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1.
Exp Parasitol ; 210: 107847, 2020 Mar.
Artigo em Inglês | MEDLINE | ID: mdl-32004535

RESUMO

Leishmaniasis is an infectious disease that has high endemicity and is among the six parasitic diseases of higher occurrence in the world. The current treatments are limited due to their toxicity, treatment resistance and high cost which have increased the search for new substances of natural origin for its therapy. Based on this, an in vitro biological and chemical investigation was carried out to evaluate the potential of Piper marginatum against Leishmania amazonesis. P. marginatum leaves were collected to obtain the essential oil (EO) and the ethanolic extract (CE). The chemical profile of the CE and fractions was obtained by 1H NMR. The analysis of the EO chemical composition was performed by GC-MS. EO, CE and fractions were submitted to antileishmanial and cytotoxicity assays against macrophages. The chromatographic profiles of EO, CE and fractions showed the presence of phenolic compounds and terpenoids, having 3,4-Methylenedioxypropiophenone as a major compound. All P. marginatum samples showed low toxicity to macrophages. The CE and the methanolic, hexane and ethyl acetate fractions had low cytotoxicity when compared to Pentamidine. All tested samples inhibited growth of L. amazonensis promastigotes. The antileishmanial activity of EO, CE and fractions were evaluated in macrophages infected with L. (L.) amazonensis and treated with the concentrations 1, 10 and 100 µg/mL for 48 h. All samples were active, but EO and CE showed superior activity against amastigote forms when compared to the promastigote forms of L. amazonensis. This work describes for the first time the antileishmanial activity of the species P. marginatum and its cytotoxicity against macrophages, suggesting that it can be an alternative source of natural products in the phytotherapeutic treatment of leishmaniasis.


Assuntos
Leishmania mexicana/efeitos dos fármacos , Leishmaniose Cutânea/tratamento farmacológico , Óleos Voláteis/farmacologia , Piper/química , Extratos Vegetais/farmacologia , Animais , Brasil/epidemiologia , Doenças Endêmicas , Cromatografia Gasosa-Espectrometria de Massas , Concentração Inibidora 50 , Leishmaniose Cutânea/epidemiologia , Leishmaniose Cutânea/parasitologia , Macrófagos/efeitos dos fármacos , Macrófagos/parasitologia , Espectroscopia de Ressonância Magnética , Camundongos , Camundongos Endogâmicos BALB C , Doenças Negligenciadas/tratamento farmacológico , Doenças Negligenciadas/epidemiologia , Doenças Negligenciadas/parasitologia , Óleos Voláteis/química , Óleos Voláteis/isolamento & purificação , Extratos Vegetais/química , Extratos Vegetais/isolamento & purificação , Folhas de Planta/química , Óleos Vegetais/química , Óleos Vegetais/isolamento & purificação , Óleos Vegetais/farmacologia
2.
Food Chem Toxicol ; 135: 110987, 2020 Jan.
Artigo em Inglês | MEDLINE | ID: mdl-31759067

RESUMO

The Piper mikanianum species were investigated by the antimicrobial potential and chemical composition. Chemical analysis was performed by gas chromatography coupled to mass spectrometry (GC/MS). The Minimum Inhibitory Concentration (MIC) as well as the 50% Inhibitory Concentration against Candida strains were determined by microdilution. The effect of the drug-oil combination was also evaluated to verify possible synergism. The Minimum Fungicidal Concentration (MFC) was evaluated by subculturing the microdilution in Petri dishes and the anti-pleomorphism potential of the oil was tested in humid chambers. Chemical analysis revealed safrol as the major compound. The results from the intrinsic activity evaluation of the oil did not reveal a clinical importance, however, it presented a synergistic effect when associated with gentamicin against the multidrug resistant E. coli strain and when associated with fluconazole against fungal strains. Moreover, the oil possessed a fungistatic effect. Total inhibition of filamentous structures occurred in both Candida species in the anti-virulence test. The P. mikanianum essential oil showed a potentiating activity of drugs for which resistance exists and an inhibitory effect of one of the main virulence factors of the Candida genus, morphological transition, which has been previously shown to be responsible for causing invasive infections in human tissues.


Assuntos
Anti-Infecciosos/farmacologia , Cromatografia Gasosa-Espectrometria de Massas/métodos , Óleos Voláteis/farmacologia , Piper/química , Candida/classificação , Candida/efeitos dos fármacos , Escherichia coli/efeitos dos fármacos , Humanos , Testes de Sensibilidade Microbiana , Especificidade da Espécie , Staphylococcus aureus/efeitos dos fármacos
3.
J Ethnopharmacol ; 247: 112255, 2020 Jan 30.
Artigo em Inglês | MEDLINE | ID: mdl-31568819

