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1.
Phytochemistry ; 171: 112233, 2020 Mar.
Artigo em Inglês | MEDLINE | ID: mdl-31911267

RESUMO

Eight previously undescribed and 15 known components, including six neolignans, two monolignan, three sesquineolignans, three dineolignans, eight phenylpropanoids, and one steroid were identified from the seed testa of Vernicia fordii. Their structures were established based on the comprehensive analysis of NMR and ECD data. The anti-neuroinflammatory effects of the isolates were evaluated through nitrite assays in LPS-induced BV2 cells. As a result, isodiverniciasin A, diverniciasin B, diverniciasin C, isoprincepin, princepin, 3, 3'-bisdemethylpinoresinol, (+)-7-epi-sesamin-dicatechol, isoamericanin A, americanin B, 7S, 8R-americanin D, 4-hydroxyl cinnamic aldehyde, 3-hydroxyl-4-methoxyl cinnamic aldehyde and 24R-6ß-hydroxy-24- ethylcholest-4-en-3-one exhibited significant inhibitory effects on nitric oxide (NO) production and isoprincepin, princepin, americanin B, and 4-hydroxyl cinnamic aldehyde suppressed the overexpression of inflammatory cytokines TNF-α, IL-1ß, and IL-6 in over-activated microglia. The results suggested that bioactive ingredients from the seed testa of V. fordii can serve as potential therapeutic agents for neurodegenerative diseases.


Assuntos
Anti-Inflamatórios/farmacologia , Euphorbiaceae/química , Inflamação/tratamento farmacológico , Fármacos Neuroprotetores/farmacologia , Compostos Fitoquímicos/farmacologia , Animais , Anti-Inflamatórios/química , Anti-Inflamatórios/isolamento & purificação , Sobrevivência Celular/efeitos dos fármacos , Células Cultivadas , Lipopolissacarídeos/antagonistas & inibidores , Lipopolissacarídeos/farmacologia , Camundongos , Conformação Molecular , Fármacos Neuroprotetores/química , Fármacos Neuroprotetores/isolamento & purificação , Nitritos/análise , Nitritos/antagonistas & inibidores , Nitritos/metabolismo , Compostos Fitoquímicos/química , Compostos Fitoquímicos/isolamento & purificação
2.
Phytochemistry ; 170: 112217, 2020 Feb.
Artigo em Inglês | MEDLINE | ID: mdl-31812109

RESUMO

Twelve ent-abietane and two ent-pimarane diterpenoids were isolated from the leaves of Croton mubango Müll. Arg. (Euphorbiaceae) collected in the Democratic Republic of the Congo. 2ß-Hydroxy-ent-abieta-7,13-dien-3-one, 15-hydroxy-ent-abieta-7,13-dien-3-one, 13α,15-dihydroxy-ent-abieta-8(14)-en-3-one, 2ß,9,13-trihydroxy-ent-abieta-7-en-3-one, 2ß,7ß-dihydroxy-ent-abieta-8,11,13-trien-3-one, 15-hydroxy-ent-abieta-8,11,13-trien-3-one and ent-pimara-8(14),15-dien-3-one and the ent-forms of the previously reported normal series diterpenoids, ent-abieta-8,11,13-trien-3-one, 7ß-hydroxy-ent-abieta-8,11,13-trien-3-one, 3α-hydroxy-ent-abieta-8,11,13-triene, 15-hydroxy-ent-abieta-8,11,13-triene and 6ß-hydroxy-ent-abieta-8,11,13-triene are reported here for the first time. Structures were established using HRESIMS, FTIR, NMR, DP4+ probability calculations and by comparison of the experimental and calculated electronic circular dichroism (ECD) spectra. Ent-pimara-8(14), 15-dien-3-one, showed antiproliferative activity against melanoma (MALME-3M), renal (UO-31) and ovarian cancer cell lines (IGROV1) at a concentration of 10-5 M in the NCI 60 screen.


Assuntos
Antineoplásicos Fitogênicos/farmacologia , Diterpenos/farmacologia , Euphorbiaceae/química , Compostos Fitoquímicos/farmacologia , Antineoplásicos Fitogênicos/química , Antineoplásicos Fitogênicos/isolamento & purificação , Linhagem Celular Tumoral , Proliferação de Células/efeitos dos fármacos , Diterpenos/química , Diterpenos/isolamento & purificação , Relação Dose-Resposta a Droga , Ensaios de Seleção de Medicamentos Antitumorais , Humanos , Conformação Molecular , Compostos Fitoquímicos/química , Compostos Fitoquímicos/isolamento & purificação , Relação Estrutura-Atividade
3.
Phytochemistry ; 170: 112213, 2020 Feb.
Artigo em Inglês | MEDLINE | ID: mdl-31786408

