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1.
Planta ; 254(6): 112, 2021 Nov 02.
Artigo em Inglês | MEDLINE | ID: mdl-34727239

RESUMO

MAIN CONCLUSION: Solanoeclepin A is a hatching stimulant for potato cyst nematode in very low (pM) concentrations. We report a highly sensitive method for the analysis of SolA in plant root exudates using UHPLC-MS/MS and show that there is considerable natural variation in SolA production in Solanum spp. corresponding with their hatching inducing activity. Potato cyst nematode (PCN) is a plant root sedentary endoparasite, specialized in the infection of solanaceous species such as potato (Solanum tuberosum) and tomato (Solanum lycopersicum). Earlier reports (Mulder et al. in Hatching agent for the potato cyst nematode, Patent application No. PCT/NL92/00126, 1996; Schenk et al. in Croat Chem Acta 72:593-606, 1999) showed that solanoeclepin A (SolA), a triterpenoid metabolite that was isolated from the root exudate of potato, induces the hatching of PCN. Its low concentration in potato root exudate has hindered progress in fully understanding its hatching inducing activity and exploitation in the control of PCN. To further investigate the role of SolA in hatching of PCN, the establishment of a highly sensitive analytical method is a prerequisite. Here we present the efficient single-step extraction and UHPLC-MS/MS based analysis for rapid determination of SolA in sub-nanomolar concentrations in tomato root exudate. This method was used to analyze SolA production in different tomato cultivars and related solanaceous species, including the trap crop Solanum sisymbriifolium. Hatching assays with PCN, Globodera pallida, with root exudates of tomato genotypes revealed a significant positive correlation between SolA concentration and hatching activity. Our results demonstrate that there is natural variation in SolA production within solanaceous species and that this has an effect on PCN hatching. The analytical method we have developed can potentially be used to support breeding for crop genotypes that induce less hatching and may therefore display reduced infection by PCN.


Assuntos
Hidrocarbonetos Aromáticos com Pontes/química , Hexanos/química , Doenças das Plantas/parasitologia , Solanum tuberosum , Tylenchoidea , Animais , Cromatografia Líquida de Alta Pressão , Cromatografia Líquida , Exsudatos e Transudatos , Melhoramento Vegetal , Raízes de Plantas/química , Solanum tuberosum/química , Espectrometria de Massas em Tandem , Tylenchoidea/patogenicidade
2.
Phytomedicine ; 93: 153748, 2021 Dec.
Artigo em Inglês | MEDLINE | ID: mdl-34628240

RESUMO

BACKGROUND: In the present work the bioactivity-guided fractionation of n-hexane extract from aerial parts of Baccharis sphenophylla (Asteraceae) against trypomastigote forms of Trypanosoma cruzi was performed. PURPOSE: To evaluate the antitrypanosomal potential of diterpenes ent­kaurenoic (1), grandifloric (2). and 15ß-tiglinoyloxy­ent-kaurenoic (3) acids, isolated from n-hexane extract from aerial parts of B. sphenophylla, and elucidate their mechanism of action against T. cruzi. METHODS/STUDY DESIGN: n-Hexane and MeOH extracts from aerial parts of B. sphenophylla were prepared and caused, respectively, 100% and 50% of death of trypomastigote forms of T. cruzi. Based on these results, the n-hexane extract was subjected to bioactivity-guided fractionation procedures to afford three related ent­kaurane diterpenoids (1-3). Based on spectrofluorometric assays and flow cytometry analysis, the mechanism of action of compounds 1 and 3 was investigated. RESULTS: Compounds 1 and 3, isolated from n-hexane extract from aerial parts of B. sphenophylla, showed potent activity against parasites with EC50 values of 10.6 µM (SI > 18.8) and 2.4 µM (SI = 34.8), respectively. On the other hand, compound 2 was inactive against trypomastigotes. In mechanism of action studies using the fluorescent probe SYTOX Green, the plasma membrane permeability was unaltered after treatment with compounds 1 and 3, but compound 1 induced a depolarization of the plasma membrane electric potential (ΔΨp). No substantial alterations were observed in the mitochondria after treatment with compound 3, but a transient hyperpolarization of the mitochondrial membrane potential (ΔΨm) by compound 1. Despite the increased ATP levels induced by compounds 1 and 3, no alterations of ROS and Ca2+ levels were registered. However, both compounds promoted a time-dependent alkalinization of the acidocalcisomes, probably contributing to an osmotic imbalance of the cell. In silico physicochemical studies of compounds 1-3 suggested that lipophilicity and molecular complexity may play an important role in the antitrypanosomal activity. Moreover, no pan-assay interference compounds (PAINS) alerts were detected for compounds 1-3. CONCLUSION: Obtained data indicated that the isolated ent­kaurane diterpenes from n-hexane extract from aerial parts of B. sphenophylla, especially compound 3, could be considered interesting prototypes for further modifications aiming the discovery of new hits against T. cruzi.


