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1.
Molecules ; 26(15)2021 Jul 28.
Artigo em Inglês | MEDLINE | ID: mdl-34361702

RESUMO

Neurodegenerative diseases have a complex nature which highlights the need for multitarget ligands to address the complementary pathways involved in these diseases. Over the last decade, many innovative curcumin-based compounds have been designed and synthesized, searching for new derivatives having anti-amyloidogenic, inhibitory of tau formation, as well as anti-neuroinflammation, antioxidative, and AChE inhibitory activities. Regarding our experience studying 3-substituted coumarins with interesting properties for neurodegenerative diseases, our aim was to synthesize a new series of curcumin-coumarin hybrid analogues and evaluate their activity. Most of the 3-(7-phenyl-3,5-dioxohepta-1,6-dien-1-yl)coumarin derivatives 11-18 resulted in moderated inhibitors of hMAO isoforms and AChE and BuChE activity. Some of them are also capable of scavenger the free radical DPPH. Furthermore, compounds 14 and 16 showed neuroprotective activity against H2O2 in SH-SY5Y cell line. Nanoparticles formulation of these derivatives improved this property increasing the neuroprotective activity to the nanomolar range. Results suggest that by modulating the substitution pattern on both coumarin moiety and phenyl ring, ChE and MAO-targeted derivatives or derivatives with activity in cell-based phenotypic assays can be obtained.


Assuntos
Antioxidantes/síntese química , Inibidores da Colinesterase/síntese química , Cumarínicos/síntese química , Curcumina/análogos & derivados , Inibidores da Monoaminoxidase/síntese química , Fármacos Neuroprotetores/síntese química , Acetilcolinesterase/metabolismo , Animais , Antioxidantes/farmacologia , Compostos de Bifenilo/antagonistas & inibidores , Butirilcolinesterase/metabolismo , Linhagem Celular Tumoral , Sobrevivência Celular/efeitos dos fármacos , Inibidores da Colinesterase/farmacologia , Cumarínicos/farmacologia , Curcumina/farmacologia , Proteínas Ligadas por GPI/metabolismo , Humanos , Peróxido de Hidrogênio/antagonistas & inibidores , Peróxido de Hidrogênio/farmacologia , Monoaminoxidase/metabolismo , Inibidores da Monoaminoxidase/farmacologia , Córtex Motor/citologia , Córtex Motor/enzimologia , Nanopartículas/química , Neurônios/citologia , Neurônios/efeitos dos fármacos , Neurônios/enzimologia , Fármacos Neuroprotetores/farmacologia , Picratos/antagonistas & inibidores , Cultura Primária de Células , Ratos , Relação Estrutura-Atividade
2.
Molecules ; 26(15)2021 Jul 28.
Artigo em Inglês | MEDLINE | ID: mdl-34361727

RESUMO

Enzymatic pretreatment of seeds is a novel approach that enhances the health benefits of the extracted oil. The study investigated the influence of the enzymatic pretreatment of seeds on the quality of oil from different pomegranate cultivars. The quality of the ultrasound-assisted (and ethanol-extracted) oil was studied, with respect to the refractive index (RI), yellowness index (YI), conjugated dienes (K232), peroxide value (PV) ρ-anisidine value (AV), total oxidation value (TOTOX), total carotenoid content (TCC), total phenolic compounds (TPC), fatty acid composition, phytosterol composition, ferric reducing antioxidant power (FRAP), and 2.2-diphenyl-1-picryl hydrazyl (DPPH) radical scavenging capacity. The seeds of three different pomegranate cultivars ('Wonderful', 'Herskawitz', and 'Acco') were digested with an equal mixture of Pectinex Ultra SPL, Flavourzyme 100 L, and cellulase crude enzymes, at a concentration, pH, temperature, and time of 1.7%, 4.5, 40 °C, and 5 h, respectively. Enzymatic pretreatment of PS increased oil yield, PV, TPC, TCC, and DPPH radical scavenging capacity, but decreased the YI. The levels of K232, AV and TOTOX, fatty acids, phytosterols, RI, and FRAP, were not significantly affected by enzymatic pretreatment of PS. Principal component analysis (PCA) established that oil extracted from the 'Acco' seed after enzymatic pretreatment had higher yield, TPC, TCC, and DPPH radical scavenging capacity. Therefore, enzyme-pretreated 'Acco' pomegranate fruit seed is a source of quality seed oil with excellent antioxidant properties.


Assuntos
Antioxidantes/isolamento & purificação , Hidrolases/química , Extração Líquido-Líquido/métodos , Óleos Vegetais/isolamento & purificação , Romã (Fruta)/química , Sementes/química , Antioxidantes/química , Antioxidantes/farmacologia , Compostos de Bifenilo/antagonistas & inibidores , Carotenoides/química , Carotenoides/isolamento & purificação , Carotenoides/farmacologia , Etanol/química , Ácidos Graxos/química , Ácidos Graxos/isolamento & purificação , Ácidos Graxos/farmacologia , Frutas/química , Alimento Funcional/provisão & distribuição , Humanos , Oxirredução , Fenóis/química , Fenóis/isolamento & purificação , Fenóis/farmacologia , Fitosteróis/química , Fitosteróis/isolamento & purificação , Fitosteróis/farmacologia , Picratos/antagonistas & inibidores , Óleos Vegetais/química , Análise de Componente Principal , Solventes/química , Sonicação/métodos
3.
Biomolecules ; 11(8)2021 07 28.
Artigo em Inglês | MEDLINE | ID: mdl-34439780

RESUMO

The aim of the study was to investigate changes in the content of biologically active compounds during the fermentation and aging of natural meads with the addition of three Cornelian cherry juices from three cultivars: 'Koralovyi', 'Podolski' and 'Yantarnyi', in the amount of 10% v/v. After the fermentation process the content of gallic and ellagic acids significantly increased, in relation to wort. Whereas the greatest losses were observed among unstable anthocyanins. The three-month aging process also reduced the content of the analyzed compounds except for ellagic acid, the content of which increased by up to 90%. The content of biologically active compounds, including iridoids and antioxidant phenolics, are constantly changing in the process of fermentation and aging of fruit meads. The studies proved that the addition of Cornelian cherry juice allows significantly enriched classic meads with new biologically active compounds, such as: exceptional iridoids (loganic acid, cornuside, loganine, sweroside), flavonols, phenolic acids and anthocyanins.