RESUMO

ETHNOPHARMACOLOGICAL RELEVANCE: Piper longum, commonly referred as 'Pippali', has found its traditional use in India, Malaysia, Singapore and other South Asian countries as an analgesic, carminative, anti-diarrhoeic, immunostimulant, post childbirth to check postpartum hemorrhage and to treat asthma, insomnia, dementia, epilepsy, diabetes, rheumatoid arthritis, asthma, spleen disorder, puerperal fever, leprosy etc. AIM OF THE REVIEW: This review offers essential data focusing on the traditional use, phytochemistry and pharmacological profile of Piper longum thereby identifying research gaps and future opportunities for investigation on this plant. MATERIALS AND METHODS: This systematic survey was accomplished as per the PRISMA guidelines. The information was collected from books, and electronic search (PubMed, Science Direct, Lilca and Scielo) during 1967-2019. RESULTS: Many phytochemicals have been identified till date, including alkaloids as its major secondary metabolites (piperine and piperlongumine), essential oil, flavonoids and steroids. These exhibit a wide range of activities including anti-inflammatory, analgesic, anti-oxidant, anti-microbial, anti-cancer, anti-parkinsonian, anti-stress, nootropic, anti-epileptic, anti-hyperglycemic, hepatoprotective, anti-hyperlipidemic, anti-platelet, anti-angiogenic, immunomodulatory, anti-arthritic, anti-ulcer, anti-asthmatic, anthelmintic action, anti-amebic, anti-fungal, mosquito larvicidal and anti-snake venom. CONCLUSION: Amongst various activities, bioscientific clarification in relation to its ethnopharmacological perspective has been evidenced mainly for anti-amebic, anthelminthic, anti-tumor and anti-diabetic activity. However, despite traditional claims, insufficient scientific validation for the treatment of insomnia, dementia, epilepsy, rheumatoid arthritis, asthma, spleen disorder, puerperal fever and leprosy, necessitate future investigations in this direction. It is also essential and critical to generate toxicological data and pharmacokinetics on human subjects so as to confirm its conceivable bio-active components in the body.


Assuntos
Etnofarmacologia/métodos , Medicina Tradicional/métodos , Piper/química , Extratos Vegetais/farmacologia , Pesquisa Médica Translacional/métodos , Etnofarmacologia/tendências , Humanos , Índia , Malásia , Extratos Vegetais/uso terapêutico , Singapura , Pesquisa Médica Translacional/tendências
4.
Mater Sci Eng C Mater Biol Appl ; 104: 109984, 2019 Nov.
Artigo em Inglês | MEDLINE | ID: mdl-31500006

RESUMO

The present investigation highlights the strong antioxidant, anticancer and larvicidal potential of green synthesized silver nanoparticles (AgNPs) using aqueous leaf extract of Piper longum L. for their diverse therapeutic applications. The optimum conditions for the synthesis of AgNPs were recorded as 1 mM AgNO3, 60 ±â€¯2 °C at pH 6 for 120 min. Synthesized AgNPs proved to be highly stable and monodispersed as characterized through various techniques. UV-Vis spectrum of biosynthesized AgNPs showed a maximum absorption peak at 420 nm. Field emission-Scanning electron microscopy (FE-SEM) and High resolution-Transmission electron microscopy (HR-TEM) micrographs showed the spherical shape of AgNPs with mean diameter size of 28.8 nm. Existence of crystallographic AgNPs was proved by X-ray diffraction (XRD) pattern analysis. Presence of phenolics, terpenoids and flavonoids compounds which act as bioreducing agents were confirmed by Fourier-transform infrared spectroscopy (FTIR) analysis. Furthermore, the AgNPs and leaf extracts prepared individually in different solvents such as methanol, ethyl acetate, chloroform, hexane and aqueous were assessed for their bio-efficacies. AgNPs showed the enhanced antioxidant (IC50 67.56 µg) and radical-scavenging activities (IC50 196.8 µg) as compared to the crude leaf extracts. Anticancer activity revealed the strong and dose-dependent cytotoxic effect of AgNPs against the HeLa cells showing maximum IC50 value being 5.27 µg/mL after 24 h and was also found to be non-toxic to normal cells (HEK). The AgNPs induced the fragmentation of DNA in the cells, indicating the occurrence of apoptosis and necrosis. Subsequently, an efficient larvae mortality was also recorded against Anopheles stephensi having LC50 and LC90 values being 8.969 and 16.102 ppm, followed by Aedes aegypti (LC50;14.791 and LC90;28.526 ppm) and Culex quinquefasciatus (LC50;18.662 and LC90;40.903 ppm) after 72 h of exposure. Besides, they showed no toxicity against Mesocyclops thermocyclopoides (non-target organism). This is the first report showing strong anti-tumorous and larvicidal activity of AgNPs synthesized using P. longum leaf extract against cervical cancer cell line and mosquito vectors causing dengue, malaria and filariasis. Based on our findings, we suggest that AgNPs derived using P. longum leaf extract possessed excellent anti-cancerous and mosquito larvicidal potential and therefore, can be bioprospected further for the management of these hazardous health diseases. This study has given a new insight for the novel drug designing after conducting experiments on the in vivo models.


