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1.
Nat Prod Res ; 37(8): 1338-1348, 2023 Apr.
Artigo em Inglês | MEDLINE | ID: mdl-34791965

RESUMO

The ethyl acetate and methanol extracts from aerial parts of Tanacetum balsamita yielded a new derivative of 1-acetyl-erivanin, namely 1-acetyl-3-epi-erivanin (17), some known compounds, namely seventeen sesquiterpene lactones, five flavonoids, four coumarins, and a steroid. All extracts displayed antibacterial activity against test microorganisms except for Escherichia coli. The methanol (TBM) extract with an IC50 value of 0.180 mg/mL exhibited good antioxidant activity against DPPH radical while all extracts showed significant anti-inflammatory activity against lipoxygenase enzyme. The ethyl acetate (TBEA) extract presented moderate activity against α-glucosidase enzyme with an IC50 of 0.808 mg/mL. The highest total phenol content with 91.050 mg GAE/g extract was found in TBM. It is the first study on the isolation of secondary metabolites as well as 5-lipoxygenase and α-glucosidase inhibitory activity of T. balsamita growing in Turkey.


Assuntos
Sesquiterpenos , Tanacetum , Metanol/química , Tanacetum/química , alfa-Glucosidases/química , Extratos Vegetais/farmacologia , Extratos Vegetais/química , Antioxidantes/química , Sesquiterpenos/farmacologia , Flavonoides/química
2.
Nat Prod Res ; 36(20): 5347-5352, 2022 Oct.
Artigo em Inglês | MEDLINE | ID: mdl-33977845

RESUMO

Tanacetum fisherae Aitch. & Hemsl. is an endemic plant growing wild in some brackish regions of Iran. Since there are not enough reports concerning the quantitative and qualitative analyses of its essential oil, it was decided to characterise the respective water-distilled oils obtained from the flowers and leaves of this medicinal plant. Characterisation of the corresponding essential oil profiles revealed that in both of the analysed oils, oxygenated monoterpenes constituted most of the chemical profiles. In this sense, the most prevailing natural compounds in the flower oils were cis-p-2-menthen-1-ol (11.2%), trans-p-2-menthen-1-ol (10.7%), trans-piperitol (7.8%), 1,8-cineole (6.1%), cis-piperitol (3.8%), α-terpineol (3.7%) and terpinene-4-ol (2.1%), whereas the main constituent components of the leaves oils were, respectively, 1,8-cineole (16.7%), cis-p-2-menthen-1-ol (14.6%), trans-p-2-menthen-1-ol (10.4%), trans-piperitol (12.8%), α-terpineol (5.4%), cis-piperitol (2.9%), borneol (2.7%), and terpinene-4-ol (2.1%). In addition, the second rank of natural compound constituting groups was due to oxygenated sesquiterpenes, as well.[Formula: see text].


Assuntos
Asteraceae , Óleos Voláteis , Sesquiterpenos , Tanacetum , Monoterpenos Cicloexânicos , Eucaliptol/análise , Flores/química , Cromatografia Gasosa-Espectrometria de Massas , Irã (Geográfico) , Monoterpenos/análise , Óleos Voláteis/química , Folhas de Planta/química , Óleos de Plantas/química , Sesquiterpenos/análise , Tanacetum/química , Água/análise
3.
Molecules ; 26(23)2021 Nov 25.
Artigo em Inglês | MEDLINE | ID: mdl-34885703

RESUMO

Traditionally, arctic Finnish Angelica (Angelica archangelica L.), marsh Labrador tea (Rhododendron tomentosum, syn. Ledum palustre) and common tansy (Tanacetum vulgare) have been used as medicinal herbs in folklore medicine. However, these underutilised plants are a source of, e.g., oil-based compounds, which could benefit many modern applications implemented by the green chemistry extraction methods, as well. We extracted Angelica, marsh Labrador tea and common tansy by non-toxic and recyclable extraction methods, i.e., hydrodistillation and supercritical carbon dioxide (scCO2) extraction; characterised the essential oils (EOs) and scCO2 extracts by combination of gas chromatography and mass spectrometry (GC-MS), and in addition, analysed the antimicrobial properties. As expected for Angelica root and common tansy inflorescence, the scCO2 extraction method produced less amount of volatile compounds compared to hydrodistillation. On the other hand, more coumarins, alkanes, fatty alcohols and fatty acids were obtained. Additionally, sesquiterpenoids palustrol and ledol were predominant compounds in both marsh Labrador tea EO and scCO2 extract. According to our results, however, all the EOs and scCO2 extracts showed broad spectrum of antimicrobial activities against the selected microbes, but the effects were extract-specific. The strongest and broadest antimicrobial activities were performed by marsh Labrador tea scCO2 extract, which showed extremely strong effect on Staphylococcusaureus subsp. aureus and strong effect on Candida albicans.


