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1.
Chem Biodivers ; 21(7): e202400670, 2024 Jul.
Artigo em Inglês | MEDLINE | ID: mdl-38747034

RESUMO

Cancer remains a significant global health concern, with mortality rates steadily rising and prompting an urgent search for effective treatments. This study focuses on the medicinal properties of plants from the Phyllanthus genus, specifically Phyllanthus amarus and Phyllanthus niruri, which have shown promise in traditional medicine. Through bioguided fractionation using preparative high-performance liquid chromatography (HPLC), bioactive compounds were isolated and identified using ultra-performance liquid chromatography coupled to time-of-flight mass spectrometry (UHPLC-QTOF-MSE) and nuclear magnetic resonance (NMR) spectroscopy. Chemometric analyses such as principal component analysis (PCA) aided in understanding metabolite distribution. Biological assays demonstrated cytotoxic activities of specific fractions against cancer cell lines, notably the PhyN 4n fraction from P. niruri, which induced S-phase cell cycle arrest and apoptosis in HL60 cells. These findings underscore the anticancer potential of Phyllanthus species and lay the groundwork for future drug development efforts. The study's integration of advanced analytical techniques, chemometrics, and biological assays provides valuable insights for harnessing natural products in the fight against cancer.


Assuntos
Antineoplásicos Fitogênicos , Apoptose , Ensaios de Seleção de Medicamentos Antitumorais , Metabolômica , Phyllanthus , Phyllanthus/química , Humanos , Antineoplásicos Fitogênicos/farmacologia , Antineoplásicos Fitogênicos/química , Antineoplásicos Fitogênicos/isolamento & purificação , Apoptose/efeitos dos fármacos , Cromatografia Líquida de Alta Pressão , Extratos Vegetais/química , Extratos Vegetais/farmacologia , Extratos Vegetais/isolamento & purificação , Linhagem Celular Tumoral , Proliferação de Células/efeitos dos fármacos , Sobrevivência Celular/efeitos dos fármacos , Relação Dose-Resposta a Droga
2.
J Chem Ecol ; 48(7-8): 660-669, 2022 Aug.
Artigo em Inglês | MEDLINE | ID: mdl-35653012

RESUMO

In most commercial pine farms in southern Brazil, black capuchin causes damage to wood and financial losses when it removes bark from some pine species to feed upon underlying vascular tissues. Therefore, this study aimed to evaluate the variability of the primary metabolites of phloem saps from 10 different species of pine by NMR spectroscopy, as well as the aroma compounds using SPME-GC-MS. Each technique provided a different set of metabolites that we can correlate to monkey predilection. The PCA showed monosaccharide (detected by NMR) and α-pinene (pine-like and resinous flavor descriptors) as attractive compounds for monkeys. On the other hand, the low content of monosaccharide and the high content of ß-phellandrene (citrus odor descriptor) was observed in less attacked pine species (P. patula). The data fusion on primary metabolites and aroma compounds corroborated the individual analyses, complementing the comprehension of the monkey predilection. Thus, P. elliottii was an avoided tree even with high content of sugars possibly due to its high content of ß-phellandrene (citrus odor). The results are useful for further behavioral studies to determine the role that each highlighted metabolite plays in chemically mediated animal-plant interactions.


Assuntos
Citrus , Pinus , Animais , Citrus/metabolismo , Cromatografia Gasosa-Espectrometria de Massas , Monossacarídeos/metabolismo , Floema/metabolismo , Pinus/química , Sapajus
3.
Food Chem ; 324: 126874, 2020 Sep 15.
Artigo em Inglês | MEDLINE | ID: mdl-32353658

RESUMO

Thermally-processed coconut water often develop a commercially-undesirable pink color, thus, NMR, UPLC-HRMS, GC-MS analyses combined with chemometrics approach were applied to evaluate chemical variations in comparison to tender water (control) that could explain such color change. Chemometrics on negative ionization mode dataset showed trimeric and A-type dimeric procyanidins, and caffeoylshikimic acid as main identified secondary metabolites induced by processing, while, control water presented mainly cytokinin trans-zeatin riboside, procyanidin dimer, caffeoylshikimic acid and trihydroxy-octadecenoic acid. Processing increased long-chain saturated palmitic and stearic fatty acids contents, meanwhile NMR analysis showed a decline in primary metabolites content as sugars fructose and glucose, and short-chain organic acids. Among the results observed for thermally processed coconut water, the increase in oligomeric procyanidins as A-type dimer and trimer may be associated with pink color development as these are precursors of anthocyanin pigment and/or by enhancing color stability of anthocyanin solutions.


