RESUMO
CONTEXT: Methanol extracts obtained from eight species belonging to four families of the Lamiales order native to Mexico were investigated for biological action. OBJECTIVE: Cytotoxicity and antioxidant activity of methanol extracts have been investigated. MATERIALS AND METHODS: Cytotoxic activity was evaluated by the sulphorhodamine B protein staining assay against KB (nasopharyngeal), HEp-2 (larynx), HF-6 (colon), MCF7 (breast), PC-3 (prostate), and Ca Ski (cervix) carcinoma cell lines. To analyze the antioxidant activity, common stable radicals chromogens, 2,2-azino-bis(3-ethylbenzthiazoline-6-sulfonic acid (ABTS+) and DPPH (1,1-diphenyl-2-picrylhydrazyl) were used. The ferric reducing antioxidant power (FRAP) and the total phenolic content of the samples were also determined. RESULTS: Some of the extracts, such as Limosella aquatica L. (Scrophulariaceae), Mimulus glabratus Kunth. (Phrymaceae), Pedicularis mexicana Zucc. ex Benth. (Orobanchaceae), and Penstemon campanulatus (Cav.) Willd. (Plantaginaceae) displayed remarkably selective cytotoxic activity. However, the extract from Veronica americana (Raf.) Schwein (Plantaginaceae) showed the highest activity with IC50 values of 1.46 and 0.169 g/ µL on PC-3 and HF-6 cells, respectively. With the exception of M. glabratus, all the extracts showed different degrees of antioxidant activity with IC50 values from 0.89 up to 1.8 in the ABTS assay; from 0.49 up to 1.25 mg/mL in the DPPH assay and with the FRAP evaluation, 36 to 68 equivalents in mM of FeSO4. V. americana also showed the highest antoxidant activity with IC50 values from 0.491 and 0.892 mg/mL, on DPPH and ABTS assays, respectively. DISCUSSION AND CONCLUSION: These findings demonstrated that the species studied have great potential cytotoxic and antioxidant activity.
Assuntos
Antineoplásicos Fitogênicos/farmacologia , Antioxidantes/farmacologia , Lamiaceae/química , Compostos de Bifenilo , Linhagem Celular Tumoral , Cromanos/química , Ensaios de Seleção de Medicamentos Antitumorais , Compostos Férricos/química , Sequestradores de Radicais Livres/farmacologia , Radicais Livres/química , Humanos , México , Oxirredução , Fenóis/química , Picratos , Extratos Vegetais/química , Extratos Vegetais/farmacologia , Espécies Reativas de Nitrogênio , Espécies Reativas de OxigênioRESUMO
As most anticancer drugs are derived from natural sources, the screening of local medicinal flora should be considered a primary step in the search for new sources for antineoplastic agents. In Mexico, more than 6000 medicinal plant species are used for the treatment of various diseases, including cancer. A multifactorial plant selection method, employing various criteria was designed and applied in order to select alternative sources of podophyllotoxin lignan analogues. For each criterion (chemotaxonomy, traditional medical uses and published scientific data), an arbitrary score system was ascribed to the species and the sum of these enabled us to compare potential candidates. The resulting selected plants were tested for cytotoxic activity and the compounds responsible for this activity were evaluated by liquid chromatography-mass spectroscopy (LC-MS). Around 50 species from the Mexican flora were initially considered. From these, six species were selected by referring to the results from the scoring system and these were then collected. Three extracts were evaluated as being highly cytotoxic against three different cancer cell lines. Finally, podophyllotoxin-like lignans could be identified by observing the fragmentation pattern on mass spectra, obtained from the LC-MS in two species: Linum scabrellum and Hyptis suaveolens.