Assuntos
Angelica archangelica/química , Óleos Voláteis/química , Rhododendron/química , Tanacetum/química , Infecções Bacterianas/tratamento farmacológico , Infecções Bacterianas/microbiologia , Candida albicans/efeitos dos fármacos , Candida albicans/patogenicidade , Dióxido de Carbono/química , Cromatografia Gasosa-Espectrometria de Massas , Óleos Voláteis/farmacologia , Extratos Vegetais/química , Extratos Vegetais/farmacologia , Staphylococcus aureus/efeitos dos fármacos , Staphylococcus aureus/patogenicidade
4.
Food Chem Toxicol ; 153: 112268, 2021 Jul.
Artigo em Inglês | MEDLINE | ID: mdl-34015423

RESUMO

The Tanacetum genus is a big treasure with the presence of biologically-active compounds and members of this genus are widely used for the treatment of several diseases in traditional medicine system. Considering this fact, we aimed to analyze the extracts from Tanacetum vulgare L. in case of chemical profiles and biological effects. Chemical characterization was performed by using UHPLC-HRMS technique and showed the presence of several phytochemical groups (107 compounds were identified, including phenolic acids, flavonoids, terpenoids and fatty acids. Biological abilities were examined by using antioxidant (DPPH, ABTS, FRAP, CUPRAC, metal chelating and phosphomolybdenum assays) and enzyme inhibition (tyrosinase, amylase, glucosidase and cholinesterase) properties. Pharmaco-toxicological investigations were also performed with the aim to identify limits of biocompatibility, anti-oxidant and neuromodulatory effects, in hypothalamic HypoE22 cells. A bioinformatic analysis was also carried to unravel the putative protein-targets for the observed biological effects. Generally, the tested hexane and hydroalcoholic extracts displayed stronger activities in antioxidant and enzyme inhibitory assays, when compared with water. In addition, multivariate analysis was performed to understand the differences in both solvents and plant parts and we clearly observed the separation of these parameters. The extracts (10 µg/mL) also stimulated DAT and inhibited TNFα and BDNF gene expression, in HypoE22 cells. In parallel, the extracts were also able to stimulate norepinephrine release from this cell line. By contrast, in the concentration range 50-100 µg/mL, the extracts reduced the HypoE22 viability, thus demonstrating cytotoxicity at concentrations 5-10 fold higher compared to those effective as neuromodulatory. Our observations manifested that T. vulgare has several beneficial effects and it can be used as a potential natural raw material for designing further health-promoting applications in nutraceutical, cosmeceutical, and pharmaceutical areas.


Assuntos
Antioxidantes/farmacologia , Inibidores Enzimáticos/farmacologia , Compostos Fitoquímicos/farmacologia , Extratos Vegetais/farmacologia , Tanacetum/química , Animais , Antioxidantes/análise , Antioxidantes/química , Antioxidantes/toxicidade , Artemia/efeitos dos fármacos , Linhagem Celular , Inibidores Enzimáticos/análise , Inibidores Enzimáticos/química , Inibidores Enzimáticos/toxicidade , Etanol/química , Flores/química , Hexanos/química , Análise Multivariada , Compostos Fitoquímicos/análise , Compostos Fitoquímicos/química , Compostos Fitoquímicos/toxicidade , Componentes Aéreos da Planta/química , Extratos Vegetais/análise , Extratos Vegetais/química , Extratos Vegetais/toxicidade , Caules de Planta/química , Mapas de Interação de Proteínas , Ratos , Solventes/química , Água/química
5.
Pol J Vet Sci ; 24(1): 159-161, 2021 Mar.
Artigo em Inglês | MEDLINE | ID: mdl-33847089

RESUMO

Ichthyophthiriasis, which is caused by Ichthyophthirius multifiliis (Ich) infections, has a severe impact on productivity in freshwater aquaculture. These infections were previously treated effectively with malachite green, a compound that is now banned on fish farms due to its carcinogenicity. To find efficacious drugs to control Ich, flowers of tansy Tanacetum vulgare were evaluated for their antiprotozoal activity. Tanacetum vulgare extract significantly reduced the survival of Ich trophonts and theronts. In vitro, the extract killed all trophonts at 3200 mg l-1, terminated tomont reproduction at 50 mg l-1, and caused mortality of all theronts at 100 mg l-1. T. vulgare extract may be a new and efficacious drug for the control of Ich.