Assuntos
Cromatografia Líquida de Alta Pressão , Cocos/química , Cromatografia Gasosa-Espectrometria de Massas , Espectroscopia de Ressonância Magnética , Espectrometria de Massas , Antocianinas/análise , Antocianinas/isolamento & purificação , Cocos/metabolismo , Cor , Citocininas/análise , Citocininas/isolamento & purificação , Frutose/análise , Frutose/isolamento & purificação , Análise de Componente Principal , Proantocianidinas/análise , Proantocianidinas/isolamento & purificação , Extração em Fase Sólida , Temperatura
4.
Microb Pathog ; 143: 104144, 2020 Jun.
Artigo em Inglês | MEDLINE | ID: mdl-32194182

RESUMO

There has been a rapid increase in the incidence and prevalence of opportunistic bacterial infections. Inappropriate use of current antibiotics has continuously contributed to the emergence of resistance to conventional antibiotic therapy. Therefore, the search for natural molecules that are able to combat infections is of great public interest, and many of these compounds with antimicrobial properties can be obtained from phytochemical studies of medicinal plants. In this context, this study reports the isolation and characterization of the flavonoid, kaempferol 7-O-ß-D-(6″-O-cumaroyl)-glucopyranoside, from Croton piauhiensis leaves. Additionally, the intrinsic antimicrobial action of the compound and its enhancement against Escherichia coli, Pseudomonas aeruginosa, and Staphylococcus aureus strains were assessed. The minimum inhibitory concentration (MIC) of the compound was determined using broth microdilution assays. To evaluate the modulatory effect of the flavonoid, the MIC of antibiotics amikacin and gentamicin, belonging to the class aminoglycosides was assessed, with and without the compound in sterile microplates. The results of intrinsic antibacterial activity tests revealed that the compound had no antibacterial activity against strains tested at concentrations <1024 µg/mL. The combination of the flavonoid at a concentration of 128 µg/mL with gentamicin presented synergistic effects against S. aureus 10 and E. coli 06, and also reduced the MIC from 16 µg/mL to 4 µg/mL and 8 µg/mL, respectively. Amikacin also showed synergistic effects against S. aureus 10 and E. coli 06. We also observed reduced MIC for both, from 128 µg/mL to 32 µg/mL; however, antagonism for P. aeruginosa increased the MIC from 16 µg/mL to 64 µg/mL. The combination of the flavonoid with the aminoglycosides may be an alternative to potentiate the expected results in treatment against S. aureus and E. coli, since their association leads to a synergistic effect, reducing the MIC of these drugs and decreasing the dose necessary for therapeutic success.


Assuntos
Antibacterianos/farmacologia , Croton/química , Quempferóis/farmacologia , Antibacterianos/administração & dosagem , Antibacterianos/isolamento & purificação , Sinergismo Farmacológico , Escherichia coli/efeitos dos fármacos , Gentamicinas/administração & dosagem , Gentamicinas/farmacologia , Quempferóis/administração & dosagem , Quempferóis/isolamento & purificação , Testes de Sensibilidade Microbiana , Folhas de Planta/química , Staphylococcus aureus/efeitos dos fármacos
5.
Zebrafish ; 17(2): 112-119, 2020 04.
Artigo em Inglês | MEDLINE | ID: mdl-32105571

