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1.
Chem Biodivers ; 21(5): e202301467, 2024 May.
Artigo em Inglês | MEDLINE | ID: mdl-38471006

RESUMO

Cervical cancer is a specific type of cancer that affects women around the world, with an incidence of 604 thousand new cases per year and 341 thousand deaths. There is a high demand for new effective antineoplastic drugs with few side effects. In this sense, recent research highlights the potential of compounds of natural origin in treating and preventing different types of cancer. Myrciaria glazioviana is a Brazilian native species belonging to the Myrtaceae family, which has previously described biological activities such as antimicrobial, anti-inflammatory, and antioxidant properties. This study aims to evaluate the anticancer activity of the dichloromethane extract (MGD) and ethyl acetate extract (MGA) of M. glazioviana leaves against human cervical cancer cell line (HeLa), as well as to identify their bioactive compounds. Using HPLC-HRESIMS technique, ten compounds were characterized in both samples: quinic acid, ellagic acid, Tri-O-methyl ellagic acid, two derivatives of Tetra-O-methyl flavellagic acid, quercetrin, Di-O-methyl ellagic acid, and three derivatives of pentamethyl coruleoellagic acid. Through MTT assays using HeLa cells and NIH/3T3 cells, it was observed that MGD and MGA were selective against tumor cells, with IC50 values of 24.31 and 12.62 µg/mL, respectively. The samples induced the tumor cell death by apoptosis, as evidenced by the activation of caspases 3/7, cell shrinkage, and pyknotic nuclei. Both samples were also able to inhibit the migration of HeLa cells after 24 hours of treatment, indicating a potential antimetastatic effect. Therefore, the present research highlights the antiproliferative and antimigratory potential of this species against HeLa cells.


Assuntos
Antineoplásicos Fitogênicos , Apoptose , Proliferação de Células , Ensaios de Seleção de Medicamentos Antitumorais , Myrtaceae , Extratos Vegetais , Neoplasias do Colo do Útero , Humanos , Células HeLa , Extratos Vegetais/farmacologia , Extratos Vegetais/química , Extratos Vegetais/isolamento & purificação , Proliferação de Células/efeitos dos fármacos , Antineoplásicos Fitogênicos/farmacologia , Antineoplásicos Fitogênicos/química , Antineoplásicos Fitogênicos/isolamento & purificação , Neoplasias do Colo do Útero/tratamento farmacológico , Neoplasias do Colo do Útero/patologia , Myrtaceae/química , Cromatografia Líquida de Alta Pressão , Apoptose/efeitos dos fármacos , Feminino , Relação Dose-Resposta a Droga , Camundongos , Folhas de Planta/química , Animais , Sobrevivência Celular/efeitos dos fármacos , Espectrometria de Massas por Ionização por Electrospray
2.
Phytochem Anal ; 35(3): 552-566, 2024 Apr.
Artigo em Inglês | MEDLINE | ID: mdl-38191126

RESUMO

INTRODUCTION: In Brazil, the plant group popularly known as "pedra-ume-caá" is used in folk medicine for the treatment of diabetes, and its raw material is commonly sold. OBJECTIVE: The aim of the study was to apply a method for chemical identification of extracts of dry pedra-ume-caá leaves using HPLC-high-resolution mass spectrometry (HRMS) and NMR and develop a multivariate model with NMR data to authenticate commercial samples. In addition, to evaluate the biological activities of the extracts. MATERIALS AND METHODS: Dry extracts of Myrcia multiflora, Myrcia amazonica, Myrcia guianensis, Myrcia sylvatica, Eugenia punicifolia leaves, and 15 commercial samples (sold in Manaus and Belém, Brazil) were prepared by infusion. All the extracts were analysed using HPLC-high-resolution mass spectrometry (HRMS), NMR, principal component analysis (PCA), and hierarchical cluster analysis (HCA). The antidiabetic effect of extracts was evaluated according to enzymatic inhibition. Their content of total phenols, cell viability, and antioxidant and antiglycation activities were also determined. RESULTS: HPLC-HRMS and NMR analysis of these extracts permitted the identification of 17 compounds. 1H NMR data combined with multivariate analyses allowed us to conclude that catechin, myricitrin, quercitrin, and gallic and quinic acids are the main chemical markers of pedra-ume-caá species. These markers were identified in 15 commercial samples of pedra-ume-caá. Additionally, only the extracts of M. multiflora and E. punicifolia inhibited α-glucosidase. All the extracts inhibited the formation of advanced glycation end products (AGEs) and showed free-radical-scavenging activity. These extracts did not present cytotoxicity. CONCLUSION: This study revealed the chemical markers of matrices, and it was possible to differentiate the materials marketed as pedra-ume-caá. Moreover, this study corroborates the potential of these species for treating diabetes.


