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1.
Fitoterapia ; 137: 104268, 2019 Sep.
Artículo en Inglés | MEDLINE | ID: mdl-31306720

RESUMEN

Solanum nigrum L. (also called as European black nightshade) has been traditionally used as folk medicine and food in some regions. Phytochemical investigations of the immature fruits of S. nigrum yielded five steroidal alkaloid glycosides (1-5), including an unprecedented nor-spirosolane type steroidal alkaloid with a five-membered ring A (1) and two novel spirosolane type steroidal alkaloid glycosides (2, 3), together with eight known phenolic compounds (6-13). Their structures were elucidated on the basis of spectroscopic and chemical methods, including IR, NMR, HR-ESI-MS, and GC analyses. Five steroidal alkaloid glycosides were tested for their potential antiproliferative effects against HL-60, U-937, Jurkat, K562, and HepG2 cell lines and inhibitory activities on nitric oxide (NO) production induced by lipopolysaccharide (LPS) in a macrophage cell line RAW 264.7. Compound 1 exhibited significant inhibition on NO production with an IC50 value of 23.4 ±â€¯2.0 µM, compared to positive control indomethacin (IC50, 47.40 ±â€¯4.50 µM). Compound 4 exhibited significant cytotoxicity against all tested cell lines.


Asunto(s)
Alcaloides/farmacología , Glicósidos/farmacología , Solanum nigrum/química , Esteroides/farmacología , Alcaloides/aislamiento & purificación , Animales , Antiinflamatorios/aislamiento & purificación , Antiinflamatorios/farmacología , Antineoplásicos Fitogénicos/aislamiento & purificación , Antineoplásicos Fitogénicos/farmacología , Línea Celular Tumoral , China , Frutas/química , Glicósidos/aislamiento & purificación , Humanos , Ratones , Estructura Molecular , Óxido Nítrico/metabolismo , Fitoquímicos/aislamiento & purificación , Fitoquímicos/farmacología , Extractos Vegetales/química , Células RAW 264.7 , Esteroides/aislamiento & purificación
2.
Steroids ; 148: 11-18, 2019 08.
Artículo en Inglés | MEDLINE | ID: mdl-31026467

RESUMEN

Phytochemical investigations on the bulbs of Chinese onion led to the isolation of three new furostanol saponins (1, 2, 5) together with seven known furostanol saponins (3, 4, 6-10). Their chemical structures were elucidated on the basis of spectroscopic and chemical methods, including IR, MS, NMR, and GC analyses. The anti-proliferative and anti-inflammatory activities of the isolates were evaluated. Compounds 7-10 showed potential anti-proliferative activities against human cancer cell lines (HepG2, A549, SPC-A-1, MGC80-3, MDA-MB-231, SW620 and CNE-1) with IC50 values below 30 µM. Compounds 4 and 7 could induce G2/M cell-cycle arrest and apoptosis through mitochondria-mediate pathway in HepG2 cells. Compounds 7 and 10 showed strong inhibitory effects against LPS induced NO production in RAW264.7 cells with IC50 values of 2.01 ±â€¯1.40 µM and 2.49 ±â€¯1.54 µM, respectively.


Asunto(s)
Antiinflamatorios/farmacología , Antineoplásicos Fitogénicos/farmacología , Apoptosis/efectos de los fármacos , Mitocondrias/efectos de los fármacos , Cebollas/química , Saponinas/farmacología , Animales , Antiinflamatorios/química , Antiinflamatorios/aislamiento & purificación , Antineoplásicos Fitogénicos/química , Antineoplásicos Fitogénicos/aislamiento & purificación , Puntos de Control del Ciclo Celular/efectos de los fármacos , Línea Celular , Proliferación Celular/efectos de los fármacos , Supervivencia Celular/efectos de los fármacos , Relación Dosis-Respuesta a Droga , Ensayos de Selección de Medicamentos Antitumorales , Células Hep G2 , Humanos , Lipopolisacáridos/antagonistas & inhibidores , Lipopolisacáridos/farmacología , Ratones , Mitocondrias/metabolismo , Conformación Molecular , Óxido Nítrico/antagonistas & inhibidores , Óxido Nítrico/biosíntesis , Células RAW 264.7 , Saponinas/química , Saponinas/aislamiento & purificación , Relación Estructura-Actividad
3.
Phytomedicine ; 42: 83-89, 2018 Mar 15.
Artículo en Inglés | MEDLINE | ID: mdl-29655701

