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1.
Chem Biodivers ; : e202400746, 2024 Jul 29.
Artigo em Inglês | MEDLINE | ID: mdl-39075724

RESUMO

Orthopterygium huaucui, commonly known as "Pate", is a medicinal shrub belonging to the Anacardiaceae family used locally to treat burns and stomach pains. Endemic to Peru, chemical studies on O. huaucui are limited. In this study, Ultra-High Performance Liquid Chromatography Quadrupole/Orbitrap Electrospray Ionization Tandem Mass Spectrometry (UHPLC Q/Orbitrap/ESI/MS/MS) was used to identify secondary metabolites in leaves, stems and fruits, and the antioxidant capacities of the different parts were compared. In addition, several compounds such as methyl gallate, gallic acid, kaempferol, quercetin, and quercetin 3-O-ß-glucuronide were successfully isolated from the methanolic extract of the leaves of this species for the first time. Untargeted UHPLC Q/Orbitrap/ESI/MS/MS analysis tentatively identified seventy-six compounds in the different parts of the plant, showing that this species as an interesting source of flavonoids, procyanidins and tannins. The phenolic content in leaves and stems was 334.31±4.34 and 295.18±6.38 gallic acid equivalents/100 g dry plant, respectively, while that of fruits was lower (99.92±5.45 mg/100 g). Leaves had twice the flavonoid content than fruits (210.38±3.85 versus 87.42±3.85 quercetin equivalents/100 g). 2,2-Diphenyl-1-picrylhydrazyl (DPPH) results indicated high antioxidant activity in all parts, with stems and leaves showing IC50 of 12.8 µg/mL, and fruits showing less activity (IC50=38.6 µg/mL). The Oxygen Radical Absorbance Capacity (ORAC) test showed higher antioxidant values in the stems (467.82±21.17 µmol Trolox equivalents/100 g). This study provides valuable information on the chemistry of O. huaucui and highlights its antioxidant potential, especially in leaves and stems.

2.
Plant Foods Hum Nutr ; 79(2): 337-343, 2024 Jun.
Artigo em Inglês | MEDLINE | ID: mdl-38358640

RESUMO

Although Phoenix dactylifera dates are traditionally consumed for their health benefits, no research has been done on the vascular response in hypertensive animals. This study evaluated the vascular relaxation of hydroalcoholic extracts from seeds of three varieties of P. dactylifera; Sukkari seed (SS), Ajwa seed (AS), and Mabroom seed (MS) on L-NAME-induced hypertension and spontaneously hypertensive rats (SHR). Results showed that all extracts (10 µg/mL) caused relaxations higher than 60% in the aortic rings precontracted with 10- 6 M phenylephrine in normotensive rats, the SS extract was the most potent. Endothelial nitric oxide (NO) pathway is involved as significantly reduced vascular relaxation in denuded-endothelium rat aorta and with an inhibitor (10- 4 M L-Nω-Nitro arginine methyl ester; L-NAME) of endothelial nitric oxide synthase (eNOS). Confocal microscopy confirmed that 10 µg/mL SS extract increases NO generation as detected by DAF-FM fluorescence in intact aortic rings. Consistent with these findings, vascular relaxation in intact aortic rings at 10 µg/mL SS extract was significantly decreased in L-NAME-induced hypertensive rats (endothelial dysfunction model), but not in SHR. In both hypertensive models, the denuded endothelium blunted the vascular relaxation. In conclusion, the hydroalcoholic extract of the seed of P. dactylifera (Sukkari, Ajwa and Mabroom varieties) presents a potent endothelium-dependent vascular relaxation, via NO, in normotensive rats as well as in two different models of hypertension. This effect could be mediated by the presence of phenolic compounds identified by UHPLC-ESI-MS/MS, such as protocatechuic acid, and caftaric acid.


Assuntos
Hipertensão , NG-Nitroarginina Metil Éster , Óxido Nítrico , Phoeniceae , Extratos Vegetais , Ratos Endogâmicos SHR , Sementes , Animais , Sementes/química , Phoeniceae/química , Extratos Vegetais/farmacologia , Hipertensão/tratamento farmacológico , Hipertensão/induzido quimicamente , Masculino , Óxido Nítrico/metabolismo , Ratos , NG-Nitroarginina Metil Éster/farmacologia , Endotélio Vascular/efeitos dos fármacos , Óxido Nítrico Sintase Tipo III/metabolismo , Vasodilatação/efeitos dos fármacos , Aorta/efeitos dos fármacos , Anti-Hipertensivos/farmacologia
3.
Molecules ; 27(22)2022 Nov 21.
Artigo em Inglês | MEDLINE | ID: mdl-36432187