RESUMO

Schinus terebinthifolius Raddi (Anacardiaceae) is popularly known in Brazil as aroeira-da-praia and has pharmacological use as an astringent, antidiarrheal, anti-inflammatory, depurative, diuretic, and antifebrile agent. Although the neuropathic antinociceptive potential of S. terebinthifolius fruits has already been investigated, this study is the first one to analyze the acute antinociceptive effect of the essential oil of S. terebinthifolius (female) leaves (EOFSt) on adult zebrafish. EOFSt was submitted to antioxidant activity evaluation by two methods (ferrous ion-chelating capacity [FIC] and ß-carotene). The animals (n = 6/group) were treated orally (20 µL) with EOFSt (0.1, 0.5, or 1.0 mg/mL) or vehicle (0.9% sodium chloride [NaCl]; 20 µL), and submitted to nociception (formalin, cinnamaldehyde, capsaicin, glutamate, acidic saline, and hypertonic saline). Possible neuromodulation mechanisms, as well motor alterations and toxicity were also evaluated. In the FIC assay, EOFSt showed ferrous ion-chelating capacity in ∼40% to 90%. Regarding the ß-carotene bleaching assay, EOFSt showed inhibition in a 58% to 80% range. Oral administration of EOFSt showed no acute toxicity and did not alter the locomotor system of aZF, and reduced the nociceptive behavior in all tested models. These effects of EOFSt were significantly similar to those of morphine, used as a positive control. The antinociceptive effect of EOFSt was inhibited by naloxone, L-NAME, ketamine, camphor, ruthenium red, and amiloride. The antinociceptive effect of the EOFSt cornea was inhibited by capsazepine. EOFSt has the pharmacological potential for acute pain treatment and this effect is modulated by the opioid system, NMDA receptors, and transient receptor potential ankyrin 1 (TRPA1), transient receptor potential vanilloid 1 (TRPV1), and acid-sensing ion channels. The EOFSt also has the pharmacological potential for corneal pain treatment and this effect is modulated by the TRPV1 channel.


Assuntos
Anacardiaceae/química , Analgésicos/farmacologia , Óleos Voláteis/farmacologia , Peixe-Zebra/fisiologia , Administração Oral , Analgésicos/química , Animais , Anti-Inflamatórios não Esteroides/química , Anti-Inflamatórios não Esteroides/farmacologia , Antioxidantes/metabolismo , Feminino , Masculino , Óleos Voláteis/química , Folhas de Planta/química
6.
Chem Biodivers ; 16(6): e1900050, 2019 Jun.
Artigo em Inglês | MEDLINE | ID: mdl-30980460

RESUMO

The development of studies on emissions of volatile organic compounds (VOCs) by inflorescence of oil palms deserves a special attention regarding the importance to reproduction success and for increase of production. This study aimed to evaluate metabolic profiling of VOCs expelled by male and female inflorescences of different oil palm species (African oil palm, Amazonian Caiaué and the interspecific hybrid BRS-Manicoré), associating the composition variability with main pollinators to improve the comprehension of the plant-insect relationship. The phenylpropanoids, terpenoids and the aliphatic hydrocarbons were predominant classes detected in inflorescences of oil palms and the major compound was estragole. This result may be correlated with attraction of Elaidobius pollinators, since these insects were not attracted by Caiaué, which emitted estragole only in trace amounts. However, Caiaué and the hybrid species were visited by other native species whose frequencies were low and their success as pollinators could not be expected.


Assuntos
Óleo de Palmeira/química , Compostos Orgânicos Voláteis/química , Animais , Arecaceae/química , Arecaceae/metabolismo , Comportamento Animal/efeitos dos fármacos , Análise por Conglomerados , Feminino , Cromatografia Gasosa-Espectrometria de Massas , Hidrocarbonetos/química , Hidrocarbonetos/farmacologia , Masculino , Óleo de Palmeira/metabolismo , Polinização , Terpenos/química , Terpenos/farmacologia , Compostos Orgânicos Voláteis/metabolismo , Compostos Orgânicos Voláteis/farmacologia , Gorgulhos/fisiologia
7.
Bol. latinoam. Caribe plantas med. aromát ; 17(3): 302-309, mayo 2018. ilus, tab
Artigo em Inglês | LILACS | ID: biblio-915398