RESUMO

Clutia lanceolata Forssk. (C. lanceolata) is a medicinal plant native to sub-Saharan Africa and the Arabian Peninsula. Phytochemical investigation of the aerial parts of C. lanceolata yielded twenty-one coumarins including methylthio and methylsulfinyl-coumarins. Thirteen of these compounds are reported here for the first time, named as cluteolin A to M. The remaining eight compounds are known but have not been associated previously with C. lanceolata. The structures of the undescribed compounds were elucidated from their 2D NMR and MS spectra. Single crystal X-ray analyses confirmed the structures of eleven compounds. As, in Saudi Arabian tradition, C. lanceolata has been reported to have anti-diabetic and anti-fungal properties, the coumarins were examined for their biological activity. Seven compounds strongly enhanced the glucose-triggered release of insulin by murine pancreatic islets, with two compounds showing more than two-fold enhancement of insulin secretion, compared with the standard drug glimepiride.


Assuntos
Cumarínicos/farmacologia , Euphorbiaceae/química , Secreção de Insulina/efeitos dos fármacos , Insulina/metabolismo , Compostos Fitoquímicos/farmacologia , Enxofre/farmacologia , Animais , Cumarínicos/química , Cumarínicos/isolamento & purificação , Masculino , Camundongos , Camundongos Endogâmicos BALB C , Compostos Fitoquímicos/química , Compostos Fitoquímicos/isolamento & purificação , Arábia Saudita , Enxofre/química , Enxofre/isolamento & purificação
4.
Fitoterapia ; 140: 104432, 2020 Jan.
Artigo em Inglês | MEDLINE | ID: mdl-31759030

RESUMO

Seven new lignans, cleistonkinins A- E (1-5), cleistonkisides A and B (6-7) were isolated from the fruits of Cleistanthus tonkinensis (Euphorbiaceae), together with five known aryltetralin lignans, cleisindoside B (8), cleistantoxin (9), cleisindoside D (10), neocleistantoxin (11) and polygamain (12). Their structures were established from spectral analysis, including mass spectrometry and 2D-NMR. The absolute configurations of 4-7 were determined by analysis of their experimental CD spectra and comparison with calculated electronic circular dichroism (ECD) spectra. Compounds 2 and 6 had selective inhibition with moderate cytotoxicity against Pan C1 and A549 cell lines, respectively. Cleistantoxin (9) was significantly active against A549, HeLa, Hep3B, Pan C1 and MCF7 cell lines while it was less cytotoxic against HeLa cells. Neocleistantoxin (11) exhibited remarkable inhibition toward A549, HeLa, MCF7 and Pan C1. This is the first report for cytotoxicity of 9 and 11 against A549, Hep3B and Pan C1 cell lines.


Assuntos
Antineoplásicos Fitogênicos/farmacologia , Euphorbiaceae/química , Frutas/química , Lignanas/farmacologia , Antineoplásicos Fitogênicos/isolamento & purificação , Linhagem Celular Tumoral , Humanos , Lignanas/isolamento & purificação , Estrutura Molecular , Compostos Fitoquímicos/isolamento & purificação , Compostos Fitoquímicos/farmacologia , Vietnã
5.
Food Chem ; 307: 125568, 2020 Mar 01.
Artigo em Inglês | MEDLINE | ID: mdl-31630021

RESUMO

Sacha inchi oil is derived from the seeds of Plukenetia volubilis L. and has great nutritional value due to its high contents of active polyunsaturated triacylglycerols (PUTAGs). In this study, we developed a methodology combined Paternò-Büchi reaction nanoelectrospray ionization mass spectrometry (PB-nanoESI-MS) and nuclear magnetic resonance (NMR) to identify CC locations and isomers of PUTAGs in sacha inchi oil. Benzophenone was used as the PB reagent, and the optimized solvent composition (methanol:chloroform = 9:1) allowed for PUTAGs and their PB products to be detected with higher intensities. In addition, we made efforts to interpret the MS2 spectra for identification lipid species. A series of C57-PUTAGs and C59-PUTAGs were detected and identified via high-resolution PB-nanoESI-MS, and the predominant PUTAGs were TAG 18:1(Δ9)_18:3(Δ9,12,15)_18:3(Δ9,12,15) and TAG 18:2(Δ9,12)_18:2(Δ9,12)_18:3 (Δ9,12,15), which demonstrated that the PB-nanoESI-MS approach in this study provides help in promoting the development of structural determination of triacylglycerols in food chemistry.