Assuntos
Baccharis , Diterpenos do Tipo Caurano , Diterpenos , Trypanosoma cruzi , Diterpenos/farmacologia , Diterpenos do Tipo Caurano/farmacologia , Hexanos
3.
Braz J Biol ; 83: e240842, 2021.
Artigo em Inglês | MEDLINE | ID: mdl-34550279

RESUMO

This research aimed to investigate various mosquitocidal activities of Chenopodium botrys whole- plant n-hexane extract against Culex quinquefasciatus. The extract showed remarkable larvicidal, pupicidal, adulticidal, oviposition deterrent and adult emergence inhibitory activities against Cx. quinquefasciatus. During the larvicidal and pupicidal activities, the 24-hour lethal concentration (LC50) of extract against 2nd instar larvae, 4th instar larvae and pupae were 324.6, 495.6 and 950.8 ppm, respectively. During the CDC (Centers for Disease Control and Prevention) bottle bioassay for adulticidal activity, the median knockdown times (KDT50) at 1.25% concentration was 123.4 minutes. During the filter paper impregnation bioassay for adulticidal activity, the KDT50 value at 0.138 mg/cm2 concentration was 48.6 minutes. The extract was fractionated into 14 fractions through silica gel column chromatography which were then combined into six fractions on the basis of similar retention factor (Rf) value. These fractions were screened for adulticidal activity by applying CDC bottle bioassay. The fraction obtained through 60:40 to 50:50% n-hexanes-chloroform mobile phase with 0.5 Rf value showed 100% adulticidal activity at 0.2% concentration. During oviposition deterrent activity, the highest concentration (1000 ppm) showed 71.3 ± 4.4% effective repellence and 0.6 ± 0.1 oviposition activity index. During adult emergence inhibition activity, the median emergence inhibition (EI50) value was 312.3 ppm. From the outcome of the present investigation, it is concluded that the n-hexane extract of C. botrys whole- plant possesses strong larvicidal, pupicidal, adulticidal, oviposition deterrent and adult emergence inhibitory activities against Cx. quinquefasciatus.


Assuntos
Chenopodium , Culex , Inseticidas , Animais , Hexanos , Inseticidas/farmacologia , Larva , Extratos Vegetais/farmacologia , Folhas de Planta
4.
Nat Commun ; 12(1): 4966, 2021 08 17.
Artigo em Inglês | MEDLINE | ID: mdl-34404784

RESUMO

Although chirality is an ever-present characteristic in biology and some artificial molecules, controlling the chirality and demystifying the chirality origin of complex assemblies remain challenging. Herein, we report two homochiral Ag14 nanoclusters with inherent chirality originated from identical rotation of six square faces on a Ag8 cube driven by intra-cluster π···π stacking interaction between pntp- (Hpntp = p-nitrothiophenol) ligands. The spontaneous resolution of the racemic (SD/rac-Ag14a) to homochiral nanoclusters (SD/L-Ag14 and SD/R-Ag14) can be realized by re-crystallizing SD/rac-Ag14a in acetonitrile, which promotes the homochiral crystallization in solid state by forming C-H···O/N hydrogen bonds with nitro oxygen atoms in pntp- or aromatic hydrogen atoms in dpph (dpph = 1,6-bis(diphenylphosphino)hexane) on Ag14 nanocluster. This work not only provides strategic guidance for the syntheses of chiral silver nanoclusters in an all-achiral environment, but also deciphers the origin of chirality at molecular level by identifying the special effects of intra- and inter-cluster supramolecular interactions.


Assuntos
Cristalização , Compostos Organometálicos/química , Fenômenos Físicos , Prata/química , Acetonitrilas/química , Cristalografia por Raios X , Hexanos , Hidrogênio , Ligação de Hidrogênio , Modelos Moleculares , Conformação Molecular , Oxigênio , Rotação
5.
Molecules ; 26(12)2021 Jun 17.
Artigo em Inglês | MEDLINE | ID: mdl-34204264

RESUMO

The present research investigated the chemical characterization and insecticidal activity of n-Hexane extracts of Epaltes divaricata (NH-EDx) along with their chief derivatives n-Hexadecanoic acid (n-HDa) and n-Octadecanoic acid (n-ODa) against the dengue vector Aedes aegypti and lepidopteran pest Spodoptera litura. Chemical screening of NH-EDx through GC-MS analysis delivered nine major derivatives, and the maximum peak area percentage was observed in n-Hexadecanoic acid (14.63%) followed by n-Octadecadienoic acid (6.73%). The larvicidal activity of NH-EDx (1000 ppm), n-HDa (5 ppm), and n-ODa (5 ppm) against the A. aegypti and S. litura larvae showed significant mortality rate in a dose-dependent way across all the instars. The larvicidal activity was profound in the A. aegypti as compared to the S. litura across all the larval instars. The sublethal dosages of NH-EDx (500 ppm), n-HDa (2.5 ppm), and n-ODa (2.5 ppm) also showed alterations in the larval/pupal durations and adult longevity in both the insect pests. The enzyme activity revealed that the α- and ß-carboxylesterase levels were decreased significantly in both the insect pests, whereas the levels of GST and CYP450 uplifted in a dose-dependent manner of NH-EDx, n-HDa, and n-ODa. Correspondingly, midgut tissues such as the epithelial layer (EL), gut lumen (GL), peritrophic matrix (Pm), and brush border membrane (BBM) were significantly altered in their morphology across both A. aegypti and S. litura against the NH-EDx and their bioactive metabolites. NH-EDx and their bioactive metabolites n-HDa and n-ODa showed significant larvicidal, growth retardant, enzyme inhibition, and midgut toxicity effects against two crucial agriculturally and medically challenging insect pest of ecological importance.