RESUMEN

BACKGROUND: Our previous study has revealed that the spirostanol saponins isolated from the rhizomes of Rohdea chinensis (Baker) N. Tanaka (synonym Tupistra chinensis Baker) (Convallariaceae) (a reputed folk medicine) exhibited potent antiproliferative activity. However, the underlying mechanism of purified saponins remains unclear. More studies are necessary to assess the apoptosis and autophagy activities of the saponins from R. chinensis and clarify their antiproliferative mechanisms. PURPOSE: The present study certificated the potential antiproliferative activity and mechanism of 5ß-spirost-25(27)-en-1ß,3ß-diol-1-O-α-L-rhamnopyranosyl-(1→2)- ß-D-xylopyranosyl-3-O-α-L-rhamnopyranoside (SPD), a spirostanol saponin from R. chinensis, against human acute promyelocytic leukemia cells (HL-60). METHODS: The antiproliferative activity of SPD in vitro was evaluated by MTT assay compared with cis-dichlorodiammineplatinum (II). The autophagic activity was assessed using MDC staining and western blot, cell apoptosis inspection was detected by Annexin V-FITC/PI double staining and the mitochondrial membrane potential was detected by JC-1 fluorescence dye combined with flow cytometry. The potential mechanisms for protein levels of apoptosis and autophagy were evaluated by western blot. RESULTS: Treatment of HL-60 cells with SPD resulted in growth inhibition (IC50 value of 2.0 ± 0.2 µM, after 48 h treatment) and induction of apoptosis and autophagy. Results from Annexin V-FITC/PI double-staining assay and mitochondrial membrane potential detection showed that apoptosis was happened after SPD treatment. The regulation of caspase-3, Bax, Bcl-2, PARP following SPD treatment contributed to the induction of mitochondria-dependent apoptosis. Meanwhile, SPD induced autophagy related with Akt/mTOR/p70S6K signaling and activated of AMPK signaling pathway. Furthermore, blocking autophagy with bafilomycin A1 reduced the cytotoxicity of SPD in HL-60 cells. CONCLUSION: The antiproliferative, apoptosis and pro-death autophagy activities of SPD suggested that spirostanol saponins from R. chinensis would be a potential cytotoxic candidate against acute promyelocytic leukemia.


Asunto(s)
Antineoplásicos Fitogénicos/farmacología , Autofagia/efectos de los fármacos , Saponinas/farmacología , Espirostanos/farmacología , Antineoplásicos Fitogénicos/química , Apoptosis/efectos de los fármacos , Caspasa 3/metabolismo , Ensayos de Selección de Medicamentos Antitumorales , Células HL-60 , Humanos , Potencial de la Membrana Mitocondrial/efectos de los fármacos , Proteínas Proto-Oncogénicas c-akt/metabolismo , Rizoma/química , Saponinas/química , Espirostanos/química , Serina-Treonina Quinasas TOR/metabolismo
4.
Fitoterapia ; 121: 229-234, 2017 Sep.
Artículo en Inglés | MEDLINE | ID: mdl-28782581

RESUMEN

Four new phenylpropanoids (1-4) along with ten known phenolics were isolated and purified from the roots of hairy fig (Ficus hirta Vahl.). Their structures were elucidated by the extensive spectroscopic analysis and chemical degradation. The anti-inflammatory activities of the purified compounds were evaluated. Results indicated that the extracts and some purified compounds exhibited pronounced inhibitory effects on the lipopolysaccharides (LPS) induced nitric oxide (NO) production in murine macrophage RAW 264.7 compared to indomethacin, which suggested that hairy fig could be served as an anti-inflammatory agent for health products.


