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1.
Chem Biodivers ; 21(6): e202400379, 2024 Jun.
Artigo em Inglês | MEDLINE | ID: mdl-38743034

RESUMO

Robusta coffee blossom honey stands as a key regional product in Dak Lak province, Vietnam. Despite its significance, there exists a dearth of scientific data for assessing its quality. This study aims to fill this gap by characterizing the physicochemical properties and biological activities of coffee blossom honeys from three distinct sub-regions within Dak Lak province, Vietnam. These activities include ferric reducing power (FRP), DPPH and ABTS radical scavenging, as well as tyrosinase inhibitory activities. Moreover, the study compares these honey samples with other popular varieties in Vietnam, such as Lychee and Longan honeys. The physicochemical parameters of the honey samples meet the standards set by Codex Alimentarius 2001. Through UPLC analysis, eleven compounds were identified, with caffeine serving as a marker for coffee honey. Furthermore, by employing multiple factor analysis (MFA), it was observed that certain physicochemical properties correlate positively with tyrosinase inhibitory, DPPH, ABTS free radicals scavenging activities, and FRP. Notably, tyrosinase inhibitory activity exhibited a positive correlation with antioxidant activity. These findings underscore the high quality of Coffea robusta honey, showcasing its potent antioxidant and tyrosinase inhibitory activities.


Assuntos
Antioxidantes , Inibidores Enzimáticos , Mel , Monofenol Mono-Oxigenase , Antioxidantes/farmacologia , Antioxidantes/química , Antioxidantes/isolamento & purificação , Benzotiazóis/antagonistas & inibidores , Benzotiazóis/química , Compostos de Bifenilo/antagonistas & inibidores , Café/química , Inibidores Enzimáticos/farmacologia , Inibidores Enzimáticos/química , Inibidores Enzimáticos/isolamento & purificação , Flores/química , Mel/análise , Monofenol Mono-Oxigenase/antagonistas & inibidores , Monofenol Mono-Oxigenase/metabolismo , Picratos/antagonistas & inibidores , Ácidos Sulfônicos/antagonistas & inibidores , Vietnã
2.
Bioorg Chem ; 119: 105551, 2022 02.
Artigo em Inglês | MEDLINE | ID: mdl-34915284

RESUMO

Oxidative stress is linked to several invasive diseases which causes significant clinical and economic impact, therefore, there is a need to develop new antioxidants. The natural products could play an important role in overcoming the current need. In the present work, the antioxidant bioassay-guided fractionation of the ethanolic extract of Inula viscosa leaves (Asteraceae) was performed using DPPH and ABTS assays affording three known compounds, which were successfully characterized as ilicic acid (1), taxifolin (2) and quercetin (3) based on 1D, 2D NMR. Compounds 2 and 3 were identified as the most active, displaying similar or higher potency against ABTS (value 41.27 for quercetin and 142.58 for taxifolin) and similar activity against DPPH (value 41.27 for quercetin and 142.58 for taxifolin) than the well-known reference, ascorbic acid (value 65.36 for quercetin and 58.43 for taxifolin) but less potency than the standard gallic acid. The discussion of SAR of the antioxidant potential revealed that the type of natural product is crucial for the activity and the substitution pattern on the flavonoid skeleton modulate the antioxidant profile. Our findings show that I. viscosa leaves may be a natural source of antioxidants and once again the role of flavonoids health benefits is more strongly endorsed.


Assuntos
Antioxidantes/farmacologia , Inula/química , Extratos Vegetais/farmacologia , Antioxidantes/química , Antioxidantes/isolamento & purificação , Benzotiazóis/antagonistas & inibidores , Relação Dose-Resposta a Droga , Estrutura Molecular , Estresse Oxidativo/efeitos dos fármacos , Extratos Vegetais/química , Extratos Vegetais/isolamento & purificação , Folhas de Planta/química , Relação Estrutura-Atividade , Ácidos Sulfônicos/antagonistas & inibidores
3.
Protein Expr Purif ; 177: 105745, 2021 01.
Artigo em Inglês | MEDLINE | ID: mdl-32896621

RESUMO

Lysozymes, which are secreted in many organisms, including invertebrates, mammals, plants, bacteria and fungus, exhibit antimicrobial, antiviral, antioxidant, and anti-inflammatory activities. Splys-i is an invertebrate-type (i-type) lysozyme isolated from Scylla paramamosain in 2017 and is involved in immune defense against bacteria. However, the antibacterial, antioxidant, and anti-inflammatory activities of Splys-i remain to be elucidated. In the current study, the expression parameters (including IPTG concentration, induction temperature, and induction duration) of Splys-i in Escherichia coli were optimized to achieve high-level yield through shake-flask cultivation with approximately 120 mg of Splys-i obtained from 1 L of LB medium. The purified Splys-i displayed low cytotoxicity to RAW264.7 macrophage cells and low hemolytic activity against erythrocytes of mouse, rat, and rabbit, respectively, and exhibited potent antibacterial activity against both Gram-positive and -negative bacteria with minimum concentrations ranging from 15 to 90 µg/mL. The antibacterial property of Splys-i was also unaffected when treated with various temperature, pHs, and salinity, respectively, and Splys-i showed resistance to proteinase digestion. Radical-scavenging rate assay (including ABTS+, DPPH, hydroyl free radical, and superoxide anion) indicated that Splys-i was an efficient antioxidant. Splys-i also exerted anti-inflammatory effect through the inhibition of IκBα and NF-κB(P65) phosphorylation, thereby reducing the secretion of pro-inflammatory cytokines. All these results suggested that Splys-i can be prepared from E. coli with potent biological property.