Assuntos
Euphorbiaceae/química , Espectroscopia de Ressonância Magnética/métodos , Óleos Vegetais/química , Espectrometria de Massas por Ionização por Electrospray/métodos , Triglicerídeos/análise , Ácidos Graxos Insaturados , Triglicerídeos/química
6.
BMC Res Notes ; 12(1): 649, 2019 Oct 07.
Artigo em Inglês | MEDLINE | ID: mdl-31590691

RESUMO

OBJECTIVES: This study examines the rationale, if any, behind combining the extracts from the fruits of Alchornea cordifolia and Pterocarpus santalinoides and aerial parts of Cassytha filiformis in the traditional treatment of diarrhoegenic bacterial infections. RESULTS: Four diarrhoegenic bacterial isolates: Salmonella typhi, Shigellae dysenteriae, Escherichia coli and Staphylococcus aureus were used and their antibiotic susceptibility screening showed that they were multi-antibiotic resistant. The extracts exhibited activity against all the test isolates with minimum inhibitory concentration values ranging from 3.125 to 12.5 mg/mL. From the checkerboard assay, the fractional inhibitory concentration indices showed that C. filiformis has antagonistic and indifference activities in combination with either P. santalinoides or A. cordifolia. This showed that the combination of extracts from the fruits of A. cordifolia and P. santalinoides and aerial parts of C. filiformis is counterproductive and invalidates any claim for positive results in the management of diarrhoegenic bacterial infections.


Assuntos
Antibacterianos/farmacologia , Euphorbiaceae/química , Lauraceae/química , Extratos Vegetais/farmacologia , Pterocarpus/química , Antibacterianos/isolamento & purificação , Combinação de Medicamentos , Farmacorresistência Bacteriana Múltipla/efeitos dos fármacos , Escherichia coli/efeitos dos fármacos , Frutas/química , Testes de Sensibilidade Microbiana , Componentes Aéreos da Planta/química , Extratos Vegetais/isolamento & purificação , Salmonella typhi/efeitos dos fármacos , Shigella dysenteriae/efeitos dos fármacos , Staphylococcus aureus/efeitos dos fármacos
7.
Artigo em Inglês | MEDLINE | ID: mdl-31596175

RESUMO

In the Philippines, the herbal medicinal product (HMP) market is flourishing due to the abundance of pharmacologically important species, and the high level of ethnomedicinal knowledge still widely accepted by the public. As such, herbal products from Antidesma bunius (L.) Spreng., locally known as bignay, are popular as medicine for various ailments of the circulatory and digestive systems. Though efficacy is guaranteed, the authenticity of the marketed products is still in question as several other herbal plants can provide the said benefits. Similar morphology between wild species also hinders species identification and contributes confusion especially to the general consumer. The authenticity of the marketed HMPs was established by means of DNA barcoding techniques which offers quick and reliable species identification by means of (1) the Basic Local Alignment Search Tool (BLASTn) and (2) the establishment of the first Standard Reference Material (SRM) Herbal barcode library for Antidesma spp. A total of 56 gene accessions from matK-psbA-trnH-rbcL sequences of 9 wild Antidesma spp. comprised the SRM which was then used to confirm the identity of 11 randomly sampled bignay-derived HMPs. Following the BLASTn and the SRM (maximum likelihood tree reconstruction) criterion, the subjected sequences revealed that only three of the 11 HMPs were authentic A. bunius-derived products. The other eight HMPs contained substitutes that were either fillers or different herbal medicinal plant not indicated in the product labels. These results indicate that product safety should be reinforced with complete HMP authentication using traditional methods supported by molecular data.


Assuntos
Código de Barras de DNA Taxonômico/normas , Euphorbiaceae/química , Contaminação de Alimentos/análise , Biblioteca Gênica , Medicina Herbária , Plantas Medicinais/química , Frutas/química
8.
Phytochemistry ; 167: 112101, 2019 Nov.
Artigo em Inglês | MEDLINE | ID: mdl-31473556

RESUMO

In an effort to identify inhibitors of Chikungunya virus (CHIKV) replication, a systematic study of 594 extracts of plant species originating from the French Guiana plateau region was performed in a virus-cell-based assay for CHIKV assay. The extract obtained from the stem bark of Sagotia racemosa was selected for its potent antiviral activity. Using a classical bioassay-guided procedure, three undescribed degraded diterpenoids, i.e. trigohowilols C and D and trigoflavidol D, as well as trigoxyphin K, stictic acid, hyperhomosekikaic acid and five known flavonoids were isolated. The structures of these compounds were elucidated by extensive NMR spectroscopic data analysis. Although trigohowilols C and D were isolated from the most active fraction they didn't show any antiviral activity. By using the Feature-Based Molecular Networking (FBMN) and Network Annotation Propagation (NAP) workflows, it has been shown that the strong anti-CHIKV activity found for this fraction might be due to the presence of analogues of 12-O-tetradecanoylphorbol-13-acetate (TPA), one of the most potent inhibitors of CHIKV replication identified to date.