Assuntos
Aedes/efeitos dos fármacos , Asteraceae/metabolismo , Extratos Vegetais/farmacologia , Spodoptera/efeitos dos fármacos , Animais , Asteraceae/efeitos dos fármacos , Culex/efeitos dos fármacos , Dengue/prevenção & controle , Hexanos/química , Inseticidas/farmacologia , Larva/efeitos dos fármacos , Mosquitos Vetores/efeitos dos fármacos , Folhas de Planta/química , Solventes/química
6.
Biomed Res Int ; 2021: 1584141, 2021.
Artigo em Inglês | MEDLINE | ID: mdl-34222467

RESUMO

Microbial infections are increasing worldwide, and the widespread emergence of antibiotic-resistant pathogens poses a severe threat to public health. Medicinal plants are well-known sources of bioactive ingredients. This study was designed to determine the antimicrobial and antioxidant activities of extracts from Platycerium stemaria. The serial exhaustive extraction method using a solvent of increasing polarity from nonpolar (hexane) to polar (water) was designed to prepare crude extracts; liquid-liquid partition was used to fractionate of active extracts. The extracts and fractions were screened for antimicrobial activity on bacteria and yeasts using the microdilution method. The antioxidant activity was done using DPPH and FRAP assays. Out of the sixteen extracts screened, four (PsHex, PsH2O(H), PsMeOH(EA), and PsMeOH) exhibited potency with minimal inhibitory concentration (MIC) values ranging from 31.25 to 500 µg/mL. Out of the four extracts, two, including PsMeOH and PsMeOH(EA), exhibited DPPH radical scavenging activity with the antiradical power of 8.94 × 10-5 and 47.96 × 10-5, respectively, and ferric reducing antioxidant power values ranging from 0.34 to 61.53 µg equivalent Vit C/g of extract. The phytochemical screening of the promising crude extracts revealed flavonoids, glycosides, phenols, tannins, terpenoids, saponins, and anthraquinones. This study reports the antimicrobial and antioxidant activities of P. stemaria for the first time. The results showed that the serial exhaustive extraction approach used in this study allowed capturing the antimicrobial and antioxidant metabolites beyond the single extraction, indicating the need for a rigorous choice of an appropriate solvent and method for extracting P. stemaria. Further investigation is needed to characterize the active ingredients present in the promising extracts.


Assuntos
Anti-Infecciosos/farmacologia , Antioxidantes/farmacologia , Extratos Vegetais/farmacologia , Polypodiaceae/metabolismo , Antioxidantes/química , Compostos de Bifenilo , Candida albicans , Hexanos/química , Técnicas In Vitro , Concentração Inibidora 50 , Klebsiella pneumoniae , Testes de Sensibilidade Microbiana , Compostos Fitoquímicos , Picratos , Extratos Vegetais/química , Folhas de Planta/química , Plantas Medicinais , Shigella flexneri , Solventes/química , Especificidade da Espécie , Staphylococcus aureus , Água/química
7.
Molecules ; 26(11)2021 May 27.
Artigo em Inglês | MEDLINE | ID: mdl-34072180

RESUMO

Herein, we prepared 1,3-dipalmitoyl-2-oleoyl glycerol (POP)-rich fats with reduced levels of diacylglycerols (DAGs), adversely affecting the tempering of chocolate, via two-step hexane fractionation of palm stearin. DAG content in the as-prepared fats was lower than that in POP-rich fats obtained by previously reported conventional two-step acetone fractionation. Cocoa butter equivalents (CBEs) were fabricated by blending the as-prepared fats with 1,3-distearoyl-2-oleoyl glycerol (SOS)-rich fats obtained by hexane fractionation of degummed shea butter. POP-rich fats achieved under the best conditions for the fractionation of palm stearin had a significantly lower DAG content (1.6 w/w%) than that in the counterpart (4.6 w/w%) prepared by the previously reported method. The CBEs fabricated by blending the POP- and SOS-rich fats in a weight ratio of 40:60 contained 63.7 w/w% total symmetric monounsaturated triacylglycerols, including 22.0 w/w% POP, 8.6 w/w% palmitoyl-2-oleoyl-3-stearoyl-rac-glycerol, 33.1 w/w% SOS, and 1.3 w/w% DAGs, which was not substantially different from the DAG content in cocoa butter (1.1 w/w%). Based on the solid-fat content results, it was concluded that, when these CBEs were used for chocolate manufacture, they blended with cocoa butter at levels up to 40 w/w%, without distinctively altering the hardness and melting behavior of cocoa butter.