Assuntos
Antineoplásicos Fitogênicos/farmacologia , Ensaios de Seleção de Medicamentos Antitumorais/métodos , Lignanas/farmacologia , Neoplasias/tratamento farmacológico , Plantas Medicinais/química , Podofilotoxina/farmacologia , Antineoplásicos Fitogênicos/química , Linhagem Celular Tumoral/efeitos dos fármacos , Cromatografia Líquida de Alta Pressão , Humanos , Lignanas/química , Lignanas/isolamento & purificação , México , Fitoterapia , Extratos Vegetais/química , Extratos Vegetais/farmacologia , Podofilotoxina/química , Podofilotoxina/isolamento & purificação , Projetos de PesquisaRESUMO
The triterpenes ursolic acid (1), 27-p-Z-coumaroyloxyursolic acid (2), 27-p-E-coumaroyloxyursolic acid, alpha-amyrine-3-palmitate and lupeol-3-palmitate were isolated through a bioactivity-guided fractionation from the acetonic extract of the aerial parts of Viburnum jucundum Morton in addition to amentoflavone, an epimeric mixture at C-2 of 2,3-dihydroamentoflavone, beta-sitosterol and beta-sitosteryl glucopyranoside. Ursolic acid (1) was the only constituent that exhibited cytotoxic activity toward three human cancer cell lines in culture. This is the first phytochemical and cytotoxic analysis performed to this plant species.
Assuntos
Antineoplásicos Fitogênicos/farmacologia , Gastroenteropatias/tratamento farmacológico , Extratos Vegetais/farmacologia , Triterpenos/farmacologia , Viburnum/química , Antineoplásicos Fitogênicos/química , Antineoplásicos Fitogênicos/isolamento & purificação , Linhagem Celular , Ensaios de Seleção de Medicamentos Antitumorais , Flavonoides/química , Flavonoides/isolamento & purificação , Flavonoides/farmacologia , Humanos , México , Extratos Vegetais/química , Plantas Medicinais , Esteróis/química , Esteróis/isolamento & purificação , Esteróis/farmacologia , Triterpenos/química , Triterpenos/isolamento & purificação , Células Tumorais Cultivadas , Ácido UrsólicoRESUMO
The novel bisabolene sesquiterpenes 3-6, were isolated from Iostephane heterophylla, using bioguided fractionation. The new compounds were determined to be (12R/12S)-12,13-epoxy-xanthorrhizols (3,4) and (12R/12S)-12,13-dihydro-12,13-dihydroxy-xanthorrizols (5,6) and their structures were characterized by analysis of spectroscopic data and by chemical correlation from xanthorrhizol (2). The stereochemistry at C-12 of 5 was deduced using the modified Mosher experiment. Some of the isolated compounds elicited activity against gram positive and gram negative bacteria, levadura and dermatophytes.
Assuntos
Anti-Infecciosos/isolamento & purificação , Asteraceae/química , Sesquiterpenos/isolamento & purificação , Antibacterianos , Anti-Infecciosos/química , Anti-Infecciosos/farmacologia , Candida albicans/efeitos dos fármacos , Cromatografia Líquida de Alta Pressão , Enterococcus faecalis/efeitos dos fármacos , Glicosídeos/química , Glicosídeos/isolamento & purificação , México , Microsporum/efeitos dos fármacos , Estrutura Molecular , Ressonância Magnética Nuclear Biomolecular , Raízes de Plantas/química , Plantas Medicinais/química , Proteus mirabilis/efeitos dos fármacos , Sesquiterpenos/química , Sesquiterpenos/farmacologia , Espectrofotometria Ultravioleta , Staphylococcus aureus/efeitos dos fármacos , Estereoisomerismo , Relação Estrutura-Atividade , Trichophyton/efeitos dos fármacosRESUMO
The cytotoxic compound moronic acid (1) and the new tetracyclic triterpene 3,4-seco-olean-18-ene-3,28-dioic acid (2), were isolated from the aerial parts of the medicinal plant Phoradendron reichenbachianum (mistletoe, Loranthaceae) through a bioassay-guided fractionation. In addition, squalene, glycerol trilinoleate, morolic acid, betulonaldehyde, betulinaldehyde, alpha-germanicol, lupeol, beta-sitosterol and beta-sitosteril glucopyranoside, were identified in this plant species. The structures were elucidated on the basis of chemical and spectroscopic evidence.
