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1.
Food Chem X ; 19: 100826, 2023 Oct 30.
Artículo en Inglés | MEDLINE | ID: mdl-37780250

RESUMEN

This study aims to analysis the structures of polysaccharides isolated from Pteridium revolutum and their antioxidant and antiglycated activities. Three novel water-soluble heteropolysaccharides, named PRP0, PRP1, and PRP2, were isolated from P. revolutum. The average molecular weight was determined by high performance gel permeation chromatography analysis as 1.04 × 106, 8.39 × 105, and 7.37 × 105 Da, respectively. Their structures were characterized using physicochemical and spectroscopic methods. The antioxidant and antiglycated activities were assayed in vitro. PRP0, PRP1, and PRP2 consist of l-Ara, l-Rha, d-Man, d-Xyl, d-Fuc, d-Gal, and d-Glc in different proportions. PRP1 mainly has a backbone of (1 â†’ 3,6)-linked d-Man and (1 â†’ 3)-linked d-Gal on main chain. PRP2 is mainly composed of (1 â†’ 2,4)-linked d-Man and (1 â†’ 3)-linked d-Gal on main chain. All polysaccharides have strong scavenging power on 2,2-difenil-1-picril-hidrazil and hydroxyl radicals and significantly antiglycated activity in Bovine serum albumin-Glucose model, which showing that the polysaccharides have potential application value on the functional food.

2.
Foods ; 11(13)2022 Jun 22.
Artículo en Inglés | MEDLINE | ID: mdl-35804650

RESUMEN

Pteridium aquilinum (L.) Kuhn (Pteridaceae family) has been widely used as a food and medicine in China and Korea. Previous studies indicate that P. aquilinum contains a variety of bioactive chemical components such as flavonoids, phenols, terpenoids, saponins, polysaccharides, and so on. In the present study, a novel polysaccharide (named as PAP-3) with average molecular weight of 2.14 × 105 Da was obtained from P. aquilinum. The structure was studied through physicochemical and spectroscopic analysis. The results indicated that PAP-3 consists of arabinose, rhamnose, fucose, galactose, mannose, and xylose in a molar ratio of 1.58:1.00:3.26:4.57:4.81:3.33. The polysaccharide is mainly composed of (1→2)-linked xylose and (1→3,6)-linked mannose on the main chain, with (1→2)-linked xylose, (1→6)-linked mannose, and (1→6)- and (1→3,6)-linked galactose as side chains. Galactose, fucose, and xylose are located at the end of the side chains. The in vitro immunomodulatory and antioxidant activities were assayed. PAP-3 has strong free-radical scavenging activity on DPPH and ABTS radicals and significant immunomodulatory activity on RAW264.7 cells. These data provide useful information for further study on the polysaccharides of P. aquilinum and their applications in the food and medical industries.

3.
Nat Prod Res ; 35(6): 945-950, 2021 Mar.
Artículo en Inglés | MEDLINE | ID: mdl-31135215

RESUMEN

Premna fulva Craib, locally known as "Zhangu" in China, is a kind of traditional medicinal plant. A phytochemical investigation on this plant led to the isolation of a novel flavonoid glycoside along with three known analogues. The chemical structure of the new compound was determined by spectral and chemical analysis as apigenin 8-C-ß-D-xylopyranoside (1). Compound 1 showed weak inhibitory activities in vitro against to four tumor cell lines (HL-60, Bcap37, SMMC7721, and P388) with IC50 values of 12.58, 19.31, 31.02, and 48.19 µg/mL, respectively. The result might be helpful to explain the application of P. fulva in Traditional Chinese Medicine.[Figure: see text].