Assuntos
Antivirais/isolamento & purificação , Antivirais/farmacologia , Vírus Chikungunya/efeitos dos fármacos , Euphorbiaceae/química , Fenantrenos/isolamento & purificação , Fenantrenos/farmacologia , Ésteres de Forbol/química , Antivirais/química , Vírus Chikungunya/fisiologia , Informática , Fenantrenos/química , Replicação Viral/efeitos dos fármacos , Fluxo de Trabalho
9.
Biomed Pharmacother ; 117: 109140, 2019 Sep.
Artigo em Inglês | MEDLINE | ID: mdl-31387195

RESUMO

Previously non-isolated compounds (scopoletin and ß-D-Glucopyranoside, (1R)-O-isopropyl 6-O-(2,3,4-tri-O-acetyl-ß-D-xylopyranosyl)-2,3,4-triacetate) were isolated from an organic extract of the Cnidoscolus chayamansa stem. Also, lupeol acetate (main compound, 49.7 mg/g of dry extract) and scopoletin (0.19 mg/g of dry extract) were quantified by HPLC analysis from this organic extract. The protective activity of the C. chayamansa organic extract against hepatotoxicity induced by antitubercular drugs [Rifampicin (50 mg/kg), Isoniazid (50 mg/kg), and Pyrazinamide (100 mg/kg)] are reported. The extract was tested at 200 and 400 mg/kg in Balb/C mice during 85 days, using silymarin (2.5 mg/kg) as positive control. Liver damage was determined using biochemical parameters (AST, ALT, ALP, CHOL, HDL TG, Urea, and CREA), histological analysis, and evaluation of oxidative stress (SOD, CAT, Gpx, Lpx and POx). The extract at both doses favored body weight gain with respect to the anti-TB group; the dose of 200 mg/kg was better. Also, the extract at both doses decreased the values of transaminases (AST, ALT) enzymes (p < 0.05) vs. anti-TB group. In oxidative stress parameters, the SOD value was decreased, as were the levels of peroxidation of lipids and oxidative protein in the group with C. chayamansa extract at 200 and 400 mg/kg vs. the anti-TB group. Histological analyses from liver showed the absence of steatosis in the extract group at 400 mg/kg, and moderate steatosis in the silymarin and extract (at 200 mg/kg) groups with respect to anti-TB group, which demonstrated a steatosis. It should be noted that during the study period, none of the treated mice died. In conclusion, the CHCl3: MeOH extract of C. chayamansa has a hepatoprotective effect against hepatotoxicity induced by anti-TB drugs.


Assuntos
Antituberculosos/efeitos adversos , Doença Hepática Induzida por Substâncias e Drogas/tratamento farmacológico , Euphorbiaceae/química , Fígado/efeitos dos fármacos , Extratos Vegetais/farmacologia , Alanina Transaminase/metabolismo , Animais , Antioxidantes/metabolismo , Aspartato Aminotransferases/metabolismo , Doença Hepática Induzida por Substâncias e Drogas/metabolismo , Fígado/metabolismo , Testes de Função Hepática/métodos , Masculino , Camundongos , Camundongos Endogâmicos BALB C , Estresse Oxidativo/efeitos dos fármacos
10.
Chemistry ; 25(49): 11574-11580, 2019 Sep 02.
Artigo em Inglês | MEDLINE | ID: mdl-31407847

RESUMO

The so-called Securinega alkaloids constitute a class of tetracyclic biologically active specialised metabolites isolated principally from subtropical plants belonging to the Phyllanthaceae family. Following a strategy based on alternative hypotheses for their biosynthesis, an easy and time-efficient divergent synthesis enabled access to twelve of those alkaloids featuring (neo)(nor)securinane skeletons. Moreover, this work permitted to reassign the absolute configurations of (+)-virosine B and (-)-episecurinol A.


