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1.
Biometals ; 37(4): 971-982, 2024 Aug.
Artigo em Inglês | MEDLINE | ID: mdl-38409305

RESUMO

The 'sacred leaf' or "Hoja Santa" (Piper auritum Kunth) has a great value for Mexican culture and has gained popularity worldwide for its excellent properties from culinary to remedies. To contribute to its heritage, in this project we proposed the green synthesis of silver oxide nanoparticles (Ag2O NPs) using an extract of "Hoja Santa" (Piper auritum) as a reducing and stabilizing agent. The synthesized Ag2O NPs were characterized by UV-Visible spectroscopy (plasmon located at 405 nm), X-ray diffraction (XRD) (particle size diameter of 10 nm), scanning electron microscopy (SEM) (particle size diameter of 13.62 ± 4.61 nm), and Fourier-transform infrared spectroscopy (FTIR) (functional groups from "Hoja Santa" attached to nanoparticles). Antioxidant capacity was evaluated using DPPH, ABTS and FRAP methods. Furthermore, the antimicrobial activity of NPs against a panel of clinically relevant bacterial strains, including both Gram-positive (Staphylococcus aureus) and Gram-negative bacteria (Salmonella Enteritidis and Escherichia coli O157:H7), was over 90% at concentrations of 200 µg/mL. Additionally, we assessed the antibiofilm activity of the NPs against Pseudomonas aeruginosa (reaching 98% of biofilm destruction at 800 µg/mL), as biofilm formation plays a crucial role in bacterial resistance and chronic infections. Moreover, we investigated the impact of Ag2O NPs on immune cell viability, respiratory burst, and phagocytic activity to understand their effects on the immune system.


Assuntos
Antibacterianos , Nanopartículas Metálicas , Testes de Sensibilidade Microbiana , Piper , Extratos Vegetais , Compostos de Prata , Staphylococcus aureus , Extratos Vegetais/química , Extratos Vegetais/farmacologia , Antibacterianos/farmacologia , Antibacterianos/química , Antibacterianos/síntese química , Compostos de Prata/química , Compostos de Prata/farmacologia , Staphylococcus aureus/efeitos dos fármacos , Piper/química , Nanopartículas Metálicas/química , Óxidos/química , Óxidos/farmacologia , Antioxidantes/farmacologia , Antioxidantes/química , Antioxidantes/síntese química , Animais , Camundongos , Salmonella enteritidis/efeitos dos fármacos , Tamanho da Partícula , Células RAW 264.7 , Escherichia coli O157/efeitos dos fármacos , Folhas de Planta/química
2.
J Nat Prod ; 87(3): 617-628, 2024 Mar 22.
Artigo em Inglês | MEDLINE | ID: mdl-38436272

RESUMO

Nature is an important source of bioactive compounds and has continuously made a large contribution to the discovery of new drug leads. Particularly, plant-derived compounds have long been identified as highly interesting in the field of aging research and senescence. Many plants contain bioactive compounds that have the potential to influence cellular processes and provide health benefits. Among them, Piper alkaloids have emerged as interesting candidates in the context of age-related diseases and particularly senescence. These compounds have been shown to display a variety of features, including antioxidant, anti-inflammatory, neuroprotective, and other bioactive properties that may help counteracting the effects of cellular aging processes. In the review, we will put the emphasis on piperlongumine and other related derivatives, which belong to the Piper alkaloids, and whose senomodulating potential has emerged during the last several years. We will also provide a survey on their potential in therapeutic perspectives of age-related diseases.


Assuntos
Alcaloides , Piper , Amidas , Alcaloides/farmacologia , Extratos Vegetais/farmacologia
3.
Biotechnol Appl Biochem ; 71(3): 670-680, 2024 Jun.
Artigo em Inglês | MEDLINE | ID: mdl-38444172

RESUMO

Piper longum L. (long pepper) is an economically and industrially important medicinal plant. However, the characterization of its volatiles has only been analyzed by gas chromatography-mass spectrometry (GC-MS). In the present study, precise characterization of P. longum fruit volatiles has been performed for the first time through advanced two-dimensional gas chromatography-time-of-flight spectrometry (GC×GC-TOFMS). A total of 146 constituents accounting for 93.79% were identified, of which 30 were reported for the first time. All these constituents were classified into alcohols (4.5%), alkanes (8.9%), alkenes (6.71%), esters (6.15%), ketones (0.58%), monoterpene hydrocarbons (1.64%), oxygenated monoterpenes (2.24%), sesquiterpene hydrocarbons (49.61%), oxygenated sesquiterpenes (13.03%), phenylpropanoid (0.23%), and diterpenes (0.2%). Among all the classes, sesquiterpene hydrocarbons were abundant, with germacrene-D (2.87% ± 0.01%) as the major one, followed by 8-heptadecene (2.69% ± 0.03%), ß-caryophyllene (2.43% ± 0.03%), n-heptadecane (2.4% ± 0.04%), n-pentadecane (2.11% ± 0.05%), and so forth. Further, 20 constituents were observed to be coeluted and separated precisely in the two-dimensional column. The investigation provides an extensive metabolite profiling of P. longum fruit volatiles, which could be helpful to improve its therapeutic potential.