RESUMO

The lichen species Lecania brialmontii, Pseudephebe pubescens, and Sphaerophorus globosus are part of the prominent lichenoflora of the Antarctic territory. In this work, we report the metabolomic identification of ethanolic extracts of these species, their antioxidant and cholinesterase enzyme inhibitory activity, and conduct a molecular docking analysis with typical compounds. Eighteen compounds were identified by UHPLC-ESI-QTOF-MS in L. brialmontii, 18 compounds in P. pubescens, and 14 compounds in S. globosus. The content of phenolic compounds was variable among the species, ranging from 0.279 to 2.821 mg AG/g, and all three species showed high inhibition potential on the cholinesterase enzymes. Molecular docking showed important interactions between AChE and BChE with the selected compounds. This study evidences the chemical fingerprint of three species of the order Lecanorales that support the continuation of the study of other biological activities and their potential for medical research.


Assuntos
Eczema , Ceratose , Líquens , Simulação de Acoplamento Molecular , Antioxidantes/farmacologia , Colinesterases
4.
Molecules ; 27(14)2022 Jul 08.
Artigo em Inglês | MEDLINE | ID: mdl-35889260

RESUMO

This study aimed to determine the in vitro cytotoxicity and understand possible cytotoxic mechanisms via an in silico study of eleven chalcones synthesized from two acetophenones. Five were synthesized from a prenylacetophenone isolated from a plant that grows in the Andean region of the Atacama Desert. The cytotoxic activity of all the synthesized chalcones was tested against breast cancer cell lines using an MTT cell proliferation assay. The results suggest that the prenyl group in the A-ring of the methoxy and hydroxyl substituents of the B-ring appear to be crucial for the cytotoxicity of these compounds. The chalcones 12 and 13 showed significant inhibitory effects against growth in MCF-7 cells (IC50 4.19 ± 1.04 µM and IC50 3.30 ± 0.92 µM), ZR-75-1 cells (IC50 9.40 ± 1.74 µM and IC50 8.75 ± 2.01µM), and MDA-MB-231 cells (IC50 6.12 ± 0.84 µM and IC50 18.10 ± 1.65 µM). Moreover, these chalcones showed differential activity between MCF-10F (IC50 95.76 ± 1.52 µM and IC50 95.11 ± 1.97 µM, respectively) and the tumor lines. The in vitro results agree with molecular coupling results, whose affinity energies and binding mode agree with the most active compounds. Thus, compounds 12 and 13 can be considered for further studies and are candidates for developing new antitumor agents. In conclusion, these observations give rise to a new hypothesis for designing chalcones with potential cytotoxicity with high potential for the pharmaceutical industry.


Assuntos
Antineoplásicos , Neoplasias da Mama , Chalcona , Chalconas , Antineoplásicos/química , Antineoplásicos/farmacologia , Neoplasias da Mama/tratamento farmacológico , Proliferação de Células , Chalcona/farmacologia , Chalconas/química , Chalconas/farmacologia , Desenho de Fármacos , Ensaios de Seleção de Medicamentos Antitumorais , Feminino , Humanos , Células MCF-7 , Simulação de Acoplamento Molecular , Estrutura Molecular , Relação Estrutura-Atividade
5.
Molecules ; 27(16)2022 Aug 16.
Artigo em Inglês | MEDLINE | ID: mdl-36014470

RESUMO

An ecofriendly extraction technology using infrared (IR) irradiation Ired-Irrad® was applied to purple corn cobs to enhance polyphenol recovery for the first time. The IR extraction efficiency was compared to that of the water bath (WB) method. Response surface methodology (RSM) using a central composite design was conducted to determine the effect of the experimental conditions (extraction time and treatment temperature) and their interactions on the total polyphenol and anthocyanin yields. Optimal extraction of total phenolic compounds (37 mg GAE/g DM) and total monomeric anthocyanins (14 mg C3G/g DM) were obtained at 63 °C for 77 min using IR as an extraction technique and water as a solvent. HPLC revealed that the recovery of peonidin 3-O-glucoside and cyanidin 3-O-glucoside was enhanced by 26% and 34%, respectively, when using IR. Finally, purple corn cobs' spray-dried extract was proven to be an important natural colorant of pickled turnip. It offers great potential for use as a healthy alternative to the carcinogenic rhodamine B synthetic dye, which was banned.