RESUMO

Vitex gardneriana Schauer (Lamiaceae) popularly known as "jaramataia", is a shrub commonly found in caatinga biome located in Northeast Brazil. In folk medicine, its leaves have been used as analgesic and anti-inflammatory agents. The chemical composition of the essential oil from leaves obtained by hydrodistillation was analyzed and identified by GC-MS and GC-FID and showing a total of 26 constituents (95.9%) being 2 monoterpenes (0.4%) and 24 sesquiterpenes (95.4%). The main constituents identified were cis-calamenene (29.7%), 6,9-guaiadiene (14.5%) and caryophyllene oxide (14.0%). The essential oil has been demonstrated high larvicidal activity against Aedes aegypti (LC50 = 28.0 µg/mL). In the evaluation of the bioassay with Artemia salina the essential oil showed LC50 = 98.11 µg/mL. In addition, the essential oil did not show cytotoxicity (IC50 > 2.50 mg/mL) by the hemolysis assay.


Vitex gardneriana Schauer (Lamiaceae) popularmente conocido como "jaramataia", es un arbusto que se encuentra comúnmente en el bioma de caatinga ubicado en el noreste de Brasil. En medicina popular, sus hojas se han utilizado como analgésicos y agentes antiinflamatorios. La composición química de los aceites esenciales de las hojas obtenidas por hidrodestilación fue analizada e identificada por GC-MS y GC-FID y mostrando un total de 26 constituyentes (95.9%) siendo 2 monoterpenos (0.4%) y 24 sesquiterpenos (95.4%). Los componentes principales fueron cis-calamenene (29.7%), 6,9-guaiadiene (14.5%) y caryophyllene oxide (14.0%). El aceite esencial ha demostrado una alta actividad larvicida contra Aedes aegypti (CL50 = 28.0 µg/mL). En la evaluación del bioensayo con Artemia salina, el aceite esencial demostró CL50 = 98.11 µg/mL. Además, el aceite esencial no mostró citotoxicidad (IC50 > 2.5 mg / mL) mediante el ensayo de hemólisis.


Assuntos
Óleos Voláteis/farmacologia , Extratos Vegetais/farmacologia , Folhas de Planta/química , Aedes/efeitos dos fármacos , Vitex/química , Terpenos/análise , Óleos Voláteis/química , Extratos Vegetais/química , Cromatografia Gasosa , Larvicidas , Larva
8.
Appl Biochem Biotechnol ; 178(6): 1167-83, 2016 Mar.
Artigo em Inglês | MEDLINE | ID: mdl-26634842

RESUMO

Ethanol production from acidic-alkaline pretreated cashew apple bagasse (CAB-OH) was investigated using separated hydrolysis and fermentation (SHF) and simultaneous saccharification and fermentation (SSF) processes. First, a screening of Kluyveromyces strains was conducted by SHF and a maximum ethanol concentration of 24.1 g L(-1) was obtained using Kluyveromyces marxianus ATCC36907, which presented similar profiles when compared to results obtained by a Saccharomyces strain. The effect of temperature on ethanol production conducted by SHF using K. marxianus ATCC36907 was investigated, and the maximum ethanol yield (YE/G) was obtained at 40 °C (0.46 g g(-1)) using a synthetic medium. In the SHF using CAB-OH hydrolysate, the maximum ethanol concentration obtained was 24.9 g L(-1), 5.92 g L(-1) h(-1) of productivity, and ethanol yield of 0.43 g g(-1) at 40 °C. Afterwards, K. marxianus ATCC36907 was used in the bioconversion of CAB-OH by SSF, and an ethanol concentration of 41.41 ± 0.2 g L(-1) was obtained using 10 % CAB-OH at 40 °C, 150 rpm and 24 h, resulting in a Y'E/G of 0.50 gE gG (-1) and an efficiency of 98.4 %, in the process conducted with cellobiase supplementation. SHF and SSF processes using CAB-OH and K. marxianus ATCC36907 can be used to ethanol production, but the SSF process required only one step to achieve the same production.


Assuntos
Anacardium/química , Celulose/química , Etanol/química , Fermentação , Hidrólise , Temperatura
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