Assuntos
Frutas , Cromatografia Gasosa-Espectrometria de Massas , Piper , Piper/química , Piper/metabolismo , Frutas/química , Frutas/metabolismo , Compostos Orgânicos Voláteis/análise , Compostos Orgânicos Voláteis/metabolismo , Compostos Orgânicos Voláteis/química
4.
Biol Pharm Bull ; 47(1): 130-137, 2024 Jan 01.
Artigo em Inglês | MEDLINE | ID: mdl-37989300

RESUMO

Since ancient times, Piper longum Linn. fruits have been recognized for exhibiting various effects, including the diaphoretic effects linked to enhanced blood flow. Piperine and piperlongumine coexist in Piper longum Linn. fruits, although the cardiovascular effects of both compounds remain elusive. We investigated their action of piperine and piperlongumine in porcine coronary arteries, comparing them to the Ca2+ channel antagonist diltiazem. Piperlongumine, unlike piperine or diltiazem, concentration-dependently inhibited basal contractile tone in endothelium-denuded coronary arteries. All three compounds inhibit tonic contractions induced by high potassium chloride (KCl) concentrations. The order of relaxation potency indexed by the half-maximal effective concentration (EC50) were as follows: diltiazem > piperlongumine > piperine. These effects were not different between endothelium-intact and -denuded preparations. In endothelial-denuded preparations, pretreatment with these compounds not only inhibited KCl-induced tonic contractions attenuated calcium chloride (CaCl2)-induced ones in a Ca2+-free medium. Histamine-induced phasic contractions in a Ca2+-free medium containing intracellular Ca2+ chelator was completely suppressed by selective inositol trisphosphate receptor antagonist and piperlongumine, whereas piperine or diltiazem do not have the same effect. These findings suggest that piperine and piperlongumine similar to diltiazem cause vasorelaxation by inhibiting both KCl- and CaCl2-induced contractions in coronary arteries, possibly through the inhibition of voltage-dependent Ca2+ channels. Piperlongumine inhibits histamine-induced contractions in a Ca2+-free medium, which is associated with the intracellular Ca2+ signaling pathway, suggesting that the relaxant effect of piperlongumine differs from that of piperine.


Assuntos
Diltiazem , Piper , Animais , Suínos , Diltiazem/farmacologia , Vasos Coronários , Frutas , Cloreto de Cálcio/farmacologia , Histamina , Cálcio/metabolismo , Cloreto de Potássio/farmacologia , Contração Muscular
5.
Cell Biochem Funct ; 42(5): e4095, 2024 Jul.
Artigo em Inglês | MEDLINE | ID: mdl-39004810

RESUMO

This study aimed to investigate the effects of the n-hexane fraction of the ethanolic seed extract of PG (NFESEPG) on hypertension induced by Nω-nitro-L-arginine methyl ester (L-NAME) in rats. Specifically, the study examined the impact of NFESEPG on blood pressure, oxidative stress markers, NO concentration, angiotensin-converting enzyme (ACE) and arginase activities, and cardiac biomarkers in hypertensive rats. The study involved collecting, identifying, and processing the PG plant to obtain the ethanolic seed extract. The extract was then partitioned with solvents to isolate the n-hexane fraction. Hypertension was induced in rats by oral administration of L-NAME for 10 days, while concurrent treatment with NFESEPG at two doses (200 and 400 mg/kg/day) was administered orally. Blood pressure was measured using a noninvasive tail-cuff method, and various biochemical parameters were assessed. Treatment with both doses of NFESEPG significantly reduced systolic and diastolic blood pressure in L-NAME-induced hypertensive rats. Additionally, NFESEPG administration increased NO concentration and decreased ACE and arginase activities, malondialdehyde (MDA) levels, and cardiac biomarkers in hypertensive rats. The findings indicate that NFESEPG effectively lowered blood pressure in hypertensive rats induced by L-NAME, potentially through mechanisms involving the modulation of oxidative stress, NO bioavailability, and cardiac biomarkers. These results suggest the therapeutic potential of NFESEPG in managing hypertension and related cardiovascular complications.


