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1.
Pan Afr Med J ; 40: 58, 2021.
Artigo em Inglês | MEDLINE | ID: mdl-34795837

RESUMO

Introduction: Marsdenia macrantha is a crucial source of traditional medicine in Northern Namibia. Its roots are used to treat various health conditions ranging from mouth infections to urinary retention. Despite its medicinal application, there is no known knowledge of its therapeutic properties. Thus, we investigated the phytochemical content and antibacterial activity of M. macrantha. Methods: M. macrantha root extracts were obtained using three different solvents (distilled water, methanol and acetone) - in the soxhlet and maceration extraction methods. Total phytochemical (terpenoid, alkaloid and/or flavonoid) content was determined by spectrophotometry. Antibacterial activity against common foodborne pathogens (Staphylococcus aureus, Escherichia coli and Salmonella typhi) was determined by both well and disc diffusion method. Results: we detected the presence of all the tested phytochemicals. Methanol gave the highest percentage yield of extraction (mean: 13.95 ± standard deviation: 0.41%) followed by water (10.92 ± 0.11%) and acetone (6.85 ± 0.23%), F-ratio=326.71 and p<0.0003. The total content determined showed that M. macrantha root extract contained more flavonoids than alkaloids (mg of standard per grams of the dry material). Antibacterial analyses showed inhibitory activity against all the selected pathogens, with the highest inhibition zone against S. typhi (19.7 ± 0.3 mm) - for the acetone-prepared root extract. There were variations in minimum inhibitory concentrations of the extracts prepared by the different solvents. Conclusion: this is the first study demonstrating the presence of phytochemicals and antibacterial properties of M. macrantha roots. Further studies are needed to isolate and characterize the phytochemicals for antibacterial application.


Assuntos
Antibacterianos/farmacologia , Marsdenia/química , Extratos Vegetais/farmacologia , Alcaloides/isolamento & purificação , Alcaloides/farmacologia , Antibacterianos/isolamento & purificação , Testes de Sensibilidade a Antimicrobianos por Disco-Difusão , Escherichia coli/efeitos dos fármacos , Flavonoides/isolamento & purificação , Flavonoides/farmacologia , Testes de Sensibilidade Microbiana , Compostos Fitoquímicos/química , Compostos Fitoquímicos/isolamento & purificação , Compostos Fitoquímicos/farmacologia , Extratos Vegetais/química , Raízes de Plantas , Salmonella typhi/efeitos dos fármacos , Solventes/química , Staphylococcus aureus/efeitos dos fármacos , Terpenos/isolamento & purificação , Terpenos/farmacologia
2.
FASEB J ; 35(11): e21985, 2021 11.
Artigo em Inglês | MEDLINE | ID: mdl-34674317

RESUMO

Inflammation is broadly recognized as an important factor in the pathogenesis of acute kidney injury (AKI), but pharmacological approaches to alleviate inflammation in AKI have not been proved successful in clinical trials. Macrophage infiltration into renal tissue promotes inflammatory responses that contribute to the pathogenesis of AKI. Suppression of renal tissue inflammatory responses is postulated to improve renal injury of patients and animals. Rhodomeroterpene (RMT) is a novel meroterpenoid isolated from the Rhododendron genus that was shown to exert anti-inflammatory action in vivo or in vitro in this study. We investigated the treatment effects of RMT on LPS-induced sepsis and two different AKI models. The results showed that pretreatment with RMT (30 mg kg-1  d-1 , ip, for 3 days) significantly inhibited acute inflammatory responses in LPS-induced septic mice. In both renal ischemia-reperfusion injury (I/R) and sepsis-induced AKI models, RMT (30 mg kg-1  d-1 , ip, for 3 days) ameliorated renal function and injury and alleviated inflammation by reducing the infiltration of immune cells, including macrophages and neutrophils. Furthermore, our study demonstrated that RMT inhibits inflammatory responses in macrophages. The anti-inflammatory effects of RMT may be due to the inactivation of the IKK/NF-κB and PI3K/PDK1/Akt inflammatory signaling pathways in macrophages. Collectively, our findings indicate that RMT ameliorates renal injury and alleviates the renal inflammatory state in different AKI models, suggesting that RMT may be a potential agent for the treatment of AKI.


Assuntos
Injúria Renal Aguda/tratamento farmacológico , Anti-Inflamatórios/farmacologia , Inflamação/tratamento farmacológico , Macrófagos/efeitos dos fármacos , Rhododendron/química , Terpenos/farmacologia , Animais , Células da Medula Óssea , Células HEK293 , Humanos , Rim/efeitos dos fármacos , Rim/patologia , Masculino , Camundongos , Camundongos Endogâmicos C57BL , Células RAW 264.7
3.
J Med Microbiol ; 70(9)2021 Sep.
Artigo em Inglês | MEDLINE | ID: mdl-34491156

