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1.
Fitoterapia ; 169: 105609, 2023 Sep.
Artículo en Inglés | MEDLINE | ID: mdl-37453701

RESUMEN

Five new flavonoid C-glycosides named desmodinosides A-E (1-5) and one known compound, apigenin 6-C-ß-d-xylopyranosyl-2''-O-ß-D-glucopyranoside (6) have been isolated from the methanol extract of the aerial parts of Desmodium heterocarpon var. stigosum. These compounds were determined by 1D and 2D-NMR and HR-MS spectroscopies. The methanol extract of this plant, in particular, demonstrated hepatoprotection and antifungal inhibition. This extract has a remarkable hepatoprotection and activity-dose response with an EC50 of 43.07 µg/mL. The hepatoprotective effect on human liver hepatoma cells (HepG2) of the isolated flavonoid C-glycosides 1-6 was observed. Desmodinosides A-C (1-3) were found to exhibit moderate hepatoprotective activity on HepG2 cells. Of these, compound 2 showed the best hepatoprotective activity with an EC50 value of 74.12 µg/mL. While compounds 1 and 3 displayed EC50 values of 271.21 and 211.99 µg/mL, respectively. Quercetin, a positive control, also caused an EC50 value of 36.42 µg/mL. In addition to having hepatoprotective effect, the methanol extract had an inhibitory effect on the growth of oomycete; it inhibited Phytophthora infestans with IC50 of 13.3 µg/mL and IC90 of 78.7 µg/mL. The oomycete inhibition was directly attributed to compounds 5 and 6, which significantly inhibited P. infestans with IC50 values of 27.4 and 24.7 µg/mL, respectively. Both 5 and 6 and methanol extract were active against P. infestanse in a dose-dependent manner. Our study demonstrated for the first time the new flavonoid C-glycosides from D. heterocarpon var. stigosum and their novel pharmacological properties. The study findings also suggest the plant extract and its metabolites could be used as a new botanical source of bioactive compounds.


Asunto(s)
Antifúngicos , Flavonoides , Humanos , Antifúngicos/farmacología , Metanol , Estructura Molecular , Glicósidos , Extractos Vegetales/química
2.
Z Naturforsch C J Biosci ; 78(5-6): 179-187, 2023 May 25.
Artículo en Inglés | MEDLINE | ID: mdl-35768067

RESUMEN

In the course of finding new antifungal natural compounds against plant pathogens, the methanol extract of Desmodium triflorum was investigated phytochemically. From n-butanol-soluble fraction, seven compounds (1-7) were isolated and structurally elucidated. Of which, six compounds belong to flavone 6- or 8-C-glycoside class (1-6). Three major compounds (1-3) exhibited moderate in vitro antifungal activity against Sclerotium rolfsii, Fusarium oxysporum f. sp. cubense, and Phytophthora palmivora. Compound 1 (IC50 = 162.1 µg/mL) was most active against S. rolfsii in a dose-dependent manner. At 300 µg/mL, compounds 1 and 2 significantly inhibited P. palmivora, whereas compound 3 lacked effectiveness. In addition, the nanoemulsion of the methanol extract with a droplet size of 12.2 nm displayed an excellent inhibition against S. rolfsii and P. palmivora compared with the normal extract. The presence of 1 (0.846%) and 2 (0.759%) in the methanol extract may attribute to the antifungal activity of D. triflorum. These results proved the potential of D. triflorum and its C-glycoside flavonoids against phytopathogenic fungi for the first time. Besides, an enhancement in the effectiveness of nanoemulsion containing D. triflorum extract against the fungi was confirmed. The structural characteristics of 1 and 2 could be considered to develop new fungicidal substances in the future.