Assuntos
Antocianinas , Brassica napus , Extratos Vegetais , Polifenóis , Tecnologia , Água , Zea mays
6.
Molecules ; 26(7)2021 Apr 06.
Artigo em Inglês | MEDLINE | ID: mdl-33917599

RESUMO

The Lamiaceae family is an important source of species among medicinal plants highly valued for their biological properties and numerous uses in folk medicine. Origanum is one of the main genera that belong to this family. The purpose of the study was to determine the phenolic composition of the Origanum vulgare extract and evaluate the antimicrobial, antioxidant, and inhibitory activities of this species that grows in the Andean region of the Atacama Desert. High-performance liquid chromatography was performed to determine the main phenols. Rosmarinic acid was identified as the predominant phenolic compound in this species (76.01 mg/100 g DW), followed by protocatechuic acid, which to our knowledge, no previous study reported similar concentrations in O. vulgare. The oregano extract exhibited a content of total phenolic (3948 mg GAE/100 g DW) and total flavonoid (593 mg QE/100 g DW) with a higher DPPH antioxidant activity (IC50 = 40.58 µg/mL), compared to the same species grown under other conditions. Furthermore, it was found to inhibit α-glucosidase activity with an IC50 value (7.11 mg/mL) lower than acarbose (129.32 mg/mL). Pseudomonas syringae and Pantoea agglomerans (both MIC 0.313 mg/mL and MBC 1.25 mg/mL) were the bacteria most susceptible to oregano extract with the lowest concentration necessary to inhibit bacterial growth. These results open the door for the potential use of this plant to manage chronic diseases, and they expand the knowledge of the species cultivated in arid environmental conditions.


Assuntos
Antibacterianos/farmacologia , Antioxidantes/farmacologia , Clima Desértico , Inibidores Enzimáticos/farmacologia , Origanum/química , Bactérias/efeitos dos fármacos , Chile , Cromatografia Líquida de Alta Pressão , Testes de Sensibilidade Microbiana , Fenóis/análise , Extratos Vegetais/química
7.
Molecules ; 25(14)2020 Jul 08.
Artigo em Inglês | MEDLINE | ID: mdl-32650373

RESUMO

Heliotropium taltalense is an endemic species of the northern coast of Chile and is used as folk medicine. The polyphenolic composition of the methanolic and aqueous extract of the endemic Chilean species was investigated using Ultrahigh-Performance Liquid Chromatography, Heated Electrospray Ionization and Mass Spectrometry (UHPLC-Orbitrap-HESI-MS). Fifty-three compounds were detected, mainly derivatives of benzoic acid, flavonoids, and some phenolic acids. Furthermore, five major compounds were isolated by column chromatography from the extract, including four flavonoids and one geranyl benzoic acid derivative, which showed vascular relaxation and were in part responsible for the activity of the extracts. Since aqueous extract of H. taltalense (83% ± 9%, 100 µg/mL) produced vascular relaxation through an endothelium-dependent mechanism in rat aorta, and the compounds rhamnocitrin (89% ± 7%; 10-4 M) and sakuranetin (80% ± 6%; 10-4 M) also caused vascular relaxation similar to the extracts of H. taltalense, these pure compounds are, to some extent, responsible for the vascular relaxation.


Assuntos
Aorta/metabolismo , Extratos Vegetais/química , Polifenóis , Vasodilatação/efeitos dos fármacos , Animais , Heliotropium/química , Masculino , Polifenóis/química , Polifenóis/farmacologia , Ratos , Ratos Sprague-Dawley
8.
Molecules ; 25(3)2020 Jan 24.
Artigo em Inglês | MEDLINE | ID: mdl-31991709

RESUMO

The infusion of the desertic plant Nolana ramosissima I.M. Johnst showed vascular smooth muscle relaxation in rat aorta and the presence of several phenolic compounds, which were detected by high resolution UHPLC-Orbitrap-HESI-MS. In addition, five flavonoids were rapidly isolated from a methanolic extract using high-performance counter-current chromatography (HPCCC). The N. ramosissima extract showed endothelium-independent relaxation effect in rat aorta. Sixty-one compounds were detected in the infusion, mainly glycosylated flavonoids, flavanones and several oxylipins, suggesting that a synergistic effect between the compounds in the extracts could be responsible for the relaxation activity. Vascular activity experiments were done in isolated organ bath. In rat aorta, a nitric oxide inhibitor did not prevent the relaxation effects of the extract; however, a selective guanylyl cyclase inhibitor partially blunted this effect. The compound 5,3'-dihydroxy-4'7-dimethoxyflavone presented higher relaxation effect than 100 µg/mL of N. ramosissima extract. The extract and the isolated metabolites from N. ramosissima can show relaxation effects on rat aorta by a mechanism that is independent of the endothelium.