RESUMO

Introduction. The increase of invasive fungal infections (IFIs) and associated treatment failure in populations at risk is driving us to look for new treatments.Hypothesis. The CIN-102 compound, derived from cinnamon essential oil, could be a new antifungal class with an activity, in particular, on strains resistant to current antifungals but also on biofilms, a factor of virulence and resistance of fungi.Aim. The aim of this study is to show the activity of CIN-102 on various strains resistant to current antifungals, on the biofilm and to determine the possibility of resistance induced with this compound.Methodology. We studied the MIC of CIN-102 and of current antifungals (voriconazole and amphotericin B) using CLSI techniques against eight different strains of three genera of filamentous fungi involved in IFIs and having resistance phenotypes to current antifungals. We also determined their effects on biofilm formation, and the induced resistance by voriconazole (VRC) and CIN-102.Results. MIC values determined for CIN-102 were between 62.5 and 250 µg ml-1. We demonstrated the antifungal effect of CIN-102 on biofilm, and more particularly on its formation, with 100 % inhibition achieved for most of the strains. CIN-102 at a sub-inhibitory concentration in the medium did not induce resistance in our strains, even after 30 generations.Conclusions. In this study we show that CIN-102 is effective against resistant filamentous fungi and against biofilm formation. In addition, our strains did not acquire a resistance phenotype against CIN-102 over time, unlike with VRC. CIN-102 is therefore an interesting candidate for the treatment of IFIs, including in cases of therapeutic failure linked to resistance, although further studies on its efficacy, safety and mechanism of action are needed.


Assuntos
Antifúngicos/farmacologia , Benzoatos/farmacologia , Biofilmes/efeitos dos fármacos , Cinamatos/farmacologia , Fungos/efeitos dos fármacos , Micoses , Terpenos/farmacologia , Anfotericina B/farmacologia , Combinação de Medicamentos , Humanos , Testes de Sensibilidade Microbiana , Micoses/tratamento farmacológico , Micoses/microbiologia , Voriconazol/farmacologia
4.
Int J Mol Sci ; 22(18)2021 Sep 13.
Artigo em Inglês | MEDLINE | ID: mdl-34576028

RESUMO

Lung cancer is one of the most common cancers and the leading cause of death in humans worldwide. Non-small-cell lung cancer (NSCLC) accounts for approximately 85% of lung cancer cases and is often diagnosed at a late stage. Among patients with NSCLC, 50% die within 1 year after diagnosis. Even with clinical intervention, the 5-year survival rate is only approximately 20%. Therefore, the development of an advanced therapeutic strategy or novel agent is urgently required for treating NSCLC. Berberine exerts therapeutic activity toward NSCLC; therefore, its activity as an antitumor agent needs to be explored further. In this study, three terpenylated-bromide derivatives of berberrubine were synthesized and their anti-NSCLC activities were evaluated. Each derivative had higher anti-NSCLCs activity than berberrubine and berberine. Among them, 9-O-gernylberberrubine bromide (B4) and 9-O-farnesylberberrubine bromide (B5) showed greater growth inhibition, cell-cycle regulation, in vitro tumorigenesis suppression, and tumor migration reduction. In addition, some degree of apoptosis and autophagic flux blocking was noted in the cells under B4 and B5 treatments. Our study demonstrates that the berberrubine derivatives, B4 and B5, exhibit impressive anti-NSCLC activities and have potential for use as chemotherapeutic agents against NSCLC.


Assuntos
Berberina/análogos & derivados , Carcinoma Pulmonar de Células não Pequenas/tratamento farmacológico , Movimento Celular/efeitos dos fármacos , Proliferação de Células/efeitos dos fármacos , Células A549 , Antineoplásicos/farmacologia , Apoptose/efeitos dos fármacos , Berberina/síntese química , Berberina/química , Berberina/farmacologia , Brometos/química , Carcinogênese/efeitos dos fármacos , Carcinoma Pulmonar de Células não Pequenas/patologia , Humanos , Terpenos/síntese química , Terpenos/farmacologia
5.
Molecules ; 26(16)2021 Aug 04.
Artigo em Inglês | MEDLINE | ID: mdl-34443305

RESUMO

The local botanical Imperata cylindrica in Cameroon was investigated for its antibacterial potency. The methanol extract afforded a total of seven compounds, including five hitherto unreported compounds comprising three flavonoids (1-3) and two C-15 isoprenoid analogues (4 and 5) together with known derivatives (6 and 7). The novelty of the flavonoids was related to the presence of both methyl and prenyl groups. The potential origin of the methyl in the flavonoids is discussed, as well as the chemophenetic significance of our findings. Isolation was performed over repeated silica gel and Sephadex LH-20 column chromatography and the structures were elucidated by (NMR and MS). The crude methanol extract and isolated compounds showed considerable antibacterial potency against a panel of multi-drug resistant (MDR) bacterial strains. The best MIC values were obtained with compound (2) against S. aureus ATCC 25923 (32 µg/mL) and MRSA1 (16 µg/mL).