Assuntos
Hexanos , Hipertensão , NG-Nitroarginina Metil Éster , Piper , Extratos Vegetais , Sementes , Animais , Extratos Vegetais/farmacologia , Extratos Vegetais/química , Hipertensão/tratamento farmacológico , Hipertensão/induzido quimicamente , Hipertensão/metabolismo , Ratos , NG-Nitroarginina Metil Éster/farmacologia , Masculino , Sementes/química , Hexanos/química , Piper/química , Pressão Sanguínea/efeitos dos fármacos , Estresse Oxidativo/efeitos dos fármacos , Ratos Wistar , Óxido Nítrico/metabolismo , Arginase/metabolismo , Peptidil Dipeptidase A/metabolismo
6.
Pestic Biochem Physiol ; 200: 105809, 2024 Mar.
Artigo em Inglês | MEDLINE | ID: mdl-38582581

RESUMO

Culex quinquefasciatus is the main vector of lymphatic filariasis in Brazil, which present resistance to commercial insecticides. Nowadays, essential oils (EOs) exhibiting larvicidal activity, such as those derived from Piper alatipetiolatum, provide a promising alternative for vector control, including Culex species. This study aimed to investigate the larvicidal activity and the oxidative stress indicators of the EO from P. alatipetiolatum in Cx. quinquefasciatus larvae. The EO was extracted from P. alatipetiolatum leaves using the hydrodistillation method, resulting in a yield of 7.2 ± 0.1%, analysed by gas chromatography coupled with spectrometry and gas chromatography coupled with flame ionization detector (GC-MS and GC-FID), and evaluated against Cx. quinquefasciatus larvae. Reactive Oxygen and Nitrogen Species (RONS), Catalase (CAT), glutathione-S-transferase (GST), acetylcholinesterase (AChE), and Thiol levels were used as oxidative stress indicators. Analysis by CG-MS and CG-FID revealed that the main compound in the EO was the oxygenated sesquiterpene ishwarone, constituting 78.6% of the composition. Furthermore, the EO exhibited larvicidal activity, ranging from 26 to 100%, with an LC50 of 4.53 µg/mL and LC90 of 15.37 µg/mL. This activity was accompanied by a significant increase in RONS production, alterations in CAT, GST, AChE activity, and thiol levels compared to the control groups (p < 0.05). To the best of our knowledge, this is the first report describing the larvicidal activity and oxidative stress induced by the EO from P. alatipetiolatum against Cx. quinquefasciatus larvae. Therefore, we propose that this EO shows promise as larvicidal agent for the effective control of Cx. quinquefasciatus larvae.


Assuntos
Aedes , Culex , Culicidae , Inseticidas , Óleos Voláteis , Piper , Animais , Óleos Voláteis/farmacologia , Óleos Voláteis/química , Larva , Acetilcolinesterase , Mosquitos Vetores , Inseticidas/farmacologia , Inseticidas/química , Compostos de Sulfidrila/farmacologia , Extratos Vegetais/farmacologia , Folhas de Planta
7.
Chem Biodivers ; 21(2): e202301522, 2024 Feb.
Artigo em Inglês | MEDLINE | ID: mdl-38085680

RESUMO

INTRODUCTION: Studies prove that the use of medicinal plants is a custom carried out by man since ancient times, the evolution of the pharmaceutical industry makes more people consume more natural products. Currently, we can observe that mouthwashes containing natural compounds have shown a growth in demand in the markets and in the professional community. OBJECTIVE: The present study aims to carry out the chemical characterization and microbiological potential of Piper mikanianum (Kunth) Steud essential oil (EOPm), providing data that allows the development of a low-cost mouthwash formulation aimed at vulnerable communities. METHODS: The evaluation of the antibacterial activity and modulator of bacterial resistance was performed by the microdilution method to determine the minimum inhibitory concentration (MIC). The chemical components were characterized by gas chromatography coupled to mass spectrometry, identified 28 constituents, in which Safrole Phenylpropanoid is the major compound, representing 72.6 % of the total composition, followed by α-pinene (10.7 %), Limonene (2 %), ß-caryophyllene (2 %), E-nerolidol (1.9 %), spathulenol (1.3 %) and camphene (1.1 %). RESULTS: The EOPm showed a MIC minimum inhibitory concentration≥1024 µg/mL for all bacterial strains used in the tests. When the EOPm modulating activity combined with chlorhexidine, mouthwash, ampicillin, gentamicin and penicillin G was evaluated against bacterial resistance, the oil showed significant synergistic activity, reducing the MIC of the products tested in combination, in percentage between 20.6 % to 98 .4 %. CONCLUSIONS: We recommend the expansion of tests with greater variation of EOPm concentration combinations and the products used in this study, as well as toxicity evaluation and in vivo tests, seeking the development of a possible low-cost mouthwash formulation accessible to the most vulnerable population.