Assuntos
Gorduras na Dieta/metabolismo , Diglicerídeos/química , Hexanos/química , Óleo de Palmeira/química , Cacau/química , Varredura Diferencial de Calorimetria , Cromatografia Líquida de Alta Pressão , Ácidos Graxos/química , Glicerol/química , Óleos Vegetais/química , Temperatura , Triglicerídeos/química
8.
Molecules ; 26(11)2021 May 28.
Artigo em Inglês | MEDLINE | ID: mdl-34071241

RESUMO

Amphipterygium adstringens (cuachalalate) contains anacardic acids (AAs) such as 6-pentadecyl salicylic acid (6SA) that show immunomodulatory and antitumor activity with minimal or no secondary adverse effects. By contrast, most chemotherapeutic agents, such as 5-fluorouracil (5-FU) and carboplatin (CbPt), induce myelosuppression and leukopenia. Here, we investigated the myeloprotective and antineoplastic potential of an AA extract or the 6SA as monotherapy or in combination with commonly used chemotherapeutic agents (5-FU and CbPt) to determine the cytoprotective action of 6SA on immune cells. Treatment of Balb/c breast tumor-bearing female mice with an AA mixture or 6SA did not induce the myelosuppression or leukopenia observed with 5-FU and CbPt. The co-administration of AA mixture or isolated 6SA with 5-FU or CbPt reduced the apoptosis of circulating blood cells and bone marrow cells. Treatment of 4T1 breast tumor-bearing mice with the AA mixture or 6SA reduced tumor growth and lung metastasis and increased the survival rate compared with monotherapies. An increased effect was observed in tumor reduction with the combination of 6SA and CbPt. In conclusion, AAs have important myeloprotective and antineoplastic effects, and they can improve the efficiency of chemotherapeutics, thereby protecting the organism against the toxic effects of drugs such as 5-FU and CbPt.


Assuntos
Ácidos Anacárdicos/química , Carboplatina/farmacologia , Fluoruracila/farmacologia , Neoplasias Mamárias Experimentais/tratamento farmacológico , Anacardiaceae , Ácidos Anacárdicos/farmacologia , Animais , Antineoplásicos/farmacologia , Apoptose , Células da Medula Óssea/metabolismo , Linhagem Celular Tumoral , Sobrevivência Celular , Citoproteção , Modelos Animais de Doenças , Feminino , Hexanos/química , Leucócitos/efeitos dos fármacos , Camundongos , Camundongos Endogâmicos BALB C , Metástase Neoplásica , Casca de Planta/metabolismo
9.
J Hazard Mater ; 419: 126330, 2021 10 05.
Artigo em Inglês | MEDLINE | ID: mdl-34171668

RESUMO

Two-phase partitioning bioreactors (TPPBs) have been extensively used for volatile organic compounds (VOCs) removal. To date, most studies have focused on improving the mass transfer of gas phases/non-aqueous phases (NAPs)/aqueous phases, whereas the NAP/biological phases and gas/biological phases transfer has been neglected. Herein, chitosan was introduced into a TPPB to increase cell surface hydrophobicity (CSH) and improve the n-hexane mass transfer. The performance and stability of the TPPB with chitosan for n-hexane biodegradation were investigated, and it was found out that the TPPB with chitosan achieved maximum removal efficiency and elimination capacity of 80.6% and 26.5 g m-3 h-1, thereby reaching much higher values than those obtained without chitosan (61.3% and 15.2 g m-3 h-1). Chitosan not only obvio usly increased cell surface hydrophobicity and cell dry biomass on the surface of silicone oil, but might also allow hydrophobic cells in aqueous phases to directly capture and biodegrade n-hexane, resulting in an obvious improvement of mass transfer from the gas phase to biomass. Stability enhancement was another attractive advantage from chitosan addition. This study might provide a new strategy for the development of TPPB in the hydrophobic VOCs treatment.


Assuntos
Quitosana , Pseudomonas mendocina , Biodegradação Ambiental , Reatores Biológicos , Hexanos
10.
Food Chem ; 361: 130067, 2021 Nov 01.
Artigo em Inglês | MEDLINE | ID: mdl-34062456

RESUMO

In this paper, new supramolecular extractants, which contained surfactant, alkane and alkanol, were designed and used to separate PQQ. After a series of tests, the optimal extractant composition was determined as benzalkalonium (C8-C16) chloride (BC): n-hexane:n-pentanol, and the highest extraction rate could reach 98%. The extraction equilibrium could be reached in five minutes. The mechanism of the extraction selectivity was inferred as an ion-pair and π-π complexation interaction between PQQ and BC, which was indicated by UV and fluorescence quenching experiments. To recycle the organic extractant, the extract was back-extracted with sodium chloride solution. After extraction, back extraction and crystallization, an isolated product with a purity of 97.5% was obtained from G. oxydans fermentation broth. The product was identified as PQQ by HPLC analysis and MS. Above all, the present research developed a simple and efficient method for the separation of PQQ from fermentation broth.