Assuntos
Antibacterianos/farmacologia , Flavonoides/farmacologia , Poaceae/química , Prenilação , Terpenos/farmacologia , Espectroscopia de Ressonância Magnética Nuclear de Carbono-13 , Flavonoides/química , Flavonoides/isolamento & purificação , Testes de Sensibilidade Microbiana , Espectroscopia de Prótons por Ressonância Magnética , Terpenos/química , Terpenos/isolamento & purificação
6.
Molecules ; 26(16)2021 Aug 13.
Artigo em Inglês | MEDLINE | ID: mdl-34443500

RESUMO

Prostaglandins are a group of important cell-signaling molecules involved in the regulation of ovarian maturation, oocyte development, egg laying and associated behaviors in invertebrates. However, the presence of prostaglandin E2 (PGE2), the key enzymes for PGE2 biosynthesis and its interference by drugs were not investigated previously in the ovary of ticks. The present study was undertaken to assess the modulation of the PGE2-mediated pathway in the eclosion blocking effect of flumethrin and terpenoid subfraction isolated from Artemisia nilagirica in Rhipicephalus annulatus ticks. The acaricidal activities and chemical profiling of the terpenoid subfraction were performed. The localization of the cyclooxygenase1 (COX1) and prostaglandin E synthase (PGES) enzymes and the quantification of PGE2 in the ovaries of the ticks treated with methanol (control), flumethrin and terpenoid subfraction were also undertaken. In addition, the vitellogenin concentration in hemolymph was also assayed. Both flumethrin and the terpenoid subfraction of A. nilagirica elicited a concentration-dependent inhibition of fecundity and blocking of hatching of the eggs. The COX1 could not be detected in the ovaries of treated and control ticks, while there was no significant difference observed in the concentration of vitellogenin (Vg) in them. The presence of PGES in the oocytes of control ticks was confirmed while the immunoreactivities against PGES were absent in the vitellogenic oocytes of ticks treated with flumethrin and terpenoid subfraction. The levels of PGE2 were below the detection limit in the ovaries of the flumethrin-treated ticks, while it was significantly lower in the ovaries of the terpenoid subfraction-treated ticks. Hence, the prostaglandin E synthase and PGE2 were identified as very important mediators for the signaling pathway for ovarian maturation and oviposition in ticks. In addition, the key enzyme for prostaglandin biosynthesis, PGES and the receptors for PGE2 can be exploited as potential drug targets for tick control. The detection of PGES by immunohistochemistry and quantification of PGE2 by LC-MSMS can be employed as valuable tools for screening newer compounds for their eclosion blocking acaricidal effects.


Assuntos
Artemisia/química , Dinoprostona/metabolismo , Piretrinas/farmacologia , Rhipicephalus/efeitos dos fármacos , Terpenos/isolamento & purificação , Terpenos/farmacologia , Animais , Anticorpos/metabolismo , Feminino , Cromatografia Gasosa-Espectrometria de Massas , Hemolinfa/metabolismo , Imersão , Ovário/efeitos dos fármacos , Ovário/enzimologia , Peroxidase/metabolismo , Prostaglandina-E Sintases/metabolismo , Vitelogeninas/metabolismo
7.
J Chem Ecol ; 47(8-9): 799-809, 2021 Sep.
Artigo em Inglês | MEDLINE | ID: mdl-34347233

RESUMO

Fall armyworm (Spodoptera frugiperda) is a major global pest of many crops, including maize (Zea mays). This insect is known to use host plant-derived volatile organic compounds to locate suitable hosts during both its adult and larval stages, yet the function of individual compounds remains mostly enigmatic. In this study, we use a combination of volatile profiling, electrophysiological assays, pair-wise choice behavioral assays, and chemical supplementation treatments to identify and assess specific compounds from maize that influence S. frugiperda host location. Our findings reveal that methyl salicylate and (E)-alpha-bergamotene are oviposition attractants for adult moths but do not impact larval behavior. While geranyl acetate can act as an oviposition attractant or repellent depending on the host volatile context and (E)-4,8-dimethyl-1,3,7-nonatriene (DMNT) is an oviposition deterrent. These compounds can also be attractive to the larvae when applied to specific maize inbreds. These data show that S. frugiperda uses different plant volatile cues for host location in its adult and larval stage and that the background volatile context that specific volatiles are perceived in, alters their impact as behavioral cues.


Assuntos
Herbivoria/efeitos dos fármacos , Oviposição/efeitos dos fármacos , Spodoptera/fisiologia , Compostos Orgânicos Voláteis/farmacologia , Zea mays/química , Animais , Compostos Bicíclicos com Pontes/isolamento & purificação , Compostos Bicíclicos com Pontes/farmacologia , Cromatografia Gasosa-Espectrometria de Massas , Larva/fisiologia , Folhas de Planta/química , Folhas de Planta/metabolismo , Análise de Componente Principal , Salicilatos/isolamento & purificação , Salicilatos/farmacologia , Spodoptera/crescimento & desenvolvimento , Terpenos/isolamento & purificação , Terpenos/farmacologia , Compostos Orgânicos Voláteis/química , Zea mays/metabolismo
8.
J Chem Ecol ; 47(8-9): 740-746, 2021 Sep.
Artigo em Inglês | MEDLINE | ID: mdl-34347235

