , Humanos , Hidroxibenzoatos/isolamento & purificação , Polônia , Sensibilidade e EspecificidadeRESUMO
The phenolic composition, as well as the antioxidant and antimicrobial activities of two poorly investigated Achillea species, Achillea lingulata Waldst. and the endemic Achillea abrotanoides Vis., were studied. To obtain a more detailed phytochemical profile, four solvents with different polarities were used for the preparation of the plant extracts whose phenolic composition was analyzed using UHPLC-MS/MS (ultra-high performance liquid chromatography-tandem mass spectrometry). The results indicate that both of the investigated Achillea species are very rich in both phenolic acids and flavonoids, but that their profiles differ significantly. Chloroform extracts from both species had the highest yields and were the most chemically versatile. The majority of the examined extracts showed antimicrobial activity, while ethanolic extracts from both species were potent against all tested microorganisms. Furthermore, the antioxidant activity of the extracts was evaluated. It was found that the ethanolic extracts possessed the strongest antioxidant activities, although these extracts did not contain the highest amounts of detected phenolic compounds. In addition, several representatives of phenolic compounds were also assayed for these biological activities. Results suggest that ethanol is a sufficient solvent for the isolation of biologically active compounds from both Achillea species. Moreover, it was shown that the flavonoids naringenin and morin are mainly responsible for these antimicrobial activities, while caffeic, salicylic, chlorogenic, p-coumaric, p-hydroxybenzoic, and rosmarinic acid are responsible for the antioxidant activities of the Achillea extracts.
Assuntos
Achillea/química , Anti-Infecciosos/isolamento & purificação , Antioxidantes/isolamento & purificação , Hidroxibenzoatos/isolamento & purificação , Compostos Fitoquímicos/isolamento & purificação , Achillea/classificação , Anti-Infecciosos/química , Anti-Infecciosos/farmacologia , Antioxidantes/química , Antioxidantes/farmacologia , Compostos de Bifenilo/antagonistas & inibidores , Cromatografia Líquida de Alta Pressão , Flavonoides/química , Flavonoides/isolamento & purificação , Flavonoides/farmacologia , Hidroxibenzoatos/química , Hidroxibenzoatos/farmacologia , Testes de Sensibilidade Microbiana , Fenóis/química , Fenóis/isolamento & purificação , Fenóis/farmacologia , Compostos Fitoquímicos/química , Compostos Fitoquímicos/farmacologia , Picratos/antagonistas & inibidores , Extratos Vegetais/química , Solventes , Especificidade da Espécie , Espectrometria de Massas em TandemRESUMO
Over the past 100 years, Salvia miltiorrhiza f. alba (Lamiaceae) (RSMA) roots have been used to cure thromboangiitis obliterans (TAO) in local clinics. This study aimed to confirm the anti-thrombotic efficacy of 12 phenolic acids obtained from RSMA and to clarify the possible underlying mechanisms. The results of quantitative real-time polymerase chain reaction (qRT-PCR) and enzyme-linked immunosorbent assay (ELISA) experiments demonstrated that most of the phenolic acids markedly inhibited PAI-1 protein and mRNA levels but increased t-PA protein and mRNA levels in TNF-α-induced EA.hy926 cells (P < 0.05 or 0.001), with lithospermic acid displaying the strongest effect. In vitro anticoagulation and antiplatelet aggregation assays showed that lithospermic acid and salvianolic acid B significantly prolonged prothrombin time (PT), activated partial thromboplastin time (APTT), decreased fibrinogen concentration (FIB), and inhibited platelet aggregation induced by adenosine diphosphate (ADP) in rat blood. Both lithospermic acid and salvianolic acid B markedly down-regulated the expression of factor Xa and factor IIa on the external surface of EA.hy926 cells and demonstrated significant anti-factor IIa and anti-factor Xa activity using chromogenic substrates in vitro. Western blot results revealed that both lithospermic acid and salvianolic acid B also significantly inhibited the expression of TF, p-p65, p-p38, and pJNK proteins induced by TNF-α. These results indicated that all of the phenolic acids appeared to have some anti-thrombotic activity, with salvianolic acid B and lithospermic acid markedly decreasing the chance of thrombosis by regulating the NF-κB/JNK/p38 MAPK signaling pathway in response to TNF-α.