Assuntos
Antineoplásicos Fitogênicos/farmacologia , Magnoliopsida/química , Ácido Oleanólico/análogos & derivados , Ácido Oleanólico/farmacologia , Triterpenos/farmacologia , Linhagem Celular , Espectroscopia de Ressonância Magnética , Estrutura Molecular , Ácido Oleanólico/química , Caules de Planta , Plantas Medicinais , Triterpenos/química , Triterpenos/isolamento & purificaçãoRESUMO
A new antimycotic steroidal saponin named SC-1 has been isolated from the leaves of Solanum chrysotrichum by bioassay-guided fractionation. The structure of SC-1 was characterized as 3-O-[beta-quinovopyranosyl(1-->6)-beta-glucopyranosyl(1-->6)-beta- glucopyranosyl]chlorogenin on the basis of spectral analyses and chemical evidence.
Assuntos
Antifúngicos , Extratos Vegetais/química , Saponinas , Solanaceae/química , Espirostanos , Antifúngicos/química , Antifúngicos/isolamento & purificação , Antifúngicos/farmacologia , Antifúngicos/uso terapêutico , Bactérias/efeitos dos fármacos , Cromatografia Líquida de Alta Pressão , Imageamento por Ressonância Magnética , Estrutura Molecular , Plantas Medicinais/química , Saponinas/química , Saponinas/isolamento & purificação , Saponinas/farmacologia , Saponinas/uso terapêutico , Espirostanos/química , Espirostanos/isolamento & purificação , Espirostanos/farmacologia , Espirostanos/uso terapêutico , Trichophyton/efeitos dos fármacosRESUMO
The bisdesmoside oleanolic acid saponin, 3-0-(methyl-beta-D-glucuronopyranosiduronoate)-28-0-beta-D-glucopyranosyl-oleanolate along with nine known compounds (two diterpenic acids, one chromene, three triterpenes, one steroidal glycoside, and two monodesmoside oleanolic acid saponins), were obtained from Viguiera decurrens roots. The chemical structure of the bisdesmoside oleanolic saponin was determined by chemical and NMR spectral evidence. A mixture of monodesmoside saponins displayed cytotoxic activity against P388 and COLON cell lines (ED50= 2.3 and 3.6 microg/ml, respectively). Two of the known compounds showed insecticidal activity against the Mexican bean beetle larvae (Epilachna varivestis).
Assuntos
Asteraceae/química , Ácido Oleanólico/química , Saponinas/isolamento & purificação , Ensaios de Seleção de Medicamentos Antitumorais , Espectroscopia de Ressonância Magnética , Raízes de Plantas/química , Saponinas/química , Saponinas/farmacologia , Espectrometria de Massas de Bombardeamento Rápido de Átomos , Células Tumorais CultivadasRESUMO
Based on traditional medicinal knowledge, it was possible to identify the plant species Solanum chrysotrichum as the source of a new antimycotic agent designated SC-1. Cell suspension batch cultures from this plant were established in shake flasks, in which the production of SC-1 was optimized, reaching values fifty times higher than those registered in field grown plants. Large-scale cultivation of the active biomass from S. chrysotrichum was established in 10 l airlift bioreactors, and productivity levels of SC-1 were increased by 60% when using a draw-fill mode in the bioreactors.
Assuntos
Extratos Vegetais/isolamento & purificação , Plantas Medicinais , Saponinas/isolamento & purificação , Biotecnologia , Células Cultivadas , Cromatografia Líquida de Alta Pressão , Humanos , México , Extratos Vegetais/farmacologia , Saponinas/farmacologiaRESUMO
A tissue culture method is described for callus formation from Galphimia glauca (Mapighiaceae) in MS (Murashige & Skoog) medium supplemented with various growth regulators. Best induction was achieved when using hypocotyls as explants in medium supplemented with 2 mg/l of 2,4-dichlorophenoxyacetic acid (2,4-D). Major cellular growth of calluses was obtained with naphthaleneacetic acid (2 mg/l) + kinetin (1 mg/l). Subcultivation of calluses using various concentrations of 2,4-D allowed the production of the sedative nor-seco-triterpenoid, galphimine B and a new related compound. The structure of the new constituent was elucidated as 6-acetoxygalphimine B. The highest accumulation of active constituent 1 (1.5 x 10(-2) dry weight) was achieved when 4 mg/l of the hormone were used, and this experimental condition allowed the detection of only galphimine B. A preliminary screening of the methanolic extracts prepared from calluses, using the isolated guinea-pig ileum as a general test system for pharmacological effects, demonstrated that the most active material was the one with the highest concentration of galphimine B. Total accumulation of this sedative triterpene, in the optimized tissue culture conditions, was in the same order of magnitude as the value quantified for wild plants (4.5 x 10(-2) dry weight).