Asunto(s)
Antiinflamatorios/farmacología , Ficus/química , Macrófagos/efectos de los fármacos , Fenoles/farmacología , Animales , Antiinflamatorios/aislamiento & purificación , Ratones , Estructura Molecular , Óxido Nítrico/metabolismo , Fenoles/aislamiento & purificación , Extractos Vegetales/química , Raíces de Plantas/química , Células RAW 264.7
5.
Phytochemistry ; 143: 81-86, 2017 Nov.
Artículo en Inglés | MEDLINE | ID: mdl-28780427

RESUMEN

Six previously undescribed piperidine alkaloids were isolated from the rhizomes of Alocasia macrorrhiza (L.) Schott. Their structures were elucidated based on 1D and 2D NMR, IR, HR-ESI-MS spectroscopic analysis and the application of a modified Mosher method. All isolated alkaloids were evaluated for cytotoxicity against five human cancer cell lines (CNE-1, Detroit 562, Fadu, MGC-803, and MCF-7) using the MTT method. Only one compound exhibited cytotoxic effects against Detroit 562, Fadu, and MCF-7 cell lines with IC50 values less than 10 µM.


Asunto(s)
Alcaloides/aislamiento & purificación , Alocasia/química , Antineoplásicos Fitogénicos/aislamiento & purificación , Medicamentos Herbarios Chinos/aislamiento & purificación , Piperidinas/aislamiento & purificación , Alcaloides/química , Alcaloides/farmacología , Antineoplásicos Fitogénicos/química , Antineoplásicos Fitogénicos/farmacología , Medicamentos Herbarios Chinos/química , Medicamentos Herbarios Chinos/farmacología , Humanos , Células MCF-7 , Estructura Molecular , Resonancia Magnética Nuclear Biomolecular , Piperidinas/química , Piperidinas/farmacología , Rizoma/química
6.
J Agric Food Chem ; 65(21): 4262-4272, 2017 May 31.
Artículo en Inglés | MEDLINE | ID: mdl-28486801

RESUMEN

Solanum nigrum L. or European black nightshade (Solanum genus) is a common weed of crops and gardens. The berries and leaves of S. nigrum L. are consumed as food or vegetable in some regions and reported to possess a range of biological activities. In this study, nine new steroidal saponins, solanigrosides Y1-Y9 (1-6, 10-12), together with seven known congeners, were isolated from the berries of S. nigrum. Their potential inhibitory effects on nitric oxide (NO) and IL-6 and IL-1ß production induced by lipopolysaccharide (LPS) in macrophages cell line RAW 264.7 were evaluated. Compound 1 exhibited significant inhibition on NO production with an IC50 value of 9.7 µM, and some compounds exhibited significant inhibition effects on the LPS-induced IL-6 and IL-1ß production. These results suggest that the steroidal saponins from berries of S. nigrum demonstrated pronounced anti-inflammatory activity and might be explored as a healthy benefit agent.


Asunto(s)
Antiinflamatorios/análisis , Extractos Vegetales/análisis , Saponinas/análisis , Solanum nigrum/química , Animales , Antiinflamatorios/farmacología , Frutas/química , Interleucina-6/inmunología , Macrófagos/efectos de los fármacos , Macrófagos/inmunología , Ratones , Óxido Nítrico/inmunología , Extractos Vegetales/farmacología , Células RAW 264.7 , Saponinas/farmacología
7.
Phytomedicine ; 28: 10-18, 2017 May 15.
Artículo en Inglés | MEDLINE | ID: mdl-28478808