RESUMO

Aphids are destructive pests, and alarm pheromones play a key role in their chemical ecology. Here, we conducted a detailed analysis of terpenoids in the vetch aphid, Megoura viciae, and its host plant Pisum sativum using gas chromatography/mass spectrometry. Four major components, (-)-ß-pinene (49.74%), (E)-ß-farnesene (32.64%), (-)-α-pinene (9.42%) and ( +)-limonene (5.24%), along with trace amounts of ( +)-sabinene, camphene and α-terpineol) (3.14%) were found in the aphid. In contrast, few terpenoids were found in the host plant, consisting mainly of squalene (66.13%) and its analog 2,3-epoxysqualene (31.59%). Quantitative analysis of the four major terpenes in different developmental stages of the aphid showed that amounts of the monoterpenes increased with increasing stage, while the sesquiterpene amount peaked in the 3rd instar. (-)-ß-Pinene was the most abundant terpene at all developmental stages. Behavioral assays using a three-compartment olfactometer revealed that the repellency of single compounds varied in a concentration-dependent manner, but two mixtures [(-)-α-pinene: (-)-ß-pinene: (E)-ß-farnesene: ( +)-limonene = 1:44.4:6.5:2.2 or 1:18.4:1.3:0.8], were repellent at all concentrations tested. Our results suggest that (-)-α-pinene and (-)-ß-pinene are the major active components of the alarm pheromone of M. viciae, but that mixtures play a key role in the alarm response. Our study contributes to the understanding of the chemical ecology of aphids and may help design new control strategies against this aphid pest.


Assuntos
Afídeos/fisiologia , Ervilhas/química , Feromônios/química , Terpenos/química , Animais , Afídeos/química , Afídeos/crescimento & desenvolvimento , Comportamento Animal/efeitos dos fármacos , Monoterpenos Bicíclicos/isolamento & purificação , Monoterpenos Bicíclicos/farmacologia , Cromatografia Gasosa-Espectrometria de Massas , Controle de Insetos/métodos , Estágios do Ciclo de Vida , Ervilhas/metabolismo , Ervilhas/parasitologia , Feromônios/análise , Feromônios/farmacologia , Sesquiterpenos/isolamento & purificação , Sesquiterpenos/farmacologia , Terpenos/análise , Terpenos/farmacologia
9.
Molecules ; 26(16)2021 Aug 06.
Artigo em Inglês | MEDLINE | ID: mdl-34443354

RESUMO

If plasma polymer thin films are to be synthesised from sustainable and natural precursors of chemically heterogeneous composition, it is important to understand the extent to which this composition influences the mechanism of polymerisation. To this end, a well-studied monoterpene alcohol, terpinen-4-ol, has been targeted for a comparative study with the naturally occurring mix of terpenes (viz. Melaleuca alternifolia oil) from which it is commonly distilled. Positive ion mode mass spectra of both terpinen-4-ol and M. alternifolia oil showed a decrease in disparities between the type and abundance of cationic species formed in their respective plasma environments as applied plasma power was increased. Supplementary biological assay revealed the antibacterial action of both terpinen-4-ol and M. alternifolia derived coatings with respect to S. aureus bacteria, whilst cytocompatibility was demonstrated by comparable eukaryotic cell adhesion to both coatings. Elucidating the processes occurring within the reactive plasmas can enhance the economics of plasma polymer deposition by permitting use of the minimum power, time and precursor pre-processing required to control the extent of monomer fragmentation and fabricate a film of the desired thickness and functionality.


Assuntos
Antibacterianos/química , Antibacterianos/farmacologia , Produtos Biológicos/química , Gases em Plasma/química , Staphylococcus aureus/efeitos dos fármacos , Terpenos/química , Terpenos/farmacologia , Melaleuca/química
10.
Fitoterapia ; 154: 105017, 2021 Oct.
Artigo em Inglês | MEDLINE | ID: mdl-34418492

RESUMO

One undescribed tetracyclic triterpene (boswellicarin A), four undescribed pentacyclic triterpenes (boswellicarterins A-C) and one undescribed prenylaromadendrane-type diterpene (boscarterin A) were isolated from the gum resin of Boswellia carterii Birdw. (Burseraceae). Their structures were elucidated from NMR and HRESIMS spectroscopic data and ECD spectra. Boswellicarterins A-C and boscarterin A displayed weak and selective cytotoxicity against three human cancer cells (HepG2, A549 and MCF-7) by MTT assay.