Assuntos
Gluconobacter oxydans/enzimologia , Cofator PQQ/isolamento & purificação , Compostos de Benzalcônio/química , Cromatografia Líquida de Alta Pressão , Fermentação , Gluconobacter oxydans/química , Hexanos/química , Espectrometria de Massas , Pentanóis , Solventes
11.
Forensic Sci Int ; 324: 110793, 2021 Jul.
Artigo em Inglês | MEDLINE | ID: mdl-34049074

RESUMO

Analysis of condom evidence commonly focusses on the detection of silicone-based lubricants, such as polydimethylsiloxane (PDMS). Although various instruments are used to analyse silicone lubricants, pyrolysis-gas chromatography coupled to mass spectrometry (py-GC-MS) is one of the few instruments that presents immediate applicability to casework. However, considering that this technique detects silicone-based evidence, it is important to evaluate the discrimination potential of the method when applied to various samples. Examination of the variability within a large sample set from an international market is needed to evaluate the most distinguishing compounds likely to be detected in casework. In this study, 70 condoms, personal hygiene products, and lubricants, were analysed using py-GC-MS. Resulting pyrograms were characterised using published spectral databases. Pyrolysates data were extracted and evaluated using multivariate techniques. Qualitative visual inspection of the data, as well as statistical analysis, revealed at least five groups within the dataset. Discrimination was based on four main oligomers, as well as six minor compounds from siloxane degradation. Condom lubricants were found to present a very regular pattern, allowing for the majority of them to be differentiated from personal lubricants.


Assuntos
Preservativos , Cromatografia Gasosa-Espectrometria de Massas , Lubrificantes/química , Pirólise , Análise Discriminante , Hexanos , Humanos , Análise de Componente Principal , Silicones , Solventes , Espectroscopia de Infravermelho com Transformada de Fourier
12.
Food Chem Toxicol ; 153: 112268, 2021 Jul.
Artigo em Inglês | MEDLINE | ID: mdl-34015423

RESUMO

The Tanacetum genus is a big treasure with the presence of biologically-active compounds and members of this genus are widely used for the treatment of several diseases in traditional medicine system. Considering this fact, we aimed to analyze the extracts from Tanacetum vulgare L. in case of chemical profiles and biological effects. Chemical characterization was performed by using UHPLC-HRMS technique and showed the presence of several phytochemical groups (107 compounds were identified, including phenolic acids, flavonoids, terpenoids and fatty acids. Biological abilities were examined by using antioxidant (DPPH, ABTS, FRAP, CUPRAC, metal chelating and phosphomolybdenum assays) and enzyme inhibition (tyrosinase, amylase, glucosidase and cholinesterase) properties. Pharmaco-toxicological investigations were also performed with the aim to identify limits of biocompatibility, anti-oxidant and neuromodulatory effects, in hypothalamic HypoE22 cells. A bioinformatic analysis was also carried to unravel the putative protein-targets for the observed biological effects. Generally, the tested hexane and hydroalcoholic extracts displayed stronger activities in antioxidant and enzyme inhibitory assays, when compared with water. In addition, multivariate analysis was performed to understand the differences in both solvents and plant parts and we clearly observed the separation of these parameters. The extracts (10 µg/mL) also stimulated DAT and inhibited TNFα and BDNF gene expression, in HypoE22 cells. In parallel, the extracts were also able to stimulate norepinephrine release from this cell line. By contrast, in the concentration range 50-100 µg/mL, the extracts reduced the HypoE22 viability, thus demonstrating cytotoxicity at concentrations 5-10 fold higher compared to those effective as neuromodulatory. Our observations manifested that T. vulgare has several beneficial effects and it can be used as a potential natural raw material for designing further health-promoting applications in nutraceutical, cosmeceutical, and pharmaceutical areas.


Assuntos
Antioxidantes/farmacologia , Inibidores Enzimáticos/farmacologia , Compostos Fitoquímicos/farmacologia , Extratos Vegetais/farmacologia , Tanacetum/química , Animais , Antioxidantes/análise , Antioxidantes/química , Antioxidantes/toxicidade , Artemia/efeitos dos fármacos , Linhagem Celular , Inibidores Enzimáticos/análise , Inibidores Enzimáticos/química , Inibidores Enzimáticos/toxicidade , Etanol/química , Flores/química , Hexanos/química , Análise Multivariada , Compostos Fitoquímicos/análise , Compostos Fitoquímicos/química , Compostos Fitoquímicos/toxicidade , Componentes Aéreos da Planta/química , Extratos Vegetais/análise , Extratos Vegetais/química , Extratos Vegetais/toxicidade , Caules de Planta/química , Mapas de Interação de Proteínas , Ratos , Solventes/química , Água/química
13.
ScientificWorldJournal ; 2021: 6623609, 2021.
Artigo em Inglês | MEDLINE | ID: mdl-33986636