Assuntos
Bebidas Alcoólicas/análise , Tecnologia de Alimentos/métodos , Mel/análise , Iridoides/química , Fenóis/química , Saccharomyces/metabolismo , Antocianinas/biossíntese , Antocianinas/química , Antocianinas/classificação , Antocianinas/isolamento & purificação , Antioxidantes/química , Antioxidantes/classificação , Antioxidantes/isolamento & purificação , Antioxidantes/metabolismo , Benzotiazóis/antagonistas & inibidores , Compostos de Bifenilo/antagonistas & inibidores , Ácido Elágico/química , Ácido Elágico/isolamento & purificação , Ácido Elágico/metabolismo , Fermentação , Flavonóis/química , Flavonóis/classificação , Flavonóis/isolamento & purificação , Flavonóis/metabolismo , Frutas/química , Sucos de Frutas e Vegetais/análise , Ácido Gálico/química , Ácido Gálico/isolamento & purificação , Ácido Gálico/metabolismo , Humanos , Iridoides/classificação , Iridoides/isolamento & purificação , Iridoides/metabolismo , Fenóis/classificação , Fenóis/isolamento & purificação , Fenóis/metabolismo , Picratos/antagonistas & inibidores , Prunus avium/química , Ácido Quínico/análogos & derivados , Ácido Quínico/química , Ácido Quínico/isolamento & purificação , Ácido Quínico/metabolismo , Ácidos Sulfônicos/antagonistas & inibidores
4.
Molecules ; 26(15)2021 Jul 29.
Artigo em Inglês | MEDLINE | ID: mdl-34361742

RESUMO

The biological activities of propolis samples are the result of many bioactive compounds present in the propolis. The aim of the present study was to determine the various chemical compounds of some selected propolis samples collected from Palestine and Morocco by the High-Performance Liquid Chromatography-Photodiode Array Detection (HPLC-PDA) method, as well as the antioxidant and antibacterial activities of this bee product. The chemical analysis of propolis samples by HPLC-PDA shows the cinnamic acid content in the Palestinian sample is higher compared to that in Moroccan propolis. The results of antioxidant activity demonstrated an important free radical scavenging activity (2,2-Diphenyl-1-picrylhydrazyl (DPPH); 2,2'-azino-bis 3-ethylbenzothiazoline-6-sulphonic acid (ABTS) and reducing power assays) with EC50 values ranging between 0.02 ± 0.001 and 0.14 ± 0.01 mg/mL. Additionally, all tested propolis samples possessed a moderate antibacterial activity against bacterial strains. Notably, Minimum Inhibitory Concentrations (MICs) values ranged from 0.31 to 2.50 mg/mL for Gram-negative bacterial strains and from 0.09 to 0.125 mg/mL for Gram-positive bacterial strains. The S2 sample from Morocco and the S4 sample from Palestine had the highest content of polyphenol level. Thus, the strong antioxidant and antibacterial properties were apparently due to the high total phenolic and flavone/flavonol contents in the samples. As a conclusion, the activities of propolis samples collected from both countries are similar, while the cinnamic acid in the Palestinian samples was more than that of the Moroccan samples.


Assuntos
Antibacterianos/química , Antioxidantes/química , Cinamatos/química , Fenóis/química , Própole/química , Animais , Antibacterianos/isolamento & purificação , Antibacterianos/farmacologia , Antioxidantes/isolamento & purificação , Antioxidantes/farmacologia , Abelhas/fisiologia , Benzotiazóis/antagonistas & inibidores , Compostos de Bifenilo/antagonistas & inibidores , Cinamatos/isolamento & purificação , Cinamatos/farmacologia , Bactérias Gram-Negativas/efeitos dos fármacos , Bactérias Gram-Negativas/crescimento & desenvolvimento , Bactérias Gram-Positivas/efeitos dos fármacos , Bactérias Gram-Positivas/crescimento & desenvolvimento , Testes de Sensibilidade Microbiana , Oriente Médio , Marrocos , Fenóis/isolamento & purificação , Fenóis/farmacologia , Picratos/antagonistas & inibidores , Polifenóis , Análise de Componente Principal , Própole/isolamento & purificação , Ácidos Sulfônicos/antagonistas & inibidores
5.
Molecules ; 26(15)2021 Jul 29.
Artigo em Inglês | MEDLINE | ID: mdl-34361745

RESUMO

The edible parts of the plants Camellia sinensis, Vitis vinifera and Withania somnifera were extensively used in ancient practices such as Ayurveda, owing to their potent biomedical significance. They are very rich in secondary metabolites such as polyphenols, which are very good antioxidants and exhibit anti-carcinogenic properties. This study aims to evaluate the anti-cancerous properties of these plant crude extracts on human liver cancer HepG2 cells. The leaves of Camellia sinensis, Withania somnifera and the seeds of Vitis vinifera were collected and methanolic extracts were prepared. Then, these extracts were subjected to DPPH, α- amylase assays to determine the antioxidant properties. A MTT assay was performed to investigate the viability of the extracts of HepG2 cells, and the mode of cell death was detected by Ao/EtBr staining and flow cytometry with PI Annexin- V FITC dual staining. Then, the protein expression of BAX and BCl2 was studied using fluorescent dye to determine the regulation of the BAX and BCl2 genes. We observed that all the three extracts showed the presence of bioactive compounds such as polyphenols or phytochemicals. The W. somnifera bioactive compounds were found to have the highest anti-proliferative activity on human liver cancer cells.


Assuntos
Antineoplásicos Fitogênicos/farmacologia , Antioxidantes/farmacologia , Camellia sinensis/química , Regulação Neoplásica da Expressão Gênica/efeitos dos fármacos , Vitis/química , Withania/química , Alcaloides/química , Alcaloides/isolamento & purificação , Antineoplásicos Fitogênicos/química , Antineoplásicos Fitogênicos/isolamento & purificação , Antioxidantes/química , Antioxidantes/isolamento & purificação , Compostos de Bifenilo/antagonistas & inibidores , Compostos de Bifenilo/química , Morte Celular/efeitos dos fármacos , Flavonoides/química , Flavonoides/isolamento & purificação , Células Hep G2 , Humanos , Picratos/antagonistas & inibidores , Picratos/química , Extratos Vegetais/química , Folhas de Planta/química , Proteínas Proto-Oncogênicas c-bcl-2/genética , Proteínas Proto-Oncogênicas c-bcl-2/metabolismo , Sementes/química , Transdução de Sinais , Taninos/química , Taninos/isolamento & purificação , Terpenos/química , Terpenos/isolamento & purificação , alfa-Amilases/genética , alfa-Amilases/metabolismo , Proteína X Associada a bcl-2/genética , Proteína X Associada a bcl-2/metabolismo
6.
Molecules ; 26(15)2021 Jul 29.
Artigo em Inglês | MEDLINE | ID: mdl-34361759

