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1.
Biotechnol Lett ; 46(5): 843-850, 2024 Oct.
Artigo em Inglês | MEDLINE | ID: mdl-38717662

RESUMO

OBJECTIVE: Evaluation of Nepeta cataria as a host with specific endogenous metabolite background for transient expression and metabolic engineering of secondary biosynthetic sequences. RESULTS: The reporter gene gfp::licBM3 as well as three biosynthetic genes leading to the formation of the cannabinoid precursor olivetolic acid were adopted to the modular cloning standard GoldenBraid, transiently expressed in two chemotypes of N. cataria and compared to Nicotiana benthamiana. To estimate the expression efficiency in both hosts, quantification of the reporter activity was carried out with a sensitive and specific lichenase assay. While N. benthamiana exhibited lichenase activity of 676 ± 94 µmol g-1 s-1, N. cataria cultivar '1000', and the cultivar 'Citriodora' showed an activity of 37 ± 8 µmol g-1 s-1 and 18 ± 4 µmol g-1 s-1, respectively. Further, combinatorial expression of genes involved in cannabinoid biosynthetic pathway acyl-activating enzyme 1 (aae1), olivetol synthase (ols) and olivetolic acid cyclase (oac) in N. cataria cv. resulted presumably in the in vivo production of olivetolic acid glycosides. CONCLUSION: Nepeta cataria is amenable to Agrobacterium-mediated transient expression and could serve as a novel chassis for the engineering of secondary metabolic pathways and transient evaluation of heterologous genes.


Assuntos
Engenharia Metabólica , Nepeta , Nepeta/genética , Nepeta/metabolismo , Nepeta/química , Engenharia Metabólica/métodos , Redes e Vias Metabólicas/genética , Nicotiana/genética , Nicotiana/metabolismo , Plantas Geneticamente Modificadas/genética , Genes Reporter , Vias Biossintéticas/genética
2.
Phytochem Anal ; 35(7): 1674-1687, 2024 Oct.
Artigo em Inglês | MEDLINE | ID: mdl-39099156

RESUMO

INTRODUCTION: Catnip (Nepeta cataria, L.) has well-documented applications in arthropod repellency because of its bioactive iridoids. Long-term stability of nepetalactones and other iridoids in N. cataria are needed to develop as effective pest repellents. OBJECTIVES: The present work intends to measure iridoid concentration over time in biomass, plant extracts, and extract solution while identifying degradative byproducts under different storage conditions. METHODOLOGY: Samples of desiccated biomass, ethanol extract, and extract in ethanol solution were stored in ambient light or darkness. Through UHPLC-QTOF/MS or UHPLC-QQQ/MS, the concentration of Z,E-nepetalactone, E,Z-nepetalactone, nepetalic acid, and dihydronepetalactone were examined over 2 years and statistically analyzed for determination of best storage practices. Degradation kinetics were applied to each analyte using graphical estimation. With targeted formula searching, degradative byproducts were identified and quantified. RESULTS: Light exposure caused significant decreases in E,Z-nepetalactone concentration in all sample types, while having no effect on Z,E-nepetalactone as it decayed more rapidly. Extract samples lost nepetalactone content faster than biomass or extract solution. Dihydronepetalactone levels were low, but never declined over 2 years. Nepetalic acid increased over some periods, depending on sample type, indicating a relationship between the acid and nepetalactone. Four degradative byproducts-nepetonic acid, dehydronepetalactone, an anhydride, and an ethanolic ester-were identified, with variable responses to light exposure. CONCLUSIONS: Protecting catnip products from light is necessary to preserve nepetalactones, and a discernable difference in nepetalactone isomer stability was discovered. Identifying Nepeta chemotypes rich in dihydronepetalactone may provide more resilient botanicals as starting materials for processing.


Assuntos
Iridoides , Nepeta , Nepeta/química , Iridoides/análise , Iridoides/química , Cromatografia Líquida de Alta Pressão/métodos , Extratos Vegetais/química , Extratos Vegetais/análise , Espectrometria de Massas/métodos , Espectrometria de Massas em Tandem/métodos , Estabilidade de Medicamentos , Biomassa , Monoterpenos Ciclopentânicos , Pironas
3.
Molecules ; 29(9)2024 Apr 26.
Artigo em Inglês | MEDLINE | ID: mdl-38731491