RESUMO

Background: Nigella sativa L (NS) is a powerful antioxidant and medicinal plant with many therapeutic applications particularly in traditional medicine for respiratory, gastrointestinal, rheumatic, and inflammatory disorders, as well as cancer. Objective: The aim of this study is to extract the active ingredients from the Moroccan Nigella sativa L and determine its antioxidant properties. We hypothesize that the separation of the compounds from Nigella sativa L has either a positive or negative effect on antioxidants. To study this, we explored different methods to simultaneously extract and separate compounds from Nigella sativa L and performed antioxidant tests (ß-carotene and DPPH) for all collected fractions. Methods: Nigella sativa L was hot-extracted by Soxhlet and mother extracts and was separated using silica column chromatography with adequate eluents. Qualitative phytochemical tests to determine the chemical families in Nigella sativa L seeds were performed on the fractions. They were also identified and characterized by GC-MS and HPLC-DAD. Then, antioxidant activity was examined by ß-carotene bleaching and DPPH radical scavenger tests. Results and Conclusion. The mother extract hexane FH generated eight different fractions (SH1-8) and the acetone extract FA generated 11 fractions (SA1-11). The FH fractions had a high percentage of fatty acids, and the FA fractions had some interesting polyphenols derivative compounds. Phytochemical screening revealed secondary metabolites such as polyphenols flavonoids, alkaloids, steroids, terpenes coumarins, tannins, and saponins. We found that only two solvents (hexane, acetone) of different polarities could easily extract and simultaneously separate the components of Nigella sativa L. The antioxidant fractions that we collected had close activity to reference compounds but were more active than the corresponding mother extracts. Moreover, several IC50 values of fractions from acetone extract were better than those from hexane. Therefore, the antioxidant activity of Nigella sativa L is more attributed to flavonoids and polyphenols than fatty acids. In summary, the separation of hexane extract presents a more pronounced positive effect for antioxidant tests than acetone extract.


Assuntos
Antioxidantes/isolamento & purificação , Flavonoides/isolamento & purificação , Extração Líquido-Líquido/métodos , Nigella sativa/química , Compostos Fitoquímicos/isolamento & purificação , Polifenóis/isolamento & purificação , Sementes/química , Acetona/química , Alcaloides/química , Alcaloides/classificação , Alcaloides/isolamento & purificação , Antioxidantes/química , Antioxidantes/classificação , Compostos de Bifenilo/antagonistas & inibidores , Cromatografia Líquida de Alta Pressão , Cumarínicos/química , Cumarínicos/classificação , Cumarínicos/isolamento & purificação , Flavonoides/química , Flavonoides/classificação , Hexanos/química , Humanos , Marrocos , Compostos Fitoquímicos/química , Compostos Fitoquímicos/classificação , Picratos/antagonistas & inibidores , Extratos Vegetais/química , Plantas Medicinais , Polifenóis/química , Polifenóis/classificação , Saponinas/química , Saponinas/classificação , Saponinas/isolamento & purificação , Solventes/química , Esteroides/química , Esteroides/classificação , Esteroides/isolamento & purificação , Taninos/química , Taninos/classificação , Taninos/isolamento & purificação , Terpenos/química , Terpenos/classificação , Terpenos/isolamento & purificação , beta Caroteno/agonistas
14.
Chem Biodivers ; 18(6): e2100120, 2021 Jun.
Artigo em Inglês | MEDLINE | ID: mdl-34008318

RESUMO

Calendula suffruticosa subsp. algarbiensis (Boiss.) Nyman is very common on the Portuguese coast, but it has only recently begun to be studied chemically and belongs to a genus of difficult taxonomic classification. To improve the knowledge on the chemical variability of this taxon and evaluate the possible use of this tool for taxonomical purposes, the aim of this work was to determine the extent of chemical variation between individuals collected in the same geographic region, and to compare with samples mixing fragments of several individuals each (populations) from different local environments. Overall, hexane extract analysis by GC/MS allowed to identify 42 compounds, eight fatty acids, 24 terpenoids, three alcohols, five alkanes, and two pollutants. Greater chemical differences were found between individuals, grown in the same region, than were found between population samples from different regions. Additionally, 25 phytochemicals were identified for this taxon for the first time and may be used for taxonomic classification, even to distinguish between subspecies of C. suffruticosa. Furthermore, plants collected near urban areas accumulated pollutants, indicating the importance of controlling local environmental conditions when C. suffruticosa cultivation is for human consumption.


Assuntos
Calendula/química , Hexanos/química , Compostos Fitoquímicos/isolamento & purificação , Extratos Vegetais/isolamento & purificação , Humanos , Compostos Fitoquímicos/química , Extratos Vegetais/química
15.
Environ Sci Pollut Res Int ; 28(35): 48141-48153, 2021 Sep.
Artigo em Inglês | MEDLINE | ID: mdl-33899147

RESUMO

Cancer is a universal health issue, and many anticancer therapeutic drugs have been isolated from natural products. This study analyzed the cytotoxic and apoptotic activity of Plectranthus amboinicus leaf hexane (PALH) extract in MDA-MB-231 (median inhibitory concentration [IC50] = 39.26 µg/mL) and MCF7 (IC50 = 89.05 µg/mL) breast cancer cell lines. Cells appeared rounded and shrunken, indicating morphological changes due to apoptosis induction. The primary constituent of PALH was phenol, 5-methyl-2-(1-methylethyl) (44%). PALH extract treatment increased the percentage of late apoptotic cells in the MDA-MB231 cell line (58% ± 1.5% at 200 µg/mL) compared to the control group, as evidenced by the activated caspase-3 and caspase-7 identified and captured by fluorescence microscopy. The relative migration rate in MDA-MB-231 cells treated with 10 µg/mL of PALH extract for 48 h was significantly lower compared to the control group. Analysis of acute (2000 mg/kg/BW) and subacute (250 and 500 mg/kg/BW) toxicity of PALH extract in mice showed no mortality or adverse effects in the kidney and liver histology compared to the control group. PALH extract can be considered nontoxic as it does not cause any adverse changes and so can be proposed as a potential breast anticancer agent.