Assuntos
Antineoplásicos Fitogênicos/farmacologia , Boswellia/química , Terpenos/farmacologia , Células A549 , Antineoplásicos Fitogênicos/isolamento & purificação , Células Hep G2 , Humanos , Células MCF-7 , Estrutura Molecular , Compostos Fitoquímicos/isolamento & purificação , Compostos Fitoquímicos/farmacologia , Resinas Vegetais/química , Terpenos/isolamento & purificação
11.
Angew Chem Int Ed Engl ; 60(41): 22270-22275, 2021 10 04.
Artigo em Inglês | MEDLINE | ID: mdl-34374477

RESUMO

Forrestiacids A (1) and B (2) are a novel class of [4+2] type pentaterpenoids derived from a rearranged lanostane moiety (dienophile) and an abietane unit (diene). These unprecedented molecules were isolated using guidance by molecular ion networking (MoIN) from Pseudotsuga forrestii, an endangered member of the Asian Douglas Fir Family. The intermolecular hetero-Diels-Alder adducts feature an unusual bicyclo[2.2.2]octene ring system. Their structures were elucidated by spectroscopic analysis, GIAO NMR calculations and DP4+ probability analyses, electronic circular dichroism calculations, and X-ray diffraction analysis. This unique addition to the pentaterpene family represents the largest and the most complex molecule successfully assigned using computational approaches to predict accurately chemical shift values. Compounds 1 and 2 exhibited potent inhibitory activities (IC50 s <5 µM) of ATP-citrate lyase (ACL), a new drug target for the treatment of glycolipid metabolic disorders including hyperlipidemia. Validating this activity 1 effectively attenuated the de novo lipogenesis in HepG2 cells. These findings provide a new chemical class for developing potential therapeutic agents for ACL-related diseases with strong links to traditional medicines.


Assuntos
ATP Citrato (pro-S)-Liase/antagonistas & inibidores , Produtos Biológicos/farmacologia , Inibidores Enzimáticos/farmacologia , Terpenos/farmacologia , ATP Citrato (pro-S)-Liase/metabolismo , Produtos Biológicos/química , Inibidores Enzimáticos/química , Humanos , Lipogênese/efeitos dos fármacos , Espectroscopia de Ressonância Magnética , Conformação Molecular , Terpenos/química
12.
Molecules ; 26(11)2021 Jun 05.
Artigo em Inglês | MEDLINE | ID: mdl-34198771

RESUMO

This study investigated within-plant variability of the main bioactive compounds in rosemary (Rosmarinus officinalis L.). Volatile terpenes, including the enantiomeric distribution of monoterpenes, and phenols were analyzed in young and mature foliar, cortical and xylem tissues. In addition, antimicrobial activity of rosmarinic acid and selected terpenes was evaluated against two rosemary pathogens, Alternaria alternata and Pseudomonas viridiflava. Data showed that total concentration and relative contents of terpenes changed in relation to tissue source and age. Their highest total concentration was observed in the young leaves, followed by mature leaves, cortical and xylem tissues. Rosmarinic acid and carnosic acid contents did not show significant differences between leaf tissues of different ages, while young and mature samples showed variations in the content of four flavonoids. These results are useful for a more targeted harvesting of rosemary plants, in order to produce high-quality essential oils and phenolic extracts. Microbial tests showed that several terpenes and rosmarinic acid significantly inhibited the growth of typical rosemary pathogens. Overall, results on antimicrobial activity suggest the potential application of these natural compounds as biochemical markers in breeding programs aimed to select new chemotypes less susceptible to pathogen attacks, and as eco-friendly chemical alternatives to synthetic pesticides.


Assuntos
Anti-Infecciosos/farmacologia , Fenóis/farmacologia , Rosmarinus/química , Terpenos/farmacologia , Alternaria/efeitos dos fármacos , Alternaria/crescimento & desenvolvimento , Anti-Infecciosos/química , Cinamatos/farmacologia , Depsídeos/farmacologia , Cromatografia Gasosa-Espectrometria de Massas , Testes de Sensibilidade Microbiana , Viabilidade Microbiana/efeitos dos fármacos , Óleos Voláteis/química , Óleos Voláteis/farmacologia , Especificidade de Órgãos , Fenóis/química , Pseudomonas/efeitos dos fármacos , Pseudomonas/crescimento & desenvolvimento , Rosmarinus/microbiologia , Terpenos/química
13.
Molecules ; 26(11)2021 Jun 02.
Artigo em Inglês | MEDLINE | ID: mdl-34199500

RESUMO

In the search of new alternatives for weed control, spices appear as an option with great potential. They are rich in bioactive natural products and edible, which might minimize toxicity hazard. Marjoram (Origanum majorana L.) is an aromatic herb that has been widely employed as a seasoning herb in Mediterranean countries. Although marjoram boasts a plethora of therapeutic properties (painkiller, antibiotic, treatment for intestinal disorders, etc.), the potential for its extracts for weed control is still to be more thoroughly explored. In order to determine their phytotoxic potential, marjoram leaves were subjected to different bioguided extraction processes, using water, ethyl acetate, acetone or methanol. The most active extract (acetone) was sequentially fractionated to identify its most active compounds. This fractionation led to the isolation and identification of 25 compounds that were classified as monoterpenes, diterpenes or flavonoids. Among them, a new compound named majoradiol and several compounds are described in marjoram for the first time. The phytotoxicity of the major compounds to etiolated wheat coleoptiles was compared against that of the commercial herbicide (Logran®), with similar or higher activity in some cases. These results confirm the extraordinary potential of the extracts from this edible plant to develop safer and more environmentally friendly herbicides.