Asunto(s)
Fungicidas Industriales , Fusarium , Antifúngicos/farmacología , Metanol , Hongos , Fungicidas Industriales/química , Extractos Vegetales/química
3.
Phytochemistry ; 202: 113300, 2022 Oct.
Artículo en Inglés | MEDLINE | ID: mdl-35798090

RESUMEN

Thirty-three natural products were isolated from the aerial parts of Antidesma bunius, Euphorbiaceae, a plant used in Vietnamese traditional medicine against rheumatoid arthritis. All compounds were reported the first time for this species, and nine constituents resembled undescribed natural products, noticeably three coumarinolignans with 2,2-dimethyl-1,3-dioxolane moiety, two cyclopeptides, and two furofuran-type lignans connected with a phenylpropanoid moiety. The individual structures were elucidated by combining NMR and MS data, and their configuration was established by NOESY and ECD experiments and NMR calculations. Compounds with sufficient amount were analyzed for their inhibition of advanced glycation endproducts (AGEs) formation, metabolites involved in many diseases like Alzheimer, joint diseases or diabetes. With IC50 values below 0.2 mM rutin and p-hydroxyphenethyl trans-ferulate showed to be moderately active, both still being 10-times more active than the positive control aminoguanidine.


Asunto(s)
Productos Biológicos , Euphorbiaceae , Euphorbiaceae/química , Productos Finales de Glicación Avanzada , Componentes Aéreos de las Plantas , Vietnam
4.
Bioorg Chem ; 117: 105445, 2021 12.
Artículo en Inglés | MEDLINE | ID: mdl-34717238

RESUMEN

During an attempt to discover insulin mimetics, thirteen new triterpenoid saponins (1-13), including three phytolaccagenic acids (1, 2, and 12) and ten serjanic acids (3-11 and 13), as aglycones were isolated from a 70% ethanol extract of leaves and stems from Pericampylus glaucus. The chemical structures of compounds 1-13 were determined through spectroscopic data analysis, including NMR, IR, and HRESIMS. All isolated compounds (1-13) were evaluated using 2-deoxy-2-[(7-nitro-2,1,3-benzoxadiazol-4-yl)amino]-d-glucose (2-NBDG) as a fluorescent-tagged glucose probe to determine their stimulatory effects on glucose uptake in differentiated 3 T3-L1 adipocyte cells. Consequently, four compounds (4, 7, 11, and 12) exhibited stimulatory effects on glucose uptake.


Asunto(s)
Hipoglucemiantes/farmacología , Insulina/metabolismo , Menispermaceae/química , Extractos Vegetales/farmacología , Saponinas/farmacología , Triterpenos/farmacología , Células 3T3-L1 , Animales , Relación Dosis-Respuesta a Droga , Glucosa/metabolismo , Hipoglucemiantes/química , Hipoglucemiantes/aislamiento & purificación , Ratones , Estructura Molecular , Extractos Vegetales/química , Extractos Vegetales/aislamiento & purificación , Hojas de la Planta/química , Tallos de la Planta/química , Saponinas/química , Saponinas/aislamiento & purificación , Relación Estructura-Actividad , Triterpenos/química , Triterpenos/aislamiento & purificación
5.
J Nat Prod ; 82(11): 2941-2952, 2019 11 22.
Artículo en Inglés | MEDLINE | ID: mdl-31626544

RESUMEN

Twelve new terpenoids (1-12) were isolated from the stems of Fissistigma polyanthoides, an anti-inflammatory medicinal plant traditionally used in Vietnam. Most of them (1-9) possess a sesquiterpenoid backbone (e.g., guaiane, germacrane, and cadinane) connected to a 2'-O-trans-cinnamoyl)-ß-d-glucopyranose moiety, which is rare in Nature. Among them, compounds 4 (5/8-fused ring) and 6 (spiran [4,5] ring) represent uncommonly rearranged sesquiterpenoids. Compounds 10-12 are a novel monoterpene and two megastigmane derivatives, respectively. The individual structures were elucidated by combining NMR and MS data, and their configuration was established in NOESY and ECD experiments. Compounds 1-9 were also examined for their potential to interact with nuclear factor-kappa B activator protein 1 (NF-κB/AP-1) signaling by using the myelomonocytic reporter cell line THP-1Blue-CD14. Compounds 1-5 showed dose-dependent inhibitory effects [IC50 13.7 µM (1) to 49.0 µM (5)] on lipopolysaccharide-stimulated cells. However, compounds 1 to 4 also negatively affected cell viability in the same concentration range, while compound 5 was less potently cytotoxic.


