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1.
J Cell Mol Med ; 25(24): 11085-11096, 2021 12.
Artículo en Inglés | MEDLINE | ID: mdl-34755444

RESUMEN

Flavonoids are bioactive secondary metabolites of plants, which exert anti-cancer effects. However, metabolism in enterocytes and the liver can influence the biological activity of flavonoids contained in the diet. Therefore, results from in vitro studies on cancer cells from the digestive tract and liver may reflect the real effects in the human body. Previously, we have found that the extract from birch buds exerts antiproliferative activity in a panel of cancer cells. In the present study, the anti-cancer activity of ten flavonoids isolated from the buds of Betula pubescens and Betula pendula was characterized. Among them, santin and cirsimaritin significantly reduced viability, proliferation and clonogenicity of gastric (AGS), colon (DLD-1) and liver (HepG2) cancer cells. Both flavonoids induced apoptosis, accompanied by activation of caspase-3, caspase-7, caspase-8 and caspase-9. Moreover, upregulation of p53 was detected only in wild-type p53 harbouring cells. Together, our results suggest that santin and cirsimaritin exhibit promising anti-cancer activity in cultures of digestive system cancer cells.


Asunto(s)
Antineoplásicos Fitogénicos/farmacología , Apoptosis/efectos de los fármacos , Betula/química , Flavonas/farmacología , Flavonoides/farmacología , Antineoplásicos Fitogénicos/química , Línea Celular Tumoral , Supervivencia Celular/efectos de los fármacos , Neoplasias del Sistema Digestivo , Relación Dosis-Respuesta a Droga , Fibroblastos/efectos de los fármacos , Fibroblastos/metabolismo , Flavonas/química , Flavonoides/química , Humanos , Estructura Molecular , Extractos Vegetales/química , Extractos Vegetales/farmacología
2.
Molecules ; 24(22)2019 Nov 09.
Artículo en Inglés | MEDLINE | ID: mdl-31717557

RESUMEN

The present study investigated the magnitude and mechanism of the cytotoxic effect on selected cancer cell lines of 3,4-seco-urs-4(23),20(30)-dien-3-oic acid (1), 3,4-seco-olean-4(24)-en-19-oxo-3-oic acid (2), and 3,4-seco-urs-4(23),20(30)-dien-19-ol-3-oic acid (3) isolated from downy birch (Betula pubescens) buds by carbon dioxide supercritical fluid extraction and gradient column chromatography. Cell viability in six human cancer lines exposed to these compounds was determined by 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) assay. Apoptosis was quantified by annexin V/propidium iodide staining of gastric cancer AGS and colorectal cancer DLD-1 cells. To evaluate the mechanism of apoptosis, the expression of apoptosis-related proteins was analyzed by Western blot. Compound 1 exhibited non-specific toxicity, while compounds 2 and 3 were specifically toxic to colon and stomach cancer cells. The toxicity of compounds 2 and 3 against these two cell lines was greater than for compound 1. Cleavage of caspase-8, -9, and -3 was found in AGS and DLD-1 cells treated with all three seco-acids, indicating the induction of apoptosis via extrinsic and intrinsic pathways. Therefore, triterpene seco-acids (1-3) decreased cell viability by apoptosis induction. AGS and DLD-1 cells were more susceptible to seco-acids with an oxidized C19 than normal fibroblasts. Hence, it made them a new group of triterpenes with potential anticancer activity.


Asunto(s)
Antineoplásicos Fitogénicos/química , Antineoplásicos Fitogénicos/farmacología , Betula/química , Triterpenos/farmacología , Apoptosis/efectos de los fármacos , Línea Celular Tumoral , Supervivencia Celular/efectos de los fármacos , Neoplasias Colorrectales/tratamiento farmacológico , Humanos , Extractos Vegetales/química , Extractos Vegetales/farmacología , Neoplasias Gástricas/tratamiento farmacológico , Triterpenos/química
3.
Microbiol Res ; 215: 76-88, 2018 Oct.
Artículo en Inglés | MEDLINE | ID: mdl-30172312