RESUMEN

BACKGROUND: Harmine, a ß-carboline alkaloid from Peganum harmala, has multiple anti-tumor activities, especially for its folk therapy for digestive system neoplasm. However, the underlying mechanism of harmine on gastric cancer remains unclear. PURPOSE: To illuminate the potential anti-tumor activity and mechanism of harmine against gastric cancer cells. METHODS/STUDY DESIGNS: The anti-proliferative activity of harmine in vitro was evaluated by MTT assay. The autophagic activity induced by harmine was assessed using GFP-LC3 transfection. FITC/PI double staining was applied for the apoptosis inspection. The mitochondrial membrane potential was detected by JC-1 fluorescence probe. The potential mechanisms for proteins level in autophagy and apoptosis were analyzed by Western blot. RESULTS: Harmine exhibited potent effects on both autophagy and apoptosis. Treatment with harmine could enhance dots of GFP-LC3 in cells. Meanwhile, the process had connection with Beclin-1, LC3-II, and p62 by the inhibition of Akt/mTOR/p70S6K signaling. However, high concentration of harmine led to apoptosis characterized by the propidium/Annexin V-positive cell pollution, cell shrunk and the collapse of mitochondrial membrane potential. The regulation of Bcl-2, Bax and the gathering of cleaved-PARP, cleaved-caspase 3 and cleaved-caspase 9 contributed to the induction of apoptosis. In addition, 10µM LY294002 (a specific inhibitor of PI3K/Akt) combination with 40µM harmine significantly increased the cytotoxicity to the gastric cancer cells and up-regulated both the apoptosis-related protein (cleaved-PARP, cleaved-caspase-3) and autophagy-related protein (Beclin-1, LC3-II, and p62). Adding the inhibitor of autophagy, 3-MA or BafA1, increased the viability of harmine-exposured gastric cancer cells, which confirmed the role of autophagy played in the gastric cancer cell death induced by harmine. CONCLUSION: Harmine might be a potent inducer of apoptosis and autophagy, which offered evidences to therapy of harmine in gastric carcinoma in the folk medicine.


Asunto(s)
Antineoplásicos Fitogénicos/farmacología , Autofagia/efectos de los fármacos , Harmina/farmacología , Neoplasias Gástricas/tratamiento farmacológico , Apoptosis/efectos de los fármacos , Proteínas Reguladoras de la Apoptosis/metabolismo , Beclina-1/metabolismo , Caspasa 3/metabolismo , Caspasa 9/metabolismo , Línea Celular Tumoral , Ensayos de Selección de Medicamentos Antitumorales/métodos , Humanos , Potencial de la Membrana Mitocondrial/efectos de los fármacos , Fosfatidilinositol 3-Quinasas/metabolismo , Transducción de Señal/efectos de los fármacos , Neoplasias Gástricas/metabolismo , Neoplasias Gástricas/patología
8.
Fitoterapia ; 117: 126-132, 2017 Mar.
Artículo en Inglés | MEDLINE | ID: mdl-28161134

RESUMEN

Five new lignanamides (1-5), and one new monoindole alkaloid (6), along with eight known compounds (7-14) were isolated and identified from the rhizomes of Alocasia macrorrhiza (giant taro). All purified compounds were evaluated for their inhibitory effects on lipopolysaccharide (LPS)-induced nitric oxide (NO) production in RAW 264.7 cells, and the antiproliferative activities against human nasopharyngeal carcinoma epithelial (CNE-1), human gastric carcinoma (MGC-803), and human breast cancer (MCF-7) cell lines by MTT method. Compounds 2, 4, 7 and 8 exhibited significant inhibitory effects on NO production with the IC50 values of 2.35±0.38, 9.20±0.94, 3.45±0.39 and 7.96±0.56µM, respectively. The results suggested the lignanamides and monoindoles might be responsible for the anti-inflammatory activity of giant taro and might be potential anti-inflammatory candidates.