Asunto(s)
Annonaceae/química , Antiinflamatorios no Esteroideos/química , Antiinflamatorios no Esteroideos/farmacología , Tallos de la Planta/química , Terpenos/química , Terpenos/farmacología , Línea Celular , Supervivencia Celular/efectos de los fármacos , Relación Dosis-Respuesta a Droga , Humanos , Lipopolisacáridos/farmacología , Espectroscopía de Resonancia Magnética , Espectrometría de Masas , Estructura Molecular , Receptor Activador del Factor Nuclear kappa-B/efectos de los fármacos , Sesquiterpenos/química , Sesquiterpenos/farmacología , Vietnam
6.
Fitoterapia ; 137: 104252, 2019 Sep.
Artículo en Inglés | MEDLINE | ID: mdl-31271787

RESUMEN

The stems of Fissistigma polyanthoides (A.DC.) Merr. are traditionally used for the treatment of rheumatism and for recuperating women after childbirth. In our continuous phytochemical investigation of this plant, four new (1, 2, 5, and 19) and fifteen known (3, 4, and 6-18) phenolic compounds were isolated. The structures of all compounds were elucidated based on extensive spectroscopic analyses (1D-, 2D-NMR, and MS), and in comparison with reported literature data. The new natural products showed to be two poly-methoxylated chalcones (1 and 2) and two flavonoid glycosides, with 19 containing an uncommon sugar moiety (quinovose). Compounds with sufficient amount were tested for their anti-oxidant activity in a cell-based assay using the human bronchial epithelial cell line BEAS-2B. The compounds' capacity to inhibit the peroxyl radical triggered formation of dichlorofluorescein (DCF) was investigated in a dose-dependent manner. Both, anti-oxidant (3, 4, 6, 8-12, and 14) and pro-oxidative (5 and 16) properties were found for the investigated substances. The half maximal concentrations (IC50) for the inhibition of ROS formation ranged between 18.8 µM and 63.5 µM. Compounds, which acted protectively in the cellular antioxidant activity (CAA) assay and did not negatively affect cell viability, could be interesting targets for further investigations.


Asunto(s)
Annonaceae/química , Antioxidantes/farmacología , Células Epiteliales/efectos de los fármacos , Fenoles/farmacología , Antioxidantes/aislamiento & purificación , Línea Celular , Chalconas/aislamiento & purificación , Chalconas/farmacología , Glicósidos/aislamiento & purificación , Glicósidos/farmacología , Humanos , Estructura Molecular , Fenoles/aislamiento & purificación , Fitoquímicos/aislamiento & purificación , Fitoquímicos/farmacología , Tallos de la Planta/química , Especies Reactivas de Oxígeno/metabolismo , Vietnam
7.
Molecules ; 24(6)2019 Mar 23.
Artículo en Inglés | MEDLINE | ID: mdl-30909559

RESUMEN

Human African trypanosomiasis (HAT), known as sleeping sickness and caused by Trypanosoma brucei, is threatening low-income populations in sub-Saharan African countries with 61 million people at risk of infection. In order to discover new natural products against HAT, thirty-seven Vietnamese essential oils (EOs) were screened for their activity in vitro on Trypanosoma brucei brucei (Tbb) and cytotoxicity on mammalian cells (WI38, J774). Based on the selectivity indices (SIs), the more active and selective EOs were analyzed by gas chromatography. The anti-trypanosomal activity and cytotoxicity of some major compounds (isolated or commercial) were also determined. Our results showed for the first time the selective anti-trypanosomal effect of four EOs, extracted from three Zingiberaceae species (Curcuma longa, Curcuma zedoaria, and Zingiber officinale) and one Lauraceae species (Litsea cubeba) with IC50 values of 3.17 ± 0.72, 2.51 ± 1.08, 3.10 ± 0.08, and 2.67 ± 1.12 nL/mL respectively and SI > 10. Identified compounds accounted for more than 85% for each of them. Among the five major components of Curcuma longa EO, curlone is the most promising anti-trypanosomal candidate with an IC50 of 1.38 ± 0.45 µg/mL and SIs of 31.7 and 18.2 compared to WI38 and J774 respectively.