RESUMEN

Matricaria is a widespread genus of flowering plants of the family Asteraceae that grow in temperate regions of Europe, Asia, America and Africa. Some of the species are also naturalized in Australia. Some species of this genus such as Chamomiles are recognized medicinal plants and cultivated in several countries for commercial purposes: to obtain its blue essence, as herbal tea, and for pharmaceutical or cosmeceutical uses. The phytochemical composition of Matricaria spp. includes volatile terpenoids (e.g., α-bisabolol, bisabolol oxide A and B, ß-trans-farnesene and chamazulene), sesquiterpene lactones such as matricin, and phenolic compounds (flavonoids, coumarins and phenolic acids). Their essential oil is obtained from the fresh or dried inflorescences by steam distillation, and additionally cohobation of the remaining water. The volatile composition of the essential oil, especially the content of the valuable components α-bisabolol and chamazulene, depends on the plant part, origin and quality of the source, genetic, and environmental factors. Moreover, other parameters, such as season of harvest and methods of extraction, can affect the extraction yield of the essential oils/extracts, their composition and, therefore, their bioactivity. Due to the importance of this genus and particularly M. recutita (M. chamomilla), this review focus on its cultivation, factor affecting essential oils' composition and their role in traditional medicine, as antibacterial agents and finally as food preservatives.


Asunto(s)
Antiinfecciosos/química , Matricaria/química , Aceites Volátiles/química , Fitoquímicos/química , Extractos Vegetales/química , Plantas Medicinales/química , Antiinfecciosos/farmacología , Azulenos/farmacología , Infecciones Bacterianas/tratamiento farmacológico , Cumarinas/metabolismo , Granjas , Flavonoides/química , Alimentos , Industria de Alimentos , Conservantes de Alimentos , Hidroxibenzoatos/química , Lactonas/farmacología , Sesquiterpenos Monocíclicos , Aceites Volátiles/farmacología , Fitoquímicos/farmacología , Extractos Vegetales/farmacología , Aceites de Plantas/química , Estaciones del Año , Sesquiterpenos/farmacología , Sesquiterpenos de Guayano
4.
PLoS One ; 13(8): e0201949, 2018.
Artículo en Inglés | MEDLINE | ID: mdl-30106978

RESUMEN

Birch buds (Gemmae Betulae) are widely used in Russian and Chinese traditional medicine mainly as a diuretic and diaphoretic agent but also as an antiseptic, anti-inflammatory and analgesic. Despite the long history of therapeutic use of birch buds in folk medicine, the existing information on their chemical composition and pharmacological effects is insufficient. This circumstance warrants further study of the chemistry and pharmacology of birch buds. The present study was designed to investigate (a) the chemical composition of buds from two species of white birch and (b) the in vitro cytotoxic effect of extracts from these sources on selected tumour cells. Extracts from Betula pubescens Ehrh. and Betula pendula Roth. buds were obtained using three different methods: carbon dioxide supercritical fluid extraction (SFE), washing of exudate covering whole buds, and extraction of milled buds with diethyl ether. The chemical composition of extracts was investigated by GC-MS. Cytotoxicity was determined by MTT assay, and cell proliferation was determined by [3H]thymidine uptake in cancer cells and normal skin fibroblasts. The GC-MS investigation identified a total of 150 substances of different classes. The chemical composition of B. pubescens and B. pendula buds differed, with bud extracts from the former containing a relatively high quantity of sesquiterpenoids and flavonoids, while the main components of extracts from the latter were triterpenoids. The results of the biological assay indicated that birch bud extracts demonstrated time- and concentration-dependent and differential cytotoxicity. The highest cytotoxic activity demonstrated bud exudates and SFE extracts obtained from both Betula species. The rich chemical composition of birch buds suggests the possibility of a wider spectrum of biological activity than previously thought. Birch bud extracts could be a promising source of compounds with cytotoxic activity against various cancers.


Asunto(s)
Antineoplásicos Fitogénicos/química , Antineoplásicos Fitogénicos/farmacología , Betula/química , Extractos Vegetales/química , Extractos Vegetales/farmacología , Línea Celular Tumoral , Proliferación Celular/efectos de los fármacos , Supervivencia Celular/efectos de los fármacos , Humanos , Concentración 50 Inhibidora , Neoplasias , Fitoquímicos/química
5.
Am J Chin Med ; 46(2): 319-337, 2018.
Artículo en Inglés | MEDLINE | ID: mdl-29433387

RESUMEN

Flavonoid compound scutellarin (Scu) is quite frequently met in the plant kingdom, particularly in the genus Scutellaria (Lamiaceae) and Erigeron (Asteraceae). The extract of the herb of Erigeron breviscapus, containing this component in high amount, has been used for many years in traditional Chinese medicine. In recent years, studies have made great progress on the usefulness of Scu for treating various diseases by testing its mechanism of action. They support the traditional use of Scu rich plant in heart and cerebral ischemia. Scu can potentially be applied in Alzheimer's disease, Helicobacter pylori infection, vascular complications of diabetes and as an inhibitor of certain carcinomas. Various methods were designed to improve its isolation from plant material, solubility, absorption and bioavailability. On the basis of recent studies, it is suggested that Scu could be a promising candidate for new natural drug and deserves particular attention in further research and development.