Assuntos
Nanopartículas Metálicas/química , Piper/química , Extratos Vegetais/química , Prata/química , Aedes/efeitos dos fármacos , Animais , Anopheles/efeitos dos fármacos , Bioengenharia/métodos , Linhagem Celular , Linhagem Celular Tumoral , Culex/efeitos dos fármacos , Células HEK293 , Células HeLa , Humanos , Inseticidas/química , Inseticidas/farmacologia , Larva/efeitos dos fármacos , Dose Letal Mediana , Extratos Vegetais/farmacologia
5.
J Photochem Photobiol B ; 199: 111604, 2019 Oct.
Artigo em Inglês | MEDLINE | ID: mdl-31473430

RESUMO

The indiscriminate use of antibiotics has made bacterial resistance an important public health problem, since many antibiotics have become ineffective. Phototherapy can be considered an alternative to reduce the abusive use of antimicrobials, thus impacting microbial resistance. The objective of this study was to determine the chemical profile and to evaluate the effect of blue LED lights on the antibacterial activity of essential oils from Piper species, as well as their aminoglycoside antibiotic activity modulation using the microdilution method to determine the Minimum Inhibitory Concentration (MIC). The antibiotic activity modulating effect of these oils was also determined using the broth microdilution method with 96-well plates which were exposed to LED light for 20 min. Chemical components were characterized by gas chromatography coupled to mass spectrometry, revealing ß-copaen-4-α-ol, germacrene A and germacrene B as major essential oil constituents for Piper arboreum (OEPar), Piper aduncum (OEPad) and Piper gaudichaudianum (OEPg), respectively. OEPar obtained a MIC of 512 µg/mL against Staphylococcus aureus and a MIC ≥ 1024 µg/mL against Escherichia coli. OEPad and OEPg showed MIC values ≥ 1024 µg/mL against the utilized strains. The essential oils modulated the effect of the antibiotics amikacin and gentamicin, with this effect being potentiated when exposed to blue LED. The blue LED light in the absence of the essential oil also showed an ability to modulate aminoglycoside antibiotic activity in this study, presenting mostly synergistic effects. In conclusion, the results obtained in this study demonstrate that photodynamic therapy using blue LED light interferes with the antibacterial action of P. arboreum, P. aduncum and P. gaudichaudianum essential oils and aminoglycoside antibiotic activity.


Assuntos
Antibacterianos/química , Óleos Voláteis/química , Fotoquimioterapia/métodos , Piper/química , Extratos Vegetais/química , Óleos Vegetais/química , Amicacina/farmacologia , Antibacterianos/farmacologia , Bactérias/efeitos dos fármacos , Avaliação Pré-Clínica de Medicamentos , Sinergismo Farmacológico , Gentamicinas/farmacologia , Luz , Testes de Sensibilidade Microbiana , Óleos Voláteis/farmacologia , Extratos Vegetais/farmacologia , Óleos Vegetais/farmacologia
6.
Bol. latinoam. Caribe plantas med. aromát ; 18(5): 527-532, sept. 2019. ilus, tab
Artigo em Inglês | LILACS | ID: biblio-1008292

RESUMO

Chemical constituents and biological activities of the aerial parts of Piper erecticaule C.DC. have been studied for the first time. Fractionation and purification of the extracts afforded aristolactam AII (1), aristolactam BII (2), piperolactam A (3), piperolactam C (4), piperolactam D (5), together with terpenoids of ß-sitosterol, ß-sitostenone, taraxerol, and lupeol. The structures of these compounds were obtained by analysis of their spectroscopic data, as well as the comparison with that of reported data. Acetylcholinesterase inhibitory activity revealed that compounds 1 and 3 showed strong AChE inhibitory effects with the percentage inhibition of 75.8% and 74.8%, respectively.


Se estudiaron por primera vez los constituyentes químicos y actividad biológica de las partes aéreas de Piper erecticaule C.DC. El fraccionamiento y la purificación de los extractos proporcionaron aristolactama AII (1), aristolactama BII (2), piperolactama A (3), piperolactama C (4), piperolactama D (5), junto con terpenoides de ß-sitosterol, ß-sitostenona, taraxerol, y el lupeol. Las estructuras de estos compuestos se obtuvieron mediante el análisis de sus datos espectroscópicos, así como mediante la comparación con datos ya informados. La actividad inhibidora de la acetilcolinesterasa reveló que los compuestos 1 y 3 mostraron un potente efecto inhibidor de la AChE con un porcentaje de inhibición del 75.8% y 74.8%, respectivamente.


Assuntos
Aporfinas/farmacologia , Acetilcolinesterase/efeitos dos fármacos , Extratos Vegetais/química , Inibidores da Colinesterase/farmacologia , Piper/química , Alcaloides/farmacologia , Aporfinas/química , Terpenos/isolamento & purificação , Inibidores da Colinesterase/química , Alcaloides Indólicos/química , Alcaloides/química , Lactamas/química
7.
J Oleo Sci ; 68(9): 923-930, 2019 Sep 04.
Artigo em Inglês | MEDLINE | ID: mdl-31413248

RESUMO

Ginkgo biloba extract (GBE) is widely used as herbal medicine. Preventive effect of GBE against dementia, including Alzheimer's disease, has been reported. The bioactive compounds in GBE that impart these beneficial effects, flavonoids and terpene lactones, have poor bioavailability. Our previous study found distribution of bioactive compounds of sesame extract in mice brain after mixing it with turmeric oil. Here, we evaluate the distribution of bioactive compounds of GBE by combining it with the mixture of sesame extract and turmeric oil (MST). The content of terpene lactones in mice serum was significantly increased in a dose-dependent manner after administration of GBE. However, the contents of terpene lactones in mice brain were not significantly changed. Concentration of ginkgolide A in mice brain increased significantly when GBE was co-administrated with MST than when GBE was administered alone. These results suggest that MST may be effective in enhancing the bioavailability of ginkgolide A in GBE.