RESUMO

Catnip (Nepeta cataria L.) plants produce a wide array of specialized metabolites with multiple applications for human health. The productivity of such metabolites, including nepetalactones, and natural insect repellents is influenced by the conditions under which the plants are cultivated. In this study, we assessed how field-grown catnip plants, transplanted after being propagated via either single-node stem cuttings or seeds, varied regarding their phytochemical composition throughout a growing season in two distinct environmental conditions (Pittstown and Upper Deerfield) in the state of New Jersey, United States. Iridoid terpenes were quantified in plant tissues via ultra-high-performance liquid chromatography with triple quadrupole mass spectrometry (UHPLC-QqQ-MS), and phenolic compounds (phenolic acids and flavonoids) were analyzed via UHPLC with diode-array detection (UHPLC-DAD). The highest contents of total nepetalactones in Pittstown were found at 6 weeks after transplanting (WAT) for both seedlings and cuttings (1305.4 and 1223.3 mg/100 g, respectively), while in Upper Deerfield, the highest contents for both propagules were at 11 WAT (1247.7 and 997.1 mg/100 g, respectively) for seed-propagated and stem cuttings). The highest concentration of nepetalactones was associated with floral-bud to partial-flowering stages. Because plants in Pittstown accumulated considerably more biomass than plants grown in Upper Deerfield, the difference in nepetalactone production per plant was striking, with peak productivity reaching only 598.9 mg per plant in Upper Deerfield and 1833.1 mg per plant in Pittstown. Phenolic acids accumulated in higher contents towards the end of the season in both locations, after a period of low precipitation, and flavone glycosides had similar accumulation patterns to nepetalactones. In both locations, rooted stem cuttings reached their maximum nepetalactone productivity, on average, four weeks later than seed-propagated plants, suggesting that seedlings have, overall, better agronomic performance.


Assuntos
Nepeta , Estações do Ano , Nepeta/química , Cromatografia Líquida de Alta Pressão , Compostos Fitoquímicos/química , Compostos Fitoquímicos/análise , Flavonoides/análise , Flavonoides/química , Monoterpenos Ciclopentânicos , Sementes/química , Sementes/crescimento & desenvolvimento , Extratos Vegetais/química , Iridoides/química , Pironas
4.
Fish Physiol Biochem ; 50(4): 1651-1665, 2024 Aug.
Artigo em Inglês | MEDLINE | ID: mdl-38801500

RESUMO

The purpose of this study was to characterize the activity of essential oils from Nepeta Cataria (EON) at concentrations of 125 µ L  L-1, 150 µ L  L-1, 175 µ L  L-1, and 200 µ L  L-1 on the behavior of loss of the posture reflex and recovery of the posture reflex and electrocardiographic activity and recording of the opercular beat of Colossoma macropomum during immersion bathing for a period of 5 min, in order to obtain a window for safe use during anesthesia. The fish (23.38 ± 3.5 g) were assigned to the following experiments: experiment 1 (latency to loss and recovery of the posture reflex): (a) 125 µ L  L-1, (b) 150 µ L  L-1, (c) 175 µ L  L-1, and (d) 200 µ L  L-1 (n = 9) per group. Experiment 2 (electrocardiographic and heartbeat recordings): (a) control group; (b) vehicle control group (2 ml of alcohol per liter of water), (c) 125 µ L  L-1, (d) 150 µ L  L-1, (e) 175 µ L  L-1, and (f) 200 µ L  L-1 (n = 9), per group. All the concentrations used showed efficacy in inducing loss of the posture reflex and reversibility with recovery of the posture reflex, but the electrocardiographic recordings indicated morphographic changes such as bradycardia during induction and p wave apiculation during recovery at the highest concentrations tested. In this way, we suggest a safe use window for short-term anesthesia with EON in the concentration range of 125 to 150 µ L  L-1 for juvenile Colossoma macropomum.


Assuntos
Nepeta , Animais , Nepeta/química , Anestesia/veterinária , Óleos Voláteis/farmacologia , Óleos Voláteis/administração & dosagem , Comportamento Animal/efeitos dos fármacos , Caraciformes/fisiologia , Eletrocardiografia/veterinária , Óleos de Plantas/farmacologia , Óleos de Plantas/administração & dosagem , Frequência Cardíaca/efeitos dos fármacos , Imersão
5.
Cell Mol Biol (Noisy-le-grand) ; 69(10): 129-135, 2023 Oct 31.
Artigo em Inglês | MEDLINE | ID: mdl-37953573

RESUMO

Pathogenic microorganisms are more or less successfully treated by synthetic chemical compounds, whose residues often cause serious health problems. Plant specialized metabolites with antimicrobial properties have for a long time been the focus of both medicine and pharmacology. This study was conducted to evaluate the in vitro antimicrobial activity of methanol extracts of selected endemic and native Iranian Nepeta species against some of the most important pathogenic bacteria and fungi. The results indicated that N. kotschyi leaf extract was the most efficient against the tested bacteria, with Pseudomonas aeruginosa being the most sensitive and fungal species were more susceptible to the extracts than bacterial strains. Nepeta spp. extracts showed a strong antifungal activity against micromycetes, except for quite resistant Aspergillus niger. Antibacterial MIC values (mg.mL-1) ranged from 0.01 (N. kotschyi) to 0.20 (N. crassifolia), while antifungal MIC values ranged from 0.02 (N. crassifolia, N. kotschyi, N. menthoides, and N. cataria) to 0.13 (N. crassifolia and N. menthoides). When compared to positive controls, in most cases the extracts performed much better. The recorded antimicrobial activity candidates the selected 4 endemic and native Iranian Nepeta spp. as prospective and promising antimicrobial agents to be used in both pharmacology and biotechnology.