Asunto(s)
Apigenina/aislamiento & purificación , Apigenina/farmacología , Apigenina/uso terapéutico , Erigeron/química , Glucuronatos/aislamiento & purificación , Glucuronatos/farmacología , Glucuronatos/uso terapéutico , Fitoterapia , Scutellaria/química , Enfermedad de Alzheimer/tratamiento farmacológico , Apigenina/química , Isquemia Encefálica/tratamiento farmacológico , Bases de Datos Bibliográficas , Angiopatías Diabéticas/tratamiento farmacológico , Gastritis/tratamiento farmacológico , Gastritis/microbiología , Glucuronatos/química , Infecciones por Helicobacter , Helicobacter pylori , Humanos , Isquemia Miocárdica/tratamiento farmacológico
6.
J Chromatogr A ; 1521: 161-166, 2017 Oct 27.
Artículo en Inglés | MEDLINE | ID: mdl-28941807

RESUMEN

The article presents for the first time the linear temperature programmed retention indices on a column with stationary phases of 5% phenylpolydimethyl silicone and the mass spectra of trimethylsilyl (TMS) derivatives of 71 glycosides (both commercial preparations and compounds extracted from plant tissues) which were not characterized earlier by these parameters. Converted to their TMS derivatives, the glycosides were thermally stable: they exhibited single peaks on their chromatograms without products of thermal decomposition. Therefore this work demonstrates the suitability of high resolution-high temperature gas chromatography (HR-HT/GC) to analyse different groups of glycosides including compounds with disaccharide moieties without the necessity of their hydrolyses. Since a limited number of commercial and plant-isolated glycosides were available, an attempt was made to assess their retention indices using the known "structure-retention relationships" approach. It was demonstrated that the retention indices of silanised glycosides and their aglycones were characterized by a linear dependence.


Asunto(s)
Técnicas de Química Analítica/métodos , Cromatografía de Gases y Espectrometría de Masas , Glicósidos/análisis , Hidrólisis , Extractos Vegetales/química , Temperatura , Compuestos de Trimetilsililo/análisis
7.
J Sep Sci ; 40(19): 3830-3838, 2017 Oct.
Artículo en Inglés | MEDLINE | ID: mdl-28779529

RESUMEN

Novel methods for the determination of polyphenolic antioxidants present in extracts from inflorescences of Cirsium vulgare (Savi) Ten. based on ultra-high performance liquid chromatography with photodiode array and chemiluminescence detection have been developed. Under the optimized conditions of chromatographic separation the analytical characteristic of the method was performed. The proposed method was successfully applied to the determination of ten polyphenols present in inflorescences of Cirsium vulgare. A comparison of the contents of analytes in extracts prepared by using various extraction media (methanol, ethanol, 70% methanol, 70% ethanol, and water) was carried out for the first time. For the postcolumn detection of scavenging activity of polyphenolic antioxidants against reactive oxygen species (H2 O2 , • OH, O2• - ) three systems based on chemiluminescence of luminol were used. A review of the current scientific literature shows that this is the first report on the application of luminol-based postcolumn detection for the on-line investigation of • OH scavenging activity. The main compound determined in extracts from inflorescences of Cirsium vulgare was apigenin 7-O-glucuronide, whereas the highest antioxidant activity was observed for chlorogenic acid, luteolin 7-O-glucoside, and apigenin.


Asunto(s)
Antioxidantes/aislamiento & purificación , Cirsium/química , Polifenoles/aislamiento & purificación , Cromatografía Líquida de Alta Presión , Inflorescencia/química , Extractos Vegetales/química
8.
Nat Prod Commun ; 12(4): 519-522, 2017 Apr.
Artículo en Inglés | MEDLINE | ID: mdl-30520586

RESUMEN

The chemical composition of Cirsium vulgare flower heads was examined. Petrol and chloroform extracts of this plant material were analyzed by GC-MS for the presence of fatty acids, phytosterols, and triterpenes. Diethyl ether, ethyl acetate, and butanol fractions of the methanolic extract were subjected to multistep - chromatographic separations, and as a result, fourteen flavonoids were obtained (1-14). All compounds were isolated from this morphological part for the first time and eleven from the plant. Among the identified components were four aglycones, eight glycosides, and two glycoside esters, derivatives of apigenin, luteolin, kaemferol, and quercetin. One of them was a rarely occurring compound apigenin 7-0-p-(6"-butyl)-glucuronide) (14). Total flavonoid content and antioxidant activity were determined in the various fractions of methanolic extract.