Assuntos
Diabetes Mellitus , Myrtaceae , Antioxidantes/química , Extratos Vegetais/química , Myrtaceae/química , Espectroscopia de Ressonância Magnética , Folhas de Planta/química
3.
Molecules ; 29(12)2024 Jun 07.
Artigo em Inglês | MEDLINE | ID: mdl-38930786

RESUMO

The present study provides a comprehensive analysis of the chemical composition of essential oils from species of the Myrcia genus and their applications. The compiled results highlight the chemical diversity and biological activities of these oils, emphasizing their potential importance for various therapeutic and industrial applications. The findings reveal that Myrcia essential oils present a variety of bioactive compounds, such as monoterpenes and sesquiterpenes, which demonstrate antimicrobial activities against a range of microorganisms, including Gram-positive and Gram-negative bacteria, as well as yeasts. Furthermore, this study highlights the phytotoxic activity of these oils, indicating their potential for weed control. The results also point to the insecticidal potential of Myrcia essential oils against a range of pests, showing their viability as an alternative to synthetic pesticides. Additionally, species of the genus Myrcia have demonstrated promising hypoglycemic effects, suggesting their potential in diabetes treatment. This comprehensive synthesis represents a significant advancement in understanding Myrcia essential oils, highlighting their chemical diversity and wide range of biological activities. However, the need for further research is emphasized to fully explore the therapeutic and industrial potential of these oils, including the identification of new compounds, understanding of their mechanisms of action, and evaluation of safety and efficacy in different contexts.


Assuntos
Óleos Voláteis , Óleos Voláteis/farmacologia , Óleos Voláteis/química , Anti-Infecciosos/farmacologia , Anti-Infecciosos/química , Inseticidas/química , Inseticidas/farmacologia , Myrtaceae/química , Humanos , Hipoglicemiantes/farmacologia , Hipoglicemiantes/química , Animais , Óleos de Plantas/farmacologia , Óleos de Plantas/química
4.
Molecules ; 29(10)2024 May 11.
Artigo em Inglês | MEDLINE | ID: mdl-38792121

RESUMO

Phenolic compounds, present in plants, provide substantial health advantages, such as antioxidant and anti-inflammatory properties, which enhance cardiovascular and cognitive well-being. Australia is enriched with a wide range of plants with phytopharmacological potential, which needs to be fully elucidated. In this context, we analyzed leaves of aniseed myrtle (Syzygium anisatum), lemon myrtle (Backhousia citriodora), and cinnamon myrtle (Backhousia myrtifolia) for their complex phytochemical profile and antioxidant potential. LC-ESI-QTOF-MS/MS was applied for screening and characterizing these Australian myrtles' phenolic compounds and the structure-function relation of phenolic compounds. This study identified 145 and quantified/semi-quantified 27 phenolic compounds in these Australian myrtles. Furthermore, phenolic contents (total phenolic content (TPC), total condensed tannins (TCT), and total flavonoids (TFC)) and antioxidant potential of phenolic extracts from the leaves of Australian myrtles were quantified. Aniseed myrtle was quantified with the highest TPC (52.49 ± 3.55 mg GAE/g) and total antioxidant potential than other selected myrtles. Catechin, epicatechin, isovitexin, cinnamic acid, and quercetin were quantified as Australian myrtles' most abundant phenolic compounds. Moreover, chemometric analysis further validated the results. This study provides a new insight into the novel potent bioactive phenolic compounds from Australian myrtles that could be potentially useful for functional, nutraceutical, and therapeutic applications.