RESUMO

Croton ferrugineus Kunth is an endemic species of Ecuador used in traditional medicine both for wound healing and as an antiseptic. In this study, fresh Croton ferrugineus leaves were collected and subjected to hydrodistillation for extraction of the essential oil. The chemical composition of the essential oil was determined by gas chromatography equipped with a flame ionization detector and gas chromatography coupled to a mass spectrometer using a non-polar and a polar chromatographic column. The antibacterial activity was assayed against three Gram-positive bacteria, one Gram-negative bacterium and one dermatophyte fungus. The radical scavenging properties of the essential oil was evaluated by means of DPPH and ABTS assays. The chemical analysis allowed us to identify thirty-five compounds representing more than 99.95% of the total composition. Aliphatic sesquiterpene hydrocarbon trans-caryophyllene was the main constituent with 20.47 ± 1.25%. Other main compounds were myrcene (11.47 ± 1.56%), ß-phellandrene (10.55 ± 0.02%), germacrene D (7.60 ± 0.60%), and α-humulene (5.49 ± 0.38%). The essential oil from Croton ferrugineus presented moderate activity against Candida albicans (ATCC 10231) with an MIC of 1000 µg/mL, a scavenging capacity SC50 of 901 ± 20 µg/mL with the ABTS method, and very strong antiglucosidase activity with an IC50 of 146 ± 20 µg/mL.


Assuntos
Anti-Infecciosos/química , Antioxidantes/química , Croton/química , Inibidores Enzimáticos/química , Óleos Voláteis/química , Folhas de Planta/química , Monoterpenos Acíclicos/química , Monoterpenos Acíclicos/isolamento & purificação , Alcenos/química , Alcenos/isolamento & purificação , Anti-Infecciosos/isolamento & purificação , Anti-Infecciosos/farmacologia , Antioxidantes/isolamento & purificação , Antioxidantes/farmacologia , Benzotiazóis/antagonistas & inibidores , Compostos de Bifenilo/antagonistas & inibidores , Candida albicans/efeitos dos fármacos , Candida albicans/crescimento & desenvolvimento , Monoterpenos Cicloexânicos/química , Monoterpenos Cicloexânicos/isolamento & purificação , Inibidores Enzimáticos/isolamento & purificação , Inibidores Enzimáticos/farmacologia , Escherichia coli/efeitos dos fármacos , Escherichia coli/crescimento & desenvolvimento , Bactérias Gram-Positivas/efeitos dos fármacos , Bactérias Gram-Positivas/crescimento & desenvolvimento , Testes de Sensibilidade Microbiana , Sesquiterpenos Monocíclicos/química , Sesquiterpenos Monocíclicos/isolamento & purificação , Picratos/antagonistas & inibidores , Sesquiterpenos Policíclicos/química , Sesquiterpenos Policíclicos/isolamento & purificação , Sesquiterpenos de Germacrano/química , Sesquiterpenos de Germacrano/isolamento & purificação , Ácidos Sulfônicos/antagonistas & inibidores , alfa-Glucosidases/química
7.
Molecules ; 26(15)2021 Jul 29.
Artigo em Inglês | MEDLINE | ID: mdl-34361766

RESUMO

Hedyosmum racemosum (Ruiz & Pav.) G. is a native species of Ecuador used in traditional medicine for treatment of rheumatism, bronchitis, cold, cough, asthma, bone pain, and stomach pain. In this study, fresh H. racemosum leaves of male and female specimens were collected and subjected to hydrodistillation for the extraction of the essential oil. The chemical composition of male and female essential oil was determined by gas chromatography-gas chromatography equipped with a flame ionization detector and coupled to a mass spectrometer using a non-polar and a polar chromatographic column. The antibacterial activity was assayed against five Gram-positive and two Gram-negative bacteria, and two dermatophytes fungi. The scavenging radical properties of the essential oil were evaluated by DPPH and ABTS assays. The chemical analysis allowed us to identify forty-three compounds that represent more than 98% of the total composition. In the non-polar and polar column, α-phellandrene was the principal constituent in male (28.24 and 25.90%) and female (26.47 and 23.90%) essential oil. Other main compounds were methyl chavicol, germacrene D, methyl eugenol, and α-pinene. Female essential oil presented a strong activity against Klebsiella pneumoniae (ATCC 9997) with an minimum inhibitory concentration (MIC) of 500 µg/mL and a scavenging capacity SC50 of 800 µg/mL.


Assuntos
Antibacterianos/química , Antioxidantes/química , Monoterpenos Cicloexânicos/química , Magnoliopsida/química , Óleos Voláteis/química , Derivados de Alilbenzenos/química , Derivados de Alilbenzenos/isolamento & purificação , Anisóis/química , Anisóis/isolamento & purificação , Antibacterianos/isolamento & purificação , Antibacterianos/farmacologia , Antioxidantes/isolamento & purificação , Antioxidantes/farmacologia , Arthrodermataceae/efeitos dos fármacos , Arthrodermataceae/crescimento & desenvolvimento , Benzotiazóis/antagonistas & inibidores , Monoterpenos Bicíclicos/química , Monoterpenos Bicíclicos/isolamento & purificação , Compostos de Bifenilo/antagonistas & inibidores , Monoterpenos Cicloexânicos/isolamento & purificação , Equador , Eugenol/análogos & derivados , Eugenol/química , Eugenol/isolamento & purificação , Feminino , Bactérias Gram-Negativas/efeitos dos fármacos , Bactérias Gram-Negativas/crescimento & desenvolvimento , Bactérias Gram-Positivas/efeitos dos fármacos , Bactérias Gram-Positivas/crescimento & desenvolvimento , Humanos , Magnoliopsida/metabolismo , Masculino , Testes de Sensibilidade Microbiana , Picratos/antagonistas & inibidores , Folhas de Planta/química , Plantas Medicinais , Sesquiterpenos de Germacrano/química , Sesquiterpenos de Germacrano/isolamento & purificação , Fatores Sexuais , Ácidos Sulfônicos/antagonistas & inibidores
8.
Molecules ; 26(15)2021 Jul 30.
Artigo em Inglês | MEDLINE | ID: mdl-34361776