Asunto(s)
Antioxidantes/química , Cirsium/química , Extractos Vegetales/química , Antioxidantes/aislamiento & purificación , Inflorescencia/química , Estructura Molecular , Extractos Vegetales/aislamiento & purificación
9.
Biomed Res Int ; 2017: 9153403, 2017.
Artículo en Inglés | MEDLINE | ID: mdl-29441354

RESUMEN

Many studies have shown that naturally occurring compounds may support prevention and treatment of various diseases, including cancer. Pharmacological investigations revealed a wide spectrum of Nigella sativa biological activities. Combining natural compounds together with synthetic drugs may increase the anticancer activity and limit severe side effects of such a treatment and may be an alternative to monotherapy. The aim of the study was to evaluate the cytotoxic and proapoptotic effects of a novel octahydropyrazino[2,1-a:5,4-a']diisoquinoline derivative and its effect in combination with Nigella sativa seed oil or extract in human gastric cancer cells (AGS). Etoposide was used as a reference. Our studies proved that combination strategy based on novel octahydropyrazino[2,1-a:5,4-a']diisoquinoline derivative (OM-90) with Nigella sativa seed oil or extract represents the strongest efficacy in AGS cancer cells as compared to monotherapy and combined treatment with Nigella sativa seed oil or extract together with etoposide. Such a combination also leads to the activation of mitochondrial pathway, which plays a significant role in molecular mechanism of induction of apoptosis by these compounds.


Asunto(s)
Nigella sativa , Extractos Vegetales/farmacología , Quinolinas/farmacología , Neoplasias Gástricas/tratamiento farmacológico , Apoptosis , Humanos , Neoplasias , Neoplasias Gástricas/patología , Células Tumorales Cultivadas
10.
Phytochem Anal ; 27(5): 277-83, 2016 Sep.
Artículo en Inglés | MEDLINE | ID: mdl-27438906

RESUMEN

INTRODUCTION: The quality of herbs is directly related to the presence of polyphenolic antioxidants. This is the first report on the quantification of individual polyphenolic constituents of Erigeron acris L. OBJECTIVE: To develop a new method using ultra-high performance liquid chromatography with photodiode array and chemiluminescence (UHPLC-PDA-CL) detection for the separation and determination of polyphenols in Erigeron acris extracts. METHODOLOGY: The methanolic extracts from leaves and inflorescences of Erigeron acris were prepared by ultrasound assisted extraction. The chromatographic separation was performed on C18 column packed with 1.7-µm particles. The post-column CL detection was based on the enhancing effect of polyphenols on the CL generated in manganese(IV)-hexametaphosphate-formaldehyde system. RESULTS: The UHPLC method allowed to separate polyphenols in a short running time (13 min), which was three times shorter compared with traditional HPLC. The CL detection was characterised by 6-48 times higher sensitivity and up to three times lower detection limits compared to PDA detection. Qualitative and quantitative differences were observed in polyphenolic composition of Erigeron acris extracts. The main components of leaves were scutellarin and chlorogenic acid, whereas in inflorescences quercetin 3-O-glucoside was predominant. CONCLUSION: Coupling of UHPLC with CL detection has been developed for the first time. This advanced chromatographic technique coupled with sensitive CL detection is a powerful approach for the investigation of polyphenolic profiles in natural products. The shorter analysis time and diminished waste generation makes the UHPLC method more environmentally friendly and more cost-effective in comparison with conventional HPLC. Copyright © 2016 John Wiley & Sons, Ltd.


Asunto(s)
Antioxidantes/análisis , Cromatografía Líquida de Alta Presión/métodos , Erigeron/química , Extractos Vegetales/farmacología , Polifenoles/análisis , Luminiscencia
11.
Nat Prod Res ; 30(4): 373-85, 2016.
Artículo en Inglés | MEDLINE | ID: mdl-25813519

RESUMEN

Viscum album L., the European mistletoe, is a common species from the Viscaceae family. This evergreen hemiparasitic shrub grows on various trees and contains diverse, biologically active substances. Its chemical composition may vary depending on the time of harvest, species of the host tree and the manufacturing process. Among well-described and most active phytochemicals identified in V. album are lectins and viscotoxins, which play substantial role in cancer treatment because of their apoptotic and cytotoxic effects. Another group of compounds found in mistletoe are phenolic acids, phenylpropanoids and flavonoids with antioxidant and anti-inflammatory activities, which decrease blood pressure. Other mistletoe components include, among others, triterpenes with cytotoxic and apoptotic properties, and phytosterols, oligo- and polysaccharides. Extracts from the plant, especially aqueous, are applied in traditional and official medicine, among others in treating hypertension or arthritis. Potentially, it can also be used as a hepatoprotective or a sedative drug.