Assuntos
Óleos Voláteis , Piper , Humanos , Óleos Voláteis/farmacologia , Óleos Voláteis/química , Antissépticos Bucais/farmacologia , Piper/química , Cromatografia Gasosa-Espectrometria de Massas , Antibacterianos/farmacologia , Antibacterianos/química , Testes de Sensibilidade Microbiana
8.
Chem Biodivers ; 21(5): e202400518, 2024 May.
Artigo em Inglês | MEDLINE | ID: mdl-38501574

RESUMO

In this study, two undescribed compounds (1 and 2), together with eight known compounds (3-10) were isolated from the aerial parts of Piper samentosum by various chromatography methods. Their chemical structures were determined to be 7'''-oxolyciumamide N (1), vitexin 2''-O-ß-D-(6'''-feruloyl)-glucopyranoside (2), 1,2-dihydro-6,8-dimethoxy-7-hydroxy-1-(3,4-dihydroxyphenyl)-N1,N2-bis-[2-(-hydroxyphenyl)ethyl]-2,3-napthalene dicarboamide (3), vitexin 6''-O-ß-D-glucopyranoside (4), vitexin 2''-O-α-L-rhamnopyranoside (5), methyl 2-hydroxybenzoate-2-O-ß-D-apiofuranosyl-(1→2)-O-ß-D-glucopyranoside (6), ficuside G (7), methyl 2-O-ß-D-glucopyranosylbenzoate (8), methyl 2,5-dihydroxybenzoate-5-O-ß-D-glucopyranoside (9), and 3,7-dimethyloct-1-ene-3,6,7-triol 6-O-ß-D-glucopyranoside (10) by spectroscopic data analysis including HR-ESI-MS, 1D-, and 2D-NMR spectra. Compounds 1-5 inhibited nitric oxide production in LPS-stimulated RAW264.7 macrophages with the IC50 values of 27.62, 74.03, 38.54, 70.39, and 44.95 µM, respectively. The NMR data of 9 were firstly reported herein.


Assuntos
Flavonas , Glucosídeos , Lipopolissacarídeos , Óxido Nítrico , Piper , Componentes Aéreos da Planta , Células RAW 264.7 , Camundongos , Animais , Óxido Nítrico/antagonistas & inibidores , Óxido Nítrico/biossíntese , Óxido Nítrico/metabolismo , Lipopolissacarídeos/farmacologia , Lipopolissacarídeos/antagonistas & inibidores , Componentes Aéreos da Planta/química , Glucosídeos/isolamento & purificação , Glucosídeos/farmacologia , Glucosídeos/química , Piper/química , Flavonas/isolamento & purificação , Flavonas/farmacologia , Flavonas/química , Amidas/química , Amidas/farmacologia , Amidas/isolamento & purificação , Estrutura Molecular
9.
Chem Biodivers ; 21(3): e202301807, 2024 Mar.
Artigo em Inglês | MEDLINE | ID: mdl-38284478

RESUMO

The Piper genus, known for its pharmacological potential, comprises 2,263 species primarily found in tropical regions. Despite recent advancements in pain therapies, the demand for more effective and well-tolerated analgesics and anti-inflammatories, particularly for chronic pain, remains. This study assessed the effects of essential oils from Piper caldense, Piper mosenii, and Piper mikanianum on nociceptive behavior induced by formalin and capsaicin, as well as their anti-inflammatory impact induced by carrageenan, using adult zebrafish models. Results indicated non-toxic essential oils with antinociceptive properties in both neurogenic and inflammatory phases of formalin-induced nociception through interaction with the TRPA1 receptor. Additionally, P. mosenii essential oil also blocked the nociceptive effect of capsaicin, a TRPV1 receptor agonist. Furthermore, essential oils from P. caldense and P. mikanianum exhibited significant anti-inflammatory effects by reducing carrageenan-induced abdominal edema. These findings highlight the pharmacological potential of Piper's essential oils as antinociceptive and anti-inflammatory agents.


Assuntos
Óleos Voláteis , Piper , Animais , Carragenina/efeitos adversos , Peixe-Zebra , Óleos Voláteis/farmacologia , Óleos Voláteis/uso terapêutico , Capsaicina , Analgésicos/farmacologia , Analgésicos/uso terapêutico , Anti-Inflamatórios/farmacologia , Anti-Inflamatórios/uso terapêutico , Extratos Vegetais/farmacologia , Formaldeído/efeitos adversos , Edema/induzido quimicamente , Edema/tratamento farmacológico
10.
Chem Biodivers ; 21(5): e202400547, 2024 May.
Artigo em Inglês | MEDLINE | ID: mdl-38507773

RESUMO

The hexane extract from twigs of Piper truncatum Vell (Piperaceae) displayed activity against Trypanosoma cruzi and was subjected to chromatographic steps to afford six dibenzylbutyrolactolic lignans, being four knowns: cubebin (1), (-)-9α-O-methylcubebin (2), (+)-9ß-O-methylcubebinin (3) and 3,4-dimethoxy-3,4-demethylenedioxycubebin (4) as well as two new, named truncatin A (5) and B (6). Initially, in vitro activity against trypomastigotes was evaluated and compounds 1, 4 and 6 exhibited EC50 values of 41.6, 21.0 and 39.6 µM, respectively. However, when tested against amastigotes, the relevant clinical form in the chronic phase of Chagas disease, compounds 1-6 displayed activities with EC50 values ranging from 1.6 to 13.7 µM. In addition, the mammalian cytotoxicity of compounds 1-6 was evaluated against murine fibroblasts (NCTC). Compounds 2, 3 and 4 exhibited reduced toxicity against NCTC cells (CC50>200 µM), resulting in SI values of>21.9,>14.5 and>121.9, respectively. Compound 4 showed the highest potency with an SI value twice superior to that determined by the standard drug benznidazole (SI>54.6) against the intracellular amastigotes. These data suggest that lignan 4 can be considered a possible scaffold for designing a new drug candidate for Chagas disease.