Assuntos
Aorta/fisiopatologia , Endotélio Vascular/fisiopatologia , Flavonoides , Extratos Vegetais/química , Solanaceae/química , Vasodilatação/efeitos dos fármacos , Animais , Feminino , Flavonoides/química , Flavonoides/isolamento & purificação , Flavonoides/farmacologia , Ratos , Ratos Sprague-Dawley
9.
Molecules ; 25(13)2020 Jun 30.
Artigo em Inglês | MEDLINE | ID: mdl-32630065

RESUMO

In the present work, the anthelmintic activity (AA) of ethanolic extracts obtained from Gliricidia sepium, Leucaena leucocephala, and Pithecellobium dulce was evaluated using the third-stage-larval (L3) exsheathment inhibition test (LEIT) and egg hatch test (EHT) on Haemonchus contortus. Extracts were tested at concentrations of 0.3, 0.6, 1.2, 2.5, 5.0, 10, 20, and 40 mg/mL. The larval exsheathment inhibition (LEI) results showed that G. sepium achieved the highest average inhibition of 91.2%, compared with 44.6% for P. dulce and 41.0% for L. leucocephala at a concentration of 40 mg/mL; the corresponding IC50 values were 22.4, 41.7, and 43.3 mg/mL, respectively. The rates of egg hatching inhibition (EHI) at a concentration of 5 mg/mL were 99.5% for G. sepium, 64.2% for P. dulce, and 54% for L. leucocephala; the corresponding IC50 values were 1.9 mg/mL for G. sepium, 3.9 mg/mL for P. dulce, and 4.3 mg/mL for L. leucocephala. The species extracts studied here were also analyzed by ultra-high performance liquid chromatography and Orbitrap high resolution mass spectrometry (UHPLC-Q/Orbitrap/MS/MS), resulting in the compounds' identification associated with AA. Glycosylated flavonoids and methoxyphenols were observed in all three species: fatty acids in G. sepium and P. dulce; phenylpropanoids, anthraquinone glycosides, amino acids and glycosylated phenolic acids in G. sepium; and flavonoids in L. leucocephala. Comparatively, G. sepium presented a greater diversity of compounds potentially active against the control of gastrointestinal nematodes, which was associated with the results obtained in the applied tests.


Assuntos
Anti-Helmínticos/farmacologia , Fabaceae/química , Fabaceae/classificação , Flavonoides/farmacologia , Haemonchus/crescimento & desenvolvimento , Larva/crescimento & desenvolvimento , Extratos Vegetais/farmacologia , Animais , Cromatografia Líquida de Alta Pressão , Haemonchus/efeitos dos fármacos , Técnicas In Vitro , Larva/efeitos dos fármacos , Espectrometria de Massas em Tandem
10.
Molecules ; 25(16)2020 Aug 17.
Artigo em Inglês | MEDLINE | ID: mdl-32824604

RESUMO

Greigia sphacelata (Ruiz and Pav.) Regel (Bromeliaceae) is a Chilean endemic plant popularly known as "quiscal" and produces an edible fruit consumed by the local Mapuche communities named as "chupón". In this study, several metabolites including phenolic acids, organic acids, sugar derivatives, catechins, proanthocyanidins, fatty acids, iridoids, coumarins, benzophenone, flavonoids, and terpenes were identified in G. sphacelata fruits using ultrahigh performance liquid chromatography-photodiode array detection coupled with a Orbitrap mass spectrometry (UHPLC-PDA-Orbitrap-MS) analysis for the first time. The fruits showed moderate antioxidant capacities (i.e., 487.11 ± 26.22 µmol TE/g dry weight) in the stable radical DPPH assay, 169.08 ± 9.81 TE/g dry weight in the ferric reducing power assay, 190.32 ± 6.23 TE/g dry weight in the ABTS assay, and 76.46 ± 3.18% inhibition in the superoxide anion scavenging assay. The cholinesterase inhibitory potential was evaluated against acetylcholinesterase (AChE) and butyrylcholinesterase (BChE). From the findings, promising results were observed for pulp and seeds. Our findings suggest that G. sphacelata fruits are a rich source of diverse secondary metabolites with antioxidant capacities. In addition, the inhibitory effects against AChE and BChE suggest that natural products or food supplements derived from G. sphacelata fruits are of interest for their neuroprotective potential.