Asunto(s)
Curcuma/química , Aceites Volátiles/farmacología , Aceites de Plantas/farmacología , Trypanosoma brucei brucei/efectos de los fármacos , África , África del Norte , Animales , Proliferación Celular/efectos de los fármacos , Cromatografía de Gases y Espectrometría de Masas , Humanos , Mamíferos , Aceites Volátiles/química , Extractos Vegetales/química , Extractos Vegetales/farmacología , Aceites de Plantas/química , Trypanosoma brucei brucei/patogenicidad , Tripanosomiasis Africana/tratamiento farmacológico , Tripanosomiasis Africana/parasitología
8.
J Pharm Biomed Anal ; 149: 66-69, 2018 Feb 05.
Artículo en Inglés | MEDLINE | ID: mdl-29101817

RESUMEN

In Vietnam and China the leaves of Urceola rosea are widely used as herbal remedy and food. However, in contrast to the plants stem, little information was available on major constituents. In this study, the first in-depth phytochemical investigation of U. rosea leaves is described, which resulted in the isolation of thirteen compounds, mainly flavonoids (kaempferol and quercetin derivatives) and triterpenes. Furthermore, an analytical procedure for the quantification of five major compounds was developed. The HPLC separation was performed on a Synergi MAX-RP column using acetonitrile and 0.1% formic acid as mobile phase. Method validation confirmed that the assay shows good linearity (R2≥0.9997), precision (intra-day R.S.D≤4.31%, inter-day R.S.D≤3.52%) and accuracy (recovery rates ranged from 96.8 to 102.6%). Detection limits were always lower than 0.07µg/mL. The analysis of several plant samples revealed distinct differences, as for example the content of total phenolics varied from 0.44 to 1.73%.


Asunto(s)
Apocynaceae/química , Cromatografía Líquida de Alta Presión/métodos , Flavonoides/análisis , Fitoquímicos/análisis , Extractos Vegetales/análisis , Apocynaceae/metabolismo , China , Cromatografía Líquida de Alta Presión/instrumentación , Flavonoides/química , Flavonoides/aislamiento & purificación , Flavonoides/metabolismo , Medicina Tradicional de Asia Oriental/métodos , Fenoles/análisis , Fenoles/química , Fenoles/aislamiento & purificación , Fitoquímicos/química , Fitoquímicos/aislamiento & purificación , Fitoquímicos/metabolismo , Extractos Vegetales/química , Hojas de la Planta/química , Reproducibilidad de los Resultados , Solventes/química , Vietnam
9.
Molecules ; 22(7)2017 Jun 27.
Artículo en Inglés | MEDLINE | ID: mdl-28654013

RESUMEN

Leishmania mexicana is one of the pathogens causing cutaneous leishmaniasis which is associated with patient morbidity. In our researches for new safe and effective treatments, thirty-seven essential oils (EOs) extracted from Vietnamese plants were screened in vitro for the first time on Leishmania mexicana mexicana(Lmm) promastigotes at the maximum concentration of 50 nL/mL. Active EOs were also analyzed for cytotoxicity on mammalian cell lines (WI38, J774) and their selectivity indices (SI) were calculated. Their composition was determined by GC-MS and GC-FID. Our results indicated that EOs extracted from Cinnamomum cassia, Zingiber zerumbet, Elsholtzia ciliata and Amomum aromaticum, possessed a moderate anti-leishmanial activity, with IC50 values of 2.92 ± 0.08, 3.34 ± 0.34, 8.49 ± 0.32 and 9.25 ± 0.64 nL/mL respectively. However, they also showed cytotoxicity with SI < 10. The most promising EO was extracted from Ocimum gratissimum, displaying an IC50 of 4.85 ± 1.65 nL/mL and SI > 10. It contained 86.5% eugenol, which was demonstrated to be effective on Lmm with IC50 of 2.57 ± 0.57 nL/mL and not toxic on mammalian cells, explaining the observed activity.


Asunto(s)
Leishmania mexicana/efectos de los fármacos , Aceites Volátiles/farmacología , Aceites de Plantas/farmacología , Animales , Línea Celular , Supervivencia Celular/efectos de los fármacos , Concentración 50 Inhibidora , Ocimum/química , Aceites Volátiles/química , Aceites Volátiles/toxicidad , Aceites de Plantas/química
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