Assuntos
Herbicidas/farmacologia , Origanum/química , Compostos Fitoquímicos/farmacologia , Fracionamento Químico , Flavonoides/química , Flavonoides/farmacologia , Herbicidas/química , Região do Mediterrâneo , Estrutura Molecular , Compostos Fitoquímicos/química , Folhas de Planta/química , Compostos de Sulfonilureia/farmacologia , Terpenos/química , Terpenos/farmacologia , Controle de Plantas Daninhas
14.
Phytochemistry ; 190: 112860, 2021 Oct.
Artigo em Inglês | MEDLINE | ID: mdl-34229223

RESUMO

Nine undescribed shikimate-conjugated meroterpenes, as well as nine known compounds, were isolated from solid cultures of the fungus Guignardia mangiferae, an endophyte obtained from the leaves of Dendrobium nobile. The structures of these undescribed compounds were characterized by analyses of their 1D and 2D NMR and HRESIMS data, and their absolute configurations were assigned by single-crystal X-ray crystallography, electronic circular dichroism (ECD) calculations, modified Mosher's method, and Mo2(OCOCH3)4-induced ECD experiments. Of these compounds, mangnardone A represents the first example of terpene-shikimate-conjugated meroterpenoid with a hydroxy group at C-5. In addition, the X-ray diffraction analysis of mangnardone I is the first example to confirm the structure of bicycloalternarene (BCA) meroterpenoid by single-crystal data. Nine undescribed meroterpenes inhibited nitric oxide (NO) production in LPS-induced RAW 264.7 cells with IC50 values in the range of 4.7-40.0 µM.


Assuntos
Ascomicetos , Terpenos , Endófitos , Estrutura Molecular , Terpenos/farmacologia
15.
Biomed Res Int ; 2021: 9929805, 2021.
Artigo em Inglês | MEDLINE | ID: mdl-34222487

RESUMO

Hydroxycitronellal (HC) is a monoterpene present in essential oils of aromatic plants of different species, obtained from semisynthesis of citronellal, and is widely used as a fragrance in cosmetics. The objective of this work was to evaluate the possible anxiolytic-like activity of HC and its possible mechanism of action using in vivo and in silico methodologies. Swiss male mice (Mus musculus) were treated with HC (12.5, 25, and 50 mg/kg, i.p.) and subjected to the rota rod, elevated plus maze, and open field tests. No significant impairments were observed in the rota rod tests for the motor activity of the animals treated with HC at 12.5, 25, and 50 mg/kg, i.p., indicating no myo-relaxing or sedative effects. In the elevated plus maze, HC (in the three doses) induced significant increases in the percentage of entries (respectively, 34.8%, 33.8%, and 38.6%) and in the length of stay (respectively, 49.9%, 56.1%, and 57.0%) in the open arms of the EPM, as well as the number of crossings in the open field tests. The mechanism of action of the compound's anxiolytic-like activity can be attributed to the involvement of GABAA receptors, and this interaction was observed in in vivo and in silico studies. For HC, the results suggest anxiolytic-like effects, possibly via modulation of the GABAergic system. The use of natural products to treat anxiety can become an alternative to existing synthetic products.


Assuntos
Ansiolíticos/farmacologia , Ansiedade/tratamento farmacológico , Aprendizagem em Labirinto/efeitos dos fármacos , Receptores de GABA-A/metabolismo , Terpenos/farmacologia , Animais , Comportamento Animal/efeitos dos fármacos , Simulação por Computador , Ligação de Hidrogênio , Hipnóticos e Sedativos/farmacologia , Tempo de Internação , Masculino , Camundongos , Simulação de Acoplamento Molecular , Atividade Motora/efeitos dos fármacos , Resultado do Tratamento
16.
Sci Rep ; 11(1): 14785, 2021 07 20.
Artigo em Inglês | MEDLINE | ID: mdl-34285252

RESUMO

Gravid female Anopheles gambiae mosquitoes identify suitable oviposition sites through a repertoire of cues, but the influence of allelochemicals, especially root phytochemicals in modulating this behavior and impacting subsequent progeny bionomics remains unexplored. We addressed these questions in the malaria vector Anopheles gambiae and its invasive host plant Parthenium hysterophorus. Using chemical analysis combined with laboratory behavioral assays, we demonstrate that a blend of terpenes, namely α-pinene, α-phellandrene, ß-phellandrene, 3-carene and (E)-caryophyllene emitted from P. hysterophorus root exudate treated-water attracted gravid females. However, fewer eggs (55%) hatched in this treatment than in control water (66%). The sesquiterpene lactone parthenin, identified in both the natural aquatic habitat harboring P. hysterophorus and root exudate-treated water was found to be responsible for the ovicidal effect. Moreover, larvae exposed to parthenin developed 2 to 3 days earlier but survived 4 to 5 days longer as adults (median larval survival time = 9 days (all replicates);11 to 12 days as adults) than the non-exposed control (median larval survival time = 11 days (reps 1 & 2), 12 days (rep 3); 6 to 7 days as adults). These results improve our understanding of the risk and benefits of oviposition site selection by gravid An. gambiae females and the role root exudate allelochemicals could play on anopheline bionomics, with potential implications in malaria transmission.