Assuntos
Plectranthus , Animais , Apoptose , Hexanos , Humanos , Células MCF-7 , Camundongos , Extratos Vegetais/toxicidade , Folhas de Planta
16.
J Oleo Sci ; 70(4): 559-570, 2021.
Artigo em Inglês | MEDLINE | ID: mdl-33814515

RESUMO

The present study evaluates the potential use of ultrasound irradiation to synthesize decyl oleate using Fermase CALBTM10000 under the solvent-free system (SFS). The optimal condition to achieve a maximum yield of 97.14% was found to be 1:2 oleic acid:decanol ratio, 1.8% (w/w) enzyme loading, 45°C temperature, 200 rpm agitation speed, 50 W power input, 50% duty cycle, 22 kHz frequency and reaction time of 25 minutes. The thermodynamic study was done to determine the change in entropy, Gibb's free energy, and change in enthalpy at various temperatures. The experimental results and kinetic study showed that the reaction followed ordered bi-bi model with kinetic parameters as rate of reaction (V max ) = 35.02 M/min/g catalyst, Michaelis constant for acid (K A ) = 34.47 M, Michaelis constant for alcohol (K B ) = 3.31 M, Inhibition constant (Ki) = 4542.4 M and sum of square error (SSE) = 0.000334. The application of ultrasound irradiation combined with biocatalyst and the absence of solvent intensified the process compared to the traditional stirring method using hexane as solvent.


Assuntos
Biocatálise , Enzimas Imobilizadas/química , Lipase/química , Ácido Oleico/síntese química , Ondas Ultrassônicas , Fenômenos Químicos , Cosméticos , Ácidos Decanoicos/química , Esterificação , Ésteres , Hexanos , Cinética , Lubrificantes , Ácido Oleico/química , Solventes , Temperatura , Termodinâmica
17.
Exp Appl Acarol ; 84(1): 263-270, 2021 May.
Artigo em Inglês | MEDLINE | ID: mdl-33860415

RESUMO

The frequent use of acaricides against the tick Rhipicephalus microplus increases the risk of development of resistance. Recent studies have revealed that Neoglaziovia variegata, an indigenous plant species known in Brazil as 'caroá', has a deleterious effect against R. microplus. In the current study, extracts of N. variegata were studied for their possible acaricidal properties. A hexane extract of N. variegata leaves was fractionated in a chromatography column and the fractions were tested in adult tick immersion tests in triplicate using three concentrations (5, 10 and 25 mg/ml). All the fractions had harmful effects on the ticks. However, three fractions were more efficaceous. Phytochemical analysis indicated that stigmast-5-en-3-ol and stigmastanol were most abundant; they might be responsible for the acaricidal effects, making them potentially useful as alternative agents to control the tick R. microplus.


Assuntos
Acaricidas , Bromeliaceae , Rhipicephalus , Infestações por Carrapato , Animais , Brasil , Hexanos , Larva , Extratos Vegetais/farmacologia , Folhas de Planta
18.
PLoS One ; 16(4): e0250118, 2021.
Artigo em Inglês | MEDLINE | ID: mdl-33930032

RESUMO

Many phytochemicals can affect the growth and development of plants and insects which can be used as biological control agents. In this study, different concentrations of crude, hexane, chloroform, butanol, and aqueous extracts of Euphorbia nivulia Buch.-Ham., an endemic plant of the Cholistan desert in South Punjab of Pakistan, were analysed for their chemical constituents. Their various concentrations were also tested for their phytotoxic and insecticidal potential against duckweed, Lemna minor L., and the dusky cotton bug, Oxycarenus hyalinipennis Costa. various polyphenols, i.e., quercetin, gallic acid, caffeic acid, syringic acid, coumaric acid, ferulic acid, and cinnamic acid were detected in different concentrations with different solvents during the phytochemical screening of E. nivulia. In the phytotoxicity test, except for 100 µg/mL of the butanol extract gave 4.5% growth regulation, no phytotoxic lethality could be found at 10 and 100 µg/mL of all the extracts. The highest concentration, 1000 µg/mL, of the chloroform, crude, and butanol extracts showed 100, 63.1, and 27.1% of growth inhibition in duckweed, respectively. In the insecticidal bioassay, the highest O. hyalinipennis mortalities (87 and 75%) were recorded at 15% concentration of the chloroform and butanol extracts of E. nivulia. In contrast, the lower concentrations of the E. nivulia extracts caused the lower mortalities. Altogether, these findings revealed that E. nivulia chloroform extracts showed significant phytotoxicity while all the extracts showed insecticidal potential. This potential can be, further, refined to be developed for bio-control agents.