Assuntos
Hipnóticos e Sedativos/metabolismo , Plantas Medicinais/metabolismo , Triterpenos/metabolismo , Animais , Técnicas de Cultura , Cobaias , Hipnóticos e Sedativos/química , Hipnóticos e Sedativos/farmacologia , Íleo/efeitos dos fármacos , Estrutura Molecular , Análise Espectral , Triterpenos/química , Triterpenos/farmacologiaRESUMO
Biological assays of Vitex trifolia L. organic extracts have shown relevant activities. Hexanic and dichloromethanic (DCM) extracts, when prepared from stems and foliage, have proved to be very toxic against several cancer cell lines in culture (SQC-1 UISO, OVCAR-5, HCT-15 COLADCAR, and KB). Also, an important antifeeding activity against the insect pest Spodoptera frugiperda (Lepidoptera: Noctuidae) was recorded. The hexanic extract from leaves completely inhibited the growth of the fungal plant pathogen Fusarium sp. within the first 2 days of the experiment, but dropped significantly at day 6 (15% inhibition). The potential of V. trifolia for several uses is discussed.
Assuntos
Bactérias/efeitos dos fármacos , Fungos/efeitos dos fármacos , Medicina Tradicional , Plantas Medicinais , Spodoptera/efeitos dos fármacos , Células Tumorais Cultivadas/efeitos dos fármacos , Vitex , Animais , Antibacterianos , Anti-Infecciosos/farmacologia , Antifúngicos/farmacologia , Antineoplásicos Fitogênicos/farmacologia , Bactérias/crescimento & desenvolvimento , Ensaios de Seleção de Medicamentos Antitumorais , Comportamento Alimentar/efeitos dos fármacos , Fungos/crescimento & desenvolvimento , Humanos , Inseticidas/farmacologia , México , Testes de Sensibilidade Microbiana , Fitoterapia , Extratos Vegetais/farmacologia , Folhas de Planta/química , Caules de Planta/química , Spodoptera/fisiologiaRESUMO
The novel melampolides (11R)-11,13-dihydro-schkuhriolide (7), (11S)-11,13-dihydro-schkuhriolide (8), and schkuhrioidiol (11), along with the known constituents, frutescin (1), schkuhriolide (2), frutescinic acid (4), allo-schkuhriolide (5), and epoxyschkuhriolide (6) were isolated from the aerial parts of Schkuhria schkuhrioides. The structures of the new compounds were determined by spectroscopic methods. Compounds 1, 2, 4, 5, and 6 displayed no significant cytotoxic or antimicrobial activities.
Assuntos
Anti-Infecciosos/farmacologia , Antineoplásicos Fitogênicos/farmacologia , Lactonas/farmacologia , Folhas de Planta/química , Plantas Medicinais/química , Sesquiterpenos/farmacologia , Animais , Anti-Infecciosos/isolamento & purificação , Antineoplásicos Fitogênicos/isolamento & purificação , Artemia , Cromatografia Líquida de Alta Pressão , Ensaios de Seleção de Medicamentos Antitumorais , Humanos , Lactonas/isolamento & purificação , Espectroscopia de Ressonância Magnética , Espectrometria de Massas , Sesquiterpenos/isolamento & purificação , Espectrofotometria Ultravioleta , Células Tumorais CultivadasRESUMO
Two new cytotoxic isoflavans, (3S)-7-hydroxy-2',3',4',5', 8-pentamethoxyisoflavan (1) and (3S)-3',7-dihydroxy-2',4',5', 8-tetramethoxyisoflavan (2), were isolated from the bark and trunks of Eysenhardtia polystachya (Leguminosae), together with the known constituents stigmasterol, isoduartin, cuneatin, 7-hydroxy-2',4', 5'-trimethoxyisoflavone, and 3,4-dimethoxy-8, 9-(methylenedioxy)pterocarpan. The structures of 1 and 2 were elucidated on the basis of spectroscopic methods. The antimicrobial, cytotoxic, and insecticidal potential of some of these compounds were evaluated. The isoflavans 1, 2, and isoduartin (2', 7-dihydroxy-3',4',8-trimethoxyisoflavan) displayed moderate cytotoxic activity against KB cell lines.