Assuntos
Disponibilidade Biológica , Encéfalo/metabolismo , Ginkgolídeos/farmacocinética , Lactonas/farmacocinética , Extratos Vegetais/farmacologia , Óleos Vegetais/farmacologia , Alcaloides/farmacologia , Animais , Benzodioxóis/farmacologia , Curcuma/química , Ginkgo biloba/química , Masculino , Camundongos , Compostos Fitoquímicos/sangue , Piper/química , Piperidinas/farmacologia , Alcamidas Poli-Insaturadas/farmacologia , Sesamum/química
8.
Molecules ; 24(17)2019 Aug 26.
Artigo em Inglês | MEDLINE | ID: mdl-31454974

RESUMO

Piper cubeba L. is the berry of a shrub that is indigenous to Java, Southern Borneo, Sumatra, and other islands in the Indian Ocean. The plant is usually used in folk traditional medicine and is an important ingredient in cooking. The purpose of this study was to isolate and purify the bioactive compounds from P. cubeba L. fractions. In addition, the isolated compounds were tested for their antibacterial and antispore activities against vegetative cells and spores of Bacillus cereus ATCC33019, B. subtilis ATCC6633, B. pumilus ATCC14884, and B. megaterium ATCC14581. The phytochemical investigation of the DCM fraction yielded two known compounds: ß-asarone (1), and asaronaldehyde (2) were successfully isolated and identified from the methanol extract and its fractions of P. cubeba L. Results showed that exposing the vegetative cells of Bacillus sp. to isolated compounds resulted in an inhibition zone with a large diameter ranging between 7.21 to 9.61 mm. The range of the minimum inhibitory concentration (MIC) was between 63.0 to 125.0 µg/mL and had minimum bactericidal concentration (MBC) at 250.0 to 500.0 µg/mL against Bacillus sp. Isolated compounds at a concentration of 0.05% inactivated more than 3-Log10 (90.99%) of the spores of Bacillus sp. after an incubation period of four hours, and all the spores were killed at a concentration of 0.1%. The structures were recognizably elucidated based on 1D and 2D-NMR analyses (1H, 13C, COSY, HSQC, and HMBC) and mass spectrometry data. Compounds 1, and 2 were isolated for the first time from this plant. In conclusion, the two compounds show a promising potential of antibacterial and sporicidal activities against Bacillus sp. and thus can be developed as an anti-Bacillus agent.


Assuntos
Aldeídos/farmacologia , Anisóis/farmacologia , Antibacterianos/farmacologia , Piper/química , Esporos Bacterianos/efeitos dos fármacos , Aldeídos/isolamento & purificação , Anisóis/isolamento & purificação , Antibacterianos/isolamento & purificação , Bacillus cereus/efeitos dos fármacos , Bacillus cereus/fisiologia , Bacillus megaterium/química , Bacillus megaterium/efeitos dos fármacos , Bacillus pumilus/efeitos dos fármacos , Bacillus pumilus/fisiologia , Bacillus subtilis/efeitos dos fármacos , Bacillus subtilis/fisiologia , Cromatografia em Camada Delgada , Medicina Tradicional , Testes de Sensibilidade Microbiana , Estrutura Molecular , Extratos Vegetais/isolamento & purificação , Extratos Vegetais/farmacologia
9.
Food Chem ; 298: 125067, 2019 Nov 15.
Artigo em Inglês | MEDLINE | ID: mdl-31260989

RESUMO

An ultra-high performance supercritical fluid chromatography-photodiode array detection-mass spectrometry (UHPSFC-MS) method for quality control of Piper longum L. has been developed and optimized. Hexane/isopropanol (70/30, v/v) was determined as the final injection solvent and methanol as the organic modifier. A design-of-experimental (DoE) approach was used to optimize column temperature, back-pressure and the gradient slope simultaneously using Trefoil CEL1 column. The back-pressure, temperature, flow rate were set at 130 bar, 32.5 °C and 1.0 mL/min, respectively. Positive electrospray ionization was used in the single ion monitoring mode. The 12 analytes were analyzed within 8 min using the optimized conditions. The linearities of the standard calibrations were satisfactory with coefficients of determination (R2) > 0.995. The recovery measured varied from 96.34% to 105.00% with relative standard deviation (RSD) ≤ 4.68%. The method was sensitive, reliable and effective, and successfully applied to simultaneous determination of 12 compounds in 28 batches of P. longum.