Assuntos
Lignanas , Piper , Tripanossomicidas , Trypanosoma cruzi , Lignanas/farmacologia , Lignanas/química , Lignanas/isolamento & purificação , Piper/química , Animais , Trypanosoma cruzi/efeitos dos fármacos , Camundongos , Tripanossomicidas/farmacologia , Tripanossomicidas/química , Tripanossomicidas/isolamento & purificação , Relação Estrutura-Atividade , Testes de Sensibilidade Parasitária , Fibroblastos/efeitos dos fármacos , Estrutura Molecular , Relação Dose-Resposta a Droga , Extratos Vegetais/química , Extratos Vegetais/farmacologia , Extratos Vegetais/isolamento & purificação , Sobrevivência Celular/efeitos dos fármacos
11.
J Asian Nat Prod Res ; 26(2): 237-247, 2024 Feb.
Artigo em Inglês | MEDLINE | ID: mdl-37812065

RESUMO

Three new phenylpropanoid glycosides, piperpubelide (1), 1-propionyl-3-hydroxy-phenyl-4-O-ß-D-glucopyranoside (2), and 1-propionyl-4-hydroxy-phenyl-3-O-ß-D-glucopyranoside (3), a new tyramine-type alkamide, puberulumine L (4), together with thirteen known compounds (5-17) were isolated from Piper puberulum (Benth.) Maxim. Their structures were elucidated by analysis of spectroscopic data involving NMR, IR, UV, and HRESIMS data. Calculated and experimental ECD was used to confirm the configuration of compound 1. Compounds 14, 16, and 17 exhibited relatively positive DPPH radical scavenging activities, with corresponding EC50 of 10.23, 24.12, and 21.83 µM, respectively. In addition, compound 5 inhibited LPS-induced NO production in BV-2 microglia with an IC50 value of 18.05 µM.


Assuntos
Glucosídeos , Piper , Glucosídeos/farmacologia , Glucosídeos/química , Piper/química , Tiramina/farmacologia , Tiramina/química , Estrutura Molecular , Glicosídeos/farmacologia , Glicosídeos/química
12.
Int J Mol Sci ; 25(10)2024 May 16.
Artigo em Inglês | MEDLINE | ID: mdl-38791458

RESUMO

Amblyomma sculptum is a species of tick in the family Ixodidae, with equids and capybaras among its preferred hosts. In this study, the acaricidal activity of the essential oil (EO) from Piper aduncum and its main component, Dillapiole, were evaluated against larvae of A. sculptum to establish lethal concentration values and assess the effects of these compounds on tick enzymes. Dillapiole exhibited slightly greater activity (LC50 = 3.38 mg/mL; 95% CI = 3.24 to 3.54) than P. aduncum EO (LC50 = 3.49 mg/mL; 95% CI = 3.36 to 3.62) against ticks. The activities of α-esterase (α-EST), ß-esterase (ß-EST), and glutathione-S-transferase (GST) enzymes in A. sculptum larvae treated with Dillapiole showed a significant increase compared to the control at all concentrations (LC5, LC25, LC50 and LC75), similar results were obtained with P. aduncum EO, except for α-EST, which did not differ from the control at the highest concentration (LC75). The results of the acetylcholinesterase (AChE) activity show an increase in enzyme activity at the two lower concentrations (LC5 and LC25) and a reduction in activity at the two higher, lethal concentrations (LC50 and LC75) compared to the control. These results suggest potential mechanisms of action for these natural acaricides and can provide guidance for the future development of potential plant-derived formulations.


Assuntos
Acaricidas , Acetilcolinesterase , Amblyomma , Óleos Voláteis , Piper , Animais , Acaricidas/farmacologia , Acetilcolinesterase/metabolismo , Compostos Alílicos , Amblyomma/efeitos dos fármacos , Amblyomma/crescimento & desenvolvimento , Benzodioxóis/farmacologia , Inibidores da Colinesterase/farmacologia , Dioxóis , Esterases/metabolismo , Glutationa Transferase/metabolismo , Inativação Metabólica , Larva/efeitos dos fármacos , Óleos Voláteis/farmacologia , Óleos Voláteis/química , Piper/química
13.
Int J Mol Sci ; 25(5)2024 Feb 28.
Artigo em Inglês | MEDLINE | ID: mdl-38474055