Assuntos
Anopheles/fisiologia , Asteraceae/química , Malária/parasitologia , Oviposição/efeitos dos fármacos , Terpenos/farmacologia , Animais , Anopheles/efeitos dos fármacos , Comportamento Animal/efeitos dos fármacos , Feminino , Humanos , Espécies Introduzidas , Mosquitos Vetores/efeitos dos fármacos , Mosquitos Vetores/fisiologia , Extratos Vegetais/química , Extratos Vegetais/farmacologia , Raízes de Plantas/química , Terpenos/química
17.
Molecules ; 26(10)2021 May 13.
Artigo em Inglês | MEDLINE | ID: mdl-34068314

RESUMO

The Myrteacae family is known as a rich source of phloroglucinols, a group of secondary metabolites with notable biological activities. Leaves of Psidium cattleianum were extracted with chloroform: methanol 8:2 to target the isolation of phloroglucinol derivatives. Isolated compounds were characterized using different spectroscopic methods: nuclear magnetic resonance (NMR), ultra-violet (UV) and mass spectrometry (MS). Two new phloroglucinols were evaluated for cytotoxicity against a panel of six human cancer cell lines, namely colorectal adenocarcinoma cells (HT-29 and HCT-116); hepatocellular carcinoma cells (HepG-2); laryngeal carcinoma (Hep-2); breast adenocarcinoma cells (MCF7 and MDA-MB231), in addition to normal human melanocytes HFB-4. Additionally, cell cycle analysis and annexin-V/FITC-staining were used to gain insights into the mechanism of action of the isolated compounds. The new phloroglucinol meroterpenoids, designated cattleianal and cattleianone, showed selective antiproliferative action against HT-29 cells with IC50's of 35.2 and 32.1 µM, respectively. Results obtained using cell cycle analysis and annexin-V/FITC-staining implicated both necrosis and apoptosis pathways in the selective cytotoxicity of cattleianal and cattleianone. Our findings suggest that both compounds are selective antiproliferative agents and support further mechanistic studies for phloroglucinol meroterpenoids as scaffolds for developing new selective chemotherapeutic agents.


Assuntos
Carcinoma/patologia , Folhas de Planta/química , Psidium/química , Terpenos/farmacologia , Apoptose/efeitos dos fármacos , Ciclo Celular/efeitos dos fármacos , Morte Celular/efeitos dos fármacos , Linhagem Celular Tumoral , Proliferação de Células/efeitos dos fármacos , Humanos , Concentração Inibidora 50 , Necrose , Terpenos/isolamento & purificação
18.
Front Immunol ; 12: 585595, 2021.
Artigo em Inglês | MEDLINE | ID: mdl-34093515

RESUMO

Introduction: Asthma is a chronic and recurring airway disease, which related to mast cell activation. Many compounds derived from Chinese herbal medicine has promising effects on stabilizing mast cells and decreasing inflammatory mediator production. Safranal, one of the active compounds from Crocus sativus, shows many anti-inflammatory properties. In this study, we evaluated the effect of safranal in ovalbumin (OVA)-induced asthma model. Furthermore, we investigate the effectiveness of safranal on stabilizing mast cell and inhibiting the production of inflammatory mediators in passive systemic anaphylaxis (PSA) model. Methods: OVA-induced asthma and PSA model were used to evaluate the effect of safranal in vivo. Lung tissues were collected for H&E, TB, IHC, and PAS staining. ELISA were used to determine level of IgE and chemokines (IL-4, IL-5, TNF-α, and IFN-γ). RNA sequencing was used to uncovers genes that safranal regulate. Bone marrow-derived mast cells (BMMCs) were used to investigate the inhibitory effect and mechanism of safranal. Cytokine production (IL-6, TNF-α, and LTC4) and NF-κB and MAPKs signaling pathway were assessed. Results: Safranal reduced the level of serum IgE, the number of mast cells in lung tissue were decreased and Th1/Th2 cytokine levels were normalized in OVA-induced asthma model. Furthermore, safranal inhibited BMMCs degranulation and inhibited the production of LTC4, IL-6, and TNF-α. Safranal inhibits NF-κB and MAPKs pathway protein phosphorylation and decreases NF-κB p65, AP-1 nuclear translocation. In the PSA model, safranal reduced the levels of histamine and LTC4 in serum. Conclusions: Safranal alleviates OVA-induced asthma, inhibits mast cell activation and PSA reaction. The possible mechanism occurs through the inhibition of the MAPKs and NF-κB pathways.