Assuntos
Alcaloides/química , Cromatografia com Fluido Supercrítico/métodos , Piper/química , Alcaloides/isolamento & purificação , Benzodioxóis/química , Benzodioxóis/isolamento & purificação , Cromatografia Líquida de Alta Pressão , Cromatografia com Fluido Supercrítico/normas , Frutas/química , Frutas/metabolismo , Limite de Detecção , Espectrometria de Massas , Metanol/química , Piper/metabolismo , Piperidinas/química , Piperidinas/isolamento & purificação , Alcamidas Poli-Insaturadas/química , Alcamidas Poli-Insaturadas/isolamento & purificação , Análise de Componente Principal , Controle de Qualidade , Solventes/química , Temperatura Ambiente
10.
Ecotoxicology ; 28(7): 763-770, 2019 Sep.
Artigo em Inglês | MEDLINE | ID: mdl-31254186

RESUMO

Euschistus heros (F.) (Hemiptera: Pentatomidae) is a soybean pest in Brazil, controlled with synthetic chemical insecticides, which may be harmful to the environment and humans, as well as to select pest resistant strains. The research for new pest control strategies such as the use of plant essential oils has been increased due to the selectivity and biodegradation of these molecules. The objective was to evaluate the cytological changes in the salivary glands, fat body and midgut of E. heros exposed to different concentrations of essential oil of Piper aduncum L. (Piperales: Piperaceae), which the main compounds were identified as myristicin 30.03%, aromadendrene 9.20%, dillapiole 8.43%, α-serinene 7.31%, tridecane 6.26%, γ-elemene 4.58% and o-cymene 4.20%. The essential oil of P. aduncum was toxic for E. heros with LD50 = 36.23 mg per insect and LD90 = 50.42 mg per insect. Cytological changes such as tissue disruption, increase in mitochondria population, and glycogen and lipid depletion occur in the fat body cells, whereas salivary glands and midgut are not affected by this essential oil. Results suggest that P. aduncum essential oil causes fat body cellular stress, which may compromise some physiological processes for the insect survival.


Assuntos
Corpo Adiposo/efeitos dos fármacos , Heterópteros/efeitos dos fármacos , Óleos Voláteis/toxicidade , Piper/química , Animais , Relação Dose-Resposta a Droga , Trato Gastrointestinal/efeitos dos fármacos , Heterópteros/crescimento & desenvolvimento , Dose Letal Mediana , Ninfa/efeitos dos fármacos , Ninfa/crescimento & desenvolvimento , Óleos Voláteis/química , Glândulas Salivares/efeitos dos fármacos
11.
Food Chem Toxicol ; 131: 110559, 2019 Sep.
Artigo em Inglês | MEDLINE | ID: mdl-31176927

RESUMO

The family Piperaceae is known for presenting in its species flavoring, healing and antimicrobial properties among others. The objective of the present study was: to study the chemical profile of the essential oil of Piper rivinoides (EOPR); to analyze its anti-bacterial and antifungal potential, as well as to evaluate the antifungal and antibiotic-modifying capacity. The chemical constituents were identified by gas chromatography with flame ionization detector (GC-FID), allowing the identification of 7 constituents of a total of 86.99%. E-Isoelemicin was identified as the main constituent of petroleum (40.81%). Clinically relevant MIC results were obtained against fungi in which the inhibitory concentration remained <256 µg/mL, as for Candida albicans 4127 (217.6 µg/mL). The association of EOPR with an antifungal showed a high synergistic affinity against the strains of C. tropicalis 40042 and 4262. We concluded that no intrinsic EOPR activity was observed at any concentrations tested against bacteria. However, EOPR associated with Gentamicin acted synergistically against S. aureus 10 and Escherichia coli 06, but with Erythromycin there was a synergistic effect against Escherichia coli 06, and antagonism with norfloxacin.


Assuntos
Antibacterianos/farmacologia , Antifúngicos/farmacologia , Óleos Voláteis/farmacologia , Piper/química , Antibacterianos/análise , Antibacterianos/química , Antifúngicos/análise , Antifúngicos/química , Candida albicans/efeitos dos fármacos , Sinergismo Farmacológico , Eritromicina/farmacologia , Escherichia coli/efeitos dos fármacos , Gentamicinas/farmacologia , Testes de Sensibilidade Microbiana , Óleos Voláteis/análise , Óleos Voláteis/química , Folhas de Planta/química , Staphylococcus aureus/efeitos dos fármacos
12.
J Diabetes Res ; 2019: 7836820, 2019.
Artigo em Inglês | MEDLINE | ID: mdl-31179342

RESUMO

Diabetes mellitus (DM) is considered the epidemic of the 21st century. Traditional medicine uses plants to treat DM; many of these have hypoglycemic effects in both animal models and diabetic patients. Our objective was to evaluate the hypoglycemic activity of Tilia americana, Borago officinalis, Chenopodium nuttalliae, and Piper sanctum on diabetic rats. The methanolic extracts of the plants under study were obtained by Soxhlet extraction. Toxicity was evaluated on Artemia salina; the antioxidant potential was evaluated using the DPPH technique. Hypoglycemic capacity at doses of 250 and 500 mg/kg was tested on Wistar rats with diabetes induced by alloxan (120 mg/kg). The toxicity on A. salina was null for the extracts of B. officinalis and P. sanctum, moderate for T. americana, and highly toxic for C. nuttalliae. The relevant extract of T. americana var. mexicana showed antioxidant activity. Three plants of the studied plants showed hypoglycemic activity: Tilia Americana (p = 0.0142), Borago officinalis (p = 0.0112), and Piper sanctum (p = 0.0078); P. sanctum was the one that showed the greatest reduction in glucose levels at a lower dose.