Assuntos
Antioxidantes , Fenóis , Extratos Vegetais , Folhas de Planta , Espectrometria de Massas em Tandem , Folhas de Planta/química , Antioxidantes/química , Antioxidantes/farmacologia , Espectrometria de Massas em Tandem/métodos , Fenóis/química , Fenóis/análise , Austrália , Extratos Vegetais/química , Extratos Vegetais/farmacologia , Cromatografia Líquida/métodos , Flavonoides/química , Flavonoides/análise , Espectrometria de Massas por Ionização por Electrospray , Myrtaceae/química
5.
Am J Bot ; 110(11): e16248, 2023 11.
Artigo em Inglês | MEDLINE | ID: mdl-37792299

RESUMO

PREMISE: Leaf subepidermal secretory cavities are a notable trait in Myrtaceae, but their formation is still controversial because of the lack of consensus on their ontogeny among authors. Knowledge about the compounds present in these cavities has grown over the last few years, demonstrating that terpenoid-rich oils are not their unique content. These two points are the focus of this study on the ontogeny, structure, and contents of secretory cavities in neotropical Myrtaceae. METHODS: We used histochemical tests and Raman analysis to verify the basic chemical composition of the cavity contents of nine species. We studied the ontogeny of glands in one species, comparing aldehyde-fixed tissues and fresh sections mounted in an inert medium. RESULTS: We observed schizogenous development and appearance of the secretory cavities and found that sample processing may induce cell breakdown, which can be misinterpreted as lysigeny. The content of these cavities contains putative terpenes, resins, carbonyl groups, and flavonoids. CONCLUSIONS: Our findings support the hypothesis that the lysigenous appearance of the oil glands is a technical artifact. These tissue distortions must be considered when interpreting the development of this type of secretory structure. Moreover, the basic analyses of chemical constituents show for the first time that the glands of neotropical Myrtaceae are potential reservoirs of some compounds such as flavonoids previously reported as novelties for a few other myrtaceous species. Because some of them are non-lipid compounds, the idea that the glands are just oil repositories is no longer applicable.


Assuntos
Myrtaceae , Terpenos , Terpenos/análise , Terpenos/metabolismo , Myrtaceae/química , Myrtaceae/metabolismo , Folhas de Planta/metabolismo , Flavonoides/análise , Óleos/análise
6.
J Enzyme Inhib Med Chem ; 38(1): 2224944, 2023 Dec.
Artigo em Inglês | MEDLINE | ID: mdl-37369580

RESUMO

Callistemon is an aromatic genus of flowering plants belonging to family Myrtaceae. The essential oils of C. subulatus leaves were collected in four seasons and analyzed using GC/MS. The oils demonstrated monoterpenes as the predominant class. Eucalyptol was the main component in all seasons; summer (66.87%), autumn (58.33%), winter (46.74%) and spring (44.63%), followed by α-pinene; spring (31.41%), winter (28.69%), summer (26.34%) and autumn (24.68%). Winter oil, the highest yield (0.53 mL/100g), was further investigated for its inhibitory activity against enzymes associated with ageing; elastase and acetylcholinesterase. It remarkably inhibited elastase and acetylcholinesterase with IC50 values of 1.05 and 0.20 µg/ml, respectively. A molecular docking study was conducted for the major oil components on the active sites of target enzymes. Eucalyptol revealed the best binding affinity for both enzymes. C. subualtus oil could be used as supplement for management of ageing disorders like skin wrinkles and dementia.


Assuntos
Myrtaceae , Óleos Voláteis , Óleos Voláteis/farmacologia , Óleos Voláteis/análise , Óleos Voláteis/química , Estações do Ano , Acetilcolinesterase , Eucaliptol/farmacologia , Eucaliptol/análise , Egito , Simulação de Acoplamento Molecular , Folhas de Planta/química , Myrtaceae/química , Elastase Pancreática
7.
Chem Biodivers ; 20(4): e202300234, 2023 Apr.
Artigo em Inglês | MEDLINE | ID: mdl-36942510

RESUMO

Six new phloroglucinol derivatives, xanchryones I-N (1-6), were isolated from the leaves of Xanthostemon chrysanthus. Compounds 1-6 are unusual phloroglucinol-amino acid hybrids constructed through C2 -N and O-C1 ' bonds forming a peculiar oxazole ring. The structures and absolute configurations of compounds 1-6 were determined by MS, NMR, and single-crystal X-ray diffraction. Moreover, the anti-inflammatory and antibacterial activities of these compounds were evaluated.