Assuntos
Antiprotozoários/farmacologia , Cilióforos/efeitos dos fármacos , Extratos Vegetais/farmacologia , Tanacetum/química , Antiprotozoários/química , Extratos Vegetais/química
6.
Bull Entomol Res ; 111(2): 190-199, 2021 Apr.
Artigo em Inglês | MEDLINE | ID: mdl-32778187

RESUMO

The Colorado potato beetle, Leptinotarsa decemlineata (Say), is one of the most destructive pest species to have developed resistance to most chemical insecticides. We determined the composition and evaluated the potential of Tanacetum parthenium L. and Tanacetum vulgare L. (Asteraceae family) essential oil (EO) application as an alternative eco-friendly control strategy against L. decemlineata. We assessed the antifeedant activity for L. decemlineata larvae and adults by estimating the damage to potato leaves treated with three concentrations of EOs dissolved in ethanol (0.125, 0.25 and 0.5%). Results showed that T. parthenium EO was more effective against larvae, and T. vulgare was more effective against adults. In an olfactometer assay, the time required to choose an untreated leaf disc did not depend on the Tanacetum species, or life stage examined. However, the concentration of EO exhibited a significant effect on the behaviour of both developmental stages. At higher EO concentrations, both third instar larvae and adults require less time to choose an untreated leaf disc. Additionally, T. parthenium EO provoked more rapid movement away from the treated leaf disc than T. vulgare, especially at the highest concentration. Successful modification of L. decemlineata behaviour by the two Tanacetum oils suggests that they possess the potential for use in potato protection.


Assuntos
Besouros/efeitos dos fármacos , Extratos Vegetais/farmacologia , Tanacetum parthenium/química , Animais , Comportamento/efeitos dos fármacos , Repelentes de Insetos/farmacologia , Larva/efeitos dos fármacos , Óleos Voláteis/farmacologia , Óleos de Plantas/farmacologia , Tanacetum/química
7.
Vopr Pitan ; 89(6): 14-22, 2020.
Artigo em Russo | MEDLINE | ID: mdl-33476494

RESUMO

Binge eating is repeated episodes of eating large amounts of sweet and fatty food in short periods. Dietary fibers, including pectin, significantly reduce the subjective ratings of hunger, and the amount of food eaten. However, studies showing the effect of dietary fibers on satiety use juices or yoghurts with added dietary fiber, or a kissel-like food. Thus, there is a lack of data on the effect of dietary fibres on binge eating of palatable food. The aim of the study was to assess the effect of tansy pectin on anxiety and the binge eating of palatable food in mice. Material and methods. 64 mice weighing 33.3±0.6 g were divided into two groups. Binge eating was induced in forty mice of the first group by consumption of sunflower halva (SH) in addition to regular chow for 24 h once a week. The total energy intake and separately the consumption of regular chow (RC) and SH were monitored. Tansy pectin in the form of an aqueous solution was administered to the mice using a gastric feeding tube (50 mg/kg body weight) before the last presentation of SH. Blood was obtained by cardiac puncture at the end of the last 24 h SH access period. The concentration of insulin and ghrelin in plasma samples were determined by the enzyme immunoassay. In animals of the second group, 24 hours after the administration of pectin, the level of anxiety and depression of mice was assayed with an open field test, a light-dark box test, an elevated plus-maze test, and a forced swim test. Throughout the study, water was used as a negative control, and imipramine at a dose of 20 mg/kg was used as a positive control. Results. Mice treated with tansy pectin ate 2.6 fold less SH within 3 h and 1.4 fold less within 24 h after oral administration of tansy pectin compared to control (water administration). Consumption of RC did not differ within 3 or 24 h. The total energy intake was 1.9 fold lower within 3 h in mice treated with tansy pectin. Within 24 h after pectin oral administration the total energy intake did not differ from control. Insulin plasma level was 2.5 fold lower and ghrelin plasma concentration was 25% higher in the mice that received pectin compared to control, at the end of the 24 h SH access period. The administration of tansy pectin was found to decrease anxietyrelated behaviour in mice. Its administration significantly increased the time spent in the central sector of the open field apparatus by 87%, the time spent in the light area of the light-dark box by 31%, and the time spent on the open arms of the elevated plus maze by 22% compared with the control. Conclusion. Overall, tansy pectin reduced the binge eating of SH representing highly palatable, sweet, and fatty food. Reduced intake SH lead to a decrease in insulin concentration. Blood level of ghrelin was increased in mice treated with tansy pectin at the end of the sweet and fatty food presentation period. Tansy pectin reduced the level of anxiety in mice.


Assuntos
Ansiedade/fisiopatologia , Bulimia/tratamento farmacológico , Carboidratos da Dieta/farmacologia , Ingestão de Energia/efeitos dos fármacos , Comportamento Alimentar/efeitos dos fármacos , Pectinas/farmacologia , Tanacetum/química , Animais , Ansiedade/tratamento farmacológico , Bulimia/fisiopatologia , Feminino , Masculino , Camundongos , Pectinas/química
8.
Med Sci Monit Basic Res ; 25: 179-186, 2019 Aug 27.
Artigo em Inglês | MEDLINE | ID: mdl-31451678