Assuntos
Antibacterianos/metabolismo , Anti-Inflamatórios/metabolismo , Antioxidantes/metabolismo , Proteínas de Artrópodes/genética , Braquiúros/química , Muramidase/genética , Sequência de Aminoácidos , Animais , Antibacterianos/farmacologia , Anti-Inflamatórios/farmacologia , Antioxidantes/farmacologia , Proteínas de Artrópodes/metabolismo , Proteínas de Artrópodes/farmacologia , Benzotiazóis/antagonistas & inibidores , Benzotiazóis/química , Compostos de Bifenilo/antagonistas & inibidores , Compostos de Bifenilo/química , Clonagem Molecular , Eritrócitos/efeitos dos fármacos , Escherichia coli/genética , Escherichia coli/metabolismo , Expressão Gênica , Vetores Genéticos/química , Vetores Genéticos/metabolismo , Concentração de Íons de Hidrogênio , Camundongos , Muramidase/metabolismo , Muramidase/farmacologia , Inibidor de NF-kappaB alfa/antagonistas & inibidores , Inibidor de NF-kappaB alfa/genética , Inibidor de NF-kappaB alfa/metabolismo , Picratos/antagonistas & inibidores , Picratos/química , Células RAW 264.7 , Coelhos , Ratos , Proteínas Recombinantes/genética , Proteínas Recombinantes/metabolismo , Proteínas Recombinantes/farmacologia , Ácidos Sulfônicos/antagonistas & inibidores , Ácidos Sulfônicos/química , Temperatura , Fator de Transcrição RelA/antagonistas & inibidores , Fator de Transcrição RelA/genética , Fator de Transcrição RelA/metabolismo
4.
Bioorg Med Chem Lett ; 41: 128000, 2021 06 01.
Artigo em Inglês | MEDLINE | ID: mdl-33798702

RESUMO

(S, S)-1-hydroxy-1-oxo-2-c,5-t-diphenylphospholane or Fiaud's acid is used as a novel and effective chiral organocatalyst for bis α-aminophosphonates synthesis with excellent diastereoselectivity and yields within short reaction time. All synthesized bis α-aminophosphonates revealed a good to excellent antifungal capacity, where the six compounds 4a, 4b, 4e, 4h, 4k and 4l are the best fungicide inhibiting the growth of Fusarium oxysporumandBotrytis cinereaby 65% to 84% with IC50 values <0.02 mg/mL. Similarly, these six products exhibited a strong antioxidant effect, whereas a low inhibition activity was obtained with both AChE and BChE. Furthermore, they displayed a very weak inhibitory activity against tyrosinase except for the compound4l.These findings suggest a possible use of these compounds as synthetic pesticides with less hazardous effects with antioxidant, and anti-tyrosinase properties.


Assuntos
Antifúngicos/farmacologia , Antioxidantes/farmacologia , Inibidores da Colinesterase/farmacologia , Acetilcolinesterase/metabolismo , Animais , Antifúngicos/síntese química , Antifúngicos/química , Antioxidantes/síntese química , Antioxidantes/química , Benzotiazóis/antagonistas & inibidores , Compostos de Bifenilo/antagonistas & inibidores , Botrytis/efeitos dos fármacos , Butirilcolinesterase/metabolismo , Inibidores da Colinesterase/síntese química , Inibidores da Colinesterase/química , Relação Dose-Resposta a Droga , Electrophorus , Fusarium/efeitos dos fármacos , Cavalos , Testes de Sensibilidade Microbiana , Estrutura Molecular , Picratos/antagonistas & inibidores , Relação Estrutura-Atividade , Ácidos Sulfônicos/antagonistas & inibidores
5.
Bioorg Med Chem ; 44: 116306, 2021 08 15.
Artigo em Inglês | MEDLINE | ID: mdl-34274550

RESUMO

A novel series of 2-styryl-5-hydroxy-4-pyrone derivatives and analogues were designed and synthesized as H3 receptor antagonism based multitarget-directed ligands (MTDLs) for AD therapy using pharmacophore-combine strategy. The 2-styryl-5-hydroxy-4-pyrone pharmacophore with metal ion chelation, antioxidation, and Aß aggregation inhibition activities was employed as the "eastern part", and a typical phenoxyalkylamine moiety was used as "central ring + western part" of the H3 receptor antagonist. The biological evaluation revealed that the majority of the target compounds demonstrated desirable multiple functions. The two most promising compounds 8a and 8b exhibited nanomolar IC50 values on H3 receptor antagonism, excellent metal ion chelating capability, more potent ABTS+ scavenging activity than Trolox, efficient Aß self-aggregation and Cu2+-induced aggregation inhibitory activities, as well as disaggregation activities against Aß self/Cu2+-induced aggregation.


Assuntos
Doença de Alzheimer/tratamento farmacológico , Antioxidantes/farmacologia , Desenho de Fármacos , Pironas/farmacologia , Receptores Histamínicos H3/metabolismo , Doença de Alzheimer/metabolismo , Peptídeos beta-Amiloides/antagonistas & inibidores , Peptídeos beta-Amiloides/metabolismo , Antioxidantes/síntese química , Antioxidantes/química , Benzotiazóis/antagonistas & inibidores , Cobre/farmacologia , Relação Dose-Resposta a Droga , Humanos , Estrutura Molecular , Agregados Proteicos/efeitos dos fármacos , Pironas/síntese química , Pironas/química , Relação Estrutura-Atividade , Ácidos Sulfônicos/antagonistas & inibidores
6.
J Pept Sci ; 27(4): e3295, 2021 Apr.
Artigo em Inglês | MEDLINE | ID: mdl-33410242

RESUMO

The red tree frog Litoria rubella from Australia has been studied for several decades showing that their dorsal skin glands secrete a number of small peptides containing a Pro-Trp sequence, known as tryptophyllin L peptides. Although peptides from many genera of Australian frogs have been reported to possess a variety of biological activities, the bioactivities of this peptide family have remained to be discovered. In this study, we investigated the antioxidant potency of a number of tryptophyllin L peptides for the first time using a joint statistical and experimental approach in which predictions based on Gaussian three-dimensional quantitative structure-activity relationship (3D-QSAR) models were employed to guide an in vitro experimental investigation. Two tryptophyllin tripeptides P-W-L (OH) and P-W-L (NH2 ) were predicted to have the Trolox equivalent antioxidant capacity (TEAC) values of 0.80 and 0.87 µM Trolox/µM peptide, respectively. With those promising results, antioxidant capabilities of five tryptophyllin L peptides with the common core Pro-Trp-Leu were synthesized and subjected to 1,1-diphenyl-2-picrylhydrazyl (DPPH), ferric reducing ability of plasma (FRAP) and 2,2'-azino-bis(3-ethylbenzothiazoline-6-sulphonic acid) radical cation (ABTS˙+ ) radical scavenging assays. The tests indicated that all the tested tryptophyllin L peptides, noticeably S-P-W-L (OH) and F-P-W-L (NH2 ), are strong ABTS˙+ radical scavengers and moderate scavengers in the other two assays. The results, thus, suggested that the tryptophyllin L peptides are likely to be a part of the skin antioxidant system helping the frog to cope with drastic change in oxygen exposure and humidity, as they inhabit over a large area of Australia with a wide climate variation.