Assuntos
Myrtaceae , Floroglucinol , Estrutura Molecular , Floroglucinol/química , Aminoácidos/análise , Myrtaceae/química , Antibacterianos/química , Folhas de Planta/química
8.
Molecules ; 28(6)2023 Mar 14.
Artigo em Inglês | MEDLINE | ID: mdl-36985610

RESUMO

Essential oils (EOs) obtained by hydro-distillation from different parts of twigs (EOT), leaves (EOL), and fruits (EOF) of Eucalyptus gunnii Hook. f. were screened for their chemical composition, insecticidal, repellence, and antibacterial properties. Based on GC and GC/MS analysis, 23 constituents were identified across the twigs, leaves, and fruits, with 23, 23, and 21 components, respectively. The primary significant class was oxygenated monoterpenes (82.2-95.5%). The main components were 1,8-cineole (65.6-86.1%), α-terpinyl acetate (2.5-7.6%), o-cymene (3.3-7.5%), and α-terpineol (3.3-3.5%). All three EOs exhibited moderate antibacterial activities. EOL was found to have higher antibacterial activity against all tested strains except Dickeya solani (CFBP 8199), for which EOT showed more potency. Globally, Dickeya solani (CFBP 8199) was the most sensitive (MIC ≤ 2 mg/mL), while the most resistant bacteria were Dickeya dadantii (CFBP 3855) and Pectobacterium carotovorum subsp. carotovorum (CFBP 5387). Fumigant, contact toxicity, and repellent bioassays showed different potential depending on plant extracts, particularly EOT and EOL as moderate repellents and EOT as a medium toxicant.


Assuntos
Eucalyptus , Repelentes de Insetos , Myrtaceae , Óleos Voláteis , Óleos Voláteis/química , Eucalyptus/química , Myrtaceae/química , Folhas de Planta/química , Repelentes de Insetos/química , Antibacterianos/química , Óleos de Plantas/química
9.
Molecules ; 28(5)2023 Mar 03.
Artigo em Inglês | MEDLINE | ID: mdl-36903602

RESUMO

Jabuticaba (Plinia cauliflora) and jambolan (Syzygium cumini) fruits are rich in phenolic compounds with antioxidant properties, mostly concentrated in the peel, pulp, and seeds. Among the techniques for identifying these constituents, paper spray mass spectrometry (PS-MS) stands out as a method of ambient ionization of samples for the direct analysis of raw materials. This study aimed to determine the chemical profiles of the peel, pulp, and seeds of jabuticaba and jambolan fruits, as well as to assess the efficiency of using different solvents (water and methanol) in obtaining metabolite fingerprints of different parts of the fruits. Overall, 63 compounds were tentatively identified in the aqueous and methanolic extracts of jabuticaba and jambolan, 28 being in the positive ionization mode and 35 in the negative ionization mode. Flavonoids (40%), followed by benzoic acid derivatives (13%), fatty acids (13%), carotenoids (6%), phenylpropanoids (6%), and tannins (5%) were the groups of substances found in greater numbers, producing different fingerprints according to the parts of the fruit and the different extracting solvents used. Therefore, compounds present in jabuticaba and jambolan reinforce the nutritional and bioactive potential attributed to these fruits, due to the potentially positive effects performed by these metabolites in human health and nutrition.


Assuntos
Myrtaceae , Syzygium , Humanos , Syzygium/química , Frutas/química , Solventes/análise , Myrtaceae/química , Antioxidantes/análise , Extratos Vegetais/química , Espectrometria de Massas em Tandem
10.
J Org Chem ; 87(7): 4788-4800, 2022 04 01.
Artigo em Inglês | MEDLINE | ID: mdl-35319897

RESUMO

Inspired by a previously reported biomimetic synthesis study, four new naturally occurring phloroglucinol trimers 1-4 with unusual 6/5/5/6/6/6-fused hexacyclic ring systems, along with two known analogues (5 and 6) and two known biogenetically related dimers (10 and 11), were isolated from Rhodomyrtus tomentosa. Their structures and absolute configurations were unambiguously elucidated by spectroscopic analysis, X-ray diffraction, and electronic circular dichroism calculation. By mimicking two potentially alternative biosynthetic pathways, the first asymmetric syntheses of 1-4 and the racemic syntheses of 5 and 6 were achieved in only five to six steps without the need for protecting groups. Furthermore, phloroglucinol dimers 10 and 11 exhibited significant in vitro antiviral activity against the respiratory syncytial virus.