Assuntos
Anti-Infecciosos , Nepeta , Antifúngicos/farmacologia , Antifúngicos/química , Nepeta/química , Irã (Geográfico) , Extratos Vegetais/farmacologia , Extratos Vegetais/química , Testes de Sensibilidade Microbiana , Anti-Infecciosos/farmacologia , Antibacterianos/farmacologia , Antibacterianos/química , Bactérias
6.
BMC Biol ; 20(1): 192, 2022 08 25.
Artigo em Inglês | MEDLINE | ID: mdl-36008824

RESUMO

BACKGROUND: It has been known for centuries that cats respond euphorically to Nepeta cataria (catnip). Recently, we have shown that Lonicera tatarica (Tatarian honeysuckle), Actinidia polygama (silver vine), and Valeriana officinalis (valerian) can also elicit this "catnip response". The aim of this study was to learn if the behavior seen in response to these plants is similar to the response to catnip. Furthermore, we studied if these responses are fixed or if there are differences between cats. While nepetalactone was identified decades ago as the molecule responsible for the "catnip response", we know that this volatile is found almost exclusively in catnip. Therefore, we also aimed to identify other compounds in these alternative plants that can elicit the blissful behavior in cats. Bioassays with 6 cats were performed in a low-stress environment, where 5 plants and 13 single compounds were each tested for at least 100 and 17 h, respectively. All responses were video recorded and BORIS software was used to analyze the cats' behavior. RESULTS: Both response duration and behavior differed significantly between the cats. While individual cats had preferences for particular plants, the behavior of individual cats was consistent among all plants. About half a dozen lactones similar in structure to nepetalactone were able to elicit the "catnip response", as were the structurally more distinct molecules actinidine and dihydroactinidiolide. Most cats did not respond to actinidine, whereas those who did, responded longer to this volatile than any of the other secondary plant metabolites, and different behavior was observed. Interestingly, dihydroactinidiolide was also found in excretions and secretions of the red fox, making this the first report of a compound produced by a mammal that can elicit the "catnip response". A range of different cat-attracting compounds was detected by chemical analysis of plant materials but differences in cat behavior could not be directly related to differences in chemical composition of the plants. Together with results of, among others, habituation / dishabituation experiments, this indicates that additional cat-attracting compounds may be present in the plant materials that remain to be discovered. CONCLUSIONS: Collectively, these findings suggest that both the personality of the cat and genetic variation in the genes encoding olfactory receptors may play a role in how cats respond to cat-attracting plants. Furthermore, the data suggest a potential distinct mechanism of action for actinidine.


Assuntos
Nepeta , Alcaloides , Animais , Comportamento Animal , Gatos , Mamíferos , Nepeta/química , Plantas , Piridinas , Terpenos
7.
Chem Biodivers ; 20(2): e202200241, 2023 Feb.
Artigo em Inglês | MEDLINE | ID: mdl-36655301

RESUMO

The mosquito repellent Nepetalactone rich Nepeta cataria L. (catmint) plant has a variety of therapeutic and industrial potential. Reports on the genetic diversity of N. cataria germplasm are minimal globally and need attention for adding a new variety into commercial cultivation. The present study, therefore, assessed the genetic diversity among thirteen half-sib genotypes of N. cataria using agro economic and phytochemical traits. The experimental set has shown substantial variation for agro economic traits studied. Among all the studied populations, fresh herb-based essential oil content ranged from 0.1 % to 0.3 %, with a grand mean of 1.67 %. However, the estimated oil yield ranged from 44.4 kg/h to 120.73 kg/h with an average of 71.34 kg/h. Among the eleven phytochemical constituents detected in different concentrations in the essential oil of experimental sets, 4aα,7α,7aα-Nepetalactone (67.9-87.5 %) constituted the significant proportion of essential oil. Altogether, based on mean comparison, the population NC8 was found to be promising for estimated oil yield and 4aα,7α,7aα-Nepetalactone content. The greater heritability estimates (h2 bs) and genetic advance as percent of mean (GAM) were observed for important economic parameters, i. e., oil content, herb yield, and oil yield. The cluster analysis revealed the least interactions between various agro economic and phytochemical variables. The microscopic study of trichome showed a positive correlation of abaxial leaf surface with essential oil content. The promising antimicrobial potential of catmint oil was also observed against human health-related pathogens. The results infer from our study provide valuable insight for genetic improvement and product development in the catmint germplasm.