RESUMO

In this study, we examined aqueous extracts of the edible mushrooms Pleurotus ostreatus (oyster mushroom) and Lentinula edodes (shiitake mushroom). Proteome analysis was conducted using LC-Triple TOF-MS and showed the expression of 753 proteins by Pleurotus ostreatus, and 432 proteins by Lentinula edodes. Bioactive peptides: Rab GDP dissociation inhibitor, superoxide dismutase, thioredoxin reductase, serine proteinase and lectin, were identified in both mushrooms. The extracts also included promising bioactive compounds including phenolics, flavonoids, vitamins and amino acids. The extracts showed promising antiviral activities, with a selectivity index (SI) of 4.5 for Pleurotus ostreatus against adenovirus (Ad7), and a slight activity for Lentinula edodes against herpes simplex-II (HSV-2). The extracts were not cytotoxic to normal human peripheral blood mononuclear cells (PBMCs). On the contrary, they showed moderate cytotoxicity against various cancer cell lines. Additionally, antioxidant activity was assessed using DPPH radical scavenging, ABTS radical cation scavenging and ORAC assays. The two extracts showed potential antioxidant activities, with the maximum activity seen for Pleurotus ostreatus (IC50 µg/mL) = 39.46 ± 1.27 for DPPH; 11.22 ± 1.81 for ABTS; and 21.40 ± 2.20 for ORAC assays. This study encourages the use of these mushrooms in medicine in the light of their low cytotoxicity on normal PBMCs vis à vis their antiviral, antitumor and antioxidant capabilities.


Assuntos
Antineoplásicos/química , Antioxidantes/química , Antivirais/química , Proteínas Fúngicas/química , Pleurotus/química , Proteoma/química , Cogumelos Shiitake/química , Aminoácidos/química , Aminoácidos/isolamento & purificação , Antineoplásicos/isolamento & purificação , Antineoplásicos/farmacologia , Antioxidantes/isolamento & purificação , Antioxidantes/farmacologia , Antivirais/isolamento & purificação , Antivirais/farmacologia , Benzotiazóis/antagonistas & inibidores , Compostos de Bifenilo/antagonistas & inibidores , Linhagem Celular Tumoral , Sobrevivência Celular/efeitos dos fármacos , Misturas Complexas/química , Flavonoides/química , Flavonoides/isolamento & purificação , Proteínas Fúngicas/classificação , Proteínas Fúngicas/isolamento & purificação , Humanos , Lectinas/química , Lectinas/isolamento & purificação , Leucócitos Mononucleares/citologia , Leucócitos Mononucleares/efeitos dos fármacos , Especificidade de Órgãos , Fenóis/química , Fenóis/isolamento & purificação , Picratos/antagonistas & inibidores , Pleurotus/metabolismo , Cultura Primária de Células , Proteoma/classificação , Proteoma/isolamento & purificação , Serina Proteases/química , Serina Proteases/isolamento & purificação , Cogumelos Shiitake/metabolismo , Ácidos Sulfônicos/antagonistas & inibidores , Superóxido Dismutase/química , Superóxido Dismutase/isolamento & purificação , Tiorredoxina Dissulfeto Redutase/química , Tiorredoxina Dissulfeto Redutase/isolamento & purificação , Vitaminas/química , Vitaminas/isolamento & purificação , Água/química
9.
J Med Chem ; 64(13): 9302-9320, 2021 07 08.
Artigo em Inglês | MEDLINE | ID: mdl-34152756

RESUMO

A series of multitarget-directed ligands (MTDLs) was designed by functionalizing a pseudo-irreversible butyrylcholinesterase (BChE) inhibitor. The obtained hybrids were investigated in vitro regarding their hBChE and hAChE inhibition, their enzyme kinetics, and their antioxidant physicochemical properties (DPPH, ORAC, metal chelating). In addition, in vitro assays were applied to investigate antioxidant effects using murine hippocampal HT22 cells and immunomodulatory effects on the murine microglial N9 cell line. The MTDLs retained their antioxidative properties compared to the parent antioxidant-moieties in vitro and the inhibition of hBChE was maintained in the submicromolar range. Representative compounds were tested in a pharmacological Alzheimer's disease (AD) mouse model and demonstrated very high efficacy at doses as low as 0.1 mg/kg. The most promising compound was also tested in BChE-/- mice and showed reduced efficacy. In vivo neuroprotection by BChE inhibition can be effectively enhanced by incorporation of structurally diverse antioxidant moieties.


Assuntos
Doença de Alzheimer/tratamento farmacológico , Antioxidantes/farmacologia , Inibidores da Colinesterase/farmacologia , Modelos Animais de Doenças , Fármacos Neuroprotetores/farmacologia , Acetilcolinesterase/metabolismo , Doença de Alzheimer/metabolismo , Animais , Antioxidantes/síntese química , Antioxidantes/química , Compostos de Bifenilo/antagonistas & inibidores , Butirilcolinesterase/deficiência , Butirilcolinesterase/metabolismo , Sobrevivência Celular/efeitos dos fármacos , Células Cultivadas , Inibidores da Colinesterase/síntese química , Inibidores da Colinesterase/química , Cromanos/síntese química , Cromanos/química , Cromanos/farmacologia , Cinamatos/síntese química , Cinamatos/química , Cinamatos/farmacologia , Relação Dose-Resposta a Droga , Humanos , Masculino , Melatonina/síntese química , Melatonina/química , Melatonina/farmacologia , Camundongos , Estrutura Molecular , Fármacos Neuroprotetores/síntese química , Fármacos Neuroprotetores/química , Picratos/antagonistas & inibidores , Relação Estrutura-Atividade
10.
Chem Biodivers ; 18(7): e2100167, 2021 Jul.
Artigo em Inglês | MEDLINE | ID: mdl-34145749

RESUMO

As part of a project aimed at investigating the Matthiola taxa endemic to Sicily (Italy), this study focused on Matthiola incana, an edible species used in the traditional medicine of various countries. Herein, the characterization of phenolic and volatile compounds, the antioxidant capacity in vitro (1,1-diphenyl-2-picrylhydrazil (DPPH), reducing power and Fe2+ chelating activity assays) and the toxicity test (Artemia salina lethality bioassay) of the hydroalcoholic extracts from the aerial parts of M. incana subsp. rupestris from Mt. Pellegrino (Palermo) and Mt. Erice (Trapani), and of M. incana subsp. pulchella are reported. The results are compared with those previously shown for M. incana subsp. incana, to achieve a comprehensive overview of the three subspecies. The HPLC-PDA/ESI-MS and SPME-GC/MS analyses led to the identification of 13 phenolics and 54 volatile compounds. Differences in the qualitative-quantitative profile of these phytochemicals have been highlighted between the M. incana subspecies. The antioxidant tests showed different activity for the extracts, which were found to possess better chelating properties. At last, none of the tested extracts displayed toxicity against brine shrimp larvae. These findings enrich the knowledge on the Matthiola taxa growing wild in Sicily, both from the strictly systematic point of view and for the possible applications as sources bioactive compounds that can be used in the nutraceutical field.