Assuntos
Euphorbia/química , Euphorbia/metabolismo , Extratos Vegetais/farmacologia , Alcaloides , Animais , Araceae/efeitos dos fármacos , Araceae/metabolismo , Artemia/efeitos dos fármacos , Euphorbia/fisiologia , Hemípteros/efeitos dos fármacos , Heterópteros/efeitos dos fármacos , Hexanos , Inseticidas/farmacologia , Paquistão , Compostos Fitoquímicos/farmacologia , Extratos Vegetais/isolamento & purificação , Extratos Vegetais/metabolismo
19.
Urologiia ; (1): 131-139, 2021 Mar.
Artigo em Russo | MEDLINE | ID: mdl-33818949

RESUMO

Based on literature data, feasibility of combined therapy with Serenoa repens extracts (including Permixon) and 1-adrenoblocators in patients with LUTS/BPH based on the pathogenesis of these drugs and clinical results was analyzed. The composition and biological activity of various SRE is influenced by the extraction method, as well as the production technology used by the manufacturer, which can lead to different results of experimental and clinical studies. The mechanism of action of SRE, including hexane extract Permixon, is multicomponent, which combines an antiandrogenic effect, influence on neurogenic regulation of urinary tract function (-adrenoreceptors, M-holinoreceptors, vanilloid receptors), anti-inflammatory and anti-edematous actions. At the same time, the effect of these preparations is not limited to the influence on the prostate gland, but can directly affect the bladder, helping to reduce functional disorders. A wider range of mechanisms of action and a possible direct effect of SRE on the bladder provides the same clinical effect as other traditionally used drugs (-blockers, 5-reductase inhibitors) with a significantly lower frequency of side effects of therapy. A number of publications demonstrate the feasibility of combined therapy with 1-adrenoblockers and SRE in patients with LUTS/BPH, especially with a high degree of urination dysfunction. Futher investigations are needed. The role of Serenoa repens extracts in the combination therapy of LUTS/BPH is still under discussion. Serenoa repens extracts monotherapy demonstrates similar effectiveness in patients with LUTS as 1-adrenoblockers and 5-reductase inhibitors. Recent studies indicate the advantages of combining Serenoa repens extracts with 1-adrenoblockers, especially in patients with moderate or severe symptoms. These advantages are associated with the multicomponent action of Serenoa repens extracts, which complements the blockade of 1-adrenergic receptors with other mechanisms of action (in particular, anti-inflammatory). The combination of drugs with different mechanisms of action, in particular, Serenoa repens extracts (Permixon) and 1-adrenoblockers has certain pathophysiologically based advantages, which allows to increase the efficiency of therapy. In addition, combination therapy is not associated with an increased rate of side effects.


Assuntos
Hiperplasia Prostática , Serenoa , Hexanos/uso terapêutico , Humanos , Masculino , Fitoterapia , Extratos Vegetais/uso terapêutico , Hiperplasia Prostática/tratamento farmacológico
20.
Molecules ; 26(5)2021 Mar 08.
Artigo em Inglês | MEDLINE | ID: mdl-33800366

RESUMO

In our previous work, the partitions (1 mg/mL) of Ageratum conyzoides (AC) aerial parts and Ixora coccinea (IC) leaves showed inhibitions of 94% and 96%, respectively, whereas their fractions showed IC50 43 and 116 µg/mL, respectively, toward Matrix Metalloproteinase9 (MMP9), an enzyme that catalyzes a proteolysis of extracellular matrix. In this present study, we performed IC50 determinations for AC n-hexane, IC n-hexane, and IC ethylacetate partitions, followed by the cytotoxicity study of individual partitions against MDA-MB-231, 4T1, T47D, MCF7, and Vero cell lines. Successive fractionations from AC n-hexane and IC ethylacetate partitions led to the isolation of two compounds, oxytetracycline (OTC) and dioctyl phthalate (DOP). The result showed that AC n-hexane, IC n-hexane, and IC ethylacetate partitions inhibit MMP9 with their respective IC50 as follows: 246.1 µg/mL, 5.66 µg/mL, and 2.75 × 10-2 µg/mL. Toward MDA-MB-231, 4T1, T47D, and MCF7, AC n-hexane demonstrated IC50 2.05, 265, 109.70, and 2.11 µg/mL, respectively, whereas IC ethylacetate showed IC50 1.92, 57.5, 371.5, and 2.01 µg/mL, respectively. The inhibitions toward MMP9 by OTC were indicated by its IC50 18.69 µM, whereas DOP was inactive. A molecular docking study suggested that OTC prefers to bind to PEX9 rather than its catalytic domain. Against 4T1, OTC showed inhibition with IC50 414.20 µM. In conclusion, this study furtherly supports the previous finding that AC and IC are two herbals with potential to be developed as triple-negative anti-breast cancer agents.


Assuntos
Neoplasias da Mama/metabolismo , Metaloproteinase 9 da Matriz/metabolismo , Inibidores de Metaloproteinases de Matriz/farmacologia , Ageratum/metabolismo , Antineoplásicos Fitogênicos/farmacologia , Linhagem Celular Tumoral , Fracionamento Químico , Dietilexilftalato/química , Dietilexilftalato/isolamento & purificação , Hexanos , Humanos , Metaloproteinase 9 da Matriz/fisiologia , Simulação de Acoplamento Molecular , Oxitetraciclina/química , Oxitetraciclina/isolamento & purificação , Extratos Vegetais/farmacologia , Folhas de Planta/efeitos dos fármacos , Rubiaceae/metabolismo
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