Assuntos
Antioxidantes/farmacologia , Oligopeptídeos/farmacologia , Relação Quantitativa Estrutura-Atividade , Animais , Antioxidantes/síntese química , Antioxidantes/química , Anuros , Benzotiazóis/antagonistas & inibidores , Compostos de Bifenilo/antagonistas & inibidores , Modelos Moleculares , Oligopeptídeos/síntese química , Oligopeptídeos/química , Picratos/antagonistas & inibidores , Ácidos Sulfônicos/antagonistas & inibidores
7.
J Fluoresc ; 31(6): 1705-1717, 2021 Nov.
Artigo em Inglês | MEDLINE | ID: mdl-34424483

RESUMO

Nanostructured fluorescent particles derived from natural molecules were prepared by a green synthesis technique employing a microwave method. The precursors citric acid (CA) and cysteine (Cys) were used in the preparation of S- and N-doped Cys carbon dots (Cys CDs). Synthesis was completed in 3 min. The graphitic structure revealed by XRD analysis of Cys CDs dots had good water dispersity, with diameters in the range of 2-20 nm determined by TEM analysis. The isoelectric point of the S, N-doped CDs was pH value for 5.2. The prepared Cys CDs displayed excellent fluorescence intensity with a high quantum yield of 75.6 ± 2.1%. Strong antimicrobial capability of Cys CDs was observed with 12.5 mg/mL minimum bactericidal concentration (MBC) against gram-positive and gram-negative bacteria with the highest antimicrobial activity obtained against Staphylococcus aureus. Furthermore, Cys CDs provided total biofilm eradication and inhibition abilities against Pseudomonas aeruginosa at 25 mg/mL concentration. Cys CDs are promising antioxidant materials with 1.3 ± 0.1 µmol Trolox equivalent/g antioxidant capacity. Finally, Cys CDs were also shown to inhibit the acetylcholinesterase (AChE) enzyme, which is used in the treatment of Alzheimer's disease, even at the low concentration of 100 µg/mL.


Assuntos
Antibacterianos/farmacologia , Antioxidantes/farmacologia , Inibidores da Colinesterase/farmacologia , Ácido Cítrico/farmacologia , Cisteína/farmacologia , Corantes Fluorescentes/farmacologia , Acetilcolinesterase/metabolismo , Antibacterianos/síntese química , Antibacterianos/química , Antioxidantes/síntese química , Antioxidantes/química , Benzotiazóis/antagonistas & inibidores , Biofilmes/efeitos dos fármacos , Carbono/química , Carbono/farmacologia , Inibidores da Colinesterase/síntese química , Inibidores da Colinesterase/química , Ácido Cítrico/química , Cisteína/química , Corantes Fluorescentes/síntese química , Corantes Fluorescentes/química , Humanos , Pseudomonas aeruginosa/efeitos dos fármacos , Pontos Quânticos/química , Staphylococcus aureus/efeitos dos fármacos , Ácidos Sulfônicos/antagonistas & inibidores
8.
Bioorg Chem ; 112: 104974, 2021 07.
Artigo em Inglês | MEDLINE | ID: mdl-34029971

RESUMO

We synthesized eleven new amiridine-piperazine hybrids 5a-j and 7 as potential multifunctional agents for Alzheimer's disease (AD) treatment by reacting N-chloroacetylamiridine with piperazines. The compounds displayed mixed-type reversible inhibition of acetylcholinesterase (AChE) and butyrylcholinesterase (BChE). Conjugates were moderate inhibitors of equine and human BChE with negligible fluctuation in anti-BChE activity, whereas anti-AChE activity was substantially dependent on N4-substitution of the piperazine ring. Compounds with para-substituted aromatic moieties (5g, 5h, and bis-amiridine 7) had the highest anti-AChE activity in the low micromolar range. Top-ranked compound 5h, N-(2,3,5,6,7,8-hexahydro-1H-cyclopenta[b]quinolin-9-yl)-2-[4-(4-nitro-phenyl)-piperazin-1-yl]-acetamide, had an IC50 for AChE = 1.83 ± 0.03 µM (Ki = 1.50 ± 0.12 and αKi = 2.58 ± 0.23 µM). The conjugates possessed low activity against carboxylesterase, indicating a likely absence of unwanted drug-drug interactions in clinical use. In agreement with analysis of inhibition kinetics and molecular modeling studies, the lead compounds were found to bind effectively to the peripheral anionic site of AChE and displace propidium, indicating their potential to block AChE-induced ß-amyloid aggregation. Similar propidium displacement activity was first shown for amiridine. Two compounds, 5c (R = cyclohexyl) and 5e (R = 2-MeO-Ph), exhibited appreciable antioxidant capability with Trolox equivalent antioxidant capacity values of 0.47 ± 0.03 and 0.39 ± 0.02, respectively. Molecular docking and molecular dynamics simulations provided insights into the structure-activity relationships for AChE and BChE inhibition, including the observation that inhibitory potencies and computed pKa values of hybrids were generally lower than those of the parent molecules. Predicted ADMET and physicochemical properties of conjugates indicated good CNS bioavailability and safety parameters comparable to those of amiridine and therefore acceptable for potential lead compounds at the early stages of anti-AD drug development.