Assuntos
Anti-Infecciosos , Nepeta , Óleos Voláteis , Humanos , Óleos de Plantas/química , Nepeta/química , Óleos Voláteis/química , Variação Genética
8.
Phytochem Anal ; 34(6): 661-679, 2023 Aug.
Artigo em Inglês | MEDLINE | ID: mdl-37387322

RESUMO

INTRODUCTION: The endemic species Nepeta cyrenaica Quézel & Zaffran, native to northeastern Libya, is valued as an important honey-bearing plant. OBJECTIVES: This study was aimed to examine the micromorphology, phytochemistry, and bioactivity of in vitro-propagated N. cyrenaica for the first time. MATERIALS AND METHODS: The leaf indumentum was examined using light and scanning electron microscopy and further characterised for histochemistry. The chemical composition of essential oil (EO) was performed using GC-MS analysis, while dichloromethane (DCM), methanol (ME), ethanol (ET), and aqueous (AQ) extracts were analysed using qualitative and quantitative LC/MS analyses. The antioxidant activities of EO and extracts were assessed using three parallel assays, while enzyme-inhibiting effects were evaluated against four enzymes. RESULTS: The leaves bear various types of glandular trichomes, with lipophilic secretion predominating. The main EO component of EO was 1,8-cineole. A considerable number of phenolics and iridoids were tentatively identified in the ME extract. Quantitative LC/MS analysis confirmed that ferulic acid, rosmarinic acid, and epigallocatechin gallate were present in the highest amount in the extracts, in which three iridoids were also quantified. Although the ME extract contained the highest amount of polyphenolics and iridoids, the DCM extract showed the best overall biological potential. Additionally, EO exerted the strongest acetylcholinesterase and tyrosinase inhibition. CONCLUSION: This study demonstrated that the endemic N. cyrenaica can be efficiently grown under in vitro conditions, where it develops various glandular trichomes that are thought to secrete and/or accumulate bioactive compounds with valuable medicinal potential.


Assuntos
Lamiaceae , Nepeta , Óleos Voláteis , Lamiaceae/química , Nepeta/química , Acetilcolinesterase , Óleos Voláteis/química , Antioxidantes/farmacologia , Antioxidantes/análise , Extratos Vegetais/química , Iridoides , Folhas de Planta/química
9.
Planta ; 256(5): 99, 2022 Oct 12.
Artigo em Inglês | MEDLINE | ID: mdl-36222913

RESUMO

MAIN CONCLUSION: Using virus-induced gene silencing, we demonstrated that the enzymes GES, ISY, and MLPL are responsible for nepetalactone biosynthesis in Nepeta cataria. Nepetalactone is the main iridoid that is found in the Nepeta genus and is well-known for its psychoactive effect on house cats. Moreover, there is a burgeoning interest into the effect of nepetalactone on insects. Although the enzymes for nepetalactone biosynthesis have been biochemically assayed in vitro, validation of the role that these enzymes have in planta has not been demonstrated. Virus-induced gene silencing (VIGS) is a silencing method that relies on transient transformation and is an approach that has been particularly successful when applied to a variety of non-model plants. Here, we use a recently designed visual-marker dependent VIGS system to demonstrate that the nepetalactone biosynthetic enzymes GES, ISY, and MLPL impact nepetalactone biosynthesis in Nepeta cataria.


Assuntos
Nepeta , Monoterpenos Ciclopentânicos , Iridoides , Nepeta/química , Nepeta/genética , Pironas/química , Pironas/farmacologia
10.
Phytother Res ; 36(6): 2481-2494, 2022 Jun.
Artigo em Inglês | MEDLINE | ID: mdl-35470926

RESUMO

Nepeta menthoides Boiss. & Buhse and Melissa officinalis are extensively used in Persian medicine for the treatment of depression. Considering the active ingredients and main phenolic compounds of these plants and possible synergistic effects, this study examined the antidepressant and antioxidant activities of aqueous extract of N. menthoides (NM) and M. officinalis (MO) in reserpinized mice alone and combination. Mice were pretreated orally for 1-week with normal saline (10 ml/kg), fluoxetine (20 mg/kg), imipramine (10 mg/kg), NM (50-100-200-400 mg/kg), MO (150-350-550-750 mg/kg), and combination (NM 50 with MO 150 mg/kg). The behavioral changes were evaluated using forced swim, tail suspension, and open field tests, 24 hr after reserpine injection (4 mg/kg) on eighth day. The amounts of active components in the extracts and catalase (CAT) as a brain oxidative stress were measured with enzyme-linked immunosorbent assay. Data showed that this combination produced a synergistic action on behaviors and a significant increase in CAT activity. High-performance liquid chromatography results showed that rosmarinic acid contents in MO and NM were 6.42 ± 1.1 and 11.03 ± 2.16 mg/g of dried extract, respectively. Total flavonoid and phenolic contents of MO were higher than NM. The findings suggest that the present combination produces an antidepressant-like effect, which is possibly triggered by its antioxidant properties.