RESUMO

Angiotensin-converting enzyme (ACE) plays a crucial role in the pathogenesis of hypertension. Piper sarmentosum Roxb., an herb known for its antihypertensive effect, lacks a comprehensive understanding of the mechanism underlying its antihypertensive action. This study aimed to elucidate the antihypertensive mechanism of aqueous extract of P. sarmentosum leaves (AEPS) via its modulation of the ACE pathway in phorbol 12-myristate-13-acetate (PMA)-induced human umbilical vein endothelial cells (HUVECs). HUVECs were divided into five groups: control, treatment with 200 µg/mL AEPS, induction 200 nM PMA, concomitant treatment with 200 nM PMA and 200 µg/mL AEPS, and treatment with 200 nM PMA and 0.06 µM captopril. Subsequently, ACE mRNA expression, protein level and activity, angiotensin II (Ang II) levels, and angiotensin II type 1 receptor (AT1R) and angiotensin II type 2 receptor (AT2R) mRNA expression in HUVECs were determined. AEPS successfully inhibited ACE mRNA expression, protein and activity, and angiotensin II levels in PMA-induced HUVECs. Additionally, AT1R expression was downregulated, whereas AT2R expression was upregulated. In conclusion, AEPS reduces the levels of ACE mRNA, protein and activity, Ang II, and AT1R expression in PMA-induced HUVECs. Thus, AEPS has the potential to be developed as an ACE inhibitor in the future.


Assuntos
Forbóis , Piper , Humanos , Anti-Hipertensivos/farmacologia , Miristatos/metabolismo , Miristatos/farmacologia , Angiotensina II/metabolismo , Células Endoteliais/metabolismo , Células Cultivadas , Peptidil Dipeptidase A/metabolismo , Receptor Tipo 1 de Angiotensina/metabolismo , RNA Mensageiro/metabolismo , Acetatos/farmacologia , Forbóis/metabolismo , Forbóis/farmacologia
14.
Molecules ; 29(5)2024 Feb 21.
Artigo em Inglês | MEDLINE | ID: mdl-38474459

RESUMO

The essential oils and aroma derived from the leaves (L), stems (St), and spikes (s) of Piper nigrum L. cv. Guajarina were extracted; the essential oils were extracted using hydrodistillation (HD), and steam distillation (SD), and the aroma was obtained by simultaneous distillation and extraction (SDE). Chemical constituents were identified and quantified using GC/MS and GC-FID. Preliminary biological activity was assessed by determining the toxicity against Artemia salina Leach larvae, calculating mortality rates, and determining lethal concentration values (LC50). The predominant compounds in essential oil samples included α-pinene (0-5.6%), ß-pinene (0-22.7%), limonene (0-19.3%), 35 linalool (0-5.3%), δ-elemene (0-10.1%), ß-caryophyllene (0.5-21.9%), γ-elemene (7.5-33.9%), and curzerene (6.9-31.7%). Multivariate analysis, employing principal component analysis (PCA) and hierarchical cluster analysis (HCA), revealed three groups among the identified classes and two groups among individual compounds. The highest antioxidant activity was found for essential oils derived from the leaves (167.9 41 mg TE mL-1). Larvicidal potential against A. salina was observed in essential oils obtained from the leaves (LC50 6.40 µg mL-1) and spikes (LC50 6.44 µg mL-1). The in silico studies demonstrated that the main compounds can interact with acetylcholinesterase, thus showing the potential molecular interaction responsible for the toxicity of the essential oil in A. salina.


Assuntos
Artrópodes , Óleos Voláteis , Piper nigrum , Piper , Sesquiterpenos , Animais , Óleos Voláteis/química , Acetilcolinesterase , Cromatografia Gasosa-Espectrometria de Massas , Piper/química , Óleos de Plantas/química
15.
Molecules ; 29(8)2024 Apr 09.
Artigo em Inglês | MEDLINE | ID: mdl-38675510

RESUMO

Piper aduncum L. is widely distributed in tropical regions and the ethnobotanical uses of this species encompass medicinal applications for the treatment of respiratory, antimicrobial, and gynecological diseases. Chemical studies reveal a diverse array of secondary metabolites, including terpenes, flavonoids, and prenylated compounds. Extracts from P. aduncum have shown antibacterial, antifungal, and larvicidal activities. Our study explores the activity of extracts and partitions against Mycobacterium tuberculosis H37Rv, as well as the chemical diversity of the bioactive partition. This marks the first investigation of the bioactive partition of P. aduncum from agroecological cultivation. The ethyl acetate partition from the ethanolic leaf extract (PAEPL) was found to be the most active. PAEPL was subjected to column chromatography using Sephadex LH-20 and the obtained fractions were analyzed using UHPLC-HRMS/MS. The MS/MS data from the fractions were submitted to the online GNPS platform for the generation of the molecular network, which displayed 1714 nodes and 167 clusters. Compounds were identified via manual inspection and different libraries, allowing the annotation of 83 compounds, including flavonoids, benzoic acid derivatives, glycosides, free fatty acids, and glycerol-esterified fatty acids. This study provides the first chemical fingerprint of an antimycobacterial sample from P. aduncum cultivated in an agroecological system.