Assuntos
Doença de Alzheimer/tratamento farmacológico , Aminoquinolinas/farmacologia , Antioxidantes/farmacologia , Inibidores da Colinesterase/farmacologia , Fármacos Neuroprotetores/farmacologia , Piperazina/farmacologia , Acetilcolinesterase/metabolismo , Doença de Alzheimer/metabolismo , Aminoquinolinas/química , Animais , Antioxidantes/síntese química , Antioxidantes/química , Benzotiazóis/antagonistas & inibidores , Butirilcolinesterase/metabolismo , Inibidores da Colinesterase/síntese química , Inibidores da Colinesterase/química , Relação Dose-Resposta a Droga , Cavalos , Humanos , Modelos Moleculares , Estrutura Molecular , Fármacos Neuroprotetores/síntese química , Fármacos Neuroprotetores/química , Estresse Oxidativo/efeitos dos fármacos , Piperazina/química , Relação Estrutura-Atividade , Ácidos Sulfônicos/antagonistas & inibidores
9.
Biotechnol Appl Biochem ; 68(3): 585-596, 2021 Jun.
Artigo em Inglês | MEDLINE | ID: mdl-32497351

RESUMO

Biosurfactants are microbial surface-active compounds with antimicrobial and antioxidant activities that display a range of physiological functions. In this study, a strain isolated from a Cameroonian fermented milk "pendidam" and identified as Lactobacillus casei subsp. casei TM1B was used for biosurfactants production. The biosurfactants produced by L. casei TM1B with molasses as the substrate had a good surface (40.77 mN/m) and emulsifying (84.50%) activities. The scavenging of the ABTS+• radical (IC50 value of 0.60 ± 0.03 mg/mL) by the biosurfactants was found to be higher than that of DPPH• radical (IC50 value of 0.97 ± 0.13 mg/mL). The maximum chelating activity of biosurfactants (82.29%) was observed at 3.5 mg/mL. The biologically active compound of the biosurfactants produced by L. casei TM1B was identified as 2,5-O-methylrhamnofuranosyl-palmitate, a novel rhamnolipid-like biosurfactant by using chemical, Fourier transform infrared spectroscopy, gas chromatography-mass spectrometry, and NMR analysis. The biosurfactants were bactericidal against several Gram-negative and Gram-positive pathogens (minimum inhibitory concentration values ranged from 3.22 to 12.83 mg/mL), and scanning electron microscope analysis revealed bacterial cell walls and membranes as main targets.


Assuntos
Antibacterianos/farmacologia , Antioxidantes/farmacologia , Bactérias Gram-Negativas/efeitos dos fármacos , Bactérias Gram-Positivas/efeitos dos fármacos , Lacticaseibacillus casei/química , Tensoativos/farmacologia , Antibacterianos/química , Antibacterianos/metabolismo , Antioxidantes/química , Antioxidantes/metabolismo , Benzotiazóis/antagonistas & inibidores , Compostos de Bifenilo/antagonistas & inibidores , Lacticaseibacillus casei/enzimologia , Lacticaseibacillus casei/isolamento & purificação , Testes de Sensibilidade Microbiana , Melaço , Picratos/antagonistas & inibidores , Ácidos Sulfônicos/antagonistas & inibidores , Tensoativos/química , Tensoativos/metabolismo
10.
J Sep Sci ; 44(23): 4237-4254, 2021 Dec.
Artigo em Inglês | MEDLINE | ID: mdl-34633763

RESUMO

The Himalayan wild berries Myrica esculenta, Duchesnea indica, Prunus cerasoides, and Berberis lycium were studied for the first time for polyphenolic compositions using high-performance liquid chromatography/electrospray ionization tandem mass spectrometry. The chemical analysis of extracts resulted in the identification of 69 polyphenols, including 11 anthocyanins, 28 phenolic acids, 19 flavanoids, 10 ellagitannins, and 1 dihydrochalcone. The caffeoylquinic acids, quercetin, kaempferol, and cyanidin are the common moieties in studied wild berries. In addition, seven phenolic compounds, that is, gallic acid, vanillic acid, caffeic acid, rutin, ferulic acid, quercetin, and myricetin were quantified. Among anthocyanins, cyanidin-3-O-glucoside was the majorly quantified anthocyanin that ranged from 2.52 to 6.18% followed by delphinidin-3-O-glucoside (0.6%-5.53%). The samples were assessed for total phenolics, total anthocyanin content, and antioxidant potential. The results showed that M. esculenta and B. lycium had the highest total phenolic and anthocyanin content and exhibited promising antioxidant activity with IC50 of 32.100 ± 0.42 and 48.44 ± 0.46 µg/mL, respectively. Principal component analysis was able to clearly differentiate between four underutilized Himalayan wild edible berries. The wide variability of polyphenolic constituents supports the consumption of these berries not only to achieve the nutrient requirements among local people but also as promising sources of antioxidants for the food industry.


Assuntos
Antioxidantes/farmacologia , Frutas/química , Polifenóis/farmacologia , Antioxidantes/química , Antioxidantes/isolamento & purificação , Benzotiazóis/antagonistas & inibidores , Compostos de Bifenilo/antagonistas & inibidores , Cromatografia Líquida de Alta Pressão , Recuperação de Fluorescência Após Fotodegradação , Picratos/antagonistas & inibidores , Polifenóis/química , Polifenóis/isolamento & purificação , Espectrometria de Massas por Ionização por Electrospray , Ácidos Sulfônicos/antagonistas & inibidores
11.
J Sep Sci ; 44(7): 1404-1420, 2021 Apr.
Artigo em Inglês | MEDLINE | ID: mdl-33464708