Assuntos
Antioxidantes/farmacologia , Brassicaceae/química , Compostos Fitoquímicos/farmacologia , Componentes Aéreos da Planta/química , Extratos Vegetais/farmacologia , Animais , Antioxidantes/química , Antioxidantes/isolamento & purificação , Artemia , Compostos de Bifenilo/antagonistas & inibidores , Compostos Fitoquímicos/química , Compostos Fitoquímicos/isolamento & purificação , Picratos/antagonistas & inibidores , Extratos Vegetais/química , Extratos Vegetais/isolamento & purificação , Sicília
11.
Chem Biodivers ; 18(7): e2100245, 2021 Jul.
Artigo em Inglês | MEDLINE | ID: mdl-33989453

RESUMO

The aim of this research was to investigate and compare the antioxidant, anti-tyrosinase, anti-aging, and anti-inflammatory activities of 16 herbal extracts for topical application in cosmetic/cosmeceutical products. Herbal plant materials were extracted by infusion in boiled water for 15 min. The total phenolic content and total flavonoid content of each extract were investigated by the Folin-Ciocalteu and aluminum chloride methods, respectively. Antioxidant activities were investigated using 2,2'-diphenyl-1-picrylhydrazyl and a ferric reducing antioxidant power assay. Anti-tyrosinase and anti-aging activities were investigated using an in vitro enzymatic-spectrophotometric method. Anti-inflammatory activities were investigated using an enzyme-linked immunosorbent assay. The findings show that the Stevia rebaudiana extract has the most significant levels of both phenols and flavonoids (p<0.05). The S. rebaudiana, Rosa damascene, and Phyllanthus emblica extracts possessed the most significant antioxidant activities (p<0.05) and a promising whitening effect with moderate anti-tyrosinase activities. Furthermore, the Echinacea purpurea extract possessed the most significant anti-collagenase (78.5±0.0 %), anti-elastase (69.0±1.4 %), and anti-hyaluronidase activity (64.2±0.3 %). The Morus alba extract possessed the most significant anti-inflammatory activity since it could inhibit the secretion of interleukin-6 and tumor necrosis factor-α (p<0.05). Therefore, these herbal extracts have promising skin benefits and have potential for use as active ingredients in cosmetic/cosmeceutical products.


Assuntos
Envelhecimento/efeitos dos fármacos , Anti-Inflamatórios/farmacologia , Antioxidantes/farmacologia , Inibidores Enzimáticos/farmacologia , Monofenol Mono-Oxigenase/antagonistas & inibidores , Extratos Vegetais/farmacologia , Anti-Inflamatórios/química , Anti-Inflamatórios/isolamento & purificação , Antioxidantes/química , Antioxidantes/isolamento & purificação , Compostos de Bifenilo/antagonistas & inibidores , Echinacea/química , Inibidores Enzimáticos/química , Inibidores Enzimáticos/isolamento & purificação , Humanos , Monofenol Mono-Oxigenase/metabolismo , Phyllanthus emblica/química , Picratos/antagonistas & inibidores , Extratos Vegetais/química , Extratos Vegetais/isolamento & purificação , Rosa/química , Pele/efeitos dos fármacos , Stevia/química
12.
Chem Biodivers ; 18(7): e2001068, 2021 Jul.
Artigo em Inglês | MEDLINE | ID: mdl-33998146

RESUMO

In Brazil, there is a large diversity of species of small edible fruits that are considered sources of nutrients and functional properties. They present a high innovation domain for the pharmaceutical, cosmetic and food industries due to their health-promoting properties. Edible fruits from Brosimum gaudichaudii (Moraceae) are widely consumed and used in folk medicine and in feed by the population of the Brazilian Cerrado. Nevertheless, detailed information on the chemical fingerprint, antiradical activity and safety aspects of these fruits is still unknown. Thus, the aim of this work was to investigate the bioactive compounds of hydroethanolic extracts of fruits from Brosimum gaudichaudii using high-performance liquid chromatography combined with mass spectrometry using electrospray ionization (HPLC ESI-MS). Eighteen different compounds, including flavonoids, coumarins, arylbenzofurans, terpenoids, stilbenes, xanthones and esters, were detected. Moreover, the study indicated that the hydroethanolic extract of fruits from B. gaudichaudii presented low scavenging activity against 2,2-diphenyl-1-picrylhydrazyl radicals (IC50 >800 µg mL-1 ) and was cytotoxic (IC50 <30 µg mL-1 ) in Chinese hamster ovary cells (CHO-K1) by an in vitro assay. This is the first report of the chemical profile, antioxidant activity and cytotoxic properties of the hydroethanolic extract of fruits from B. gaudichaudii.


Assuntos
Antineoplásicos Fitogênicos/farmacologia , Antioxidantes/farmacologia , Moraceae/química , Extratos Vegetais/farmacologia , Animais , Antineoplásicos Fitogênicos/química , Antineoplásicos Fitogênicos/isolamento & purificação , Antioxidantes/química , Antioxidantes/isolamento & purificação , Compostos de Bifenilo/antagonistas & inibidores , Brasil , Linhagem Celular , Sobrevivência Celular/efeitos dos fármacos , Cricetulus , Frutas/química , Humanos , Estrutura Molecular , Picratos/antagonistas & inibidores , Extratos Vegetais/química , Extratos Vegetais/isolamento & purificação , Plantas Comestíveis/química
13.
Chem Biodivers ; 18(7): e2100238, 2021 Jul.
Artigo em Inglês | MEDLINE | ID: mdl-34033700