Assuntos
Bromeliaceae/química , Inibidores da Colinesterase/farmacologia , Cromatografia Líquida de Alta Pressão/métodos , Compostos Fitoquímicos/química , Compostos Fitoquímicos/farmacologia , Extratos Vegetais/farmacologia , Espectrometria de Massas em Tandem/métodos , Acetilcolinesterase , Butirilcolinesterase/química , Inibidores da Colinesterase/química , Frutas/química , Proteínas Ligadas por GPI/antagonistas & inibidores , Humanos , Extratos Vegetais/química
11.
Molecules ; 25(21)2020 Nov 05.
Artigo em Inglês | MEDLINE | ID: mdl-33167456

RESUMO

Mangifera indica Linn popularly known as mango is used in folk medicine to treat gastrointestinal disorders. The aim of this study was to identify the metabolomic composition of lyophilized extract of mango leaf (MIE), to evaluate the antioxidant activity on several oxidative stress systems (DPPH, FRAP, TBARS, and ABTS), the spasmolytic and antispasmodic activity, and intestinal protective effect on oxidative stress induced by H2O2 in rat ileum. Twenty-nine metabolites were identified and characterized based on their ultra-high-performance liquid chromatography (UHPLC) high-resolution orbitrap mass spectrometry, these include: benzophenone derivatives, xanthones, phenolic acids, fatty acids, flavonoids and procyanidins. Extract demonstrated a high antioxidant activity in in-vitro assays. MIE relaxed (p < 0.001) intestinal segments of rat pre-contracted with acetylcholine (ACh) (10-5 M). Pre-incubation of intestinal segments with 100 µg/mL MIE significantly reduced (p < 0.001) the contraction to H2O2. Similar effects were observed with mangiferin and quercetin (10-5 M; p < 0.05) but not for gallic acid. Chronic treatment of rats with MIE (50 mg/kg) for 28 days significantly reduced (p < 0.001) the H2O2-induced contractions. MIE exhibited a strong antioxidant activity, spasmolytic and antispasmodic activity, which could contribute to its use as an alternative for the management of several intestinal diseases related to oxidative stress.


Assuntos
Antioxidantes/farmacologia , Íleo/efeitos dos fármacos , Mangifera/química , Extratos Vegetais/farmacologia , Folhas de Planta/química , Animais , Benzofenonas/química , Benzotiazóis/química , Compostos de Bifenilo/química , Cromatografia Líquida de Alta Pressão , Ácido Gálico/farmacologia , Peróxido de Hidrogênio/química , Peroxidação de Lipídeos , Masculino , Metabolômica , Modelos Biológicos , Estresse Oxidativo , Parassimpatolíticos/farmacologia , Compostos Fitoquímicos/farmacologia , Picratos/química , Quercetina/farmacologia , Ratos , Ácidos Sulfônicos/química , Substâncias Reativas com Ácido Tiobarbitúrico/química , Xantonas/química
12.
Molecules ; 24(6)2019 Mar 19.
Artigo em Inglês | MEDLINE | ID: mdl-30893865

RESUMO

The decoction of the local plant Baccharis grisebachii is used as a digestive, gastroprotective, external cicatrizing agent and antiseptic in Argentine. A lyophilized decoction (BLD) from the aerial parts of this plant was evaluated regarding its anti-ulcer, antioxidant and cytotoxic activities and the bioactivities were supported by UHPLC-MS metabolome fingerprinting which revealed the presence of several small bioactive compounds. The antioxidant properties were evaluated by DPPH, TEAC, FRAP and lipoperoxidation inhibition in erythrocytes methods, and the antibacterial activity was evaluated according to the Clinical and Laboratory Standards Institute (CLSI) guidelines. The BLD showed a moderate free radical scavenging activity in the DPPH (EC50 = 106 µg/mL) and lipid peroxidation in erythrocytes assays (67%, at 250 µg/mL). However, the BLD had the highest gastroprotective effect at a dose of 750 mg/kg with a ninety-three percent inhibition of damage through a mechanism that involve NO and prostaglandins using the ethanol-induced gastric damage in a standard rat model. On the other hand, BLD does not induce cytotoxic changes on human tumor and no-tumor cell lines at the concentrations assayed. Regarding the metabolomic analysis, thirty-one compounds were detected and 30 identified based on UHPLC-OT-MS including twelve flavonoids, eleven cinnamic acid derivatives, one coumarin, one stilbene and two other different phenolic compounds. The results support that the medicinal decoction of Baccharis grisebachii is a valuable natural product with gastroprotective effects and with potential to improve human health that opens a pathway for the development of important phytomedicine products.