Asunto(s)
Alocasia/química , Antiinflamatorios/química , Indoles/química , Lignanos/química , Animales , Antiinflamatorios/aislamiento & purificación , Antineoplásicos Fitogénicos/química , Antineoplásicos Fitogénicos/aislamiento & purificación , Línea Celular Tumoral , Humanos , Indoles/aislamiento & purificación , Lignanos/aislamiento & purificación , Lipopolisacáridos , Ratones , Estructura Molecular , Óxido Nítrico/metabolismo , Células RAW 264.7 , Rizoma/química
9.
J Agric Food Chem ; 64(40): 7475-7480, 2016 Oct 12.
Artículo en Inglés | MEDLINE | ID: mdl-27643634

RESUMEN

Mango (Mangifera indica L.) is a succulent tropical fruit. Bioactive phytochemical investigation has been carried out to the leaves of mango. Three new benzophenone glycosides, along with 14 known compounds, were purified and identified. The novel benzophenones were elucidated to be 2,4,4',6-tetrahydroxy-3'-methoxybenzophenone-3-C-ß-d-glucopyranoside (1), 4,4',6-trihydroxybenzophenone-2-O-α-l-arabinofuranoside (7), and 4',6-dihydroxy-4-methoxybenzophenone-2-O-(2″),3-C-(1″)-1″-desoxy-α-l-fructofuranoside (11). The α-glucosidase inhibitory, NO production inhibitory, and antioxidant activities were assessed for the purified benzophenones and triterpenoids. Some benzophenones showed moderate α-glucosidase and NO inhibitory activities. The IC50 value of the α-glucosidase inhibitory of isolated compounds 1, 13, and 14 were 284.93 ± 20.29, 239.60 ± 25.00, and 297.37 ± 8.12 µM, respectively. Most compounds showed moderate effects to reduce the NO content in 50 and 100 µM. The above results of bioactivity powerfully demonstrated the phytochemicals from mango, especially benzophenones, probably partially rational for its antidiabetes and anti-inflammatory.


Asunto(s)
Benzofenonas/farmacología , Inhibidores de Glicósido Hidrolasas/farmacología , Mangifera/química , Óxidos de Nitrógeno/metabolismo , Animales , Antiinflamatorios no Esteroideos/química , Antiinflamatorios no Esteroideos/farmacología , Antioxidantes/química , Antioxidantes/farmacología , Benzofenonas/química , Línea Celular , Evaluación Preclínica de Medicamentos/métodos , Inhibidores de Glicósido Hidrolasas/química , Macrófagos/efectos de los fármacos , Espectroscopía de Resonancia Magnética , Ratones , Estructura Molecular , Hojas de la Planta/química , alfa-Glucosidasas/metabolismo
10.
Sci Rep ; 6: 31633, 2016 08 17.
Artículo en Inglés | MEDLINE | ID: mdl-27530890

RESUMEN

Tupistra chinensis is widely distributed in southwestern China and its rhizome is a famous folk medicine for the treatment of carbuncles and pharyngitis. Its chemical identity of potent antiproliferative and anti-inflammatory constituents has been carried out in this study. Twenty-three polyhydroxylated spirostanol saponins, including nine novels, were isolated and identified. The new spirostanol saponins were elucidated as spirost-25(27)-en-1ß,2ß,3ß,4ß,5ß-pentol-2-O-ß-D-xylopyranoside (1), spirost-25(27)- en-1ß,2ß,3ß,4ß,5ß-pentol-2-O-α-L-arabinopyranoside (2), spirost-25(27)-en- 1ß,3α,5ß-triol (12), spirost-25(27)-en-1ß,3α,4ß,5ß,6ß-pentol (13), spirost-25(27)-en- 1ß,2ß,3ß,5ß-tetraol-5-O-ß-D-glucopyranoside (16), 5ß-spirost-25(27)-en-1ß,3ß-diol- 3-O-ß-D-glucopyranosyl-(1 → 4)-ß-D-glucopyranoside (17), (25R)-5ß-spirostan- 1ß,3ß-diol-3-O-ß-D-glucopyranosyl-(1 → 6)-ß-D-glucopyranoside (18), (25R)-5ß- spirostan-1ß,3ß-diol-3-O-ß-D-fructofuranosyl-(2 → 6)-ß-D-glucopyranoside (19), 5ß-spirost-25(27)-en-3ß-ol-3-O-ß-D-glucopyranosyl-(1 → 4)-ß-D-glucopyranoside (20). The antiproliferative effects against seven human cancer cell lines and inhibitory activities on nitric oxide (NO) production induced by lipopolysaccharide (LPS) in a macrophage cell line RAW 264.7 were assayed for all the isolated compounds. Compounds 17, 19 and 21 exhibited potential antiproliferative activities against all of human cancer cell lines tested. Compounds 21 showed significant inhibition on NO production with IC50 values of 11.5 µM. These results showed that the spirostanol saponins isolated from the dried rhizomes of T. chinensis have potent antiproliferative and anti-inflammatory activities and T. chinensis might be used as anticancer and.anti-inflammatory supplement.