Assuntos
Melissa , Nepeta , Animais , Antidepressivos/farmacologia , Antioxidantes/análise , Antioxidantes/farmacologia , Melissa/química , Camundongos , Nepeta/química , Fenóis/análise , Extratos Vegetais/química , Reserpina
11.
Molecules ; 27(20)2022 Oct 19.
Artigo em Inglês | MEDLINE | ID: mdl-36296649

RESUMO

Catnip (Nepeta cataria L.) is of scientific interest largely due to the production of nepetalactones, volatile iridoid terpenes with strong arthropod repellent activity. However, the plant can also produce other bioactive volatile iridoids, such as nepetalic acid (NA), nepetalactam (NT) and dihydronepetalactone (DHNL) that have not been studied extensively. Germplasm studies on plants that can produce such compounds are scarce. The present study evaluated the chemical diversity of catnip genotypes with a focus on NA, NT and DHNL. A total of 34 genotypes were harvested at different times over two years. The ethanolic extract of the plants was screened for iridoids by ultra-high-performance liquid chromatography/triple quadrupole mass spectrometry. CR9 × CR3 genotype had the highest value for biomass yield, while cultivar CR9 had the highest value for accumulated NA. Genotype UK.2 had the highest value for accumulated NT yield and CR5 had the highest value for accumulated DHNL. Overall, patented cultivars and elite selections performed better than other less studied genotypes. Harvest time influenced the accumulation of secondary metabolites differentially for the genotypes. This is the first germplasm study with a focus on these iridoid compounds, yet more studies are necessary as genotype characterization is essential for breeding and standardization of products for industry.


Assuntos
Nepeta , Óleos Voláteis , Nepeta/genética , Nepeta/química , Terpenos , Iridoides , Melhoramento Vegetal , Extratos Vegetais/química , Genótipo , Óleos Voláteis/química
12.
Molecules ; 26(1)2021 Jan 03.
Artigo em Inglês | MEDLINE | ID: mdl-33401536

RESUMO

BACKGROUND: The red-complex bacteria are one of the most significant complexes found simultaneously in subgingival plaque next to the periodontal pocket. The current antibacterial treatment is not adequate, and multidrug resistance to it is developing. Henceforth, the antibacterial effect of the ethanolic extract of Nepeta deflersiana was put to test against red-complex bacteria in patients with chronic periodontitis. METHODS: Well diffusion and micro broth dilution procedure by Alamar blue were applied to assess the zone of inhibition (ZOI), the minimum inhibitory concentration (MIC), and the minimum bactericidal concentration (MBC). Anti-virulence efficacies of the plant extract that comprise of adherence and formation of biofilms were examined by the process of adherence and biofilm production assay. RESULTS: The crude extract of Nepeta deflersiana exhibited significant inhibitory outcome against periodontopathic bacteria with noteworthy MIC (0.78-3.12 mg/mL), inhibitory zone (12-20 mm), as well as MBC (3.12-12.50 mg/mL). The N. deflersiana extract inhibited bacterial adhesion ranging from 41% to 52%, 53% to 66%, and 60% to 79% at the given MIC × 0.5, MIC × 1, and MIC × 2 in succession. Substantial suppression was also developed in the biofilm production of the investigated periodontopathic strains following exposure to numerous concentrations of N. deflersianan extract for a period of 24 and 48 h. CONCLUSION: These outcomes divulge a new concept that N. deflersiana extract can be utilized to manufacture valuable antibacterial compounds to treat chronic and acute periodontitis. This identifies N. deflersiana as an essential natural source for future drug development.


Assuntos
Antibacterianos , Bactérias/crescimento & desenvolvimento , Microbiota/efeitos dos fármacos , Nepeta/química , Doenças Periodontais/microbiologia , Extratos Vegetais , Antibacterianos/química , Antibacterianos/farmacologia , Humanos , Doenças Periodontais/tratamento farmacológico , Extratos Vegetais/química , Extratos Vegetais/farmacologia
13.
Molecules ; 26(23)2021 Dec 06.
Artigo em Inglês | MEDLINE | ID: mdl-34885973