Assuntos
Antioxidantes/química , Baccharis/química , Compostos de Bifenilo/química , Cromatografia Líquida de Alta Pressão , Cinamatos/química , Flavonoides/química , Células HCT116 , Humanos , Peroxidação de Lipídeos , Espectrometria de Massas , Picratos/química
14.
J Enzyme Inhib Med Chem ; 33(1): 936-944, 2018 Dec.
Artigo em Inglês | MEDLINE | ID: mdl-29734888

RESUMO

UHPLC/ESI/MS identification of organic compounds is the first step in the majority of screening techniques for the characterization of biologically active metabolites in natural sources. This paper describes a method for the fast identification and characterisation of secondary metabolites in Leptocarpha rivularis DC. (Palo negro) extracts by HPLC/UV (DAD)-Mass Spectrometry (HPLC/MS). The plant is used for the treatment of several diseases since pre-hispanic Mapuche times. Thirty-seven compounds were detected in the aqueous edible extract for the first time including 4 sesquiterpenes, 10 flavonoids, 9 oxylipins, 2 organic acids, and 11 phenolic acids. In addition, phenolic content antioxidant and cholinesterase inhibitory activities were measured for the first time using the edible infusion. The total polyphenol content of the infusion was 230.76 ± 2.5 mmol GAE/kg dry weight, while the antioxidant activity was 176.51 ± 28.84; 195.28 ± 4.83; and 223.92 ± 2.95 mmol TE/kg dry weight, for the DPPH, ABTS, and FRAP assays, respectively. The cholinesterase inhibitory activity was 7.38 ± 0.03 and 5.74 ± 0.06 mmol GALAE/kg, for the inhibition of acetylcholinesterase AChE and BChE, respectively, showing that this plant is a candidate for the isolation of compounds that can be useful for the treatment of neurodegenerative diseases. Furthermore, this plant could serve also as a raw material for the production of dietary supplements, due to its content of polyphenolic compounds.


Assuntos
Antioxidantes/farmacologia , Asteraceae/química , Produtos Biológicos/farmacologia , Compostos de Bifenilo/antagonistas & inibidores , Inibidores da Colinesterase/farmacologia , Picratos/antagonistas & inibidores , Acetilcolinesterase/metabolismo , Antioxidantes/química , Antioxidantes/isolamento & purificação , Produtos Biológicos/química , Produtos Biológicos/isolamento & purificação , Butirilcolinesterase/metabolismo , Inibidores da Colinesterase/química , Inibidores da Colinesterase/isolamento & purificação , Cromatografia Líquida de Alta Pressão , Relação Dose-Resposta a Droga , Flavonoides/química , Flavonoides/isolamento & purificação , Flavonoides/farmacologia , Hidroxibenzoatos/química , Hidroxibenzoatos/isolamento & purificação , Hidroxibenzoatos/farmacologia , Estrutura Molecular , Oxilipinas/química , Oxilipinas/isolamento & purificação , Oxilipinas/farmacologia , Sesquiterpenos/química , Sesquiterpenos/isolamento & purificação , Sesquiterpenos/farmacologia , Espectrometria de Massas por Ionização por Electrospray , Relação Estrutura-Atividade
15.
Molecules ; 23(4)2018 Mar 29.
Artigo em Inglês | MEDLINE | ID: mdl-29596368

RESUMO

The seriated extracts of petroleum ether (PE-E), dichloromethane (DCM-E) and methanol extracts (MeOH-E) from the aerial parts of the native South American plant Tetraglochin ameghinoi (Rosaceae), were evaluated regarding their antioxidant and antibacterial activities. The antioxidant properties were evaluated by free radical scavenging methods (DPPH and TEAC), ferric-reducing antioxidant power (FRAP) and lipoperoxidation in erythrocytes (LP), while the antibacterial activity was performed against Gram-positive and Gram-negative bacteria according to the Clinical and Laboratory Standards Institute (CLSI) guidelines. The chemical and biological analyses of this plant are very important since this bush is currently used in traditional medicine as a cholagogue and digestive. The polar MeOH-E showed the highest antioxidant activities (17.70 µg/mL in the DPPH assay, 381.43 ± 22.38 mM TE/g extract in the FRAP assay, 387.76 ± 91.93 mg TE/g extract in the TEAC assay and 93.23 + 6.77% in the LP assay) and it was selected for chromatographic isolation of its components. These components were found to be four acetophenones, including the new phloracetophenone glucoside: 4',6',-dihydroxy-2'-O-(6″-acetyl)-ß-d-glucopyranosylacetophenone or IUPAC name: (6-(2-acetyl-3,5-dihydroxyphenoxy)-3,4,5-trihydroxytetrahydro-2H-pyran-2-yl)methyl acetate, whose structure was elucidated by NMR and MS methods. In addition, twenty-six compounds, including five of these acetophenone derivatives, two sugars, six flavonoids, eleven phenolic acids and two triterpenes, were identified based on UHPLC-OT-MS and PDA analysis on the MeOH-E. The results support the medicinal use of the plant.