Assuntos
Anticoagulantes/farmacologia , Hidroxibenzoatos/farmacologia , Salvia miltiorrhiza/química , Fator de Necrose Tumoral alfa/antagonistas & inibidores , Animais , Anticoagulantes/química , Anticoagulantes/isolamento & purificação , Sobrevivência Celular/efeitos dos fármacos , Células Cultivadas , Células Endoteliais/efeitos dos fármacos , Células Endoteliais/metabolismo , Humanos , Hidroxibenzoatos/química , Hidroxibenzoatos/isolamento & purificação , Proteínas Quinases JNK Ativadas por Mitógeno/antagonistas & inibidores , Proteínas Quinases JNK Ativadas por Mitógeno/genética , Proteínas Quinases JNK Ativadas por Mitógeno/metabolismo , Sistema de Sinalização das MAP Quinases/efeitos dos fármacos , NF-kappa B/antagonistas & inibidores , NF-kappa B/genética , NF-kappa B/metabolismo , Tempo de Protrombina , Ratos , Ratos Wistar , Fator de Necrose Tumoral alfa/metabolismo , Proteínas Quinases p38 Ativadas por Mitógeno/antagonistas & inibidores , Proteínas Quinases p38 Ativadas por Mitógeno/genética , Proteínas Quinases p38 Ativadas por Mitógeno/metabolismoRESUMO
The oil recovery from Alyanak apricot kernel was 36.65% in control (unroasted) and increased to 43.77% in microwave-roasted kernels. The total phenolic contents in extracts from apricot kernel were between 0.06 (oven-roasted) and 0.20 mg GAE/100 g (microwave-roasted) while the antioxidant activity varied between 2.55 (oven-roasted) and 19.34% (microwave-roasted). Gallic acid, 3,4-dihydroxybenzoic acid, (+)-catechin and 1,2-dihydroxybenzene were detected as the key phenolic constituents in apricot kernels. Gallic acid contents varied between 0.53 (control) and 1.10 mg/100 g (microwave-roasted) and 3,4-dihydroxybenzoic acid contents were between 0.10 (control) and 0.35 mg/100 g (microwave-roasted). Among apricot oil fatty acids, palmitic acid contents ranged from 4.38 (oven-roasted) to 4.76% (microwave-roasted); oleic acid contents were between 65.73% (oven-roasted) and 66.15% (control) and linoleic acid contents varied between 26.55 (control) and 27.12% (oven-roasted).
Assuntos
Antioxidantes/análise , Catequina/isolamento & purificação , Catecóis/isolamento & purificação , Ácido Gálico/isolamento & purificação , Hidroxibenzoatos/isolamento & purificação , Ácidos Linoleicos/isolamento & purificação , Micro-Ondas , Ácido Oleico/isolamento & purificação , Óleos de Plantas/análise , Óleos de Plantas/isolamento & purificação , Prunus armeniaca/química , Sementes/químicaRESUMO
This study reports the inâ vitro anticoagulation activity of acetonic extract (AE) of 42 lichen species and the identification of potential bioavailable anticoagulant compounds from Umbilicaria decussata as a competent anticoagulant lichen species. Lichens' AEs were evaluated for their anticoagulant activity by monitoring activated partial thromboplastin time (APTT) and prothrombin time (PT) assays. A strong, positive correlation was observed between total phenolics concentration (TPC) of species and blood coagulation parameters. U. decussata was the only species with the longest clotting time in both APTT and PT assays. The research was moved forward by performing inâ vivo assays using rats. The results corroborated the dose-dependent impact of U. decussata's AE on rats' clotting time. Major secondary metabolites of U. decussata and their plasma-related bioavailability were also investigated using LC-ESI-MS/MS. Atranol, orsellinic acid, D-mannitol, lecanoric acid, and evernic acid were detected as possible bioavailable anticoagulants of U. decussata. Our findings suggest that U. decussata might be a potential anticoagulant lichen species that can be used for the prevention or treatment of coagulation-related issues such as cardiovascular diseases (CVDs).