RESUMO

Plants belonging to Euphorbia L. genus are considered very interesting from a medicinal point of view due to their diverse metabolites and bioactivities. The essential oil (EO) of Euphorbia mauritanica L. is not studied up to date. Therefore, the present study aimed to explore the chemical profile of this EO and evaluate its antioxidant, cytotoxic, and allelopathic potentialities. The EO was extracted from the whole plant via hydrodistillation and then, analyzed by gas chromatography/mass spectrometry (GC/MS). The correlation of E. mauritanica with the other Euphorbia plants was established using chemometric analysis. The antioxidant activity was determined based on scavenging of the free radical, 1,1-diphenyl-2-picrylhydrazyl (DPPH) and 2,2'-azinobis(3-ethylbenzothiazoline-6-sulfonic acid) (ABTS). The anti-proliferation of the EO on the Hep G2 and MCF-7 cells was evaluated. Finally the allelopathic activity of the EO was assessed against the two noxious weeds, Dactyloctenium aegyptium and Urospermum picroides. Forty-one compounds were identified using GC/MS analysis, with an abundance of terpenoids (91.54 %) that were categorized into mono- (30.75 %), sesqui- (15.23 %), and diterpenes (45.56 %). Interestingly, the results revealed the preponderance of diterpenoid constituents although they are rarely found in the EOs of the plant kingdom. The major compounds were (3E)-cembrene A (18.66 %), verticiol (17.05 %), limonene (7.91 %), eucalyptol (7.26 %), α-pinene (5.61 %), neo-cembrene A (3.52 %), kaur-16-ene (3.24 %), and cembrene (3.09 %). The EO showed moderate antioxidant activity where it attained IC50 values of 83.34 and 64.21 µg mL-1 for DPPH and ABTS compared to 23.01 and 19.23 µg mL-1 for ascorbic acid as standard, respectively. The EO exhibited very weak cytotoxic effect on MCF-7 and Hep G2 cells. The EO showed significant allelopathic activities against the weeds D. aegyptium and U. picroides in a concentration-dependent manner. EO was found more effective against U. picroides than D. aegyptium with IC50 values of 0.79, 0.45, and 0.67 mg mL-1 and 1.17, 0.55, and 1.08 mg mL-1 for germination, root, and shoot growth, respectively. Due to the high content of diterpenes in E. mauritanica, further study is recommended for more characterization of pure forms of the identified diterpenes as well as evaluating their bioactivity either solely or synergistically.


Assuntos
Alelopatia/efeitos dos fármacos , Antineoplásicos Fitogênicos/farmacologia , Antioxidantes/farmacologia , Diterpenos/farmacologia , Euphorbia/química , Óleos Voláteis/química , Antineoplásicos Fitogênicos/química , Antineoplásicos Fitogênicos/isolamento & purificação , Antioxidantes/química , Antioxidantes/isolamento & purificação , Benzotiazóis/antagonistas & inibidores , Compostos de Bifenilo/antagonistas & inibidores , Proliferação de Células/efeitos dos fármacos , Sobrevivência Celular/efeitos dos fármacos , Diterpenos/química , Diterpenos/isolamento & purificação , Ensaios de Seleção de Medicamentos Antitumorais , Humanos , Picratos/antagonistas & inibidores , Ácidos Sulfônicos/antagonistas & inibidores , Células Tumorais Cultivadas
14.
Chem Biodivers ; 18(6): e2100053, 2021 Jun.
Artigo em Inglês | MEDLINE | ID: mdl-33932088

RESUMO

The Cistaceae family is well represented in Sardinia, and the Cistus genus is widely used in traditional medicine. Nowadays only few studies have been performed on this genus vegetating in Sardinia in spite of its ethnobotanical importance. Moreover, in the past there have been conflicting opinions among botanists for the exact assignment of the species growing in Sardinia. We started several years ago to carried out studies on this genus and in the present study was to evaluate the in vitro activity of several samples of Cistus salvifolius L., Cistus monspeliensis L., and Cistus albidus L. collected in Sardinia as antimicrobial agents against Escherichia coli, Staphylococcus aureus, and four Candida species and their antioxidant activity using DPPH, ABTS, and FRAP assays. Furthermore, the phenolic content and composition of the extracts were first evaluated. Using statistical multivariate analysis on the complete metabolomics profile of all Cistus species growing wild in Sardinia, we confirmed the botanical classification, and we observed an interesting correlation between metabolomics profile and antioxidant activity.


Assuntos
Antibacterianos/farmacologia , Antifúngicos/farmacologia , Antioxidantes/farmacologia , Cistus/química , Fenóis/farmacologia , Extratos Vegetais/farmacologia , Antibacterianos/análise , Antibacterianos/metabolismo , Antifúngicos/análise , Antifúngicos/metabolismo , Antioxidantes/análise , Antioxidantes/metabolismo , Benzotiazóis/antagonistas & inibidores , Compostos de Bifenilo/antagonistas & inibidores , Candida/efeitos dos fármacos , Escherichia coli/efeitos dos fármacos , Itália , Metabolômica , Testes de Sensibilidade Microbiana , Análise Multivariada , Fenóis/análise , Fenóis/metabolismo , Picratos/antagonistas & inibidores , Extratos Vegetais/análise , Extratos Vegetais/metabolismo , Staphylococcus aureus/efeitos dos fármacos , Ácidos Sulfônicos/antagonistas & inibidores
15.
Future Med Chem ; 13(11): 975-991, 2021 06.
Artigo em Inglês | MEDLINE | ID: mdl-33896215

RESUMO

Background: Considering emerging drug resistance in microbes, this work is focused on the synthesis of azole hybrids as novel antimicrobials. Materials & methods: The triazole derivatives were prepared using azide alkyne cycloaddition reaction. The antimicrobial potential of these compounds was evaluated by serial dilution method. Results: A series of azole hybrids containing benzimidazole-1,2,3-triazole skeleton was designed and synthesized via click reaction. Compound 4s showed notable antimicrobial activity against Staphylococcus aureus and Candida albicans (MIC 0.0165 µmol/ml), and 4q gives remarkable radical scavenging activity (IC50 0.0092 µmol/ml). The compounds 4a, 4k, 4o, 4s, 4x. 4m, 4n, 4s, 4t and 4x are commendable antibacterial and antifungal molecules, even better than established drugs. Molecular docking reveals that compound 4s binds with tyrosyl-tRNA synthetase residues through two H-bonds. Conclusion: Compounds 4s and 4k may be considered valuable lead compounds for further optimization as antimicrobial drugs.