Assuntos
Piper , Extratos Vegetais , Espectrometria de Massas em Tandem , Piper/química , Cromatografia Líquida de Alta Pressão/métodos , Extratos Vegetais/química , Extratos Vegetais/farmacologia , Mycobacterium tuberculosis/efeitos dos fármacos , Folhas de Planta/química , Flavonoides/química , Flavonoides/análise , Testes de Sensibilidade Microbiana
16.
Molecules ; 29(13)2024 Jun 23.
Artigo em Inglês | MEDLINE | ID: mdl-38998933

RESUMO

Piper attenuatum Buch-Ham, a perennial woody vine belonging to the Piperaceae family, is traditionally used in Southeast Asia for treating various ailments such as malaria, headache, and hepatitis. This study described the isolation and identification of three new compounds, piperamides I-III (1-3), which belong to the maleimide-type alkaloid skeletons, along with fifteen known compounds (4-18) from the methanol extract of the aerial parts of P. attnuatum. Their chemical structures were elucidated using spectroscopic methods (UV, IR, ESI-Q-TOF-MS, and 1D/2D NMR). All the isolates were evaluated for their ability to inhibit IL-6 activity in the human embryonic kidney-Blue™ IL-6 cell line and their cytotoxic activity against ovarian cancer cell lines (SKOV3/SKOV3-TR) and chemotherapy-resistant variants (cisplatin-resistant A2780/paclitaxel-resistant SKOV3). The compounds 3, 4, 11, 12, 17, and 18 exhibited IL-6 inhibition comparable to that of the positive control bazedoxifene. Notably, compound 12 displayed the most potent anticancer effect against all the tested cancer cell lines. These findings highlight the importance of researching the diverse activities of both known and newly discovered natural products to fully unlock their potential therapeutic benefits.


Assuntos
Antineoplásicos Fitogênicos , Interleucina-6 , Neoplasias Ovarianas , Piper , Componentes Aéreos da Planta , Extratos Vegetais , Humanos , Interleucina-6/metabolismo , Piper/química , Feminino , Linhagem Celular Tumoral , Neoplasias Ovarianas/tratamento farmacológico , Neoplasias Ovarianas/patologia , Componentes Aéreos da Planta/química , Extratos Vegetais/farmacologia , Extratos Vegetais/química , Antineoplásicos Fitogênicos/farmacologia , Antineoplásicos Fitogênicos/química , Antineoplásicos Fitogênicos/isolamento & purificação , Estrutura Molecular , Proliferação de Células/efeitos dos fármacos
17.
Molecules ; 29(8)2024 Apr 12.
Artigo em Inglês | MEDLINE | ID: mdl-38675573

RESUMO

The repellent capacity against Sitophilus zeamais and the in vitro inhibition on AChE of 11 essential oils, isolated from six plants of the northern region of Colombia, were assessed using a modified tunnel-type device and the Ellman colorimetric method, respectively. The results were as follows: (i) the degree of repellency (DR) of the EOs against S. zeamais was 20-68% (2 h) and 28-74% (4 h); (ii) the IC50 values on AChE were 5-36 µg/mL; likewise, the %inh. on AChE (1 µg/cm3 per EO) did not show any effect in 91% of the EO tested; (iii) six EOs (Bursera graveolens-bark, B. graveolens-leaves, B. simaruba-bark, Peperomia pellucida-leaves, Piper holtonii (1b*)-leaves, and P. reticulatum-leaves) exhibited a DR (53-74%) ≥ C+ (chlorpyrifos-61%), while all EOs were less active (8-60-fold) on AChE compared to chlorpyrifos (IC50 of 0.59 µg/mL). Based on the ANOVA/linear regression and multivariate analysis of data, some differences/similarities could be established, as well as identifying the most active EOs (five: B. simaruba-bark, Pep. Pellucida-leaves, P. holtonii (1b*)-leaves, B. graveolens-bark, and B. graveolens-leaves). Finally, these EOs were constituted by spathulenol (24%)/ß-selinene (18%)/caryophyllene oxide (10%)-B. simaruba; carotol (44%)/dillapiole (21%)-Pep. pellucida; dillapiole (81% confirmed by 1H-/13C-NMR)-P. holtonii; mint furanone derivative (14%)/mint furanone (14%)-B. graveolens-bark; limonene (17%)/carvone (10%)-B. graveolens-leaves.