RESUMO

BACKGROUND With the continued demand for new, effective, and safe endodontic therapies, the aim of this study was assessment of efficiency of the ethyl acetate (EthOAc) extract of Tanacetum vulgare (L.) against Candida albicans. MATERIAL AND METHODS The antifungal effectiveness of the EthOAc extract of T. vulgare was determined using the agar disk diffusion method. The inhibition zones induced by the EthOAc extract were compared after 5 minutes, 60 minutes, and 24 hours to those induced by standard solutions (2% chlorhexidine, saturated calcium hydroxide, and 2% sodium hypochlorite). Statistical analysis of the results was performed using the Kruskal-Wallis test and one-way ANOVA. RESULTS The inhibition zone of chlorhexidine against C. albicans was 30.3-19.3 mm, but in combination with EthOAc extract (100 mg/mL) of T. vulgare, this inhibition was from 32.7-30 mm, indicating that this combination exerted a marked synergistic effect against C. albicans. The inhibition zone of sodium hypochlorite (69.7-65 mm) was higher than the inhibition zone of EthOAc extract and chlorhexidine. The combination of EthOAc extract with sodium hypochlorite resulted in a loss of antifungal activity. Furthermore, the activity of the EthOAc extract against C. albicans was decreased after mixing the extract with dentine at a concentration of 25 mg/50 µL (30.3-20.7 mm). The EthOAc extract did not show a genotoxic effect on lymphocyte cells. CONCLUSIONS The EthOAc extract of T. vulgare may be a useful tool to discover natural bioactive agents that have antifungal activity against C. albicans and could be used as endodontic therapies.


Assuntos
Acetatos/química , Antifúngicos/farmacologia , Candida albicans/efeitos dos fármacos , Extratos Vegetais/farmacologia , Tanacetum/química , Candida albicans/crescimento & desenvolvimento , Dentina/metabolismo , Sinergismo Farmacológico , Humanos , Linfócitos/efeitos dos fármacos , Testes de Sensibilidade Microbiana , Mutagênicos/toxicidade
9.
Planta Med ; 85(5): 424-430, 2019 Mar.
Artigo em Inglês | MEDLINE | ID: mdl-30620946

RESUMO

A phytochemical investigation of extracts from flowers and aerial parts of Tanacetum sonbolii afforded 7 new germacranolide sesquiterpene lactones. The structures were established by a combination of 1- and 2-dimensional nuclear magnetic resonance spectroscopy, high-resolution mass spectrometry, and electronic circular dichroism. The in vitro antiprotozoal activity of the compounds against Trypanosoma brucei rhodesiense and cytotoxicity against rat myoblast (L6) cells were determined. Compounds 4: and 5: showed IC50 values of 5.1 and 10.2 µM and selectivity indices of 3.9 and 4.0, respectively.


Assuntos
Antiprotozoários/farmacologia , Lactonas/farmacologia , Sesquiterpenos de Germacrano/farmacologia , Tanacetum/química , Trypanosoma brucei rhodesiense/efeitos dos fármacos , Animais , Linhagem Celular , Flores/química , Concentração Inibidora 50 , Lactonas/química , Espectroscopia de Ressonância Magnética , Espectrometria de Massas , Mioblastos/efeitos dos fármacos , Componentes Aéreos da Planta/química , Ratos , Sesquiterpenos de Germacrano/química
10.
Nat Prod Res ; 33(9): 1379-1382, 2019 May.
Artigo em Inglês | MEDLINE | ID: mdl-29768020

RESUMO

Chemical diversity of the essential oils of twenty wild populations of Tanacetum polycephalum Sch. Bip., was investigated. The aerial parts of T. polycephalum were collected at full flowering stage from West Azerbaijan Province of Iran, air-dried; hydrodistilled to produce essential oils. The essential oils were analyzed by GC-FID and GC-MS. A total of forty compounds were identified accounting for 96.4-99.9% of the total oils. The most principal compounds were cis-thujone (0-82.3%), trans-thujone (0-79.8%), camphor (1.3-75.0%), 1,8-cineole (4.5-43.3%), borneol (1.0-36.2%) and bornyl acetate (0-26.8%). Hierarchical cluster analysis based on the percentages (>0.5%) of the essential oils components was carried out to determine the chemical diversity among the populations studied. The cluster analysis resulted in the identification of four main chemotypes namely: 'camphor + 1,8-cineole', 'mixed', 'cis-thujone' and 'trans-thujone'.


Assuntos
Óleos Voláteis/química , Óleos de Plantas/química , Tanacetum/química , Monoterpenos Bicíclicos , Canfanos/análise , Cânfora/análise , Análise por Conglomerados , Cromatografia Gasosa-Espectrometria de Massas , Irã (Geográfico) , Monoterpenos/análise , Óleos Voláteis/análise , Componentes Aéreos da Planta/química , Óleos de Plantas/análise
11.
Nat Prod Res ; 33(12): 1787-1790, 2019 Jun.
Artigo em Inglês | MEDLINE | ID: mdl-29405745

RESUMO

The composition and antimicrobial activity of the essential oil of Tanacetum walteri were studied. Aerial flowering parts of plant were collected from North Khorasan Province of Iran and the essential oil was isolated by hydrodistillation and analysed by GC-FID and GC-MS. Antimicrobial activity of the essential oil was determined by disc diffusion and MIC and MBC determination. Thirty-five compounds were identified in the oil of T. walteri accounting for 94.4% of the total oil. Thymol (22.5%), 1,8-cineole (8.2%), umbellulone (6.9%), α-bisabolol (6.3%) and camphor (5.3%) were as the principal constituents. The highest antimicrobial activity of the essential oil was observed against Staphylococcus aureus, Enterococcus faecalis and Klebsiella pneumoniae with MIC value of 0.63 mg/mL. The inhibitory effect of the essential oil of T. walteri could be attributed mainly to the high levels of phenolic compound thymol and oxygenated terpenes in essential oil.