Assuntos
Borago/química , Chenopodium/química , Hipoglicemiantes/farmacologia , Piper/química , Extratos Vegetais/farmacologia , Tilia/química , Animais , Antioxidantes/farmacologia , Artemia/efeitos dos fármacos , Glicemia/efeitos dos fármacos , Diabetes Mellitus Experimental/tratamento farmacológico , Concentração de Íons de Hidrogênio , Masculino , Medicina Tradicional , Compostos Fitoquímicos/farmacologia , Ratos , Ratos Wistar , Água do Mar
13.
J Med Food ; 22(8): 861-873, 2019 Aug.
Artigo em Inglês | MEDLINE | ID: mdl-31241395

RESUMO

Plant extracts are gaining more attention as therapeutic agents against inflammation. In this study, four different widely used herbals were selected, such as holy basil leaf, sesame seed, long pepper, and cubeb pepper. We have evaluated the anti-inflammatory action of an aqueous extract from these herbs and tested their effects on monocyte-derived macrophages (MDMs). MDMs were pre-treated with these extracts individually for 2 h, followed by lipopolysaccharide (LPS) stimulation for 24 h and pro-inflammatory gene expression was analyzed. Also, we studied the effect of these extracts on the oxidation of low-density lipoprotein (LDL) by enzymatic (Myeloperoxidase) and non-enzymatic (copper) reactions. All extracts attenuated LPS-induced inflammation and also were able to inhibit the oxidation of LDL. These beneficial actions of extracts led us to identify molecules present in the extracts. A liquid chromatography-high resolution mass spectrometric analysis was performed to identify the chemical composition of extracts. Wide range of molecules were identified across all the extracts, short-chain organic acids, phenolic acids and derivatives, piperine and its structural homologues, eugenol, rosmarinic acid, flavonoids and their glucosides, and others. This study opens a door for future studies on non-pharmacological natural therapeutics that will be useful for consumers and producers, as well as industries utilizing bioactive compounds.


Assuntos
Anti-Inflamatórios/química , Anti-Inflamatórios/farmacologia , Extratos Vegetais/química , Extratos Vegetais/farmacologia , Plantas Medicinais/química , Linhagem Celular , Avaliação Pré-Clínica de Medicamentos , Flavonoides/química , Flavonoides/farmacologia , Humanos , Inflamação/tratamento farmacológico , Inflamação/genética , Inflamação/imunologia , Macrófagos/efeitos dos fármacos , Macrófagos/imunologia , Ocimum basilicum/química , Piper/química , Sesamum/química
14.
J Mass Spectrom ; 54(7): 634-642, 2019 Jul.
Artigo em Inglês | MEDLINE | ID: mdl-31144377

RESUMO

Natural 2H-chromenes were isolated from the crude extract of Piper aduncum (Piperaceae) and analyzed by electrospray ionization tandem mass spectrometry (ESI-MS/MS) applying collision-induced dissociation. Density functional theory (DFT) calculations were used to explain the preferred protonation sites of the 2H-chromenes based on thermochemical parameters, including atomic charges, proton affinity, and gas-phase basicity. After identifying the nucleophilic sites, the pathways were proposed to justify the formation of the diagnostic ions under ESI-MS/MS conditions. The calculated relative energy for each pathway was in good agreement with the energy-resolved plot obtained from ESI-MS/MS data. Moreover, the 2H-chromene underwent proton attachment on the prenyl moiety via a six-membered transition state. This behavior resulted in the formation of a diagnostic ion due to 2-methylpropene loss. These studies provide novel insights into gas-phase dissociation for natural benzopyran compounds, indicating how reactivity is correlated to the intrinsic acid-base equilibrium and structural aspects, including the substitution pattern on the aromatic moiety. Therefore, these results can be applied in the identification of benzopyran derivatives in a variety of biological samples.


Assuntos
Benzopiranos/química , Modelos Químicos , Piper/química , Benzopiranos/isolamento & purificação , Íons , Estrutura Molecular , Prótons , Espectrometria de Massas por Ionização por Electrospray , Espectrometria de Massas em Tandem
15.
Molecules ; 24(10)2019 May 15.
Artigo em Inglês | MEDLINE | ID: mdl-31096694

RESUMO

In this study, we evaluated antioxidant, antihyperuricemic, and herbicidal activities of essential oils (EOs) from Piper cubeba Bojer and Piper nigrum L.; two pepper species widely distributed in tropics, and examined their chemical compositions. Dried berries of P. cubeba and P. nigrum were hydro-distilled to yield essential oil (EO) of 1.23 and 1.11% dry weight, respectively. In the antioxidant assay, the radical scavenging capacities of P. cubeba EO against DPPH and ABTS free radicals were 28.69 and 24.13% greater than P. nigrum, respectively. In the antihyperuricemic activity, P. cubeba EO also exhibited stronger inhibitory effects on xanthine oxidase (IC50 = 54.87 µg/mL) than P. nigrum EO (IC50 = 77.11 µg/mL). In the herbicidal activity, P. cubeba EO showed greater inhibition on germination and growth of Bidens pilosa and Echinochloa crus-galli than P. nigrum EO. Besides, P. cubeba EO decreased 15.98-73.00% of photosynthesis pigments of B. pilosa and E. crus-galli, while electrolyte leakages, lipid peroxidations, prolines, phenolics, and flavonoids contents were increased 10.82-80.82% at 1.93 mg/mL dose. Gas chromatography-mass spectrometry (GC-MS) and liquid chromatography-electrospray ionization-mass spectrometry (LC-ESI-MS) analyses revealed that P. nigrum and P. cubeba EOs principally possessed complex mixtures of monoterpenes and sesquiterpenes. Terpinen-4-ol (42.41%), α-copaene (20.04%), and γ-elemene (17.68%) were the major components of P. cubeba EO, whereas ß-caryophyllene (51.12%) and ß-thujene (20.58%) were the dominant components of P. nigrum EO. Findings of this study suggest both P. cubeba and P. nigrum EOs were potential to treat antioxidative stress and antihyperuricemic related diseases. In addition, the EOs of the two plants may be useful to control B. pilosa and E. crus-galli, the two invasive and problematic weeds in agriculture practice.