Assuntos
Antibacterianos/farmacologia , Antifúngicos/farmacologia , Antioxidantes/farmacologia , Azóis/farmacologia , Candida albicans/efeitos dos fármacos , Desenvolvimento de Medicamentos , Staphylococcus aureus/efeitos dos fármacos , Antibacterianos/síntese química , Antibacterianos/química , Antifúngicos/síntese química , Antifúngicos/química , Antioxidantes/síntese química , Antioxidantes/química , Azóis/síntese química , Azóis/química , Compostos de Bifenilo/antagonistas & inibidores , Testes de Sensibilidade Microbiana , Simulação de Acoplamento Molecular , Estrutura Molecular , Picratos/antagonistas & inibidores
16.
Bioorg Chem ; 111: 104837, 2021 06.
Artigo em Inglês | MEDLINE | ID: mdl-33812281

RESUMO

A new series of urea/thiourea derivatives have been efficiently synthesized from the reaction of L-3-hydroxytyrosine with selective isocyanates/isothiocyanates and characterized by Infra-red, proton & carbon-13 nuclear magnetic resonance spectral and mass spectrometry studies. All the synthesized compounds have been screened for their antioxidant activity by 1,1-diphenyl1-2-picrylhydrazyl radical assay, ferric reducing antioxidant power assay and also studied their molecular docking interaction profiles against 1N8Q and 3NRZ enzymatic proteins. The in vitro antioxidant activity has further supported by quantitative structure activity relationship, absorption, distribution, metabolism, and excretion & toxicity studies, bioactivity studies & enzyme inhibition assay and identified that they were potentially bound to ASP490 & ASP361 aminoacid residue in chain A of 1N8Q protein and GLN1194 aminoacid residue in chain L of 3NRZ protein and are responsible for potential antioxidant activity. It is proved that urea derivatives linked with 4-fluoro & 4-nitro and thiourea derivatives linked with 3-chloro & 4-fluoro have exhibited promising antioxidant activity. In eventual synthesized compounds have been identified as potential blood-brain barrier penetrable compounds and proficient central nervous system active neuro-protective antioxidant agents as they have envisaged as easily penetrable to blood-brain barrier thresholds, a neuroprotective property.


Assuntos
Antioxidantes/farmacologia , Biologia Computacional , Tirosina/farmacologia , Ureia/farmacologia , Antioxidantes/síntese química , Antioxidantes/química , Compostos de Bifenilo/antagonistas & inibidores , Relação Dose-Resposta a Droga , Compostos Férricos/antagonistas & inibidores , Simulação de Acoplamento Molecular , Estrutura Molecular , Picratos/antagonistas & inibidores , Relação Estrutura-Atividade , Tirosina/síntese química , Tirosina/química , Ureia/análogos & derivados , Ureia/química
17.
Bioorg Chem ; 111: 104900, 2021 06.
Artigo em Inglês | MEDLINE | ID: mdl-33894429

RESUMO

Due to their unique pharmacological characteristics, methylxanthines are known as therapeutic agents in a fascinating range of medicinal scopes. In this report, we aimed to examine some biological effects of previously synthesized 8-alkylmercaptocaffeine derivatives. Cytotoxic and antioxidative activity of 8-alkylmercaptocaffeine derivatives were measured in malignant A549, MCF7, and C152 cell lines. Assessment of cGMP levels and caspase-3 activity were carried out using a colorimetric competitive ELISA kit. Computational approaches were employed to discover the inhibitory mechanism of synthesized compounds. Among the twelve synthesized derivatives, three compounds (C1, C5, and C7) bearing propyl, heptyl, and 3-methyl-butyl moieties showed higher and more desirable cytotoxic activity against all the studied cell lines (IC50 < 100 µM). Furthermore, C5 synergistically enhanced cisplatin-induced cytotoxicity in MCF-7 cells (CI < 1). Both C5 and C7 significantly increased caspase-3 activity and intracellular cGMP levels at specific time intervals in all studied cell lines (P < 0.05). However, these derivatives did not elevate LDH leakage (P > 0.05) and exhibited no marked ameliorating effects on oxidative damage (P > 0.05). Computational studies showed that H-bond formation between the nitrogen atom in pyrazolo[4,3-D] pyrimidine moiety with Gln817 and creating a hydrophobic cavity result in the stability of the alkyl group in the PDE5A active site. We found that synthesized 8-alkylmercaptocaffeine derivatives induced cell death in different cancer cells through the cGMP pathway. These findings will help us to get a deeper insight into the role of methylxanthines as useful alternatives to conventional cancer therapeutics.


Assuntos
Antineoplásicos/farmacologia , Antioxidantes/farmacologia , Cafeína/farmacologia , Simulação de Acoplamento Molecular , Antineoplásicos/síntese química , Antineoplásicos/química , Antioxidantes/síntese química , Antioxidantes/química , Compostos de Bifenilo/antagonistas & inibidores , Cafeína/análogos & derivados , Cafeína/química , Proliferação de Células/efeitos dos fármacos , Células Cultivadas , Relação Dose-Resposta a Droga , Ensaios de Seleção de Medicamentos Antitumorais , Humanos , Estrutura Molecular , Picratos/antagonistas & inibidores , Relação Estrutura-Atividade
18.
Molecules ; 26(6)2021 Mar 13.
Artigo em Inglês | MEDLINE | ID: mdl-33805815

RESUMO

The phenolic composition, as well as the antioxidant and antimicrobial activities of two poorly investigated Achillea species, Achillea lingulata Waldst. and the endemic Achillea abrotanoides Vis., were studied. To obtain a more detailed phytochemical profile, four solvents with different polarities were used for the preparation of the plant extracts whose phenolic composition was analyzed using UHPLC-MS/MS (ultra-high performance liquid chromatography-tandem mass spectrometry). The results indicate that both of the investigated Achillea species are very rich in both phenolic acids and flavonoids, but that their profiles differ significantly. Chloroform extracts from both species had the highest yields and were the most chemically versatile. The majority of the examined extracts showed antimicrobial activity, while ethanolic extracts from both species were potent against all tested microorganisms. Furthermore, the antioxidant activity of the extracts was evaluated. It was found that the ethanolic extracts possessed the strongest antioxidant activities, although these extracts did not contain the highest amounts of detected phenolic compounds. In addition, several representatives of phenolic compounds were also assayed for these biological activities. Results suggest that ethanol is a sufficient solvent for the isolation of biologically active compounds from both Achillea species. Moreover, it was shown that the flavonoids naringenin and morin are mainly responsible for these antimicrobial activities, while caffeic, salicylic, chlorogenic, p-coumaric, p-hydroxybenzoic, and rosmarinic acid are responsible for the antioxidant activities of the Achillea extracts.