Assuntos
Alcaloides/biossíntese , Alcaloides/química , Euphorbiaceae/química , Euphorbiaceae/metabolismo , Mesilatos/química , Conformação Molecular , Estereoisomerismo
11.
Artigo em Inglês | MEDLINE | ID: mdl-31314740

RESUMO

Background We investigated the effects of a polyherbal formulation prepared from the extracts of Mondia whitei (Periplocaceae), Dracaena arborea (Dracaenaceae), and Bridelia ferruginea (Euphorbiaceae) (MDB) on the sexual behavior of normal rats (NR) and prediabetic rats (PR). Methods Male Wistar rats were administered with drinking fructose solution (21%) or tap water for 16 weeks. After induction of prediabetic status, NR (n = 30) and PR (n = 30) were randomly distributed into 10 groups of six animals each and orally treated with distilled water (10 mL/kg), sildenafil citrate (5 mg/kg), or MDB (50, 100, or 500 mg/kg) for 21 days. Sexual behavior parameters per series (S) of ejaculation were evaluated on days 1, 7, 14, and 21. Results Drinking fructose solution (21%) induced prediabetic status in rats, characterized by a significant (p < 0.01) increase in glycemia by 43.41% compared with the control group. MDB improved sexual performances of NR and PR by increasing the mount frequency (MF) and the intromission frequency (IF) as well as the number of rats capable of ejaculating. For instance, the MF and the IF were significantly increased in animals administered with MDB for 7 (50 mg/kg, S1 and S2), 14 (100 mg/kg, S3), or 21 days (100 or 500 mg/kg, S2). This increase was more pronounced on days 7 and 14 in NR and PR treated with sildenafil citrate or MDB extracts, respectively. Conclusions The mixture of MDB improved sexual activity in NR and PR. This result may further justify the traditional use of these plants as sexual performance enhancers.


Assuntos
Apocynaceae/química , Dracaena/química , Euphorbiaceae/química , Extratos Vegetais/farmacologia , Estado Pré-Diabético/tratamento farmacológico , Comportamento Sexual Animal/efeitos dos fármacos , Comportamento Sexual/efeitos dos fármacos , Animais , Ejaculação/efeitos dos fármacos , Masculino , Ratos , Ratos Wistar
12.
Food Chem ; 298: 125045, 2019 Nov 15.
Artigo em Inglês | MEDLINE | ID: mdl-31261002

RESUMO

In this study, sacha inchi oil (SIO) (Plukenetia volubilis L.) was microencapsulated via complex coacervation of ovalbumin (OVA) and sodium alginate (AL), and the microcapsule properties were characterized. The omega-3 content in the SIO was evaluated after in vitro gastric simulation and microencapsulation. The coacervate complex between OVA and AL was evaluated based on electrostatic interactions and developed for use as a wall material via the SIO microencapsulation process. The best mass ratio for the biopolymers (OVA:AL) was 4:1 at pH 3.8, and the complex exhibited a thermal resistance at 189.86 °C. The SIO microcapsules showed a high encapsulation efficiency of approximately 94.12% in the ratio (OVA:AL) of 1:1. Furthermore, microencapsulated SIO presented resistance under gastric conditions with a low release of acyl (ω-3) units. These results demonstrate that it is possible to use OVA:AL as encapsulating agents to protect bioactive compounds and to improve the thermal behavior of microcapsules.


Assuntos
Composição de Medicamentos/métodos , Euphorbiaceae/metabolismo , Óleos Vegetais/química , Alginatos/química , Varredura Diferencial de Calorimetria , Cápsulas/química , Euphorbiaceae/química , Ácidos Graxos Ômega-3/química , Concentração de Íons de Hidrogênio , Ovalbumina/química , Eletricidade Estática
13.
Andrologia ; 51(9): e13359, 2019 Oct.
Artigo em Inglês | MEDLINE | ID: mdl-31353623

RESUMO

The effect of the methanolic extract of Alchornea cordifolia leaves on the fertility of senescent male rats was assessed in this study. 40 rats received daily distilled water, testosterone, 200 and 400 mg/kg of extract of Alchornea cordifolia. The reproductive organs weight, the gonadotropins, testosterone and cholesterol level, the sperm parameters, histology of the testes and epididymis were assessed. The weight of testes and prostate (400 mg/kg) significantly increased (p < 0.05) as well as the level of FHS (p < 0.001), LH and testosterone (p < 0.01) at a dose of 400 mg/kg, respectively, while the cholesterol decreased at a dose of 200 mg/kg (p < 0.05) and 400 mg/kg (p < 0.01) respectively. The testes and epididymis were full of spermatozoa particularly at a dose of 400 mg/kg. The sperm count and morphology significantly increased at both doses of 200 mg/kg (p < 0.01; p < 0.001) and 400 mg/kg (p < 0.001; p < 0.01) respectively. The sperm motion (PROG, VAP, VSL, VCL) (p < 0.001), (ALH, BCF) (p < 0.05) increased at a dose of 200 mg/kg and decreased at a dose of 400 mg/ kg. The overall results provide the strong evidence of the fertility potential of the methanolic extract of Alchornea cordifolia leaves in senescent male rats.


