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1.
Mini Rev Med Chem ; 15(10): 809-36, 2015.
Artículo en Inglés | MEDLINE | ID: mdl-25553426

RESUMEN

Malaria is one of the most important tropical diseases since more than 40% of the world population is at risk. This disease is endemic to more than 100 nations and remains one of the main leading causes of death in children less than five years of age worldwide. Natural product-derived compounds have played a major role in drug discovery, often as prototypes to obtain more active semi synthetic derivatives. Antimalarial pharmacotherapy is a significant example of plant-derived medicines, such as quinine and artemisinin. This review highlights studies on terpenes and their semi synthetic derivatives from natural sources with antimalarial activity reported in the literature during eleven years (2002-2013). A total of 114 compounds are found among terpenes and their semi synthetic derivatives. Cytotoxicity of the compounds is also found in this review. Furthermore, the physicochemical properties of the terpenes addressed are discussed based on seven well established descriptors, which provide a useful source for the elaboration of a terpene library of antimalarial compounds.


Asunto(s)
Antimaláricos/síntesis química , Productos Biológicos/química , Terpenos/química , Animales , Antimaláricos/química , Antimaláricos/toxicidad , Artemisininas/síntesis química , Artemisininas/química , Artemisininas/farmacología , Productos Biológicos/aislamiento & purificación , Productos Biológicos/toxicidad , Supervivencia Celular/efectos de los fármacos , Humanos , Plantas Medicinales/química , Plantas Medicinales/metabolismo , Plasmodium falciparum/efectos de los fármacos , Relación Estructura-Actividad , Terpenos/síntesis química , Terpenos/toxicidad
2.
Genet Mol Res ; 13(3): 7725-35, 2014 Sep 26.
Artículo en Inglés | MEDLINE | ID: mdl-25299086

RESUMEN

Theobroma cacao L. contains more than 500 different chemical compounds some of which have been traditionally used for their antioxidant, anti-carcinogenic, immunomodulatory, vasodilatory, analgesic, and antimicrobial activities. Spontaneous aerobic fermentation of cacao husks yields a crude husk extract (CHE) with antimicrobial activity. CHE was fractioned by solvent partition with polar solvent extraction or by silica gel chromatography and a total of 12 sub-fractions were analyzed for chemical composition and bioactivity. CHE was effective against the yeast Saccharomyces cerevisiae and the basidiomycete Moniliophthora perniciosa. Antibacterial activity was determined using 6 strains: Staphylococcus aureus, Staphylococcus epidermidis, and Bacillus subtilis (Gram-positive) and Pseudomonas aeruginosa, Klebsiella pneumoniae, and Salmonella choleraesuis (Gram-negative). At doses up to 10 mg/mL, CHE was not effective against the Gram-positive bacteria tested but against medically important P. aeruginosa and S. choleraesuis with a minimum inhibitory concentration (MIC) of 5.0 mg/mL. Sub-fractions varied widely in activity and strongest antibacterial activity was seen with CHE8 against S. choleraesuis (MIC of 1.0 mg/mL) and CHE9 against S. epidermidis (MIC of 2.5 mg/mL). All bioactive CHE fractions contained phenols, steroids, or terpenes, but no saponins. Fraction CHE9 contained flavonoids, phenolics, steroids, and terpenes, amino acids, and alkaloids, while CHE12 had the same compounds but lacked flavonoids.


Asunto(s)
Antiinfecciosos/farmacología , Cacao/química , Fermentación , Extractos Vegetales/farmacología , Antiinfecciosos/química , Bacterias/efectos de los fármacos , Cromatografía en Gel , Hongos/efectos de los fármacos , Pruebas de Sensibilidad Microbiana , Extractos Vegetales/química
3.
Pharmazie ; 67(4): 288-92, 2012 Apr.
Artículo en Inglés | MEDLINE | ID: mdl-22570933