Assuntos
Myrtaceae , Floroglucinol , Biomimética , Dicroísmo Circular , Estrutura Molecular , Myrtaceae/química , Floroglucinol/química
11.
Chem Biodivers ; 19(6): e202200356, 2022 Jun.
Artigo em Inglês | MEDLINE | ID: mdl-35581725

RESUMO

Four pairs of cinnamoyl-ß-triketone derivative enantiomers, (+)- and (-)-xanthostones A-D ((+)- and (-)-1-4), were isolated from Xanthostemon chrysanthus. Compounds 1 and 2 feature a new rearranged cinnamoyl-phloroglucinol scaffold fused with a cinnamyl-ß-triketone framework. Compounds 1, 3, and 4 are the first examples of natural products with a peculiar phenethyl-pyranone acid unit. Their structures with absolute configurations were determined by spectroscopic data, X-ray diffraction analysis and electronic circular dichroism (ECD) calculation. Interestingly, these novel compounds showed a tautomeric behavior in solution, which was revealed by NMR spectroscopy and density functional theory calculation. A plausible biosynthetic pathway toward xanthostones A-D was proposed. Additionally, the anti-inflammatory and antibacterial activities of xanthostones A-D were evaluated.


Assuntos
Myrtaceae , Anti-Inflamatórios , Dicroísmo Circular , Estrutura Molecular , Myrtaceae/química , Floroglucinol/química , Estereoisomerismo
12.
Chem Biodivers ; 19(6): e202200198, 2022 Jun.
Artigo em Inglês | MEDLINE | ID: mdl-35485995

RESUMO

Chagas Disease (CD), caused by flagellate protozoan Trypanosoma cruzi, is a Neglected Tropical Diseases (NTD) that affect approximately seven million people worldwide with a restrict therapeutical arsenal. In the present study, the essential oils from 18 Myrtaceae species were extracted, chemically dereplicated, and evaluated in vitro against T. cruzi. From these, eight essential oils were considered promising (IC50 <10 µg/mL and SI>10) against the protozoan: Eugenia florida, E. acutata, E. widgrenii, Calyptranthes brasilienses, C. widgreniana, Plinia cauliflora, Campomanesia xanthocarpa, and Psidium guajava. Multivariate data analysis pointed out (E)-caryophyllene, α-humulene, limonene, caryophyllene oxide, and α-copaene playing an important role in the anti-T. cruzi activity. The obtained results demonstrated the potential of essential oils of Myrtaceae species as valuable sources of bioactive compounds against T. cruzi.


Assuntos
Doença de Chagas , Myrtaceae , Óleos Voláteis , Trypanosoma cruzi , Brasil , Ecossistema , Florestas , Humanos , Myrtaceae/química , Óleos Voláteis/química , Folhas de Planta/química
13.
Molecules ; 27(17)2022 Aug 25.
Artigo em Inglês | MEDLINE | ID: mdl-36080231

RESUMO

The Myrtaceae family is one of the most representative in the Amazon. Several species have high added-value pharmacological potential. In order to contribute to the knowledge of the aromatic profile of Myrtaceae species from the Amazon, the present study presents the first report on the productivity, chemical composition, and antioxidant profile of the essential oil (EO) of Myrcia paivae. Dry leaves of the species were submitted to hydrodistillation to obtain their EO. The EO performance was calculated on a moisture-free basis and the analysis of the chemical profile was carried out by GC/MS. The determination of the antioxidant capacity was assessed by means of the antioxidant capacity equivalent to the inhibition Trolox of the ABTS•+ and DPPH• radicals. The results indicate that EO performance was equivalent to 1.69%. As for the chemical composition, hydrocarbon monoterpenes were predominant in the sample (>77%); terpinolene (14.70%), α-phellandrene (14.69%), γ-terpinene (9.64%), sylvestrene (7.62%), α-thujene (6.46%), and α-pinene (6.39%) were the constituents with higher content. Regarding the antioxidant capacity, the results show that the EO presented good results in the inhibition of ABTS•+ (0.886 ± 0.226 mM L−1) and DPPH• (2.90 ± 0.083 mM L−1), which can be attributed to the high monoterpene content in the sample.