Assuntos
Envelhecimento/fisiologia , Euphorbiaceae/química , Fertilidade/efeitos dos fármacos , Extratos Vegetais/administração & dosagem , Animais , Relação Dose-Resposta a Droga , Epididimo/efeitos dos fármacos , Epididimo/fisiologia , Fertilidade/fisiologia , Masculino , Metanol/química , Modelos Animais , Extratos Vegetais/isolamento & purificação , Folhas de Planta/química , Ratos , Ratos Wistar , Contagem de Espermatozoides , Motilidade Espermática/efeitos dos fármacos , Motilidade Espermática/fisiologia , Espermatozoides/efeitos dos fármacos , Espermatozoides/fisiologia , Testículo/efeitos dos fármacos , Testículo/fisiologia
14.
Phytomedicine ; 63: 153033, 2019 Oct.
Artigo em Inglês | MEDLINE | ID: mdl-31352284

RESUMO

BACKGROUND: The emergence of antibiotic resistant microorganisms presents a worldwide problem that requires novel antibiotic and non-antibiotic strategies, and biofilm formation is a mechanism of drug resistance utilized by diverse microorganisms. The majority of microorganisms live in biofilms that help their survival against starvation, antimicrobial agents, and immunological defense systems. Therefore, it is important novel compounds be identified that inhibit biofilm formation and cell survival without drug resistance. STUDY DESIGN: In this study, the antimicrobial and antibiofilm activities of five prenylated flavanones (Okinawan propolins) isolated from fruits of Macaranga tanarius (L.) were investigated against 14 microorganisms including 10 pathogens. RESULTS: Of these five propolins, propolin D at 5-10 µg/ml significantly inhibited biofilm formation by three Staphylococcus aureus strains, a Staphylococcus epidermidis strain, and a Candida albicans with MICs from 10 to 50 µg/ml, and in C. albicans, propolin D was found to inhibit biofilm formation by reducing cell aggregation and downregulated the expressions of hypha/biofilm-related genes including ECE1 and HWP1. Interestingly, at sub-MIC concentrations (10-50 µg/ml), propolin D significantly inhibited biofilm formation by enterohemorrhagic E. coli O157:H7, uropathogenic E. coli O6:H1, and Acinetobacter baumannii without affecting planktonic cell growth, but did not inhibit biofilm formation by a commensal E. coli K-12 strain, three probiotic Lactobacillus plantarum strains, or two Pseudomonas aeruginosa strains. And, propolin D reduced fimbriae production by E. coli O157:H7 and repressed gene expression of curli fimbriae genes (csgA and csgB). Also, propolin D was minimally toxic in a Caenorhabditis elegans nematode model. CONCLUSION: These findings show that prenylated flavanones, especially propolin D from Macaranga tanarius (Okinawan propolis), should be considered potential candidates for the development of non-toxic antibacterial and antifungal agents against persistent microorganisms.


Assuntos
Antibacterianos/farmacologia , Antifúngicos/farmacologia , Euphorbiaceae/química , Flavanonas/farmacologia , Flavonoides/farmacologia , Animais , Antibacterianos/química , Antibacterianos/toxicidade , Antifúngicos/química , Antifúngicos/toxicidade , Biofilmes/efeitos dos fármacos , Caenorhabditis elegans/efeitos dos fármacos , Candida albicans/efeitos dos fármacos , Candida albicans/fisiologia , Avaliação Pré-Clínica de Medicamentos , Escherichia coli O157/efeitos dos fármacos , Flavanonas/química , Flavanonas/toxicidade , Flavonoides/química , Flavonoides/toxicidade , Testes de Sensibilidade Microbiana , Prenilação , Pseudomonas aeruginosa/efeitos dos fármacos , Pseudomonas aeruginosa/fisiologia , Staphylococcus aureus/efeitos dos fármacos , Staphylococcus aureus/fisiologia , Testes de Toxicidade
15.
Molecules ; 24(12)2019 Jun 25.
Artigo em Inglês | MEDLINE | ID: mdl-31242603

RESUMO

Macrocyclic diterpenoids produced by plants of the Euphorbiaceae family are of considerable interest due to their high structural diversity; and their therapeutically relevant biological properties. Over the last decade many studies have reported the ability of macrocyclic diterpenoids to inhibit in cellulo the cytopathic effect induced by the chikungunya virus. This review; which covers the years 2011 to 2019; lists all macrocyclic diterpenoids that have been evaluated for their ability to inhibit viral replication. The structure-activity relationships and the probable involvement of protein kinase C in their mechanism of action are also detailed.