Asunto(s)
Antiinflamatorios/farmacología , Antineoplásicos Fitogénicos/farmacología , Asparagaceae/química , Saponinas/farmacología , Espirostanos/farmacología , Antiinflamatorios/aislamiento & purificación , Antineoplásicos Fitogénicos/aislamiento & purificación , Línea Celular Tumoral , Proliferación Celular/efectos de los fármacos , China , Medicamentos Herbarios Chinos/aislamiento & purificación , Medicamentos Herbarios Chinos/farmacología , Células Hep G2 , Humanos , Células K562 , Espectroscopía de Resonancia Magnética , Estructura Molecular , Óxido Nítrico/biosíntesis , Plantas Medicinales/química , Rizoma/química , Saponinas/aislamiento & purificación , Espirostanos/aislamiento & purificación
11.
Int J Nanomedicine ; 9: 1347-65, 2014.
Artículo en Inglés | MEDLINE | ID: mdl-24648733

RESUMEN

Near-infrared fluorescence (NIRF) imaging is an attractive modality for early cancer detection with high sensitivity and multi-detection capability. Due to convenient modification by conjugating with moieties of interests, NIRF probes are ideal candidates for cancer targeted imaging. Additionally, the combinatory application of NIRF imaging and other imaging modalities that can delineate anatomical structures extends fluorometric determination of biomedical information. Moreover, nanoparticles loaded with NIRF dyes and anticancer agents contribute to the synergistic management of cancer, which integrates the advantage of imaging and therapeutic functions to achieve the ultimate goal of simultaneous diagnosis and treatment. Appropriate probe design with targeting moieties can retain the original properties of NIRF and pharmacokinetics. In recent years, great efforts have been made to develop new NIRF probes with better photostability and strong fluorescence emission, leading to the discovery of numerous novel NIRF probes with fine photophysical properties. Some of these probes exhibit tumoricidal activities upon light radiation, which holds great promise in photothermal therapy, photodynamic therapy, and photoimmunotherapy. This review aims to provide a timely and concise update on emerging NIRF dyes and multifunctional agents. Their potential uses as agents for cancer specific imaging, lymph node mapping, and therapeutics are included. Recent advances of NIRF dyes in clinical use are also summarized.


Asunto(s)
Colorantes Fluorescentes/uso terapéutico , Nanopartículas/uso terapéutico , Neoplasias/diagnóstico , Neoplasias/terapia , Animales , Antineoplásicos/administración & dosificación , Sistemas de Liberación de Medicamentos , Colorantes Fluorescentes/química , Humanos , Nanopartículas del Metal/química , Nanopartículas del Metal/uso terapéutico , Ratones , Nanomedicina , Nanopartículas/química , Nanotecnología/tendencias , Fotoquimioterapia , Fototerapia , Puntos Cuánticos/química , Puntos Cuánticos/uso terapéutico , Espectroscopía Infrarroja Corta
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