Assuntos
Anticoagulantes/farmacologia , Líquens/química , Extratos Vegetais/farmacologia , Anticoagulantes/química , Anticoagulantes/isolamento & purificação , Benzaldeídos/química , Benzaldeídos/isolamento & purificação , Benzaldeídos/farmacologia , Coagulação Sanguínea/efeitos dos fármacos , Testes de Coagulação Sanguínea , Relação Dose-Resposta a Droga , Hidroxibenzoatos/química , Hidroxibenzoatos/isolamento & purificação , Hidroxibenzoatos/farmacologia , Manitol/química , Manitol/isolamento & purificação , Manitol/farmacologia , Extratos Vegetais/química , Extratos Vegetais/isolamento & purificação , Resorcinóis/química , Resorcinóis/isolamento & purificação , Resorcinóis/farmacologia , Salicilatos/química , Salicilatos/isolamento & purificação , Salicilatos/farmacologiaRESUMO
Nine new ß-resorcylic acid derivatives, (15S)-de-O-methyllasiodiplodin (1), (13S,15S)-13-hydroxy-de-O-methyllasiodiplodin (2), (14S,15S)-14-hydroxy-de-O-methyllasiodiplodin (3), (13R,14S,15S)-13,14-dihydroxy-de-O-methyllasiodiplodin (4), ethyl (S)-2,4-dihydroxy-6-(8-hydroxynonyl)benzoate (5), ethyl 2,4-dihydroxy-6-(8-hydroxyheptyl)benzoate (6), ethyl 2,4-dihydroxy-6-(4-methoxycarbonylbutyl)benzoate (7), 3-(2-ethoxycarbonyl-3,5-dihydroxyphenyl)propionic acid (8), and isobutyl (S)-2,4-dihydroxy-6-(8-hydroxynonyl)benzoate (9), together with a known ethyl 2,4-dihydroxy-6-(8-oxononyl)benzoate (10) were obtained from Lasiodiplodia theobromae GC-22. The structures of these compounds were elucidated by extensive spectroscopic analyses. Compounds 1, 3, and 6 showed growth inhibitory effects against Digitaria ciliaris. Conversely, treatment with compounds 5, 6, 7, 9, and 10 stimulated elongation activity toward the root of Lactuca sativa. These data expand the repertoire of new ß-resorcylic acid derivatives that may function as lead compounds in the synthesis of new agrochemical agents.
Assuntos
Agroquímicos/farmacologia , Ascomicetos/química , Digitaria/efeitos dos fármacos , Hidroxibenzoatos/farmacologia , Lactuca/efeitos dos fármacos , Agroquímicos/química , Agroquímicos/isolamento & purificação , Digitaria/crescimento & desenvolvimento , Hidroxibenzoatos/química , Hidroxibenzoatos/isolamento & purificação , Lactuca/crescimento & desenvolvimento , Estrutura Molecular , Raízes de Plantas/efeitos dos fármacos , Raízes de Plantas/crescimento & desenvolvimento , EstereoisomerismoRESUMO
Twelve hitherto unknown tandem prenylated p-hydroxybenzoic acid derivatives, namely, oberoniamyosurusins A-L, together with five known derivatives, were isolated from an EtOH extract of the whole parts of the plant Oberonia myosurus. Compounds 10, 13, and 17 exhibited moderate inhibitory activity against Staphylococcus aureus subsp. aureus ATCC29213 with MIC50 values ranging from 7.6 to 23 µg/mL. To determine the biosynthetic pathway of this class of tandem prenyl-substituted compounds, the full-length transcriptome of O. myosurus was sequenced, yielding 19.09 Gb of clean data and 10â¯949 nonredundant sequences. Two isoforms of p-hydroxybenzoic acid prenyltransferases were annotated and functionally characterized as the enzymes that might be involved in the biosynthesis of nervogenic acid (13) in Pichia pastoris.