Assuntos
Antivirais/farmacologia , Vírus Chikungunya/efeitos dos fármacos , Vírus Chikungunya/fisiologia , Diterpenos/química , Diterpenos/farmacologia , Euphorbiaceae/química , Extratos Vegetais/farmacologia , Replicação Viral/efeitos dos fármacos , Animais , Antivirais/química , Febre de Chikungunya/tratamento farmacológico , Febre de Chikungunya/virologia , Humanos , Estrutura Molecular , Extratos Vegetais/química , Relação Estrutura-Atividade
16.
Molecules ; 24(9)2019 May 13.
Artigo em Inglês | MEDLINE | ID: mdl-31086098

RESUMO

Natural daphnane diterpenoids, mainly distributed in plants of the Thymelaeaceae and Euphorbiaceae families, usually include a 5/7/6-tricyclic ring system with poly-hydroxyl groups located at C-3, C-4, C-5, C-9, C-13, C-14, or C-20, while some special types have a characteristic orthoester motif triaxially connectedat C-9, C-13, and C-14. The daphnane-type diterpenoids can be classified into five types: 6-epoxy daphnane diterpenoids, resiniferonoids, genkwanines, 1-alkyldaphnanes and rediocides, based on the oxygen-containing functions at rings B and C, as well as the substitution pattern of ring A. Up to now, nearly 200 daphnane-type diterpenoids have been isolated and elucidated from the Thymelaeaceae and Euphorbiaceae families. In-vitro and in-vivo experiments of these compounds have shown that they possess a wide range of biological activities, including anti-HIV, anti-cancer, anti-leukemic, neurotrophic, pesticidal and cytotoxic effects. A comprehensive account of the structural diversity is given in this review, along with the cytotoxic activities of daphnane-type diterpenoids, up to April 2019.


Assuntos
Diterpenos/química , Euphorbiaceae/química , Thymelaeaceae/química , Animais , Fármacos Anti-HIV/química , Antineoplásicos/química , Humanos , Estrutura Molecular
17.
J Med Food ; 22(8): 851-860, 2019 Aug.
Artigo em Inglês | MEDLINE | ID: mdl-31074673

RESUMO

Aberrant crypt foci (ACF) is the precursor lesion of colorectal carcinogenesis (CRC), one of the most common malignancies in the world. Many studies have reported that people with higher phytochemical intake are at a reduced risk of developing ACF. One example of the botanical potential of preventive plant products is Cnidoscolus aconitifolius (CA), commonly known as Chaya. This study evaluated the phenolic profile of CA and the effects of the daily consumption of CA leaf infusion on the formation of ACF, histopathological lesions, and molecular biomarkers after azoxymethane (AOM) and dextran sulfate sodium (DSS) induced premalignant colon lesions in rats treated with for 16 and 32 weeks. The phenolic composition of the CA infusion was identified by reversed phase-high performance liquid chromatography-diode array detection (RP-HPCC-DAD). After sacrifice, a 4 cm segment was collected from the distal part of the colon and stained with methylene blue to look for ACF. Furthermore, 4 µm of colon, liver, and kidney was collected and stained with hematoxylin and eosin for histopathological analysis, along with 7 µm of colon for immunohistochemistry analysis. Eleven phenolic compounds were identified in the infusions, and ACF formation was reduced by 29.5% at the subchronic and by 64.6% at chronic stages. Lesions on kidney, liver, and colon tissue were also reduced. Our data suggest that CA treatment has preventive effects against AOM-/DSS-induced premalignant colon lesions in colon rats at the promotion level, inhibiting the cell proliferation of early neoplastic lesions and colonic inflammation through the decrease of ß-catenin by 41.8% at the subchronic stage and 29% at the chronic stage, along with a 46.2% reduction of cyclooxygenase 2 (COX-2) at long term, despite a high expression of NF-κB (30.3% at the subchronic stage and 22.8% at the chronic stage).


Assuntos
Focos de Criptas Aberrantes/prevenção & controle , Euphorbiaceae/química , Extratos Vegetais/administração & dosagem , Substâncias Protetoras/administração & dosagem , Focos de Criptas Aberrantes/induzido quimicamente , Focos de Criptas Aberrantes/patologia , Animais , Azoximetano/efeitos adversos , Colo/efeitos dos fármacos , Colo/patologia , Sulfato de Dextrana/efeitos adversos , Modelos Animais de Doenças , Humanos , Masculino , Extratos Vegetais/química , Folhas de Planta/química , Substâncias Protetoras/química , Ratos , Ratos Sprague-Dawley
18.
Fitoterapia ; 134: 151-157, 2019 Apr.
Artigo em Inglês | MEDLINE | ID: mdl-30825571