RESUMO

Ribes meyeri leaves are used as traditional Kazakh medicine in China. However, no study on the characterization of the phenolic compounds in R. meyeri leaves has been reported, resulting in the lack of quality control measures and poor standardization. This study was conducted to identify the phenolic compounds in R. meyeri leaves and evaluate their antioxidant and antidiabetic activities. A total of 77 phenolics were tentatively identified by liquid chromatography coupled with quadrupole time-of-flight tandem mass spectrometry. Ultra-high performance liquid chromatography coupled with triple quadrupole mass spectrometry was applied to simultaneously quantify 12 phenolics in R. meyeri leaves. Rutin, epigallocatechin, isoquercitrin, epicatechin, protocatechuic acid, and kaempferol-3-O-rutinoside were abundant in the R. meyeri leaves. The methanol extract and four different extracts enhanced the glucose uptake in 3T3-L1 adipocytes. The ethyl acetate extracts showed a total phenolic content of 966.89 ± 3.59 mg gallic acid equivalents/g, a total flavonoid content of 263.58 ± 17.09 mg catechin equivalents/g, and good protein-tyrosine phosphatase-1B inhibitory activities (IC50 : 0.60 ± 0.03 µg/mL). To our knowledge, this work is the first to identify and quantify the major phenolics in R. meyeri leaves.


Assuntos
Antioxidantes/farmacologia , Inibidores Enzimáticos/farmacologia , Fenóis/farmacologia , Ribes/química , Células 3T3-L1 , Animais , Antioxidantes/análise , Benzotiazóis/antagonistas & inibidores , Compostos de Bifenilo/antagonistas & inibidores , Cromatografia Líquida de Alta Pressão , Inibidores Enzimáticos/análise , Glicosídeo Hidrolases/antagonistas & inibidores , Glicosídeo Hidrolases/metabolismo , Humanos , Camundongos , Fenóis/análise , Picratos/antagonistas & inibidores , Proteína Tirosina Fosfatase não Receptora Tipo 1/antagonistas & inibidores , Proteína Tirosina Fosfatase não Receptora Tipo 1/metabolismo , Ácidos Sulfônicos/antagonistas & inibidores , Espectrometria de Massas em Tandem
12.
J Sep Sci ; 44(20): 3777-3788, 2021 Oct.
Artigo em Inglês | MEDLINE | ID: mdl-34418299

RESUMO

A combinative method using high-performance liquid chromatography-electrochemical detection for fingerprinting and quantitative analysis was developed and successfully applied for the quality evaluation of Lophatherum gracile Brongn leaves collected from 21 geographical locations in China. In the fingerprint analysis, 18 common peaks were observed among the 21 samples, and 10 peaks were identified. Simultaneous quantification of the 10 components was conducted to interpret the variations in these compounds among the L. gracile Brongn leaves originating from different geographical locations. The correlation between the chromatograms and the antioxidant activities of the samples was further studied. The results indicated a linear correlation between the antioxidant activity and the total common peak areas of the fingerprints obtained by high-performance liquid chromatography-electrochemical detection. Importantly, it was found that high-performance liquid chromatography-electrochemical detection fingerprinting can not only determine the quantities of individual components present in such samples but also evaluate the antioxidant activities of the samples. The developed method is a valuable reference for the further study and development of L. gracile Brongn.


Assuntos
Antioxidantes/farmacologia , Medicamentos de Ervas Chinesas/farmacologia , Técnicas Eletroquímicas , Compostos Fitoquímicos/farmacologia , Extratos Vegetais/farmacologia , Poaceae/química , Antioxidantes/análise , Benzotiazóis/antagonistas & inibidores , Compostos de Bifenilo/antagonistas & inibidores , Cromatografia Líquida de Alta Pressão , Medicamentos de Ervas Chinesas/análise , Compostos Fitoquímicos/análise , Picratos/antagonistas & inibidores , Extratos Vegetais/análise , Ácidos Sulfônicos/antagonistas & inibidores
13.
J Enzyme Inhib Med Chem ; 36(1): 618-626, 2021 Dec.
Artigo em Inglês | MEDLINE | ID: mdl-33557639

RESUMO

Feijoa sellowiana leaves and fruits have been investigated as a source of diverse bioactive metabolites. Extract and eight metabolites isolated from F. sellowiana leaves were evaluated for their enzymatic inhibitory activity against α-glucosidase, amylase, tyrosinase, acetylcholinestrerase and butyrylcholinesterase both in vitro and in silico. Feijoa leaves' extract showed strong antioxidant activity and variable levels of inhibitions against target enzymes with a strong anti-tyrosinase activity (115.85 mg Kojic acid equivalent/g). Additionally, α-tocopherol emerged as a potent inhibitor of AChE and BChE (5.40 & 10.38 mmol galantamine equivalent/g, respectively). Which was further investigated through molecular docking and found to develop key enzymatic interactions in AChE and BChE active sites. Also, primetin showed good anti BChE (11.70 mmol galantamine equivalent/g) and anti-tyrosinase inhibition (90.06 mmol Kojic acid equivalent/g) which was also investigated by molecular docking studies. Highlights Isolation of eight bioactive constituents from Feijoa sellowiana leaves. In vitro assays using different enzymatic drug targets were investigated. In silico study was performed to define compound interactions with target proteins. Feijoa leaf is an excellent source of anti-AChE and antityrosinase bioactives.


Assuntos
Antioxidantes/farmacologia , Inibidores Enzimáticos/farmacologia , Feijoa/química , Simulação de Acoplamento Molecular , Monofenol Mono-Oxigenase/antagonistas & inibidores , Extratos Vegetais/farmacologia , Acetilcolinesterase/metabolismo , Animais , Antioxidantes/química , Antioxidantes/isolamento & purificação , Benzotiazóis/antagonistas & inibidores , Compostos de Bifenilo/antagonistas & inibidores , Butirilcolinesterase/metabolismo , Relação Dose-Resposta a Droga , Electrophorus , Inibidores Enzimáticos/química , Inibidores Enzimáticos/isolamento & purificação , Cavalos , Estrutura Molecular , Monofenol Mono-Oxigenase/metabolismo , Picratos/antagonistas & inibidores , Extratos Vegetais/química , Extratos Vegetais/isolamento & purificação , Folhas de Planta/química , Saccharomyces cerevisiae/enzimologia , Relação Estrutura-Atividade , Ácidos Sulfônicos/antagonistas & inibidores , Suínos , alfa-Amilases/antagonistas & inibidores , alfa-Amilases/metabolismo , alfa-Glucosidases/metabolismo
14.
Chem Biodivers ; 18(10): e2100300, 2021 Oct.
Artigo em Inglês | MEDLINE | ID: mdl-34375021