RESUMEN

Entire seeds of Chenopodium quinoa Willd are a rich protein source and are also well-known for their high saponin content. Due to their amphiphily quinoa saponins are able to form intricate micellar aggregates in aqueous media. In this paper we study the aggregates formed by self-association of these compounds from two quinoa saponin fractions (FQ70 and FQ90) as well as several distinctive nanostructures obtained after their complexation with different ratios of cholesterol (CHOL) and phosphatidylcholine (PC). The FQ70 and FQ90 fractions were obtained by reversed-phase preparative chromatography. The structural features of their resulting aggregates were determined by Dynamic Light Scattering (DLS) and Transmission Electron Microscopy (TEM). Novel nanosized spherical vesicles formed by self-association with mean diameter about 100-200 nm were observed in FQ70 aqueous solutions whereas worm-like micelles an approximate width of 20 nm were detected in FQ90 aqueous solutions. Under experimental conditions similar to those reported for the preparation of Quillaja saponaria ISCOM matrices, tubular and ring-like micelles arose from FQ70:CHOL:PC and FQ90:CHOL:PC formulations, respectively. However, under these conditions no cage-like ISCOM matrices were observed. The saponin composition of FQ70 and FQ90 seems to determine the nanosized structures viewed by TEM. Phytolaccagenic acid, predominant in FQ70 and FQ90 fractions, is accountable for the formation of the nanosized vesicles and tubular structures observed by TEM in the aqueous solutions of both samples. Conversely, ring-like micelles observed in FQ90:CHOL:PC complexes can be attributed to the presence of less polar saponins present in FQ90, in particular those derived from oleanolic acid.


Asunto(s)
Chenopodium quinoa/química , Saponinas/análisis , Química Farmacéutica , Colesterol/química , Luz , Micelas , Microscopía Electrónica de Transmisión , Nanopartículas/química , Fosfolípidos/química , Extractos Vegetales/química , Dispersión de Radiación , Soluciones , Agua
4.
Mini Rev Med Chem ; 11(10): 857-80, 2011 Sep.
Artículo en Inglés | MEDLINE | ID: mdl-21762102

RESUMEN

Saponins can be classified as triterpenoid (C30) or steroidal (C27), based on their carbon nucleus (aglycone). Sugar residues are linked to the aglycone, conferring an amphiphilic nature on these molecules, which is relevant for their biological activities. Saponins include a large variety of molecules that find several applications in pharmacology. Saponins have been shown to display immunoadjuvant, anti-inflammatory, antiplatelet, hypocholesterolemic, antitumoral, anti-HIV, antibacterial, insecticide, fungicide and anti-leishmanial activities. Anti-inflammatory medicines are increasingly demanded to treat various forms of arthritis in aging and obese populations and to help reduce the doses and duration of conventional corticotherapy with less side effects and without immunosuppression. The vaccine market for both human and veterinary uses is close to US$ 15 billion, progressively inflated by the recurrent threat of global pandemics.This paper provides an overview of recent advances (main focus on the last five years) on plant saponins that show anti-inflammatory and/or immunoadjuvant activities: source plants, isolation procedures, mechanism of action and biotechnological approaches towards sustainable production of bioactive saponins. Special attention is given to ginseng and Quillaja saponins. Strategies based on plant cultivation, cell and tissue culture, elicitation, and metabolic engineering for improved production of saponins are described. Future directions for research in the field and strategies to overcome bottlenecks are also discussed.


Asunto(s)
Adyuvantes Inmunológicos/química , Antiinflamatorios/química , Plantas Medicinales/química , Saponinas/biosíntesis , Adyuvantes Inmunológicos/aislamiento & purificación , Animales , Antiinflamatorios/aislamiento & purificación , Biotecnología , Humanos , Células Vegetales/metabolismo , Raíces de Plantas/citología , Raíces de Plantas/metabolismo , Saponinas/química , Saponinas/farmacología
5.
Phytother Res ; 25(12): 1783-8, 2011 Dec.
Artículo en Inglés | MEDLINE | ID: mdl-21480409

RESUMEN

Five saponins purified from the leaves of three Ilex species (saponins 1 and 2 from I. dumosa; saponin 3 from I. argentina; saponin 4 from I. paraguariensis) and from Passiflora alata (saponin 5) were evaluated for their in vitro haemolytic activity and in vivo immunostimulatory ability in a mouse model using tetanus toxoid (TT) as a model antigen. The assayed saponins showed very weak or no haemolytic activity over the tested concentration range. Mice were immunized twice with TT formulated with pure saponins 1-5, or with a mixture of saponins from Quillaja saponaria, aluminum hydroxide gel or saline, which were used as controls. The elicited humoral response was evaluated by means of the time course of specific serum antibody levels up to day 131 post-priming (total IgG and isotypes); the cellular response was tested through a delayed-type hypersensitivity (DTH) assay. The assayed saponins, in particular saponins 3 and 5, showed an adjuvant effect similar to that of alum for all tested parameters. The immunostimulating potential of these compounds deserves further investigation, especially taking into account that some Ilex spp. and Passiflora alata are native crops of widespread use and economical importance in Latin America.