Assuntos
Antibacterianos/farmacologia , Óleos Voláteis/química , Tanacetum/química , Antibacterianos/química , Antifúngicos/química , Antifúngicos/farmacologia , Cânfora/análise , Candida albicans/efeitos dos fármacos , Avaliação Pré-Clínica de Medicamentos/métodos , Enterococcus faecalis/efeitos dos fármacos , Eucaliptol/análise , Cromatografia Gasosa-Espectrometria de Massas , Irã (Geográfico) , Klebsiella pneumoniae/efeitos dos fármacos , Testes de Sensibilidade Microbiana , Sesquiterpenos Monocíclicos , Monoterpenos , Óleos Voláteis/farmacologia , Sesquiterpenos/análise , Staphylococcus aureus/efeitos dos fármacos , Timol/análise
12.
J Chromatogr A ; 1543: 73-80, 2018 Mar 30.
Artigo em Inglês | MEDLINE | ID: mdl-29499840

RESUMO

The knowledge about the activity of polyacetylenes was extended by their new acetylcholinesterase inhibition and antibacterial activity against plant pathogenic bacteria. For this discovery, an utmost streamlined workflow, which we consider to be of high potential in the field of natural product or superfood search was developed. It demonstrates the combined power of biological, biochemical and chemical fingerprints. Bioactive components of tansy (Tanacetum vulgare L.) root extract were profiled and identified by high-performance thin-layer chromatography hyphenated with in situ effect-directed analysis, chemical derivatizations and high-resolution mass spectrometry (HPTLC-UV/Vis/FLD-EDA-HRMS). The effect-directed profiling was performed using four bacterial bioassays including two plant pathogens, an antioxidant assay and acetyl- and butyrylcholinesterase inhibitory assays. The chromatographic, spectral and powerful mass spectrometric study of zones that exerted substantial antibacterial and/or antioxidant and/or acetylcholinesterase inhibitory effects allowed these multi-potent zones to be identified as polyacetylenes. Five polyacetylene compounds were assigned to be 2-non-1-ene-3,5,7-triynyl-3-vinyl-oxirane, 2-(2,4-hexadiynylidene)-3,4-epoxy-1,6-dioxaspiro[4.5]decane, trans- and cis-2-(2,4-hexadiynylidene)-1,6-dioxaspiro[4.5]dec-3-ene and tetradeca-2,4,6-triine-8-en-12-one. This study clearly showed the advantage of the combined use of different ionization sources, i.e. electrospray ionization via an elution-head based interface and also the Direct Analysis in Real Time interface, for HRMS analysis of compounds from the same class with very similar chromatographic behavior and polarity.


Assuntos
Extratos Vegetais/farmacologia , Poli-Inos/farmacologia , Tanacetum/química , Acetilcolinesterase/metabolismo , Antibacterianos/análise , Antioxidantes/farmacologia , Bactérias/efeitos dos fármacos , Inibidores da Colinesterase/isolamento & purificação , Inibidores da Colinesterase/farmacologia , Cromatografia em Camada Fina , Ativação Enzimática/efeitos dos fármacos , Espectrometria de Massas , Extratos Vegetais/química , Raízes de Plantas/química
13.
Pak J Pharm Sci ; 30(6): 2047-2052, 2017 Nov.
Artigo em Inglês | MEDLINE | ID: mdl-29175772

RESUMO

In the present study hydrodistilled essential oil and total methanol extracts of Tanacetum argenteum subsp. flabellifolium have been evaluated for their antimicrobial and antioxidant effects. The chemical composition of the oil and the crude extract were determined by GC/FID, GC/MS and LC/DAD/ESI-MS systems respectively. ß-thujone (47.1%), α-pinene (19.1%) and α-thujone (10.5%) were the main compounds of the essential oil while the 5-Ocaffeoylquinic acid, 1,5-O-dicaffeoylquinic acid, 4,5-O-dicaffeoylquinic acid were identified as flavonoid content of the crude extract. The oil and the methanol extract were demonstrated moderate antimicrobial effects (MIC range; 0,062-2,0 mg/mL) against 21 different pathogenic micro organism. Total phenolic content was determined as 63 mg GAE in g extract and the DPPH radical scavenging effect was determined as 0.16 mg/mL (IC50) and TEAC was determined as 0.21mMol.