Assuntos
Antineoplásicos Fitogênicos/isolamento & purificação , Benzopiranos/isolamento & purificação , Isoflavonas , Plantas Medicinais/química , Animais , Anti-Infecciosos/isolamento & purificação , Anti-Infecciosos/farmacologia , Antineoplásicos Fitogênicos/farmacologia , Benzopiranos/farmacologia , Ensaios de Seleção de Medicamentos Antitumorais , Humanos , Inseticidas/isolamento & purificação , Espectroscopia de Ressonância Magnética , Espectrometria de Massas , México , Camundongos , Testes de Sensibilidade Microbiana , Conformação Molecular , Espectrofotometria Infravermelho , Espectrofotometria Ultravioleta , Spodoptera , Texas , Células Tumorais CultivadasRESUMO
Crude extracts from nine plants widely used in Mexican traditional medicine for the treatment of cancer have been subjected to a bioscreening study to detect cytotoxic activity against human tumor cells. Three different extracts (petroleum ether, ethylacetate, and methanol) from each plant species, were tested towards KB, HCT-15 COLADCAR and UISO-SQC-1 cell cultures. The results showed that three plants Colubrina macrocarpa (Cav.) Don (Rhamnaceae), Acacia pennatula (Schltdl. and Cham.) Benth (Leguminosae) and Hemiangium excelsum (HBK.) Smith (Hippocrateaceae), exhibited important cytotoxic activity showing a certain degree of selectivity against the tested cells in culture.
Assuntos
Antineoplásicos Fitogênicos/farmacologia , Plantas Medicinais/química , Humanos , Medicina Tradicional , México , Células Tumorais CultivadasRESUMO
Twelve methanolic plant extracts from botanical species used in traditional medicine in Morelos, México to cure infectious diseases have been subjected to a screening study to detect potential antimicrobial activity against Staphylococcus aureus, Escherichia coli, Pseudomonas aeruginosa and Candida albicans. The antimicrobial activity of the products was evaluated using colonies growing in solid medium, establishing the minimal concentration required to inhibit their in vitro growth (MIC). The results showed that extracts from Eucalyptus globolus Labill, Punica granatum L., Artemisia mexicana Wild., and Bocconia arborea Watt. possess strong in vitro antimicrobial activity against the tested microorganisms.
Assuntos
Candidíase/tratamento farmacológico , Infecções por Escherichia coli/tratamento farmacológico , Extratos Vegetais/uso terapêutico , Plantas Medicinais , Infecções por Pseudomonas/tratamento farmacológico , Infecções Estafilocócicas/tratamento farmacológico , Ensaio de Unidades Formadoras de Colônias , Medicina Tradicional , Metanol/química , México , Testes de Sensibilidade Microbiana , Especificidade da EspécieRESUMO
From the methanolic extract of the whole plants of Bidens pilosa the new beta-D-glucopyranosyloxy-3-hydroxy-6(E)-tetradecen-8, 10,12-triyne besides a known polyine has been isolated and identified mainly by IR and NMR methods. The new compound showed overgrowing action against normal and transformed human cell lines in culture.