Assuntos
Inibidores da Colinesterase , Repelentes de Insetos , Óleos Voláteis , Sesquiterpenos Policíclicos , Animais , Acetilcolinesterase/metabolismo , Inibidores da Colinesterase/farmacologia , Inibidores da Colinesterase/química , Colômbia , Repelentes de Insetos/farmacologia , Repelentes de Insetos/química , Óleos Voláteis/farmacologia , Óleos Voláteis/química , Piper/química , Óleos de Plantas/farmacologia , Óleos de Plantas/química , Sesquiterpenos Policíclicos/química , Sesquiterpenos Policíclicos/farmacologia , Gorgulhos/enzimologia , Gorgulhos/efeitos dos fármacos , Sesquiterpenos de Eudesmano/química , Sesquiterpenos de Eudesmano/farmacologia , Sesquiterpenos/química , Sesquiterpenos/farmacologia
18.
Environ Geochem Health ; 46(5): 172, 2024 Apr 09.
Artigo em Inglês | MEDLINE | ID: mdl-38592578

RESUMO

Advancement in bioinspired alloy nanomaterials has a crucial impact on fuel cell applications. Here, we report the synthesis of PtPd alloy nanoclusters via the hydrothermal method using Piper longum extract, representing a novel and environmentally friendly approach. Physicochemical characteristics of the synthesized nanoclusters were investigated using various instrumentation techniques, including X-ray photoelectron spectroscopy, X-ray diffraction, and High-Resolution Transmission electron microscopy. The electrocatalytic activity of the biogenic PtPd nanoclusters towards the oxidation of formic acid and methanol was evaluated chronoamperometry and cyclic voltammetry studies. The surface area of the electrocatalyst was determined to be 36.6 m2g-1 by Electrochemical Surface Area (ECSA) analysis. The biologically inspired PtPd alloy nanoclusters exhibited significantly higher electrocatalytic activity compared to commercial Pt/C, with specific current responses of 0.24 mA cm - 2 and 0.17 mA cm - 2 at synthesis temperatures of 180 °C and 200 °C, respectively, representing approximately four times higher oxidation current after 120 min. This innovative synthesis approach offers a promising pathway for the development of PtPd alloy nanoclusters with enhanced electrocatalytic activity, thereby advancing fuel cell technology towards a sustainable energy solution.


Assuntos
Formiatos , Metanol , Piper , Ligas , Extratos Vegetais
19.
Crit Rev Food Sci Nutr ; 63(16): 2840-2850, 2023.
Artigo em Inglês | MEDLINE | ID: mdl-34609267

RESUMO

Brain aging is one of the unavoidable aspects of geriatric life. As one ages, changes such as the shrinking of certain parts (particularly the frontal cortex, which is vital to learning and other complex mental activities) of the brain may occur. Consequently, communications between neurons are less effective, and blood flow to the brain could also decrease. Efforts made at the biological level for repair become inadequate, leading to the accumulation of ß-amyloid peptide in the brain faster than its probable degradation mechanism, resulting in cognitive malfunction. Subsequent clinical usage of drugs in battling related brain-aging ailments has been associated with several undesirable side effects. However, recent research has investigated the potential use of natural compounds from food in combating such occurrences. This review provides information about the use of Piper guineense (black pepper) as a possible agent in managing brain aging because of its implications for practical brain function. P. guineense contains an alkaloid (piperine) reported to be an antioxidant, anti-depressant, and central nervous system stimulant. This alkaloid and other related compounds are neuroprotective agents that reduce lipid oxidation and inhibit tangles in the brain tissues.


Assuntos
Alcaloides , Piper nigrum , Piper , Piper nigrum/química , Piper/química , Benzodioxóis/química , Benzodioxóis/farmacologia , Alcamidas Poli-Insaturadas/química , Alcamidas Poli-Insaturadas/farmacologia , Encéfalo
20.
J Appl Microbiol ; 134(3)2023 Mar 01.
Artigo em Inglês | MEDLINE | ID: mdl-36737421

RESUMO

AIMS: Fusarium graminearum is a toxic fungus that affects food and feed crops. Piper sarmentosum extract (PSE) is a potential source of anti-mildew natural products for the food and feed industry due to its various pharmacological properties. In this study, we evaluated the antifungal activity and untargeted metabolomics analysis of PSE against F. graminearum. METHODS AND RESULTS: Antifungal activity was evaluated using the mycelium growth rate method. Untargeted metabolomics analysis of PSE was performed using ultra high-performance liquid chromatography-tandem mass spectrometry (UPLC-MS/MS). The results showed that PSE (1 and 2 mg ml-1) possesses inhibitory activity against F. graminearum, and a total of 17 compounds that including 8 alkaloids, 3 phenols, 3 lipids, and 3 organic acids might be the antifungal markers in PSE. Metabolomics analysis further revealed that PSE could significantly increase the levels of guanosine, guanine, adenosine, and L-isoleucine in fungi, which are related to purine and L-isoleucine metabolic pathways. CONCLUSIONS: PSE is a promising anti-mildew agent that inhibits the growth of F. graminearum in food and feed. PSE (1 and 2 mg ml-1) may exert antifungal properties by inhibiting fungal purine nucleotide synthesis and enhancing the level of L-isoleucine compared with the control groups.


Assuntos
Fusarium , Piper , Antifúngicos/farmacologia , Piper/química , Cromatografia Líquida , Isoleucina/metabolismo , Espectrometria de Massas em Tandem , Fungos
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