Assuntos
Antibacterianos/farmacologia , Antifúngicos/farmacologia , Antioxidantes/farmacologia , Óleos Voláteis/farmacologia , Extratos Vegetais/farmacologia , Óleos de Plantas/farmacologia , Tanacetum , Antibacterianos/isolamento & purificação , Antifúngicos/isolamento & purificação , Antioxidantes/isolamento & purificação , Bactérias/efeitos dos fármacos , Bactérias/crescimento & desenvolvimento , Compostos de Bifenilo/química , Candida/efeitos dos fármacos , Candida/crescimento & desenvolvimento , Cromatografia Líquida , Cromatografia Gasosa-Espectrometria de Massas , Metanol/química , Testes de Sensibilidade Microbiana , Óleos Voláteis/isolamento & purificação , Picratos/química , Extratos Vegetais/isolamento & purificação , Óleos de Plantas/isolamento & purificação , Solventes/química , Espectrometria de Massas por Ionização por Electrospray , Tanacetum/química
14.
Food Chem Toxicol ; 105: 355-369, 2017 Jul.
Artigo em Inglês | MEDLINE | ID: mdl-28472675

RESUMO

Neurotoxic thujones (α- and ß-diastereoisomers) are common constituents of plant essential oils. In this study, we employed a statistical approach to determine the contribution of thujones to the overall observed behaviour-modulating and toxic effects of essential oils (Salvia officinalis L., Artemisia absinthium L., Thuja occidentalis L. and Tanacetum vulgare L.) containing these monoterpene ketones. The data from three in vivo neuropharmacological tests on rats (open field, light-dark, and diazepam-induced sleep), and toxicity assays (brine shrimp, and antimicrobial activity against a panel of microorganisms), together with the data from detailed chemical analyses, were subjected to a multivariate statistical treatment to reveal the possible correlation(s) between the content of essential-oil constituents and the observed effects. The results strongly imply that the toxic and behaviour-modulating activity of the oils (hundreds of constituents) should not be associated exclusively with thujones. The statistical analyses pinpointed to a number of essential-oil constituents other than thujones that demonstrated a clear correlation with either the toxicity, antimicrobial effect or the activity on CNS. Thus, in addition to the thujone content, the amount and toxicity of other constituents should be taken into consideration when making risk assessment and determining the regulatory status of plants in food and medicines.


Assuntos
Artemisia absinthium/química , Óleos Voláteis/toxicidade , Óleos de Plantas/toxicidade , Salvia officinalis/química , Tanacetum/química , Thuja/química , Animais , Artemisia absinthium/toxicidade , Cromatografia Gasosa-Espectrometria de Massas , Masculino , Óleos Voláteis/análise , Óleos de Plantas/análise , Ratos , Ratos Wistar , Salvia officinalis/toxicidade , Tanacetum/toxicidade , Thuja/toxicidade
15.
J Biomater Sci Polym Ed ; 28(3): 293-311, 2017 02.
Artigo em Inglês | MEDLINE | ID: mdl-27929366

RESUMO

Pectin hydrogel particles (PHPs) were prepared by ionotropic gelation of low methylesterified pectin of Tanacetum vulgare L. with calcium ions. Wet PHPs prepared from TVF exhibited a smaller diameter and the lower weight as well as exhibited the best textural properties in terms of hardness and elasticity compared to the PHPs prepared from commercial low methylesterified pectin (CU701) used for comparison. Upon air drying, PHPs prepared from CU701 became small and dense microspheres whereas the dry PHPs prepared from TVF exhibited a drop-like shape. The morphology of dry PHPs determined by scanning electron microscopy revealed that the surface of the TVF beads exhibited fibred structures, whereas the PHPs prepared from CU701 exhibited a smooth surface. The characterization of surface roughness using atomic force microscopy indicated less roughness profile of the PHPs prepared from TVF than CU701. PHPs prepared from TVF were found to possess in vitro resistance to successive incubations in simulated gastric (SGF), intestinal (SIF), and colonic fluid (SCF) at 37 °C for 2, 4 and 18 h, respectively. The PHPs prepared from CU701 swelled in SGF and then lost their spherical shape and were fully disintegrated after 4 h of incubation in SIF. The PHPs from TVF, which were subjected to treatment with SGF, SIF and SCF, were found to adsorb microbial ß-glucuronidase (ßG) in vitro. The data obtained offered the prospect for the development of the PHPs from TVF as sorbents of colonic ßG for the inhibition of re-absorption of estrogens.