RESUMO

Cyclodextrin inclusion complexes have been successfully used to encapsulate essential oils, improving their physicochemical properties and pharmacological effects. Besides being well-known for its effects on cats and other felines, catnip (Nepeta cataria) essential oil demonstrates repellency against blood-feeding pests such as mosquitoes. This study evaluates the tick repellency of catnip oil alone and encapsulated in ß-cyclodextrin, prepared using the co-precipitation method at a 1:1 molar ratio. The physicochemical properties of this inclusion complex were characterized using GC-FID for encapsulation efficiency and yield and SPME/GC-MS for volatile emission. Qualitative assessment of complex formation was done by UV-Vis, FT-IR, 1H NMR, and SEM analyses. Catnip oil at 5% (v/v) demonstrated significant tick repellency over time, being comparable to DEET as used in commercial products. The prepared [catnip: ß-CD] inclusion complex exerted significant tick repellency at lower concentration of the essential oil (equivalent of 1% v/v). The inclusion complex showed that the release of the active ingredient was consistent after 6 h, which could improve the effective repellent duration. These results demonstrated the effective tick repellent activity of catnip essential oil and the successful synthesis of the inclusion complex, suggesting that ß-CDs are promising carriers to improve catnip oil properties and to expand its use in repellent formulations for tick management.


Assuntos
Portadores de Fármacos/química , Repelentes de Insetos/farmacologia , Nepeta/química , Óleos Voláteis/farmacologia , Óleos de Plantas/farmacologia , Carrapatos/efeitos dos fármacos , beta-Ciclodextrinas/química , Animais , Comportamento Animal/efeitos dos fármacos , DEET/farmacologia , Composição de Medicamentos/métodos , Liberação Controlada de Fármacos , Feminino , Masculino
14.
Molecules ; 26(18)2021 Sep 15.
Artigo em Inglês | MEDLINE | ID: mdl-34577074

RESUMO

Nepeta bracteata Benth. is used clinically to treat tracheal inflammation, coughs, asthma, colds, fevers, adverse urination, and other symptoms, along with functions in clearing heat and removing dampness. However, there have been few studies characterizing the material basis of its efficacy. Therefore, the aim of this study was to screen for compounds with anti-inflammatory activities in N. bracteata Benth. Using silica gel, ODS C18, and Sephadex LH-20 column chromatography, as well as semipreparative HPLC, 10 compounds were separated from N. bracteata Benth. extract, including four new diterpenoids (1-4), one amide alkaloid (5), and five known diterpenoids (6-10). The structures of all the isolates were elucidated by HR-ESI-MS, NMR, and CD analyses. Using lipopolysaccharide (LPS)-stimulated RAW 264.7 cells, we investigated the anti-inflammatory activities of compounds 1-10. It is worth noting that all were able to inhibit nitric oxide (NO) production with IC50 values < 50 µM and little effect on RAW 264.7 macrophage viability. Compounds 2 and 4 displayed remarkable inhibition with IC50 values of 19.2 and 18.8 µM, respectively. Meanwhile, screening on HCT-8 cells demonstrated that compounds 2 and 4 also had moderate cytotoxic activities with IC50 values of 36.3 and 41.4 µM, respectively, which is related to their anti-inflammatory effects.


Assuntos
Abietanos/farmacologia , Anti-Inflamatórios/farmacologia , Nepeta/química , Extratos Vegetais/farmacologia , Abietanos/química , Abietanos/toxicidade , Animais , Anti-Inflamatórios/química , Anti-Inflamatórios/toxicidade , Linhagem Celular Tumoral , Sobrevivência Celular/efeitos dos fármacos , Humanos , Concentração Inibidora 50 , Lipopolissacarídeos/toxicidade , Camundongos , Óxido Nítrico/metabolismo , Extratos Vegetais/química , Extratos Vegetais/toxicidade , Células RAW 264.7
15.
Molecules ; 25(17)2020 Aug 20.
Artigo em Inglês | MEDLINE | ID: mdl-32825223

RESUMO

Nepeta curviflora Boiss. (Syrian catnip) is native to the Middle East. This medicinal plant is commonly used against nervous disorders, rheumatic pains, and high blood pressure. Herbal infusions prepared from various Nepeta spp. are extensively consumed as functional food. However, limited information has been known about the phenolic constituents of Syrian catnip. In this study, two acylated flavone 7-O-glucuronides, apigenin 7-O-(2″-O-(2‴-(E-caffeoyl)-ß-glucuronopyranosyl)-ß-glucuronopyranoside) (1) and luteolin 7-O-(2″-O-(2‴-(E-caffeoyl)-ß-glucuronopyranosyl)-ß-glucuronopyranoside) (2), along with the known phenolic compounds rosmarinic acid, caffeic acid, apigenin, and apigenin 7-O-ß-glucopyranoside were isolated from the aerial parts of N. curviflora. The characterizations of these compounds were based on high-resolution mass spectrometry, UV, and extensive use of multidimensional NMR spectroscopy. The new compounds (1 and 2) were identified in the unmodified state and as dimethylesters.