Asunto(s)
Adyuvantes Inmunológicos/farmacología , Ilex/química , Passiflora/química , Saponinas/inmunología , Compuestos de Alumbre/farmacología , Animales , Hemólisis , Hipersensibilidad Tardía/inmunología , Inmunidad Celular , Inmunidad Humoral , Masculino , Ratones , Ratones Endogámicos BALB C , Quillaja/química , Saponinas/farmacología , Toxoide Tetánico
6.
Pharmazie ; 65(9): 650-6, 2010 Sep.
Artículo en Inglés | MEDLINE | ID: mdl-21038841

RESUMEN

A new chemical structure, the 4,2',4",2'''-tetrahydroxy-6',6'''-dimethoxy-4'-O-4'''- bichalcone, named achyrobichalcone was isolated and identified from an Achyrocline satureioides spray-dried powder (SDP80). The thermal and photo stability of this new compound as well as that of the main polyphenols present in the spray dried powder, quercetin, luteolin, 3-O-metylquercetin and the corresponding kinetics of degradation are reported. In the long-term testing (30 +/- 2 degrees C/75 +/- 5% RH, 12 months), the total polyphenols contained in SDP80 demonstrated to be stable, remaining higher than 90% after a 12 month exposure. The photo stability testing revealed that all polyphenols were stable for 48 h when SDP80 was conditioned in amber or transparent flasks and exposed to UV-C radiation (light express LE UV, 254 nm, 30W). In contrast, when unprotected, the polyphenols demonstrated to be sensitive to both, thermal stress testing (80 +/- 2 degrees C), for 14 days and to UV-C radiation. Luteolin showed to be the most stable against UVC light and 3-O-methylquercetin against temperature. The achyrobichalcone demonstrated to be the more unstable against both, temperature and light. The kinetics of polyphenol thermal degradation (80 +/- 2 degrees C, 49 days) and photodegradation (UV-C radiation, 96 h) followed, 2nd and 1st order reaction, respectively.


Asunto(s)
Achyrocline/química , Chalconas/análisis , Chalconas/efectos de la radiación , Cromatografía Líquida de Alta Presión , Desecación , Estabilidad de Medicamentos , Etanol , Calor , Cinética , Luz , Espectroscopía de Resonancia Magnética , Fenoles/análisis , Fenoles/efectos de la radiación , Extractos Vegetales/análisis , Polvos , Estándares de Referencia , Solventes
7.
Fitoterapia ; 78(2): 112-9, 2007 Feb.
Artículo en Inglés | MEDLINE | ID: mdl-17215089

RESUMEN

The aqueous leaves extracts of Passiflora alata (100-300 mg/kg, i.p.) and Passiflora edulis (100-1000 mg/kg, i.p.) possess a significant antiinflammatory activity on carrageenan-induced pleurisy in mice. Treatment with the extracts inhibited leukocyte migration and reduced the formation of exudate. Moreover, a significant inhibition of myeloperoxidase and adenosine-deaminase activities was observed at the doses tested (100 or 250 mg/kg, i.p.). At the same doses, a significant decrease of serum C-reactive protein was observed.


Asunto(s)
Antiinflamatorios no Esteroideos/farmacología , Passiflora , Fitoterapia , Extractos Vegetales/farmacología , Pleuresia/tratamiento farmacológico , Animales , Antiinflamatorios no Esteroideos/administración & dosificación , Antiinflamatorios no Esteroideos/uso terapéutico , Proteína C-Reactiva/efectos de los fármacos , Carragenina , Modelos Animales de Enfermedad , Relación Dosis-Respuesta a Droga , Femenino , Masculino , Ratones , Extractos Vegetales/administración & dosificación , Extractos Vegetales/uso terapéutico , Hojas de la Planta , Pleuresia/sangre , Pleuresia/inducido químicamente
8.
Rev. bras. farmacogn ; 12(2): 85-93, jul.-dez. 2002. ilus, tab
Artículo en Portugués | LILACS | ID: lil-526498

RESUMEN

Os relatos encontrados na literatura científica sobre a composição química e atividades farmacológicas do gênero Pfaffia spp. são apresentados. Os estudos sobre esse gênero são ainda bastante escassos, sendo assim, o uso racional de espécies de Pfaffia, com finalidade terapêutica ainda depende de conhecimento aprofundado de suas propriedades farmacológicas e do desenvolvimento de tecnologias de produção e controle de qualidade.