Assuntos
Óleos Voláteis/química , Óleos Voláteis/farmacologia , Compostos Fitoquímicos/química , Compostos Fitoquímicos/farmacologia , Piper nigrum/química , Piper/química , Antioxidantes/química , Antioxidantes/farmacologia , Relação Dose-Resposta a Droga , Flavonoides/química , Flavonoides/farmacologia , Peroxidação de Lipídeos/efeitos dos fármacos , Fenol/química , Fenol/farmacologia , Extratos Vegetais/química , Extratos Vegetais/farmacologia , Prolina/química , Prolina/farmacologia , Xantina Oxidase/antagonistas & inibidores , Xantina Oxidase/química
16.
Biotech Histochem ; 94(7): 498-513, 2019 Oct.
Artigo em Inglês | MEDLINE | ID: mdl-31064227

RESUMO

Essential oils are a promising alternative to insecticides. We investigated the LD50 of oils extracted from Piper corcovadensis, P. marginatum, and P. arboreum after 48 h topical contact with Spodoptera frugiperda larvae using morphometry, histochemistry and immunohistochemistry of the midgut and fat body. Chromatography revealed that E-caryophyllene was the principal compound common to the Piper species. The essential oils of P. corcovadensis, P. marginatum and P. arboreum caused deleterious changes in the midgut of S. frugiperda larvae. P. corcovadensis oil produced the lowest LD50 and significant histopathological alterations including elongation of the columnar cells, formation of cytoplasmic protrusions, reduction in carbohydrate, increased apoptotic index and decreased cell proliferation. P. arboreum oil caused histopathological alterations similar to P. corcovadensis, but caused the highest rate of cell proliferation and increased regenerative cells, which indicated rapid regeneration of the epithelium. Our findings demonstrated the insecticidal potential of P. corcovadensis for control of S. frugiperda owing to the significant damage it inflicted on S. frugiperda midgut.


Assuntos
Corpo Adiposo/efeitos dos fármacos , Corpo Adiposo/patologia , Óleos Voláteis/farmacologia , Piper/metabolismo , Animais , Sistema Digestório/metabolismo , Sistema Digestório/patologia , Corpo Adiposo/metabolismo , Inseticidas/metabolismo , Inseticidas/farmacologia , Larva/efeitos dos fármacos , Óleos Voláteis/química , Piper/química , Óleos Vegetais/metabolismo , Óleos Vegetais/farmacologia , Spodoptera
17.
J Pharm Pharmacol ; 71(7): 1162-1171, 2019 Jul.
Artigo em Inglês | MEDLINE | ID: mdl-31049982

RESUMO

OBJECTIVES: To explore effective extraction method and to find active constituents, we investigated the biological activity of three extracts and isolated active compounds from the fruits of Piper longum L. METHODS: Three extracts from the fruits were obtained by reflux, ultrasonic and supercritical fluid extraction, respectively. Active compounds were isolated by the bioassay-guided method. The anti-inflammatory activity, antiproliferation activity and cytotoxicity were evaluated. The apoptosis was detected by Hoechst 33258 staining assay. The relevant proteins were investigated by Western blot assay. KEY FINDINGS: The anti-inflammatory activity and cytotoxicity of supercritical fluid extract (SE) were stronger than those of the other two extracts. Among all isolated compounds, the anti-inflammatory activity of eight compounds was stronger than that of indomethacin, and compounds 8, 9, 11, 14 and 15 were found to possess anti-inflammatory effect for the first time. Compounds 1, 2, 3 and 14 exhibited significant cytotoxicity against cancer cells. SE and piperine were found to reduce colony formation, inhibit cell migration and promote apoptosis through increasing cleaved PARP and the ratio of Bax/Bcl-2. CONCLUSIONS: The anti-inflammatory and antitumour effects of SE were better than those of the other two extracts. The compounds responsible for the activity were elucidated. SE and piperine inhibit cell growth through apoptosis.