Asunto(s)
Extractos Vegetales/farmacología , Extractos Vegetales/uso terapéutico , Viscum album/química , Animales , Antineoplásicos Fitogénicos/farmacología , Antineoplásicos Fitogénicos/uso terapéutico , Antioxidantes , Humanos
12.
Nat Prod Res ; 30(6): 665-71, 2016.
Artículo en Inglés | MEDLINE | ID: mdl-25982243

RESUMEN

The effects of polyolefinic compound from roots of Cirsium palustre, (Z)-8,9-epoxyheptadeca-1,11,14-triene (EHT) on collagen biosynthesis, prolidase activity, expression of insulin-like growth factor receptor (IGF-IR), ß1 integrin, MAP kinases (pERK1/2), the transcription factors such as nuclear factor kappa B (NF-κB) and hypoxia-inducible factor-1α (HIF-1α) were evaluated in human dermal fibroblasts treated with micromolar concentrations (40-200 µM) for 24 h. It was found that EHT-dependent inhibition of collagen biosynthesis was accompanied by parallel inhibition in prolidase activity. Since IGF-I is the most potent regulator of both processes and prolidase is regulated by ß1 integrin signalling, the effect of EHT on IGF-IR and ß1 integrin receptor expressions were evaluated. Exposure of the cells to EHT contributed to distinct increase in IGF-IR and slight increase in ß1 integrin receptor expressions. It was accompanied by decrease in expression of pERK1/2, HIF-1α and NF-κB. EHT-dependent inhibition of collagen biosynthesis results from inhibition of prolidase activity, the enzyme involved in collagen biosynthesis.


Asunto(s)
Colágeno/biosíntesis , Dipeptidasas/metabolismo , Fibroblastos/efectos de los fármacos , Polienos/farmacología , Alquenos/farmacología , Células Cultivadas , Cirsium/química , Compuestos Epoxi/farmacología , Quinasas MAP Reguladas por Señal Extracelular/metabolismo , Fibroblastos/enzimología , Humanos , Subunidad alfa del Factor 1 Inducible por Hipoxia/metabolismo , Factor I del Crecimiento Similar a la Insulina/metabolismo , Integrina beta1/metabolismo , Estructura Molecular , FN-kappa B/metabolismo , Aceites Volátiles/química , Aceites de Plantas/química , Raíces de Plantas/química , Receptores de Somatomedina/metabolismo
13.
Talanta ; 133: 38-44, 2015 Feb.
Artículo en Inglés | MEDLINE | ID: mdl-25435224

RESUMEN

The first method for the simultaneous determination of polyphenolic antioxidants in extracts from leaves of Cirsium palustre based on high performance liquid chromatography combined with flow injection chemiluminescence detection (HPLC-FI-CL) has been developed. The extracts were prepared by using methanol as extraction medium and two types of extraction methods (reflux and ultrasound assisted extraction). The post-column CL determination of polyphenols was based on their enhancing effect on the chemiluminescence intensity generated in manganese(IV)-hexametaphosphate-formaldehyde system in a phosphoric acid medium. Main antioxidants determined in C. palustre leaves were eriodictyol-7-O-glucoside, luteolin-7-O-glucoside and 6-hydroxyluteolin-7-O-glucoside belonging to flavonoids, and chlorogenic acid belonging to phenolic acids. Chromatographic separation was carried out on a C18 column with gradient elution by using a mobile phase containing 0.25% (v/v) phosphoric acid in water (solvent A) and 100% methanol (solvent B). Under the optimized conditions of chromatographic separation and CL detection the validation of the method was performed. The calibration curves showed good linearity in the concentration range from 0.5 to 40 µg mL(-1). The HPLC-FI-CL method was successfully applied to the determination of four polyphenolic compounds in methanolic extracts from leaves of C. palustre. The accuracy of the developed method was confirmed by the comparison of the results with those obtained by an HPLC-PDA method. The relative error of determination does not exceed 6.1%. However, the HPLC-FI-CL method is characterized by 40-65 times higher sensitivity compared to the HPLC-PDA method.