Assuntos
Achillea/química , Anti-Infecciosos/isolamento & purificação , Antioxidantes/isolamento & purificação , Hidroxibenzoatos/isolamento & purificação , Compostos Fitoquímicos/isolamento & purificação , Achillea/classificação , Anti-Infecciosos/química , Anti-Infecciosos/farmacologia , Antioxidantes/química , Antioxidantes/farmacologia , Compostos de Bifenilo/antagonistas & inibidores , Cromatografia Líquida de Alta Pressão , Flavonoides/química , Flavonoides/isolamento & purificação , Flavonoides/farmacologia , Hidroxibenzoatos/química , Hidroxibenzoatos/farmacologia , Testes de Sensibilidade Microbiana , Fenóis/química , Fenóis/isolamento & purificação , Fenóis/farmacologia , Compostos Fitoquímicos/química , Compostos Fitoquímicos/farmacologia , Picratos/antagonistas & inibidores , Extratos Vegetais/química , Solventes , Especificidade da Espécie , Espectrometria de Massas em Tandem
19.
Molecules ; 26(7)2021 Apr 01.
Artigo em Inglês | MEDLINE | ID: mdl-33916097

RESUMO

Depression and anxiety are major mental health problems in all parts of the world. These illnesses are associated with a number of risk factors, including oxidative stress. Psychotropic drugs of a chemical nature have demonstrated several side effects that elevated the impact of those illnesses. Faced with this situation, natural products appear to be a promising alternative. The aim of this study was to evaluate the anxiolytic and antidepressant effects of the Petroselinum sativum polyphenols in vivo, as well as its correlated antioxidant properties in vitro. Anxiolytic activity of the extract (50 and 100 mg/kg) was evaluated using the open field and the light-dark chamber tests, while the antidepressant activity was evaluated using the forced swimming test. The antioxidant activity of the extract was evaluated by the 2,2-diphenyl-1-picrylhydrazyl (DPPH) free radical test and the FRAP (iron-reducing capacity) test. The phenolic extract showed very powerful anxiolytic and antidepressant-like effects, especially at a dose of 100 mg/kg, decreasing the depressive behavior in mice (decreased immobility time) and also the anxiolytic behavior (tendency for discovery in the center and illuminated areas) better even than those of paroxetine and bromazepam (classic drugs) concomitant with those results the extract also showed an important antioxidant capacity. These preliminary results suggest that Petroselinum sativum exhibits anxiolytic and antidepressant potential for use as a complement or independent phytomedicine to treat depression and anxiety.


Assuntos
Ansiolíticos/farmacologia , Antidepressivos/farmacologia , Antioxidantes/farmacologia , Petroselinum/química , Extratos Vegetais/farmacologia , Polifenóis/farmacologia , Animais , Ansiolíticos/química , Antidepressivos/química , Antioxidantes/química , Ansiedade/tratamento farmacológico , Comportamento Animal/efeitos dos fármacos , Compostos de Bifenilo/antagonistas & inibidores , Depressão/tratamento farmacológico , Modelos Animais de Doenças , Relação Dose-Resposta a Droga , Aprendizagem em Labirinto/efeitos dos fármacos , Picratos/antagonistas & inibidores , Extratos Vegetais/química , Polifenóis/química , Ratos , Ratos Wistar
20.
Molecules ; 26(7)2021 Mar 28.
Artigo em Inglês | MEDLINE | ID: mdl-33800622

RESUMO

Croton hirtus L'Hér methanol extract was studied by NMR and two different LC-DAD-MSn using electrospray (ESI) and atmospheric pressure chemical ionization (APCI) sources to obtain a quali-quantitative fingerprint. Forty different phytochemicals were identified, and twenty of them were quantified, whereas the main constituents were dihydro α ionol-O-[arabinosil(1-6) glucoside] (133 mg/g), dihydro ß ionol-O-[arabinosil(1-6) glucoside] (80 mg/g), ß-sitosterol (49 mg/g), and isorhamnetin-3-O-rutinoside (26 mg/g). C. hirtus was extracted with different solvents-namely, water, methanol, dichloromethane, and ethyl acetate-and the extracts were assayed using different in vitro tests. The methanolic extracts presented the highest 1,1-diphenyl-2-picrylhydrazyl (DPPH), 2,2'-azino-bis(3-ethylbenzothiazoline)-6-sulfonic acid (ABTS), and ferric reducing antioxidant power (FRAP) values. All the tested extracts exhibited inhibitory effects on acetylcholinesterase (AChE) and butyrylcholinesterase (BChE), with a higher activity observed for dichloromethane (AChE: 5.03 and BChE: 16.41 mgGALAE/g), while the methanolic extract showed highest impact against tyrosinase (49.83 mgKAE/g). Taken together, these findings suggest C. hirtus as a novel source of bioactive phytochemicals with potential for commercial development.


Assuntos
Antioxidantes/química , Inibidores da Colinesterase/química , Croton/química , Glucosídeos/química , Compostos Fitoquímicos/química , Fitosteróis/química , Terpenos/química , Acetatos/química , Acetilcolinesterase/química , Acetilcolinesterase/metabolismo , Antioxidantes/classificação , Antioxidantes/isolamento & purificação , Benzotiazóis/antagonistas & inibidores , Benzotiazóis/química , Compostos de Bifenilo/antagonistas & inibidores , Compostos de Bifenilo/química , Butirilcolinesterase/química , Butirilcolinesterase/metabolismo , Inibidores da Colinesterase/isolamento & purificação , Croton/metabolismo , Glucosídeos/classificação , Glucosídeos/isolamento & purificação , Humanos , Metanol/química , Cloreto de Metileno/química , Compostos Fitoquímicos/classificação , Compostos Fitoquímicos/isolamento & purificação , Fitosteróis/classificação , Fitosteróis/isolamento & purificação , Picratos/antagonistas & inibidores , Picratos/química , Extratos Vegetais/química , Solventes/química , Relação Estrutura-Atividade , Ácidos Sulfônicos/antagonistas & inibidores , Ácidos Sulfônicos/química , Terpenos/classificação , Terpenos/isolamento & purificação , Água/química
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