RESUMO

Trillium govanianum rhizomes are traditionally consumed as a raw powder and decoction for the treatment of health complications. Hence, the present study aimed to investigate whether aqueous and alcoholic extracts of T. govanianum rhizomes under hot and cold extraction conditions have similar or dissimilar chemical, nutrient, and antioxidant profiles. The total phenolics, flavonoids, carbohydrates, proteins, fats, and energy values were estimated in all the conditionally prepared samples. The total phenolics (21.23±1.4 mg GAE/g extract), flavonoids (70.57±3.24 mg RE/g extract) were found higher in hot ethanolic extract (TGHEt), while cold water extract (TGGC) showed higher nutrients including amino acids (10.545±0.219 mg/g) and nucleosides (1.803±0.018 mg/g). The nutrient energy value (2.60 and 2.49 Kcal/g extract) was higher in cold and hot ethanolic extracts. Further, TGHEt scavenged the DPPH. (IC50 ; 870±22 µg/mL) and ABTS.+ (IC50 ; 80±1.49 µg/mL) effectively and proved its highest antioxidant activity compared to other samples. In LC/MS/MS-based metabolite profiling, twenty-six metabolites (fatty acids, steroidal saponins, triterpene saponins, ecdysteroid hormones) were confirmed with mass fragmentation and literature, while one hundred nine metabolites were identified using the METLIN database. The principal component analysis showed clustering of hot condition extracts while cold extracts were differentially located in quadrants. The heatmaps exhibited the associations and differences between metabolite composition, solvents, and extraction conditions. The identified metabolites speculatively predicted the biosynthesis pathway of T. govanianum. Findings also illustrated that T. govanianum is a source of bioactive nutritional components and saponins. The current metabolite profiling of T. govanianum will help in its agricultural and biotechnological interventions for higher quality produce.


Assuntos
Antioxidantes/farmacologia , Extratos Vegetais/farmacologia , Trillium/química , Antioxidantes/química , Antioxidantes/metabolismo , Benzotiazóis/antagonistas & inibidores , Compostos de Bifenilo/antagonistas & inibidores , Picratos/antagonistas & inibidores , Extratos Vegetais/química , Extratos Vegetais/metabolismo , Ácidos Sulfônicos/antagonistas & inibidores
15.
Chem Biodivers ; 18(6): e2000947, 2021 Jun.
Artigo em Inglês | MEDLINE | ID: mdl-33848051

RESUMO

The ultrasound-assisted extraction (UAE) parameters of total water-soluble polysaccharides (TABPs) from Acanthopanaxbrachypus fruit were optimized by Box-Behnken design (BBD) and response surface methodology (RSM). Physicochemical, structural, and functional properties of TABPs were investigated by chemical analysis, inductively coupled plasma optical emission spectrometry (ICP-OES), high performance liquid chromatography (HPLC), scanning electron microscopy (SEM), Fourier transform infrared spectroscopy (FT-IR), thermogravimetric analysis (TGA), water-holding capacity (WHC), oil-holding capacity (OHC), emulsion capacity (EC), emulsion stability (ES), as well as DPPH. and ABTS.+ scavenging assays. The results showed that the maximal UAE-yield of TABPs was 3.81±0.18 % under the optimal conditions (ultrasonic power 325 W, extraction temperature 47 °C, extraction time 22 min). TABPs was rich in some beneficial element (Mg, K, Fe, Zn and Na) but little in harmful elements (Hg, Cd, As and Pb), and displayed rough surface with flake-like features and large dents, contained 93.89±0.08 % of total carbohydrate with more different monosaccharides including glucose, galactose, rhamnose, arabinose, mannose, xylose, and uronic acid in a molar ratio of 8.83 : 7.90 : 4.74 : 4.55 : 2.80 : 2.39 : 1.00, respectively. TABPs exhibited broad weight distribution (11.2-133.5 kDa), excellent thermal stability (>280 °C), WHC (0.61±0.08 g water/g sample) and OHC (4.53±0.12 g oil/g sample), as well as higher EC (43.75±1.23 %) and ES (38.32±1.50 %). Furthermore, TABPs also displayed remarkable scavenging activities on DPPH. and ABTS.+ in vitro. These findings provide a scientific basis for the applications of TABPs in functional additives for food, medicine, and cosmetics.


Assuntos
Antioxidantes/isolamento & purificação , Eleutherococcus/química , Frutas/química , Polissacarídeos/isolamento & purificação , Ondas Ultrassônicas , Antioxidantes/química , Antioxidantes/farmacologia , Benzotiazóis/antagonistas & inibidores , Compostos de Bifenilo/antagonistas & inibidores , Fenômenos Químicos , Tamanho da Partícula , Picratos/antagonistas & inibidores , Polissacarídeos/química , Polissacarídeos/farmacologia , Solubilidade , Ácidos Sulfônicos/antagonistas & inibidores , Água/química
16.
Chem Biodivers ; 18(3): e2000864, 2021 Mar.
Artigo em Inglês | MEDLINE | ID: mdl-33533083

RESUMO

Veronicastrum axillare polysaccharides (VAP) were isolated by cellulase-assisted digestion. The optimum conditions (2 % cellulase, 47 °C for 2.5 h, then, 95 °C for 2.5 h, pH 4.1, solid/liquid ratio 1 : 7.6) were identified by a combination of single factor optimization and response surface DOE (design of experiment) methods, and achieved a yield of 4.7 %. Treatment with 1 % TCA for 10 min, then, 2 % DEAE-cellulose removed protein and colored impurities. Purified VAP retained most of the radical-scavenging activities and GES-1 cell protection capability in vitro, indicating VAP were the key active components of V. axillare. Some molecular features were identified by FT-IR and NMR analyses. The molecular weight was estimated from DOSY NMR experiments to be around 21 kDa. There were 6.3 % uronic acid residues in the VAP. The constituent sugars after TFA hydrolysis were identified by HPLC to include glucose, arabinose, rhamnose, galactose, and xylose in a molar ratio of 405 : 259 : 82 : 42 : 1.