Assuntos
Flavonoides , Glucuronídeos , Nepeta/química , Componentes Aéreos da Planta/química , Flavonoides/química , Flavonoides/isolamento & purificação , Glucuronídeos/química , Glucuronídeos/isolamento & purificação
16.
J Chem Ecol ; 45(7): 626-637, 2019 Jul.
Artigo em Inglês | MEDLINE | ID: mdl-31257561

RESUMO

Since the first reports of damage by Drosophila suzukii, the spotted-wing Drosophila (SWD), over a decade ago in Europe, widespread efforts have been made to understand both the ecology and the evolution of this insect pest, especially due to its phylogenetic proximity to one of the original model organisms, D. melanogaster. In addition, researchers have sought to find economically viable solutions for the monitoring and management of this agricultural pest, which has now swept across much of Europe, North America and Asia. In a new direction of study, we present an investigation of plant-based chemistry, where we search for natural compounds that are structurally similar to known olfactory cues from parasitoid wasps that in turn are well-described ovipositional avoidance cues for many Drosophila species. Here we test 11 plant species across two plant genera, Nepeta and Actinidia, and while we find iridoid compounds in both, only those odorants from Actinidia are noted to be detected by the insect antenna, and in addition, found to be behaviorally active. Moreover, the Actinidia extracts resulted in oviposition avoidance when they were added to fruit samples in the laboratory. Thus we propose the possible efficacy of these plants or their extracted chemistry as a novel means for establishing a cost-effective integrated pest management strategy towards the control of this pest fly.


Assuntos
Actinidia/química , Produtos Biológicos/química , Drosophila/fisiologia , Controle de Insetos/métodos , Nepeta/química , Actinidia/metabolismo , Actinidia/parasitologia , Animais , Produtos Biológicos/farmacologia , Produtos Agrícolas , Drosophila/efeitos dos fármacos , Drosophila/crescimento & desenvolvimento , Cromatografia Gasosa-Espectrometria de Massas , Nepeta/metabolismo , Nepeta/parasitologia , Oviposição/efeitos dos fármacos , Folhas de Planta/química , Folhas de Planta/metabolismo , Folhas de Planta/parasitologia
17.
Molecules ; 24(9)2019 Apr 30.
Artigo em Inglês | MEDLINE | ID: mdl-31052163

RESUMO

The n-butanolic extract, from an Iranian specimen of Nepeta asterotricha Rech. f. (NABE), displayed anti-inflammatory effects on lipopolysaccharide (LPS)-stimulated J774A.1 macrophages, which reduced nitrites and cytokines production. Bioassay guided fractionation of the extract led to the isolation of four iridoid glycosides, including a new one known as nepetamoside (1), one hexenyl-diglycoside, and some polyphenol and flavonoid components. None of the isolated iridoid components displayed significant effects on nitrites formation in an in vitro LPS-induced model of inflammation, thus suggesting that the plant anti-inflammatory effect is probably due to a synergistic action among its constituents.


Assuntos
Nepeta/química , Compostos Fitoquímicos/química , Compostos Fitoquímicos/farmacologia , Extratos Vegetais/química , Extratos Vegetais/farmacologia , Animais , Sobrevivência Celular/efeitos dos fármacos , Fracionamento Químico , Citocinas/metabolismo , Macrófagos/efeitos dos fármacos , Macrófagos/metabolismo , Estrutura Molecular , Compostos Fitoquímicos/isolamento & purificação , Extratos Vegetais/isolamento & purificação , Análise Espectral
18.
Phytother Res ; 32(2): 185-198, 2018 Feb.
Artigo em Inglês | MEDLINE | ID: mdl-29044858

RESUMO

Medicinal plants have always had great value for the human population due to their valuable constituents and potential bioactivities. The objective of this review is to present an updated overview of an important medicinal plant genus Nepeta L., from the family Lamiaceae, revealing its traditional utilization, biological activity, phytoconstituents, and mechanisms of action. For this purpose, a literature survey was carried out by using SciFinder, ScienceDirect, Scopus, PubMed, and Web of Science followed by a revision of the bibliographies of the related articles. We have described and analyzed the role of plants in drug discovery and the importance of Nepeta species. Information on the utilization purposes of Nepeta species in folk medicine has been emphasized, and scientific studies on the biological effects and secondary metabolites are addressed. Nepeta species are characterized by terpenoid-type compounds and phenolic constituents, which exert several activities such as an antimicrobial, repellent against major pathogen vector mosquitoes, insecticide, larvicide against Anopheles stephensi, cytotoxic anticarcinogen, antioxidant, anticonvulsant, analgesic, anti-inflammatory agent, and antidepressant, revealing its importance in medicinal and agricultural fields. On the basis of numerous studies, the Nepeta genus demonstrates remarkable therapeutic effects against various diseases. However, clinical studies are warranted to confirm preclinical findings.