Assuntos
Myrtaceae , Óleos Voláteis , Antioxidantes/química , Monoterpenos/análise , Myrtaceae/química , Óleos Voláteis/química , Extratos Vegetais/química , Folhas de Planta/química
14.
Molecules ; 27(15)2022 Jul 22.
Artigo em Inglês | MEDLINE | ID: mdl-35897853

RESUMO

The essential oil (EO) of Calycolpus goetheanus (Myrtaceae) specimens (A, B, and C) were obtained through hydrodistillation. The analysis of the chemical composition of the EOs was by gas chromatography coupled with mass spectrometry CG-MS, and gas chromatography coupled with a flame ionization detector CG-FID. The phytotoxic activity of those EOs was evaluated against two weed species from common pasture areas in the Amazon region: Mimosa pudica L. and Senna obtusifolia (L.) The antioxidant capacity of the EOs was determined by (DPPH•) and (ABTS•+). Using molecular docking, we evaluated the interaction mode of the major EO compounds with the molecular binding protein 4-hydroxyphenylpyruvate dioxygenase (HPPD). The EO of specimen A was characterized by ß-eudesmol (22.83%), (E)-caryophyllene (14.61%), and γ-eudesmol (13.87%), while compounds 1,8-cineole (8.64%), (E)-caryophyllene (5.86%), δ-cadinene (5.78%), and palustrol (4.97%) characterize the chemical profile of specimen B's EOs, and specimen C had α-cadinol (9.03%), δ-cadinene (8.01%), and (E)-caryophyllene (6.74%) as the majority. The phytotoxic potential of the EOs was observed in the receptor species M. pudica with percentages of inhibition of 30%, and 33.33% for specimens B and C, respectively. The EOs' antioxidant in DPPH• was 0.79 ± 0.08 and 0.83 ± 0.02 mM for specimens A and B, respectively. In the TEAC, was 0.07 ± 0.02 mM for specimen A and 0.12 ± 0.06 mM for specimen B. In the results of the in silico study, we observed that the van der Waals and hydrophobic interactions of the alkyl and pi-alkyl types were the main interactions responsible for the formation of the receptor-ligand complex.


Assuntos
Herbicidas , Myrtaceae , Óleos Voláteis , Antioxidantes/química , Antioxidantes/farmacologia , Cromatografia Gasosa-Espectrometria de Massas , Herbicidas/farmacologia , Simulação de Acoplamento Molecular , Myrtaceae/química , Óleos Voláteis/química , Óleos Voláteis/farmacologia , Compostos Fitoquímicos/química , Compostos Fitoquímicos/farmacologia
15.
Molecules ; 27(15)2022 Jul 31.
Artigo em Inglês | MEDLINE | ID: mdl-35956846

RESUMO

The essential oil of Backhousia citriodora, commonly known as lemon myrtle oil, possesses various beneficial properties due to its richness in bioactive compounds. This study aimed to characterize the chemical profile of the essential oil isolated from leaves of Backhousia citriodora (BCEO) and its biological properties, including antioxidant, antibacterial, and antibiofilm activities. Using gas chromatography-mass spectrometry, 21 compounds were identified in BCEO, representing 98.50% of the total oil content. The isomers of citral, geranial (52.13%), and neral (37.65%) were detected as the main constituents. The evaluation of DPPH radical scavenging activity and ferric reducing antioxidant power showed that BCEO exhibited strong antioxidant activity at IC50 of 42.57 µg/mL and EC50 of 20.03 µg/mL, respectively. The antibacterial activity results showed that BCEO exhibited stronger antibacterial activity against Gram-positive bacteria (Staphylococcus aureus and Staphylococcus epidermidis) than against Gram-negative bacteria (Escherichia coli and Klebsiella pneumoniae). For the agar disk diffusion method, S. epidermidis was the most sensitive to BCEO with an inhibition zone diameter of 50.17 mm, followed by S. aureus (31.13 mm), E. coli (20.33 mm), and K. pneumoniae (12.67 mm). The results from the microdilution method showed that BCEO exhibited the highest activity against S. epidermidis and S. aureus, with the minimal inhibitory concentration (MIC) value of 6.25 µL/mL. BCEO acts as a potent antibiofilm agent with dual actions, inhibiting (85.10% to 96.44%) and eradicating (70.92% to 90.73%) of the biofilms formed by the four tested bacteria strains, compared with streptomycin (biofilm inhibition, 67.65% to 94.29% and biofilm eradication, 49.97% to 89.73%). This study highlights that BCEO can potentially be a natural antioxidant agent, antibacterial agent, and antibiofilm agent that could be applied in the pharmaceutical and food industries. To the best of the authors' knowledge, this is the first report, on the antibiofilm activity of BCEO against four common nosocomial pathogens.