Assuntos
Antioxidantes/farmacologia , Medicamentos de Ervas Chinesas/farmacologia , Polissacarídeos/farmacologia , Antioxidantes/química , Antioxidantes/isolamento & purificação , Benzotiazóis/antagonistas & inibidores , Compostos de Bifenilo/antagonistas & inibidores , Linhagem Celular , Sobrevivência Celular/efeitos dos fármacos , Relação Dose-Resposta a Droga , Medicamentos de Ervas Chinesas/química , Medicamentos de Ervas Chinesas/isolamento & purificação , Etanol/antagonistas & inibidores , Etanol/farmacologia , Humanos , Picratos/antagonistas & inibidores , Polissacarídeos/química , Polissacarídeos/isolamento & purificação , Estereoisomerismo , Relação Estrutura-Atividade , Ácidos Sulfônicos/antagonistas & inibidores
17.
Chem Biodivers ; 18(10): e2100356, 2021 Oct.
Artigo em Inglês | MEDLINE | ID: mdl-34398524

RESUMO

The aim of the present study was to quantify selected phenolic compounds, determine antioxidant activity and enzyme inhibitory effects of the aerial parts of Alkanna trichophylla Hub.-Mor. (A. trichophylla) and Convolvulus galaticus Rost.ex Choisy (C. galaticus) extracts prepared by homogenizer-assisted extraction (HAE), maceration (MAC) and infusion techniques. This is the first time such study has been designed to validate the phytochemical composition and bioactivity of these plants. Multivariate analysis was conducted on collected data. Rutin and caffeoylquinic acid derivatives were the most significant compounds in A. trichophylla and C. galaticus, respectively. The highest antioxidant activity of A. trichophylla was mostly exhibited by HAE/methanolic extracts as determined by DPPH, ABTS, FRAP (51.39, 112.70 and 145.73 mg TE/g, respectively) and phosphomolybdenum (2.05 mmol TE/g) assays. However, significant antioxidant activities varied within the extracts of C. galaticus. HAE/methanolic extract of A. trichophylla significantly depressed AChE (2.70 mg GALAE/g), BChE (5.53 mg GALAE/g) and tyrosinase (26.34 mg KAE/g) activities and that of C. galaticus inhibited AChE (2.04 mg GALAE/g), tyrosinase (31.25 mg KAE/g) and α-amylase (0.53 mmol ACAE/g) activities significantly. We concluded that HAE was the most efficient extraction technique as high yield of compounds and promising bioactivities were recorded from extracts prepared. Multivariate analysis showed that types of solvents influenced recovery of compounds and biological activities. This research study can be used as one methodological starting point for further investigation on these plants as all results are clearly promising and open the door to further research challenges such as cytotoxicity evaluation, molecular docking analysis, and more screening of pharmacological actions.


Assuntos
Antioxidantes/farmacologia , Boraginaceae/química , Convolvulus/química , Inibidores Enzimáticos/farmacologia , Extratos Vegetais/farmacologia , Plantas Medicinais/química , Acetilcolinesterase/metabolismo , Agaricales/enzimologia , Antioxidantes/química , Antioxidantes/isolamento & purificação , Benzotiazóis/antagonistas & inibidores , Compostos de Bifenilo/antagonistas & inibidores , Butirilcolinesterase/metabolismo , Inibidores Enzimáticos/química , Inibidores Enzimáticos/isolamento & purificação , Humanos , Monofenol Mono-Oxigenase/antagonistas & inibidores , Monofenol Mono-Oxigenase/metabolismo , Picratos/antagonistas & inibidores , Extratos Vegetais/química , Extratos Vegetais/isolamento & purificação , Saccharomyces cerevisiae/enzimologia , Ácidos Sulfônicos/antagonistas & inibidores , Turquia , alfa-Amilases/antagonistas & inibidores , alfa-Amilases/metabolismo
18.
Chem Biodivers ; 18(6): e2100054, 2021 Jun.
Artigo em Inglês | MEDLINE | ID: mdl-33915032

RESUMO

Eugenia copacabanensis and Myrciaria tenella are present in restingas of the Atlantic Forest, but little information is available about their chemical and biological potential. In this context, the hexane, dichloromethane, ethyl acetate and butanol fractions from the leaves of methanolic extract were analyzed by GC/MS and HPLC-DAD and the antioxidant potential was determined by DPPH and ABTS assays and using a Saccharomyces cerevisiae model. Dereplication allowed the identification of 68 compounds, 42 and 41 of which, respectively, are first reported here for E. copacabanensis and M. tenella. In vivo results revealed that the ethyl acetate and butanol fractions showed expressive antioxidant protection in the BY4741 and Δgsh1 strains, with greater impact on glutathione-deficient cells. With a high diversity of phenolic compounds, these polar fractions of E. copacabanensis and M. tenella leaves are potential protectors against intracellular oxidative stress.