Assuntos
Medicina Tradicional/métodos , Nepeta/química , Fitoterapia/métodos , Plantas Medicinais/efeitos dos fármacos , Humanos
19.
BMC Vet Res ; 13(1): 70, 2017 Mar 16.
Artigo em Inglês | MEDLINE | ID: mdl-28302120

RESUMO

BACKGROUND: Olfactory stimulation is an often overlooked method of environmental enrichment for cats in captivity. The best known example of olfactory enrichment is the use of catnip, a plant that can cause an apparently euphoric reaction in domestic cats and most of the Pantherinae. It has long been known that some domestic cats and most tigers do not respond to catnip. Although many anecdotes exist of other plants with similar effects, data are lacking about the number of cats that respond to these plants, and if cats that do not respond to catnip respond to any of them. Furthermore, much is still unknown about which chemicals in these plants cause this response. METHODS: We tested catnip, silver vine, Tatarian honeysuckle and valerian root on 100 domestic cats and observed their response. Each cat was offered all four plant materials and a control, multiple times. Catnip and silver vine also were offered to nine tigers. The plant materials were analyzed by gas chromatography coupled with mass spectrometry to quantify concentrations of compounds believed to exert stimulating effects on cats. RESULTS: Nearly all domestic cats responded positively to olfactory enrichment. In agreement with previous studies, one out of every three cats did not respond to catnip. Almost 80% of the domestic cats responded to silver vine and about 50% to Tatarian honeysuckle and valerian root. Although cats predominantly responded to fruit galls of the silver vine plant, some also responded positively to its wood. Of the cats that did not respond to catnip, almost 75% did respond to silver vine and about one out of three to Tatarian honeysuckle. Unlike domestic cats, tigers were either not interested in silver vine or responded disapprovingly. The amount of nepetalactone was highest in catnip and only present at marginal levels in the other plants. Silver vine contained the highest concentrations of all other compounds tested. CONCLUSIONS: Olfactory enrichment for cats may have great potential. Silver vine powder from dried fruit galls and catnip were most popular among domestic cats. Silver vine and Tatarian honeysuckle appear to be good alternatives to catnip for domestic cats that do not respond to catnip.


Assuntos
Actinidia , Felidae/fisiologia , Lonicera , Nepeta , Valeriana , Actinidia/química , Fatores Etários , Animais , Comportamento Animal , Gatos , Monoterpenos Ciclopentânicos , Ciclopentanos , Feminino , Lonicera/química , Lynx/fisiologia , Masculino , Nepeta/química , Feromônios , Pironas , Olfato , Tigres , Valeriana/química
20.
Pak J Pharm Sci ; 30(2(Suppl.)): 625-634, 2017 Mar.
Artigo em Inglês | MEDLINE | ID: mdl-28650332

RESUMO

The success of antioxidant therapy in hyperthyroidism implies that disease is mediated by oxidative stress, which is known as one of the causing agents of ageing, degenerative diseases, and cancer. The main objective of our study was to determine possible protective effects of methanolic extract of N. rtanjensis in triiodothyronine (T3)-induced DNA breaks of human lymphocytes under in vitro conditions, based upon plant antioxidant capacity related to its phytochemical profile, mainly its polyphenolic complex. The total phenolic and flavonoid content and the antioxidant activity using in vitro 1,1-dyphenyl-2- picrylhydrazyl reagent (DPPH) was determined in methanolic extracts of plant leaves and flowers. The phenolic compound content of 62.73±1.80mg of GaA/g, exhibited solid antioxidant activity (IC50= 112.59±0.95µg/ml). The antigenotoxic activity of 0.2, 0.5 and 1.0mg/ml N. rtanjensis methanol extracts mixture with 100µM of T3 was studied in human lymphocytes in vitro using the Comet assay. It is supposed that the antigenotoxicity of N. rtanjensis methanol extracts was caused by high presence of chlorogenic acid, rosmarinic acid and rutin, all known as efficient antioxidant bioactive compounds, which were determined by ultrahigh-pressure liquid chromatograph with MS/MS Mass Spectroscopy (UHPLC/-HESI-MS / MS).


Assuntos
Antioxidantes/farmacologia , Dano ao DNA , Linfócitos/efeitos dos fármacos , Nepeta/química , Fenóis/análise , Extratos Vegetais/farmacologia , Ácido Clorogênico/análise , Cinamatos/análise , Depsídeos/análise , Relação Dose-Resposta a Droga , Flavonoides/análise , Flores/química , Humanos , Extratos Vegetais/análise , Folhas de Planta/química , Rutina/análise , Tri-Iodotironina , Ácido Rosmarínico
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