Assuntos
Myrtaceae , Óleos Voláteis , Antibacterianos/química , Antibacterianos/farmacologia , Antioxidantes/química , Antioxidantes/farmacologia , Biofilmes , Escherichia coli , Testes de Sensibilidade Microbiana , Myrtaceae/química , Óleos Voláteis/química , Staphylococcus aureus , Staphylococcus epidermidis
16.
Plant Foods Hum Nutr ; 77(3): 340-344, 2022 Sep.
Artigo em Inglês | MEDLINE | ID: mdl-35902483

RESUMO

Phenolic compounds in camu-camu (Myrciaria dubia) have received interest due to their health-promoting effects. However, these compounds have been poorly investigated in the different parts of the camu-camu fruit (pulp, peel, and seeds). This study aimed to optimize the solvent composition for extraction of phenolic compounds from pulp, peels, and seeds of camu-camu through a simplex-centroid mixture design. Then, the profile of phenolic compounds in samples of camu-camu pulp, peels, and seeds from different regions in Brazil and South America was determined by UPLC-ESI-MS/MS. Aqueous ethanol (80%, v/v) yielded the highest extraction for the pulp and peel, while aqueous methanol (50%, v/v) was selected for the seed. Camu-camu parts had p-coumaric acid, catechin, epicatechin, luteolin, rutin, and quercetin, with catechin as the major compound in the pulp, peels, and seeds of all the evaluated samples. The peel showed lower concentrations of these compounds compared with the pulp and the seed; the content of phenolic compounds also differed according to the geographic region. These results broaden the knowledge on phytochemical extraction and composition of camu-camu pulp, peel, and seed and may guide future applications of their extracts in the food industry.


Assuntos
Catequina , Myrtaceae , Brasil , Catequina/análise , Frutas/química , Myrtaceae/química , Fenóis/análise , Extratos Vegetais/química , Espectrometria de Massas em Tandem
17.
Bioorg Chem ; 117: 105404, 2021 12.
Artigo em Inglês | MEDLINE | ID: mdl-34749116

RESUMO

Alzheimer's disease (AD) diagnoses are greatly increasing in frequency as the global population ages, highlighting an urgent need for new anti-AD strategies. With the aim to search for human acetylcholinesterase (hAChE) inhibitors from the species of Myrtaceae family, ten acylphloroglucinol trimers (APTs), including eight new APTs, callistemontrimers A-H (1a, 1b, 2a, 2b, 3a, 3b, 4b, and 5b), and two naturally occurring ones (4a and 5a), along with one reported triketone-acylphloroglucinol-monoterpene adduct (6), were obtained and structurally characterized from the hAChE inhibitory acetone extract of Callistemon salignus seeds. The structures and their absolute configurations for new APTs were unequivocally established via the detailed interpretation of extensive spectroscopic data (HRESIMS and NMR), ECD calculations, and single crystal X-ray diffraction, whereas the absolute configurations of known APTs were determined by further chiral separation, and calculated ECD calculations. The results of hAChE inhibitory assay revealed that an enantiomeric mixture of 2a/2b, 2a, and 2b are good hAChE inhibitors with IC50 values of 1.22 ±â€¯0.23, 2.28 ±â€¯0.19, and 4.96 ±â€¯0.39 µM, respectively. Molecular docking was used to uncover the modes of interactions for bioactive compounds with the active site of hAChE. In addition, 2 and 6 displayed moderate neurite outgrowth-promoting effects with differentiation rates of 6.16% and 6.19% at a concentration of 1.0 µM, respectively.