Assuntos
Trato Gastrointestinal/metabolismo , Glucuronidase/química , Hidrogéis/química , Pectinas/química , Adsorção , Animais , Materiais Biomiméticos/metabolismo , Camundongos , Células NIH 3T3 , Pectinas/metabolismo , Tanacetum/química
16.
Nat Prod Commun ; 11(5): 579-82, 2016 May.
Artigo em Inglês | MEDLINE | ID: mdl-27319121

RESUMO

Tanacetum huronense (Lake Huron tansy), which is native to the upper Midwest region of USA and Canada, was examined for the presence of anticancer compounds using an in vitro human tumor cell proliferation inhibition assay, with glioblastoma derived cell line U-87 MG. Bioassay-directed purification of the ethyl acetate extract of the aerial portion of this plant identified six active sesquiterpenoid lactones (1-6). Among these, compounds 5 and 6 are new structural analogs. One of the most abundant isolates, tanacin (4), exhibited the greatest inhibition with an IC50 value of 4.5 µg/mL.


Assuntos
Antineoplásicos Fitogênicos/isolamento & purificação , Flavonoides/isolamento & purificação , Glioblastoma/tratamento farmacológico , Fitoterapia , Tanacetum/química , Antineoplásicos Fitogênicos/química , Linhagem Celular Tumoral , Ensaios de Seleção de Medicamentos Antitumorais , Flavonoides/uso terapêutico , Humanos , Lactonas/química , Lactonas/isolamento & purificação , Extratos Vegetais/uso terapêutico , Sesquiterpenos/química , Sesquiterpenos/isolamento & purificação
17.
Nat Prod Res ; 30(20): 2291-8, 2016 Oct.
Artigo em Inglês | MEDLINE | ID: mdl-27018200

RESUMO

The methanolic extract of the Tanacetum gracile afforded the isolation of new sesquiterpene lactone, named gracilone (1) along with four known compounds as 14α-taraxeran-3-one (2), 14α-taraxeran-3-ol (3), apigenin (4) and ß-sitosterol (5). The structure of compound 1 was elucidated on the basis of 1D, 2D NMR and MS spectroscopic analysis. Antimicrobial, antioxidant and anticancer activities of all compounds were evaluated, from which gracilone (1) showed a moderate antibacterial activity, while apigenin (4) showed comparatively more antibacterial activity against both gram-positive and gram-negative tested strains.


Assuntos
Antibacterianos/farmacologia , Antineoplásicos Fitogênicos/farmacologia , Antioxidantes/farmacologia , Lactonas/isolamento & purificação , Sesquiterpenos/isolamento & purificação , Tanacetum/química , Antibacterianos/química , Antineoplásicos Fitogênicos/química , Antioxidantes/química , Antioxidantes/isolamento & purificação , Linhagem Celular Tumoral , Avaliação Pré-Clínica de Medicamentos/métodos , Humanos , Concentração Inibidora 50 , Lactonas/química , Lactonas/farmacologia , Espectroscopia de Ressonância Magnética , Espectrometria de Massas , Estrutura Molecular , Sesquiterpenos/química , Sesquiterpenos/farmacologia , Sitosteroides/isolamento & purificação , Sitosteroides/farmacologia
18.
J Chromatogr A ; 1422: 310-317, 2015 Nov 27.
Artigo em Inglês | MEDLINE | ID: mdl-26499972

RESUMO

Two tansy (Tanacetum vulgare L.) essential oils were obtained by steam distillation of the capitula with subsequent liquid-liquid extraction (oil 1) or with use of an auxiliary phase for the trapping of the steam components (oil 2). These oils were investigated against Bacillus subtilis F1276, B. subtilis spizizenii (DSM 618), Xanthomonas euvesicatoria, Pseudomonas syringae pv. maculicola, Ralstonia solanacearum strain GMI1000 and Aliivibrio fischeri, using the coupling of high-performance thin-layer chromatography to direct bioautography (HPTLC-DB). Using this method with the potato and tomato pathogen R. solanacearum is shown for the first time. Due to the advanced extraction process, oil 2 was richer in components and provided more inhibition zones. The main bioactive components were identified by scanning HPTLC-Direct Analysis in Real Time mass spectrometry (HPTLC-DART-MS) and solid-phase microextraction gas chromatography electron impact MS (SPME-GC-EI-MS) as cis- and trans-chrysanthenol as well as trans-chrysanthenyl acetate. cis-Chrysanthenol exhibited antibacterial effects against all tested bacteria, whereas trans-chrysanthenol inhibited B. subtilis, R. solanacearum and A. fischeri. trans-Chrysanthenyl acetate was an inhibitor for X. euvesicatoria, R. solanacearum and A. fischeri. Although HPTLC-DART-MS resulted in a comparable fragmentation, the ionization characteristics and the recorded mass spectra clearly showed that DART is a softer ionization technique than EI. It is also more affected by ambient conditions and thus prone to additional oxidation products.