Asunto(s)
Cromatografía Líquida de Alta Presión/instrumentación , Cirsium/química , Extractos Vegetales/química , Polifenoles/análisis , Antioxidantes/análisis , Diseño de Equipo , Análisis de Inyección de Flujo/instrumentación , Límite de Detección , Luminiscencia , Mediciones Luminiscentes/instrumentación , Hojas de la Planta/química
14.
Phytother Res ; 28(9): 1399-405, 2014 Sep.
Artículo en Inglés | MEDLINE | ID: mdl-24643916

RESUMEN

Ten flavonoids belonging to the subclasses of flavones, flavanones and aurones were isolated from methanolic extract of Cirsium palustre leaves after multistep chromatographic separation. Their structures were elucidated with spectroscopic methods. All compounds, except for luteolin 7-O-glucoside, were isolated for the first time. Four compounds-eriodictyol 7-O-glucoside (6), 6-hydroxyluteolin 7-O-glucoside (11), scutellarein 7-O-glucoside (12) and pedalitin (14)-were tested for their effect on collagen expression in normal human dermal fibroblasts. Among them, compound 11 at 40 µM and compound 14, at all concentrations used (1, 20, 40 µM), significantly enhanced the level of total collagen secreted into the medium. Furthermore, compound 11 significantly stimulated type I collagen expression, whereas compound 14 activated type I and III collagen expression at the mRNA level, depending on concentration. MMP-2 activity was inhibited by all study compounds, with the greatest effect recorded with compound 14 at 20 µM. The lack of effect on collagen content in the medium of compound 6- and compound 12-treated cells, besides an increase in COL1A1 and COL1A2 expression, might be caused by diminished expression of HSP47 gene, resulting in decreased procollagen secretion. Future study of compounds 11 and 14 for their potential therapeutic use in conditions connected with collagen biosynthesis deficiency is required.


Asunto(s)
Cirsium/química , Colágeno/biosíntesis , Fibroblastos/efectos de los fármacos , Flavonoides/farmacología , Extractos Vegetales/farmacología , Fibroblastos/metabolismo , Humanos , Metaloproteinasa 2 de la Matriz/metabolismo , Extractos Vegetales/química , Hojas de la Planta/química , Piel/citología
15.
Food Chem ; 152: 155-61, 2014.
Artículo en Inglés | MEDLINE | ID: mdl-24444920

RESUMEN

It was found that weak chemiluminescence of manganese(IV)-hexametaphosphate-formaldehyde system was greatly enhanced by plant polyphenolic compounds. Based on this finding, a new flow injection chemiluminescence method (FI-CL) was developed for the determination of the total content of polyphenols in plant extracts. The calibration graph obtained for standard solutions of 6-hydroxyluteolin 7-O-glucoside (6OHLG) was linear in the range 0.001-0.8 µg mL(-1). The method was simple, rapid (203 samples h(-1)) and sensitive with a detection limit of 0.25 ng mL(-1). The FI-CL method was successfully applied to the determination of the total polyphenols content (as 6OHLG equivalents) in methanolic, ethyl acetate and aqueous extracts from leaves of Cirsium palustre (L.). Two types of solvent extraction methods (reflux and ultrasound assisted extraction) were used and compared in terms of extraction efficiency. A positive, significant linear correlation between the results obtained by FI-CL method and spectrophotometric methods was observed.


Asunto(s)
Cirsium/química , Mediciones Luminiscentes/métodos , Extractos Vegetales/análisis , Hojas de la Planta/química , Polifenoles/análisis , Manganeso/química
16.
Talanta ; 96: 216-22, 2012 Jul 15.
Artículo en Inglés | MEDLINE | ID: mdl-22817953

RESUMEN

The determination of the sum of flavonoid compounds in extracts from inflorescences (expressed as mgL(-1) of apigenin) and leaves (expressed as mgL(-1) of linarin) of Cirsium oleraceum and Cirsium rivulare species by flow injection system with chemiluminescence detection (FI-CL) has been carried out. The method is based on the strong enhancement by polyphenols occurring in both plants of the CL signal generated by the reaction of cerium(IV) with rhodamine 6G in a sulfuric acid medium. Under the optimized conditions, the linear working ranges of 0.1-10 and 2.5-50µmolL(-1) were obtained for apigenin and linarin, respectively. The developed method is simple, sensitive with the detection limits of 38nmolL(-1) (apigenin) and 840nmolL(-1) (linarin) and offers high sample throughput (up to 300 samples per hour). The relative standard deviation was 0.62% and 3.75% for 10 measurements of 5µmolL(-1) apigenin and linarin, respectively. The proposed method has been successfully applied to determine the flavonoids/antioxidant levels in aqueous and methanolic extracts from inflorescences and leaves of C. oleraceum and C. rivulare. A possible mechanism of the enhancement of cerium(IV)-rhodamine 6G CL system by polyphenols was briefly discussed. For comparative studies, the antioxidant activity of C. oleraceum and C. rivulare extracts was also evaluated by spectrophotometric 1,1-diphenyl-2-picryl-hydrazyl (DPPH) radical scavenging method.