Assuntos
Antioxidantes/metabolismo , Metaboloma/fisiologia , Metabolômica , Rosaceae/metabolismo , Antioxidantes/química , Rosaceae/química
16.
Molecules ; 23(9)2018 Sep 15.
Artigo em Inglês | MEDLINE | ID: mdl-30223578

RESUMO

Forty-three metabolites including several methoxylated flavonoids, tremetones, and ent-clerodane diterpenes were accurately identified for the first time in the ethanolic extract of P. quadrangularis by means of hyphenated UHPLC-quadrupole Orbitrap mass spectrometry, and seven isolated compounds were tested regarding gastroprotective activity using the HCl/EtOH-induced lesion model in mice. A new tremetone (compound 6) is reported based on spectroscopic evidence. The isolated clerodanes and tremetones showed gastroprotective activity in a mouse model, evidenced by compound 7 (p-coumaroyloxytremetone), which showed the highest gastroprotective activity (76%), which was higher than the control drug lansoprazole (72%). Our findings revealed that several constituents of this plant have gastroprotective activity, and particularly, p-coumaroyloxytremetone could be considered as a lead molecule to explore new gastroprotective agents. This plant is a rich source of biologically active tremetones and terpenoids which can support the ethnobotanical use of the plant.


Assuntos
Antiulcerosos/administração & dosagem , Asteraceae/química , Benzofuranos/administração & dosagem , Diterpenos Clerodânicos/administração & dosagem , Úlcera Gástrica/tratamento farmacológico , Animais , Antiulcerosos/química , Antiulcerosos/farmacologia , Benzofuranos/química , Benzofuranos/farmacologia , Modelos Animais de Doenças , Diterpenos Clerodânicos/química , Diterpenos Clerodânicos/farmacologia , Etanol/efeitos adversos , Ácido Clorídrico/efeitos adversos , Lansoprazol/administração & dosagem , Lansoprazol/uso terapêutico , Camundongos , Estrutura Molecular , Extratos Vegetais/química , Úlcera Gástrica/induzido quimicamente
17.
Molecules ; 22(11)2017 Oct 30.
Artigo em Inglês | MEDLINE | ID: mdl-29084151

RESUMO

Lichens are symbiotic associations of fungi with microalgae and/or cyanobacteria. Lichens belonging to the Parmeliaceae family comprise 2700 species of lichens, including the Parmotrema genus which is composed of 300 species. The metabolites of this genus include depsides, depsidones, phenolics, polysaccharides, lipids, diphenylethers and dibenzofurans, which are responsible for the biological activities reported including antidiabetic, antihelmintic, anticancer, antioxidant, antibacterial, anti-inflammatory, antimitotic, antitumoral, antifungal, and antioxidant enzyme inhibitory. Due to scarce knowledge of metabolomic profiles of Parmotrema species (P. andinum and P. robustum), a full metabolome study based on ultra-high performance liquid chromatography- diode array detector-electrospray ionization-quadrupole-orbitrap-mass-spectrometry (UHPLC-DAD-ESI-Q-orbitrap MS) was performed for a comprehensive characterization of their substances. From the methanolic extracts of these species, a total of 54 metabolites were identified for the first time using this hyphenated technique, including thirty compounds in P. andinum, and thirty-seven in P. robustum. Moreover, two compounds were not identified as known compounds, and could be new structures, according to our data. This report shows that this technique is effective and accurate for rapid chemical identification of lichen substances and the compounds identified could serve as chemotaxonomic markers to differentiate these ruffle lichens.


Assuntos
Metabolômica/métodos , Metanol/química , Parmeliaceae/química , Cromatografia Líquida de Alta Pressão , Estrutura Molecular , Espectrometria de Massas por Ionização por Electrospray , Espectrometria de Massas em Tandem
18.
Saudi Pharm J ; 25(7): 1032-1039, 2017 Nov.
Artigo em Inglês | MEDLINE | ID: mdl-29158712

RESUMO

High-resolution mass spectrometry is currently used to determine the mass of biologically active compounds in medicinal plants and food and UHPLC-Orbitrap is a relatively new technology that allows fast fingerprinting and metabolomics analysis. Forty-two metabolites including several phenolic acids, flavonoids, coumarines, tremetones and ent-clerodane diterpenes were accurately identified for the first time in the resin of the medicinal plant Parastrephia lucida (Asteraceae) a Chilean native species, commonly called umatola, collected in the pre-cordillera and altiplano regions of northern Chile, by means of UHPLC-PDA-HR-MS. This could be possible by the state of the art technology employed, which allowed well resolved total ion current peaks and the proposal of some biosynthetic relationships between the compounds detected. Some mayor compounds were also isolated using HSCCC. The ethanolic extract showed high total polyphenols content and significant antioxidant capacity. Furthermore, several biological assays were performed that determined the high antioxidant capacity found for the mayor compound isolated from the plant, 11- p-coumaroyloxyltremetone.