Assuntos
Inibidores da Colinesterase/farmacologia , Floroglucinol/farmacologia , Acetilcolinesterase/metabolismo , Inibidores da Colinesterase/química , Inibidores da Colinesterase/isolamento & purificação , Humanos , Simulação de Acoplamento Molecular , Myrtaceae/química , Floroglucinol/análogos & derivados , Floroglucinol/isolamento & purificação , Estereoisomerismo , Relação Estrutura-Atividade
18.
Bioorg Chem ; 107: 104519, 2021 02.
Artigo em Inglês | MEDLINE | ID: mdl-33293058

RESUMO

Chemical investigation of the twigs and leaves of Rhodomyrtus tomentosa led to the isolation and structural identification of a novel polymethylated phloroglucinol meroterpenoid (PPM) featuring a 6/6/6/6 tetracyclic system, rhotomentodione F (1), five new polymethylated polycyclic phloroglucinols (PPPs) with a rare bis-furan framework, rhotomentosones A-E (2-6), and one new adduct composed of an acylphloroglucinol and two ß-triketone units, rhotomentosone F (7), as well as five known analogues (8-12). Their structures and absolute configurations were unambiguously determined by comprehensive spectroscopic data and electronic circular dichroism (ECD) calculations. All isolates were evaluated for their anti-inflammatory and acetylcholinesterase (AChE) inhibitory activities. Compound 6 displayed significant AChE inhibitory effect with an IC50 value of 8.68 µM. Further molecular docking studies of 6 revealed that the interactions with AChE residues Ser125, Glu202, and Tyr133 are crucial for AChE inhibitory activity. The current study not only enriches the chemical diversity of phloroglucinols in Myrtaceae species, but also provides potential lead compounds for the further design and development of new AChE inhibitors to treat Alzheimer's disease.


Assuntos
Acetilcolinesterase/metabolismo , Anti-Inflamatórios/farmacologia , Inibidores da Colinesterase/farmacologia , Myrtaceae/química , Floroglucinol/análogos & derivados , Floroglucinol/farmacologia , Animais , Anti-Inflamatórios/química , Anti-Inflamatórios/metabolismo , Inibidores da Colinesterase/química , Inibidores da Colinesterase/metabolismo , Humanos , Camundongos , Simulação de Acoplamento Molecular , Estrutura Molecular , Floroglucinol/metabolismo , Folhas de Planta/química , Ligação Proteica , Células RAW 264.7
19.
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
20.
Molecules ; 26(23)2021 Nov 27.
Artigo em Inglês | MEDLINE | ID: mdl-34885788

RESUMO

Myrciaria floribunda, also known as rumberry, is a tree native to the Brazilian Atlantic Forest, where its fruits have the potential for commercial use. This study evaluates the antioxidant potential, determines the phytochemical profile, and chemically characterizes the rumberry fruit. Accessions were sampled from the Rumberry Active Germplasm Bank of the Federal University of Alagoas, Brazil. Physical characteristics, chemical characteristics, and phenolic compound content were analyzed. Chemical profile characterization was carried out using PSMS. Accessions had an average weight of 0.86 g. Accession AC137 presented a higher pulp yield (1.12 g). AC132 and AC156 had larger fruits, AC137 showed greater firmness (5.93 N), and AC160 had a higher and total phenolic content ratio (279.01 ± 11.11). Orange-colored accessions scored higher in evaluated parameters, except for AC160 for phenolic content. Thirty-two compounds were identified on positive ionization mode and 42 compounds on negative ionization mode using PSMS. Flavonoids, followed by the derivatives of benzoic acid, sugars, and phenylpropanoids, were the most prominent. Myricitrin, quercitrin, and catechin stand out as flavonoids that have been reported in previous studies with antioxidant and antimicrobial properties, in addition to health and therapeutical benefits, demonstrating the potential of the rumberry fruit.


Assuntos
Fenômenos Químicos , Ecótipo , Espectrometria de Massas , Myrtaceae/química , Papel , Fenóis/análise
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