Asunto(s)
Antioxidantes/análisis , Cerio/química , Cirsium/química , Flavonoides/análisis , Mediciones Luminiscentes/métodos , Extractos Vegetales/química , Rodaminas/química , Antioxidantes/química , Antioxidantes/aislamiento & purificación , Compuestos de Bifenilo/química , Flavonoides/química , Flavonoides/aislamiento & purificación , Análisis de Inyección de Flujo , Mediciones Luminiscentes/instrumentación , Metanol/química , Picratos/química , Hojas de la Planta/química , Ácidos Sulfúricos/química , Ultrasonido
17.
Nat Prod Commun ; 7(2): 269-72, 2012 Feb.
Artículo en Inglés | MEDLINE | ID: mdl-22474978

RESUMEN

The composition of the essential oils of Cirsium palustre and C. rivulare and their antiproliferative activity against breast adenocarcinoma cells (MCF-7 and MDA-MBA-231) were investigated. The essential oils obtained by hydro-distillation from the roots (yield 0.2 and 0.1% v/w, respectively), leaves and inflorescences (yield below 0.01%), were analyzed by gas chromatography coupled with mass spectrometry (GC-MS). The composition of the essential oils in the respective organs of each plant differed considerably. On the other hand, similarities were observed in the composition of root and leaf oils. In C. palustre and C. rivulare root oil, 50 and 39 constituents were identified, accounting for 95.3% and 92.4% of the total content. The main components were aplotaxene and its derivatives, representing 78.6% and 46.6% of the total content. In leaf oils of both species, 59 and 49 compounds, respectively, were identified, representing 67.4% and 78.3% of the total content. The major constituents were beta-damascenone (4.1% and 13.4%, respectively) and beta-ionone (6.7% and 5.3%, respectively). Short-chain saturated and unsaturated aliphatic alcohols and aldehydes constituted another important group of compounds (17.7% and 9.0%, respectively). The essential oils of the roots have moderate anti-proliferative activity, with IC50 values ranging from 110 to 140 microg/mL. These concentrations were below the level able to inhibit the proliferation of healthy cells.


Asunto(s)
Antineoplásicos Fitogénicos/farmacología , Cirsium/química , Aceites Volátiles/farmacología , Aceites de Plantas/farmacología , Adenocarcinoma/tratamiento farmacológico , Antineoplásicos Fitogénicos/química , Neoplasias de la Mama/tratamiento farmacológico , Línea Celular Tumoral , Femenino , Fibroblastos/efectos de los fármacos , Humanos , Aceites Volátiles/química , Aceites de Plantas/química
18.
J Ethnopharmacol ; 129(2): 261-6, 2010 May 27.
Artículo en Inglés | MEDLINE | ID: mdl-20363311

RESUMEN

AIM OF THE STUDY: Cirsium rivulare (Jacq.) All. (Asteraceae) is a herbaceous perennial plant occurring in Central Europe. It has been traditionally used in Polish folk medicine to treat anxiety. In the present study methanolic extracts from flowers and leaves of Cirsium rivulare containing flavonoid compounds linarin, pectolinarin, apigenin, hispidulin, their glycosides and a newly isolated compound isokaemferide 7-O-(6''-methylglucuronide) were studied for anxiolytic and pro-cognitive properties. MATERIALS AND METHODS: Male Wistar rats (150-160 g) were used. They were treated orally with standardized methanol extracts of flowers and leaves of Cirsium rivulare and subsequently tested for memory in passive avoidance (PA) and object recognition (OR) tests. Auxiliary tests for motor (open field, OF) and emotional (elevated 'plus' maze, EPM) effects of the above treatments were also employed. RESULTS: We found that the extract from flowers of Cirsium rivulare, in addition to its anxiolytic effects as measured in the EPM, improves memory of the appetitively (by curiosity, OR) and aversively (by footshook, PA) motivated tasks. This is in contrast to classical anxiolytics as for example benzodiazepines that typically impair memory. The extract from leaves of Cirsium rivulare showed some anxiolytic properties in the EPM, and no effect in both cognitive tests. The examined extracts of Cirsium rivulare did not affect psychomotor exploratory activity of rats tested in the OF. CONCLUSIONS: These results suggest that the flavonoids from Cirsium rivulare possess anxiolytic and pro-cognitive effects, the extract from flowers being more pro-cognitive and that from the leaves more anxiolytic.