Assuntos
Alcinos/química , Antibacterianos/química , Antineoplásicos Fitogênicos/química , Glucosídeos/química , Inseticidas/química , Plantas Medicinais , Alcinos/isolamento & purificação , Alcinos/farmacologia , Animais , Antibacterianos/isolamento & purificação , Antibacterianos/farmacologia , Antineoplásicos Fitogênicos/isolamento & purificação , Antineoplásicos Fitogênicos/toxicidade , Bactérias/efeitos dos fármacos , Linhagem Celular , Sobrevivência Celular/efeitos dos fármacos , Glucosídeos/isolamento & purificação , Glucosídeos/farmacologia , Humanos , Inseticidas/isolamento & purificação , Células KB , Larva , Leucemia P388 , Espectroscopia de Ressonância Magnética , Medicina Tradicional , México , Camundongos , Testes de Sensibilidade Microbiana , Estrutura Molecular , Extratos Vegetais , Espectrofotometria Infravermelho , Spodoptera , Células Tumorais CultivadasRESUMO
Mimosa tenuiflora (Willd.) Poiret (Leguminosae) was micropropagated throughin vitro culture of axillary buds on Murashige and Skoog (MS) medium. Shoot formation was achieved when the media were supplemented with 0.1 mg.L(-1) IAA + 3 mg.L(-1) KN.In vitro rooting of regenerated shoots was achieved when 0.1 mg.L(-1) KN was combined with 1 mg.L(-1) IBA in the absence of IAA. Ninety-four percent of the rooted plants were succesfully adapted to field conditions and grown in the soil. A total of 180 trees grown under these conditions were obtained over a one-year period.
RESUMO
To evaluate the survival of plant tissue in an animal environment, cultured calli from a Mexican medicinal plant (Mimosa tenuiflora Poir.) were transplanted under sterile conditions into the subcutaneous tissue of rats. Microscopic studies of grafted areas were carried out at the 30th, 60th and 120th days after transplantation. Histological evidence of plant graft survival was found in specimens of all groups. during the first month of subcutaneous grafting a moderate inflammatory reaction around the callus was observed characterized by the presence of polymorphonuclear cells and some macrophages and the formation of a fibrous capsule. Nevertheless, the plant grafts remained viable and a decrease of the inflammatory reaction around the callus was observed in the specimens during the following months. In the fourth month specimens the formation of blood vessels inside the grafted plant tissue was observed. Once removed from rats, plant tissues showed high viability according to the fluorescein test. These calli were then transferred to the original in vitro medium showing growth capacity during the following weeks. These results demonstrate, for the first time, that cultivated cells of higher plants survive in an animal environment, suggesting the possibility to utilize pharmacologically active plant transplants in animals, a technique proposed here as inter-regni transplants. Further studies are required to explore this new field of research that opens numerous questions about plant-animal cellular interaction.
Assuntos
Transplante de Células , Sobrevivência de Enxerto , Plantas Medicinais/citologia , Transplante Heterólogo , Animais , Células Cultivadas , Procedimentos Cirúrgicos Dermatológicos , Masculino , Ratos , Ratos WistarRESUMO
Methanolic extracts of 141 different botanical species, used in traditional medicine in the Highland of Chiapas for the treatment of gastrointestinal and respiratory diseases, were submitted to pharmacological testing in order to evaluate the spasmolytic action on electrically-stimulated guinea pig ileum. Of these species, 33.3% showed an inhibition of reflex greater than 80% at a bath concentration of 250 µg/ml. Of the active species, 40.4% belong to the Asteraceae family. Of the active samples, 59.5% were obtained from leaves. The results identify a group of interesting plants, that could be considered for future experimental investigation.
RESUMO
Twelve pure compounds originally obtained through a systematic chemotaxonomical study with Mexican plants of the Asteraceae, were subjected to a cytotoxic and in vitro antimicrobial screening. Three different cell lines in culture (KB, KB-VI and P388) were used in the cytotoxicity assay, while antimicrobial activity was tested against Gram-positive and Gram-negative bacteria, as well as Candida albicans. Of the twelve terpenoids tested, only taraxasterol showed antimicrobial activity against Staphylococcus aureus. The significant cytotoxic activity exhibited by five sesquiterpene lactones, and the moderate cytotoxicity of an eudesmane, is discussed.