Assuntos
Antifúngicos/farmacologia , Antioxidantes/farmacologia , Eugenia/química , Myrtaceae/química , Compostos Fitoquímicos/farmacologia , Folhas de Planta/química , Antifúngicos/análise , Antioxidantes/análise , Benzotiazóis/antagonistas & inibidores , Compostos de Bifenilo/antagonistas & inibidores , Testes de Sensibilidade Microbiana , Modelos Biológicos , Compostos Fitoquímicos/análise , Picratos/antagonistas & inibidores , Saccharomyces cerevisiae/efeitos dos fármacos , Saccharomyces cerevisiae/crescimento & desenvolvimento , Ácidos Sulfônicos/antagonistas & inibidores
19.
Chem Biodivers ; 18(12): e2100706, 2021 Dec.
Artigo em Inglês | MEDLINE | ID: mdl-34636484

RESUMO

The present work describes medicinal potential and secondary metabolic picture of the methanol extract (PP-M) of Polygonum plebeium R.Br. and its fractions; hexane (PP-H), ethyl acetate (PP-E) and water (PP-W). In total bioactive component estimation, highest contents of phenolic (89.38±0.27 mgGAE/g extract) and flavonoid (51.21±0.43 mgQE/g extract) were observed in PP-E, and the same fraction exhibited the highest antioxidant potential in DPPH (324.80±4.09 mgTE/g extract), ABTS (563.18±11.39 mgTE/g extract), CUPRAC (411.33±15.49 mgTE/g extract) and FRAC (369.54±1.70 mgTE/g extract) assays. In Phosphomolybdenum activity assay, PP-H and PP-E showed nearly similar potential, however, PP-H was the most active (13.54±0.24 mgEDTAE/g extract) in metal chelating activity assay. PP-W was the stronger inhibitor (4.03±0.05 mgGALAE/g extract) of the enzyme AChE, while PP-H was potent inhibitor of BChE (5.62±0.27 mg GALAE/g extract). Interestingly, PP-E was inactive against BChE. Against tyrosinase activity, PP-E was again the most active fraction with inhibitory value of 71.89±1.44 mg KAE/g extract, followed by the activity of PP-M and PP-W. Antidiabetic potential was almost equally distributed among PP-M, PP-H and PP-E. For mapping the chemodiversity of P. plebeium, PP-M was analyzed through UHPLC/MS, which led to the identification of more than 50 compounds. Flavonoids were the main components derived from isovitexin, kaempferol and luteolin however, gallic acid, protocatechuic acid, gingerols and lyoniresinol 9'-sulfate were among important bioactive phenols. These findings prompted to conclude that Polygonum plebeium can be a significant source to offer new ingredient for nutraceuticals and functional foods.


Assuntos
Antioxidantes/farmacologia , Inibidores da Colinesterase/farmacologia , Inibidores de Glicosídeo Hidrolases/farmacologia , Compostos Fitoquímicos/farmacologia , Polygonum/química , Acetilcolinesterase/metabolismo , Antioxidantes/química , Antioxidantes/isolamento & purificação , Benzotiazóis/antagonistas & inibidores , Compostos de Bifenilo/antagonistas & inibidores , Butirilcolinesterase/metabolismo , Inibidores da Colinesterase/química , Inibidores da Colinesterase/isolamento & purificação , Inibidores de Glicosídeo Hidrolases/química , Inibidores de Glicosídeo Hidrolases/isolamento & purificação , Humanos , Compostos Fitoquímicos/química , Compostos Fitoquímicos/isolamento & purificação , Picratos/antagonistas & inibidores , Ácidos Sulfônicos/antagonistas & inibidores , alfa-Glucosidases/metabolismo
20.
Chem Biodivers ; 18(9): e2100278, 2021 Sep.
Artigo em Inglês | MEDLINE | ID: mdl-34227240

RESUMO

This work aimed to investigate, for the first time, the chemical composition, antioxidant, antiparasitic, cytotoxicity, and antimicrobial activities of the aromatic plant Limonium oleifolium Mill. essential oil (EO) and organic extracts. L. oleifolium aerial parts essential oil was analyzed by GC-FID and GC-MS, and 46 constituents representing 98.25±1.12 % of the oil were identified. γ-Muurolene (10.81±0.07 %), cis-caryophyllene (7.71±0.06 %), o-cymene (7.07±0.01 %) and α-copaene (5.02±0.05 %) were the essential oil main compounds. The antioxidant activity of L. oleifolium EO and organic extracts (MeOH, CHCl3 , AcOEt, BuOH) was explored using 2,2-diphenyl-1-picrylhydrazyl (DPPH), ABTS, ß-carotene/linoleic acid, cupric reducing antioxidant capacity (CUPRAC), and ferric reducing power assays. The results showed that L. oleifolium EO exhibit antioxidant capacity (IC50 =17.40±1.32 µg/mL for DPPH assay, IC50 =29.82±1.08 µg/mL for ß-carotene assay, IC50 =25.23±1.01 µg/mL for ABTS assay, IC50 =9.11±0.08 µg/mL for CUPRAC assay and IC50 =19.41±2.06 mg/mL for reducing power assay). Additionally, the EO showed significant activity against trophozoite form of Acanthamoeba castellanii (IC50 =7.48±0.41 µg/mL) and promastigote form of Leishmania amazonensis (IC50 =19.36±1.06 µg/mL) and low cytotoxicity on murine macrophages (LC50  90.23±1.09 µg/mL), as well as good antimicrobial activity against Staphylococcus aureus, Escherichia coli, Klebsiella oxytoca, and Pseudomonas aeruginosa. These results suggest that L. oleifolium essential oil is a valuable source of bioactive compounds presenting antioxidant, antiparasitic, and antimicrobial activities. Furthermore, it is considered nontoxic.


Assuntos
Antibacterianos/farmacologia , Antioxidantes/farmacologia , Antiparasitários/farmacologia , Extratos Vegetais/farmacologia , Plumbaginaceae/química , Acanthamoeba castellanii/efeitos dos fármacos , Animais , Antibacterianos/química , Antibacterianos/isolamento & purificação , Antioxidantes/química , Antioxidantes/isolamento & purificação , Antiparasitários/química , Antiparasitários/isolamento & purificação , Bactérias/efeitos dos fármacos , Benzotiazóis/antagonistas & inibidores , Compostos de Bifenilo/antagonistas & inibidores , Linhagem Celular , Sobrevivência Celular/efeitos dos fármacos , Leishmania/efeitos dos fármacos , Macrófagos/efeitos dos fármacos , Camundongos , Testes de Sensibilidade Microbiana , Testes de Sensibilidade Parasitária , Picratos/antagonistas & inibidores , Extratos Vegetais/química , Extratos Vegetais/isolamento & purificação , Ácidos Sulfônicos/antagonistas & inibidores
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