Asunto(s)
Ansiolíticos/uso terapéutico , Cirsium/química , Flavonoides/uso terapéutico , Glucurónidos/uso terapéutico , Memoria/efectos de los fármacos , Fitoterapia , Extractos Vegetales/uso terapéutico , Animales , Ansiolíticos/aislamiento & purificación , Ansiolíticos/farmacología , Ansiedad/tratamiento farmacológico , Reacción de Prevención/efectos de los fármacos , Benzodiazepinas , Conducta Exploratoria , Flavonoides/aislamiento & purificación , Flavonoides/farmacología , Flores , Glucurónidos/aislamiento & purificación , Glucurónidos/farmacología , Masculino , Aprendizaje por Laberinto/efectos de los fármacos , Motivación , Extractos Vegetales/química , Extractos Vegetales/farmacología , Hojas de la Planta , Ratas , Ratas Wistar
19.
Nat Prod Res ; 24(6): 554-61, 2010 Apr.
Artículo en Inglés | MEDLINE | ID: mdl-20397105

RESUMEN

In this study, antimicrobial properties and toxicity of extracts from Cirsium spp.: Cirsium arvense, C. oleraceum, C. palustre, C. rivulare and C. vulgare in combination with sodium picolinate (PS) or sodium benzoate (BS), were investigated. Three micro-organisms were used: Staphylococcus aureus, Bacillus subtilis and Pseudomonas aeruginosa. Minimum inhibitory concentration (MIC) of extracts was found at 1.56-50.0 mg mL(-1). Unlike the case of BS, adding PS to extracts from flowers of C. palustre and C. arvense enhanced their antimicrobial effect on S. aureus (MIC from 6.25-12.5 mg mL(-1) to 1.25-5.0 mg mL(-1)). An MTT test was used to study toxicity effects. The extracts from C. palustre or C. arvense mixed with PS had a concentration-dependent, slightly cytotoxic or stimulating effect on the viability of normal human skin fibroblasts. The total phenolic content (TPC) of samples varied from 44 to 178 mg gallic acid equivalent per 1 g of extract. The highest TPC was observed in C. palustre (l) and C. oleraceum (f). Our results did not show any correlation between antimicrobial activities and TPC. Cirsium palustre (f) and C. arvense (f) extracts were analysed by gas chromatography/mass spectrometry (GC/MS). About 30 compounds were found to be present in extracts from two Cirsium species in amounts of not less than 0.2% of TIC.


Asunto(s)
Antibacterianos/farmacología , Cirsium/química , Quelantes del Hierro/farmacología , Ácidos Picolínicos/farmacología , Extractos Vegetales/farmacología , Antibacterianos/análisis , Cirsium/toxicidad , Sinergismo Farmacológico , Fibroblastos/efectos de los fármacos , Flores/química , Humanos , Pruebas de Sensibilidad Microbiana , Extractos Vegetales/química , Extractos Vegetales/toxicidad , Hojas de la Planta/química , Plantas Medicinales/química , Plantas Medicinales/toxicidad , Benzoato de Sodio/farmacología
20.
Nat Prod Res ; 22(18): 1583-8, 2008 Dec.
Artículo en Inglés | MEDLINE | ID: mdl-19085412

RESUMEN

Crude aqueous extracts from leaves of Cirsium arvense, C. oleraceum, C. palustre, C. rivulare and C. vulgare were investigated. The content of tannins in mentioned sources, determined by the weight method with hide powder, varied between 1 and 7.63%. Total phenolic content, analysed by using Folin-Ciocalteau's method, ranged between 54 and 96 mg g(-1), was expressed as milligrams of gallic acid per gram of dry extract. Phenolic acids were identified by HPLC method. Antimicrobial activity of those extracts was examined. Cirsium palustre extract was the most active against investigated microorganisms. It was observed that the content of small-molecular phenolic compounds had greater influence on the activity of extracts than tannins. The total antioxidant activity indicated by radical cation 2,2'-azini-di-(3-ethylbenzthiazoline sulphonate) ABTS(*+), expressed as total antioxidant status (TAS) ranged from 2.31 to 2.78 mM L(-1).


Asunto(s)
Antiinfecciosos/aislamiento & purificación , Antiinfecciosos/farmacología , Antioxidantes/aislamiento & purificación , Antioxidantes/farmacología , Cirsium/química , Flavonoides/aislamiento & purificación , Flavonoides/farmacología , Fenoles/aislamiento & purificación , Fenoles/farmacología , Plantas Medicinales/química , Antiinfecciosos/química , Antioxidantes/química , Bacillus subtilis/efectos de los fármacos , Candida albicans/efectos de los fármacos , Flavonoides/química , Ácido Gálico , Pruebas de Sensibilidad Microbiana , Fenoles/química , Hojas de la Planta/química , Polifenoles , Pseudomonas aeruginosa/efectos de los fármacos , Staphylococcus aureus/efectos de los fármacos , Taninos/análisis
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