Assuntos
Alérgenos/imunologia , Asma/etiologia , Cicloexenos/farmacologia , Mastócitos/efeitos dos fármacos , Mastócitos/imunologia , Ovalbumina/efeitos adversos , Terpenos/farmacologia , Animais , Anti-Inflamatórios/administração & dosagem , Anti-Inflamatórios/farmacologia , Asma/tratamento farmacológico , Asma/metabolismo , Asma/patologia , Degranulação Celular/efeitos dos fármacos , Degranulação Celular/imunologia , Cicloexenos/administração & dosagem , Citocinas/metabolismo , Modelos Animais de Doenças , Suscetibilidade a Doenças , Feminino , Imunoglobulina E/imunologia , Mediadores da Inflamação/metabolismo , Mastócitos/metabolismo , Camundongos , NF-kappa B/metabolismo , Ovalbumina/imunologia , Transdução de Sinais/efeitos dos fármacos , Terpenos/administração & dosagem
19.
Biomed Pharmacother ; 140: 111592, 2021 Aug.
Artigo em Inglês | MEDLINE | ID: mdl-34088572

RESUMO

Annonaceae family has broad uses in herbal medicine for treatment of several diseases, whether through seeds' or leaves' extracts. The present study investigates the antiproliferative and antitumor activity of Annona cherimola aqueous leaf (AAL) extract/infusion in acute myeloid leukemia (AML) cell lines in vitro. High-resolution LC-MS was first used to analyze the composition of the aqueous extract. Cell proliferation assay, Annexin V staining, cell cycle analysis, dual Annexin V/PI staining, cell death quantification by ELISA, ROS level detection and Western Blotting were then performed to elucidate the therapeutic effects of AAL extract. The results obtained revealed a potent antioxidant activity of AAL extract. Moreover, the extract exhibited dose- and time-dependent antiproliferative effects on AML cell lines by decreasing cell viability with an IC50 of 5.03% (v/v) at 24 h of treatment of KG-1 cells. This decrease in viability was accompanied with a significant increase in apoptotic cell death with cell cycle arrest and flipping of the phosphatidylserine from the inner to the outer leaflet of the cell membrane. The respective overexpression and downregulation of proapoptotic proteins like cleaved caspase-8, cleaved PARP-1 and Bax and antiapoptotic proteins like Bcl-2 further validated the apoptotic pathway induced by AAL on AML cells. Finally, LC-MS revealed the presence of several compounds like fatty acids, terpenes, phenolics, cinnamic acids and flavonoids that could contribute to the antioxidant and anti-cancer effects of this herbal infusion. In addition to the generally known nutritional effects of the Annona cherimola fruit and leaves, the presented data validates the antioxidant and anti-cancerous effects of the leaf infusion on AML cell lines, proposing its potential therapeutic use against acute myeloid leukemia with future in vivo and clinical trials.


Assuntos
Annona/química , Apoptose/efeitos dos fármacos , Leucemia Mieloide Aguda/tratamento farmacológico , Compostos Fitoquímicos/farmacologia , Extratos Vegetais/farmacologia , Folhas de Planta/química , Antioxidantes/metabolismo , Pontos de Checagem do Ciclo Celular/efeitos dos fármacos , Linhagem Celular Tumoral , Proliferação de Células/efeitos dos fármacos , Sobrevivência Celular/efeitos dos fármacos , Células Cultivadas , Flavonoides/farmacologia , Humanos , Leucemia Mieloide Aguda/metabolismo , Leucócitos Mononucleares/efeitos dos fármacos , Leucócitos Mononucleares/metabolismo , Sementes/química , Terpenos/farmacologia
20.
Molecules ; 26(9)2021 May 10.
Artigo em Inglês | MEDLINE | ID: mdl-34068647

RESUMO

The anticancer activity of terretonin N (1) and butyrolactone I (2), obtained from the thermophilic fungus Aspergillus terreus TM8, was intensively studied against prostate adenocarcinoma (PC-3) and ovary adenocarcinoma (SKOV3) human cell lines. According to this study, both compounds showed potent cytotoxicity towards ovarian adenocarcinoma cells (SKOV3) with IC50 1.2 and 0.6 µg/mL, respectively. With respect to metastatic prostate cells (PC-3), the two compounds 1 and 2 showed a significantly promising cytotoxicity effect with IC50 of 7.4 and 4.5 µg/mL, respectively. The tested fungal metabolites showed higher rates of early and late apoptosis with little or no necrotic apoptotic pathway in all treated prostate adenocarcinoma (PC-3) and ovary adenocarcinoma (SKOV3) human cell lines, respectively. The results reported in this study confirmed the promising biological properties of terretonin N (1) and butyrolactone I (2) as anticancer agents via the induction of cellular apoptosis. However, further studies are needed to elucidate the molecular mechanism by which cellular apoptosis is induced in cancer cells.


Assuntos
4-Butirolactona/análogos & derivados , Apoptose/efeitos dos fármacos , Aspergillus/química , Neoplasias Ovarianas/patologia , Neoplasias da Próstata/patologia , Terpenos/farmacologia , 4-Butirolactona/química , 4-Butirolactona/farmacologia , Linhagem Celular Tumoral , Núcleo Celular/efeitos dos fármacos , Núcleo Celular/metabolismo , Forma Celular/efeitos dos fármacos , Feminino , Humanos , Concentração Inibidora 50 , Masculino , Terpenos/química
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