19.
Molecules ; 21(3): 245, 2016 Feb 23.
Artigo em Inglês | MEDLINE | ID: mdl-26907248

RESUMO

Mass spectrometry has become a method of choice to characterize bioactive compounds in biological samples because of its sensitivity and selectivity. Hybrid ultra-HPLC hyphenated with Orbitrap mass analyzer is an innovative state of the art technology that allows fast and accurate metabolomic analyses. In this work the metabolites of a Chilean mistletoe endemic to the VIII region of Chile were investigated for the first time using UHPLC mass analysis (UHPLC-PDA-HESI-Orbitrap MS(n)). The anthocyanins, together with the non-pigmented phenolics were fingerprinted and correlated with the antioxidant capacities measured by the bleaching of the DPPH radical, the ferric reducing antioxidant power (FRAP), the superoxide anion scavenging activity assay (SA), and total content of phenolics, flavonoids and anthocyanins measured by spectroscopic methods. Six anthocyanins were identified, and among them, the 3-O-glycosides of delphinidin and cyanidin were the major ones. In addition, several phenolic acids (including feruloylquinic acid, feruloyl glucose, chlorogenic acid) and several flavonols (luteolin, quercetin, apigenin, isorhamnetin and glycoside derivatives) were also identified. The mistletoe leaves showed the highest antioxidant activity as measured by the DPPH radical bleaching, ferric reducing antioxidant power and superoxide anion scavenging activity tests (13.38 ± 0.47 µg/mL, 125.32 ± 5.96 µmolTE/g DW and 84.06 ± 4.59 at 100 µg/mL, respectively).


Assuntos
Antocianinas/química , Antioxidantes/química , Flavonoides/química , Flavonóis/química , Hidroxibenzoatos/química , Erva-de-Passarinho/química , Antocianinas/isolamento & purificação , Antioxidantes/isolamento & purificação , Compostos de Bifenilo/antagonistas & inibidores , Chile , Cromatografia Líquida de Alta Pressão/métodos , Flavonoides/isolamento & purificação , Flavonóis/isolamento & purificação , Hidroxibenzoatos/isolamento & purificação , Picratos/antagonistas & inibidores , Extratos Vegetais/química , Folhas de Planta/química , Espectrometria de Massas em Tandem/métodos
20.
Molecules ; 21(1): 92, 2016 Jan 15.
Artigo em Inglês | MEDLINE | ID: mdl-26784158

RESUMO

A small Chilean variety of pears growing in the town of Toconao, an oasis located at the northeastern edge of the Salar de Atacama, northern Chile, was studied by means of modern PDA and high resolution mass spectral data (UHPLC-PDA-HESI-orbitrap-MS/MS). In addition, the antioxidant features of the fruits were compared with the varieties Packhman's Triumph and Abate Fetel and correlated with the presence of phenolic compounds. The non-pigmented phenolics were fingerprinted and related to the antioxidant capacities measured by the bleaching of the DPPH radical, the ferric reducing antioxidant power (FRAP), the superoxide anion scavenging activity assay (SA), and total content of phenolics and flavonoids measured by spectroscopic methods. The machine allowed a fast separation of 15 min employing a flow rate of 1 mL per minute and could accurately identify 25 compounds, including several isorhamnetin derivatives and phenolic acids, present in the peel and pulps of this Chilean variety for the first time. The compounds were monitored using a wavelength range of 210-800 nm. The native small Chilean pear showed the highest antioxidant activity measured as the bleaching of the DPPH radical, the ferric reducing antioxidant power and superoxide anion scavenging activity (8.61 ± 0.65 µg/mL, 712.63 ± 12.12 micromols trolox equivalents (µmol/TE)/100 g FW, and 82.89% ± 2.52% at 100 µg/mL, respectively).


Assuntos
Antioxidantes/isolamento & purificação , Flavonoides/isolamento & purificação , Frutas/química , Fenóis/isolamento & purificação , Pyrus/química , Quercetina/análogos & derivados , Antioxidantes/química , Antioxidantes/metabolismo , Compostos de Bifenilo/antagonistas & inibidores , Compostos de Bifenilo/química , Chile , Cromatografia Líquida de Alta Pressão/instrumentação , Cromatografia Líquida de Alta Pressão/métodos , Clima Desértico , Flavonoides/biossíntese , Flavonoides/química , Fenóis/química , Fenóis/metabolismo , Picratos/antagonistas & inibidores , Picratos/química , Extratos Vegetais/química , Pyrus/metabolismo , Quercetina/biossíntese , Quercetina/química , Quercetina/isolamento & purificação , Superóxidos/antagonistas & inibidores , Superóxidos/química , Espectrometria de Massas em Tandem/instrumentação , Espectrometria de Massas em Tandem/métodos
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