This review summarizes available chemical and pharmacological data about Pfaffia genre. Scientific studies about these species are still lacking, and their therapeutical rational use depends on the availability of more informations about their pharmacological properties and the development of production and control quality technologies.

9.
Phytother Res ; 15(2): 162-4, 2001 Mar.
Artículo en Inglés | MEDLINE | ID: mdl-11268119

RESUMEN

Several species of the genus Passiflora, known in Brazil as "maracujá", have widespread use in folk medicine as sedatives and tranquillizers. The anxiolytic activity of hydroethanol extracts of P. alata and P. edulis leaves was evaluated using the elevated plus-maze test. The extracts presented anxiolytic activity in dosages around 50, 100 and 150 mg/kg.


Asunto(s)
Ansiolíticos/farmacología , Aprendizaje por Laberinto/efectos de los fármacos , Plantas Medicinales , Rosales , Animales , Relación Dosis-Respuesta a Droga , Masculino , Extractos Vegetales/farmacología , Hojas de la Planta , Ratas , Ratas Wistar
10.
Phytochemistry ; 42(4): 1119-22, 1996 Jul.
Artículo en Inglés | MEDLINE | ID: mdl-8688185

RESUMEN

The structure of matesaponin 5, a novel saponin isolated from the leaves of the Ilex paraguariensis, was established as ursolic acid-3-0-{beta-D-glucopyranosyl-(1->3)-[alpha-L-rhamnopyranosyl-(1->2)]-alpha-L- arabino pyranosyl}-(28->1)-beta-D-glucopyranosyl-(1->4)-beta-D-glucopyranosyl-(1 ->6)-beta-D-glucopyranosyl] ester.


Asunto(s)
Plantas Medicinales , Saponinas/química , Triterpenos , Conformación de Carbohidratos , Secuencia de Carbohidratos , Espectroscopía de Resonancia Magnética , Datos de Secuencia Molecular , Estructura Molecular , Extractos Vegetales , Hojas de la Planta , Saponinas/aislamiento & purificación , América del Sur , Espectrometría de Masa Bombardeada por Átomos Veloces
11.
J Nat Prod ; 58(3): 438-41, 1995 Mar.
Artículo en Inglés | MEDLINE | ID: mdl-7775986

RESUMEN

The leaves of Ilex paraguariensis have yielded three new saponins named matesaponins 2, 3, and 4 [1-3], which have been characterized by chemical and nmr methods as ursolic acid 3-O-[beta-D-glucopyranosyl-(1-->3)-[alpha-L-rhamnopyranosyl- (1-->2)]]-alpha-L-arabinopyranosyl]-(28-->1)-beta-D-glucopyranosyl ester, ursolic acid 3-O-[beta-D-glucopyranosyl-(1-->3)-alpha-L-arabinopyranosyl]-(28-- >1)- [beta-D-glucopyranosyl-(1-->6)-beta-D-glucopyranosyl]ester, and ursolic acid 3-O-[beta-D-glucopyranosyl-(1-->3)-[alpha-L- rhamnopyranosyl-(1-->2)]]-alpha-L-arabinopyranosyl]-(28-->1)-[beta -D- glucopyranosyl-(1-->6)-beta-D-glucopyranosyl]ester, respectively.


Asunto(s)
Plantas Medicinales/química , Saponinas/síntesis química , Saponinas/aislamiento & purificación , Triterpenos/aislamiento & purificación , Acetilación , Secuencia de Carbohidratos , Hidrólisis , Espectroscopía de Resonancia Magnética , Datos de Secuencia Molecular , Hojas de la Planta/química , Saponinas/farmacología , América del Sur , Espectrometría de Masa Bombardeada por Átomos Veloces
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