Assuntos
Anti-Inflamatórios/farmacologia , Antineoplásicos/farmacologia , Piper/química , Extratos Vegetais/farmacologia , Alcaloides/farmacologia , Anti-Inflamatórios/toxicidade , Antineoplásicos/toxicidade , Apoptose/efeitos dos fármacos , Benzodioxóis/farmacologia , Linhagem Celular , Linhagem Celular Tumoral , Movimento Celular/efeitos dos fármacos , Frutas/química , Humanos , Macrófagos , Piperidinas/farmacologia , Extratos Vegetais/isolamento & purificação , Extratos Vegetais/toxicidade , Alcamidas Poli-Insaturadas/farmacologia , Proteínas Proto-Oncogênicas c-bcl-2/metabolismo
18.
Molecules ; 24(7)2019 Apr 07.
Artigo em Inglês | MEDLINE | ID: mdl-30959974

RESUMO

Piper species are aromatic plants used as spices in the kitchen, but their secondary metabolites have also shown biological effects on human health. These plants are rich in essential oils, which can be found in their fruits, seeds, leaves, branches, roots and stems. Some Piper species have simple chemical profiles, while others, such as Piper nigrum, Piper betle, and Piper auritum, contain very diverse suites of secondary metabolites. In traditional medicine, Piper species have been used worldwide to treat several diseases such as urological problems, skin, liver and stomach ailments, for wound healing, and as antipyretic and anti-inflammatory agents. In addition, Piper species could be used as natural antioxidants and antimicrobial agents in food preservation. The phytochemicals and essential oils of Piper species have shown strong antioxidant activity, in comparison with synthetic antioxidants, and demonstrated antibacterial and antifungal activities against human pathogens. Moreover, Piper species possess therapeutic and preventive potential against several chronic disorders. Among the functional properties of Piper plants/extracts/active components the antiproliferative, anti-inflammatory, and neuropharmacological activities of the extracts and extract-derived bioactive constituents are thought to be key effects for the protection against chronic conditions, based on preclinical in vitro and in vivo studies, besides clinical studies. Habitats and cultivation of Piper species are also covered in this review. In this current work, available literature of chemical constituents of the essential oils Piper plants, their use in traditional medicine, their applications as a food preservative, their antiparasitic activities and other important biological activities are reviewed.


Assuntos
Compostos Fitoquímicos/química , Compostos Fitoquímicos/farmacologia , Piper/química , Anti-Infecciosos/química , Anti-Infecciosos/farmacologia , Antiparasitários/química , Antiparasitários/farmacologia , Ecossistema , Conservação de Alimentos , Medicina Tradicional , Óleos Voláteis/química , Óleos Voláteis/farmacologia , Piper/classificação , Extratos Vegetais/química , Extratos Vegetais/farmacologia
19.
Parasite ; 26: 23, 2019.
Artigo em Inglês | MEDLINE | ID: mdl-30994444

RESUMO

Aedes aegypti, the main arbovirus vector of the Yellow fever, Dengue, Chikungunya and Zika viruses, is widely distributed in tropical and subtropical areas throughout the world. Preventive control efforts have been implemented worldwide aimed at reducing its impact on human health. The recent reduction of chemicals available for vector control due to their negative impact on the environment and human health and the increase in mosquito resistance to insecticides have driven the research community to identify and evaluate sustainable alternatives to synthetic insecticides. In this study, the potential larvicidal effect of essential oils extracted from Ocimum campechianum, Ocotea quixos and Piper aduncum were tested in vitro. GC and GC-MS analyses showed that the main compounds were eugenol (18%), 1,8-cineole (39%) and dillapiole (48%), respectively. Susceptibility to essential oils was measured according to the WHO protocol. After 24 h, the mean percentage mortality ranged from 2.7 to 100% for P. aduncum, from 2.2 to 100% for O. campechianum, and from 2.9 to 100% for O. quixos. The highest potential was displayed by P. aduncum, followed by O. campechianum and O. quixos, with LC50 values of 25.7, 69.3 and 75.5 ppm, respectively. The rapid and effective larvicidal activity of these three oils led us to consider these results to be promising, also considering the possibility of local cultivation of these plants in tropical and subtropical areas and the simple technology for their large-scale preparation and production. Further studies are needed to evaluate the individual components and their activity as larvicides.


Assuntos
Aedes/efeitos dos fármacos , Ocimum/química , Ocotea/química , Óleos Voláteis/farmacologia , Piper/química , Extratos Vegetais/farmacologia , Animais , Larva/efeitos dos fármacos , Mosquitos Vetores/efeitos dos fármacos , Extratos Vegetais/química
20.
Fitoterapia ; 134: 340-345, 2019 Apr.
Artigo em Inglês | MEDLINE | ID: mdl-30840916

RESUMO

A phytochemical investigation of the ethanolic extract of leaves from Piper pseudoarboreum led to the isolation of 3-chlorosintenpyridone 1, an unprecedented chlorinated piperamide, together with the known compounds 2-12. Their structures were established based on 1D and 2D (COSY, ROESY, HMQC, and HMBC) NMR spectroscopy, in addition to high resolution mass spectrometry. The proposed biosynthetic pathway of compound 1 is discussed. Compounds 1-12 were tested in vitro for their leishmanicidal potential against promastigote stages of Leishmania amazonensis, L braziliensis, L. guyanensis and L. infantum. Two compounds from this series, the alkamide 1 (IC50 3.4-5.2 µM) and the fatty acid 9 (IC50 18.7-29.6 µM) displayed higher or similar potency to Miltefosine, used as the reference drug.


Assuntos
Alcaloides/farmacologia , Antiprotozoários/farmacologia , Cloro/química , Piper/química , Alcaloides/isolamento & purificação , Antiprotozoários/isolamento & purificação , Leishmania/efeitos dos fármacos , Estrutura Molecular , Peru , Compostos Fitoquímicos/isolamento & purificação , Compostos Fitoquímicos/farmacologia , Folhas de Planta/química
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