RESUMO

Bioassay-guided fractionation of the leaves of Macaranga barteri collected from Nigeria led to the isolation of three previously undescribed cytotoxic stilbenes, macabartebenes A-C (1-3), together with six known compounds including prenylated stilbenes: vedelianin (4), schweinfurthin G (5), and mappain (7), prenylated flavonols: 8-prenylkaempferol (6), and broussoflavonol F (8), and the geranylated flavonol, isomacarangin (9). The cytotoxicity of the compounds was evaluated against four human cancer cell lines, with vinblastine as the positive control and DMSO vehicle as the negative control. Vedelianin (IC50 = 0.32-0.54 µM) displayed the greatest antiproliferative activity across the panel of cancer cell lines amongst the compounds, while macabartebene A (IC50 = 0.60-0.79 µM) was the most potent of the previously unreported compounds. The compounds displayed varying selectivity towards the cancer cell lines compared to the normal human prostate cell line. The findings of this study revealed that M. barteri leaves contain several cytotoxic compounds.


Assuntos
Antineoplásicos Fitogênicos/farmacologia , Euphorbiaceae/química , Flavonóis/farmacologia , Estilbenos/farmacologia , Antineoplásicos Fitogênicos/isolamento & purificação , Bioensaio , Linhagem Celular Tumoral , Fracionamento Químico , Ensaios de Seleção de Medicamentos Antitumorais , Flavonóis/isolamento & purificação , Humanos , Estrutura Molecular , Nigéria , Compostos Fitoquímicos/isolamento & purificação , Compostos Fitoquímicos/farmacologia , Folhas de Planta/química , Estilbenos/isolamento & purificação
19.
J Pharm Biomed Anal ; 169: 293-302, 2019 May 30.
Artigo em Inglês | MEDLINE | ID: mdl-30901623

RESUMO

As extensively active compounds, coumarins are rarely reported on the phytochemistry of the genus Trigonostemon. We herein proposed a fast strategy for analysis and separation of antitumoral active coumarins from the twigs of T. lutescens. Rapid Resolution liquid chromatography coupled with diode array detection and electrospray ionization mass spectrometry (RRLC-DAD-ESI-MS) analysis indicated the existence of coumarins in the twig extracts. Bioactivity guided phytochemical analysis assays revealed that the twig extract contained some active components that significantly inhibited cancer cell viability. Accordingly, a series of coumarins including a new furanocoumarin have been isolated from the twigs of T. lutescens by semi-preparative chromatographic separation. All compounds, especially furan-type coumarins, were reported for the first time from the genus Trigonostemon. The proposed strategy, by combining RRLC-DAD-ESI-MS based and bioactivity guided phytochemical analysis, exemplify a fast method for screening and identifying active components from raw extracts of herbs.


Assuntos
Cumarínicos/química , Euphorbiaceae/química , Compostos Fitoquímicos/química , Extratos Vegetais/química , Linhagem Celular Tumoral , Sobrevivência Celular/efeitos dos fármacos , Cromatografia Líquida de Alta Pressão/métodos , Cumarínicos/farmacologia , Células HCT116 , Células HeLa , Células Hep G2 , Humanos , Compostos Fitoquímicos/farmacologia , Extratos Vegetais/farmacologia , Espectrometria de Massas por Ionização por Electrospray/métodos
20.
Pak J Pharm Sci ; 32(1): 143-152, 2019 Jan.
Artigo em Inglês | MEDLINE | ID: mdl-30772803

RESUMO

The efficacy of Chrozophora plicata and Trianthema portuclacastrum extracts was investigated against Trogoderma granarium at 10%, 20% and 30% concentrations and 2, 4 and 6 days of exposure periods. It was found that T. portuclacastrum extract caused significantly higher larval mortality (37.47%) than C. plicata (27.03%). Maximum number of T. granarium larvae (91.11% and 82.22%) was repelled when exposed to 30% concentration. A significant reduction in percentage larval emergence was also found in F1 generation. A decrease in the activity of Acetylcholine Esterase (AChE), Acid Phosphatase (ACP), Alkaline Phosphatase (AKP), α-Carboxyl and ß-Carboxyl was also found. The FTIR analysis showed the presence of polyphenolic compounds in T. portuclacastrum extract. The overall results revealed that T. portuclacastrum extract was very effective against T. granarium than C. plicata.


Assuntos
Aizoaceae , Besouros/efeitos dos fármacos , Euphorbiaceae , Inseticidas/farmacologia , Controle de Pragas/métodos , Extratos Vegetais/farmacologia , Plantas Daninhas , Aizoaceae/química , Animais , Besouros/crescimento & desenvolvimento , Besouros/metabolismo , Relação Dose-Resposta a Droga , Euphorbiaceae/química , Inseticidas/isolamento & purificação , Larva/efeitos dos fármacos , Extratos Vegetais/isolamento & purificação , Plantas Daninhas/química
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