Assuntos
Cromatografia em Camada Fina , Espectrometria de Massas , Óleos Voláteis/química , Extratos Vegetais/química , Tanacetum/química , Antibacterianos/análise , Antibacterianos/isolamento & purificação , Antibacterianos/farmacologia , Bactérias/efeitos dos fármacos , Compostos Bicíclicos com Pontes/isolamento & purificação , Compostos Bicíclicos com Pontes/farmacologia , Monoterpenos/isolamento & purificação , Monoterpenos/farmacologia
19.
Cell Physiol Biochem ; 36(3): 988-1003, 2015.
Artigo em Inglês | MEDLINE | ID: mdl-26087920

RESUMO

BACKGROUND: Tanacetum polycephalum L. Schultz-Bip is a member of the Asteraceae family. This study evaluated the chemopreventive effect of a T. polycephalum hexane extract (TPHE) using in in vivo and in vitro models. METHODS AND RESULTS: Five groups of rats: normal control, cancer control, TPHE low dose, TPHE high dose and positive control (tamoxifen) were used for the in vivo study. Histopathological examination showed that TPHE significantly suppressed the carcinogenic effect of LA7 tumour cells. The tumour sections from TPHE-treated rats demonstrated significantly reduced expression of Ki67 and PCNA compared to the cancer control group. Using a bioassay-guided approach, the cytotoxic compound of TPHE was identified as a tricyclic sesquiterpene lactone, namely, 8ß- hydroxyl- 4ß, 15- dihydrozaluzanin C (HDZC). Signs of early and late apoptosis were observed in MCF7 cells treated with HDZC and were attributed to the mitochondrial intrinsic pathway based on the up-regulation of Bax and the down-regulation of Bcl-2. HDZC induced cell cycle arrest in MCF7 cells and increased the expression of p21 and p27 at the mRNA and protein levels. CONCLUSION: This results of this study substantiate the anticancer effect of TPHE and highlight the involvement of HDZC as one of the contributing compounds that act by initiating mitochondrial-mediated apoptosis.


Assuntos
Anticarcinógenos/farmacologia , Antineoplásicos Fitogênicos/farmacologia , Regulação Neoplásica da Expressão Gênica , Lactonas/farmacologia , Neoplasias Mamárias Experimentais/tratamento farmacológico , Sesquiterpenos/farmacologia , Tanacetum/química , Animais , Anticarcinógenos/isolamento & purificação , Antineoplásicos Fitogênicos/isolamento & purificação , Apoptose/efeitos dos fármacos , Inibidor de Quinase Dependente de Ciclina p21/agonistas , Inibidor de Quinase Dependente de Ciclina p21/genética , Inibidor de Quinase Dependente de Ciclina p21/metabolismo , Inibidor de Quinase Dependente de Ciclina p27/agonistas , Inibidor de Quinase Dependente de Ciclina p27/genética , Inibidor de Quinase Dependente de Ciclina p27/metabolismo , Feminino , Humanos , Lactonas/isolamento & purificação , Células MCF-7 , Neoplasias Mamárias Experimentais/genética , Neoplasias Mamárias Experimentais/metabolismo , Neoplasias Mamárias Experimentais/patologia , Potencial da Membrana Mitocondrial/efeitos dos fármacos , Mitocôndrias/efeitos dos fármacos , Mitocôndrias/metabolismo , Transplante de Neoplasias , Extratos Vegetais/química , Proteínas Proto-Oncogênicas c-bcl-2/antagonistas & inibidores , Proteínas Proto-Oncogênicas c-bcl-2/genética , Proteínas Proto-Oncogênicas c-bcl-2/metabolismo , RNA Mensageiro/genética , RNA Mensageiro/metabolismo , Ratos , Ratos Sprague-Dawley , Sesquiterpenos/isolamento & purificação , Transdução de Sinais , Proteína X Associada a bcl-2/agonistas , Proteína X Associada a bcl-2/genética , Proteína X Associada a bcl-2/metabolismo
20.
Nat Prod Commun ; 10(3): 403-5, 2015 Mar.
Artigo em Inglês | MEDLINE | ID: mdl-25924515

RESUMO

Foliar flavonoids of Tanacetum vulgare var. boreale were isolated. Eight flavonoid glycosides, 7-O-glucosides of apigenin, luteolin, scutellarein and 6- hydroxyluteolin, and 7-O-glucuronides of apigenin, luteolin, chrysoeriol and eriodictyol were identified. Moreover, eight flavonoid aglycones, apigenin, luteolin, hispidulin, nepetin, eupatilin, jaceosidin, pectolinarigenin and axillarin were also isolated and identified. The flavonoid composition of two varieties of T. vulgare, i.e. var. boreale and var. vulgare, were compared. All samples of var. boreale and one sample of var. vulgare had the same flavonoid pattern, and could be distinguished from almost all the samples of var. vulgare. Thus, the occurrence of chemotypes, which are characterized by either the presence or absence of scutellarein 7-O-glucoside, eriodictyol 7-O-glucuronide and pectolinarigenin was shown in T. vulgare sensu lato.


Assuntos
Flavonoides/química , Folhas de Planta/química , Tanacetum/química , Demografia
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