Asunto(s)
Flavonoides/farmacología , Glicósidos/farmacología , Lamiaceae/química , Antineoplásicos Fitogénicos/farmacología , Apigenina/farmacología , Espectroscopía de Resonancia Magnética con Carbono-13 , Muerte Celular/efectos de los fármacos , Línea Celular Tumoral , China , Flavonoides/química , Glicósidos/química , Humanos , Fitoquímicos/química , Fitoquímicos/farmacología , Extractos Vegetales/química , Plantas Medicinales/química , Prohibitinas , Espectroscopía de Protones por Resonancia Magnética
4.
Mini Rev Med Chem ; 20(12): 1101-1117, 2020.
Artículo en Inglés | MEDLINE | ID: mdl-29189150

RESUMEN

Withanolides are a group of highly oxygenated steroids derived from a C28 ergostane skeleton, and have attracted significant scientific interest due to their complex structural features and multiple bioactivities. More than 170 new natural withanolides were isolated and identified in the last 5 years. This review provides a comprehensive summary of the structural, biological and pharmacological activities of these new compounds.


Asunto(s)
Antiinfecciosos/química , Witanólidos/química , Animales , Antozoos/química , Antozoos/metabolismo , Antiinfecciosos/farmacología , Citocinas/metabolismo , Datura/química , Datura/metabolismo , Ergosterol/análogos & derivados , Ergosterol/química , Macrófagos/citología , Macrófagos/efectos de los fármacos , Macrófagos/metabolismo , Conformación Molecular , Withania/química , Withania/metabolismo
5.
Int J Biol Macromol ; 133: 564-574, 2019 Jul 15.
Artículo en Inglés | MEDLINE | ID: mdl-31004640

RESUMEN

Dendrobium devonianum has been used as herbal medicines and nutraceutical products since ancient time in China. However, its chemical composition and pharmacological mechanisms are not fully known. In present studies, by chemical purification and characteristic identification, we discovered a novel polysaccharide from D. devonianum, which was designated as DvP-1 with molecular weights of 9.52 × 104 Da. DvP-1 is a homogeneous heteropolysaccharide consisting of D-mannose and d-glucose in the molar ration of 10.11: 1. The main glycosidic linkages were ß-1, 4-Manp, which were substituted with acetyl groups at the O-2, O-3 and/or O-6 positions. DvP-1 was found to directly stimulate the activation of macrophages in vitro, as evidenced by inducing morphologic change, thereby promoting the production of cytokines TNF-α, IL-6 and NO, and enhancing the pinocytic activity of macrophages. By establishing a zebrafish model, we also found that DvP-1 could alleviate vinorelbine-induced decrease of macrophages in vivo. Further findings indicated that DvP-1 activated macrophages through several toll-like receptors (TLRs), but mainly through TLR4. DvP-1 served as a TLR4 agonist and induced ERK, JNK, p38, and IκB-α phosphorylation, suggesting the activation of MAPK and NFκB signaling pathways downstream of TLR4. These findings could help us further understand the immunomodulating effects of D. devonianum in Chinese medicines or health foods for immunocompromised persons. They also show the medicinal value of DvP-1 for the treatment of cancer and infectious diseases caused by TLR4 dysfunction.


Asunto(s)
Dendrobium/química , Macrófagos/efectos de los fármacos , Macrófagos/inmunología , Polisacáridos/farmacología , Receptor Toll-Like 4/agonistas , Animales , Proliferación Celular/efectos de los fármacos , Citocinas/biosíntesis , Macrófagos/citología , Ratones , Monosacáridos/análisis , Polisacáridos/química , Células RAW 264.7 , Bazo/inmunología , Vinorelbina/farmacología , Pez Cebra
6.
Phytochemistry ; 154: 73-76, 2018 Oct.
Artículo en Inglés | MEDLINE | ID: mdl-30006090

RESUMEN

Three undescribed aporphine alkaloids laurodionine B (1), illigerine A (2), and N-formyl-laurolitsine (3) were isolated from the methanolic extracts of the Chinese medicinal plant, Illigera aromatica, together with three known analogues (4-6). The chemical structures of 1-6 were identified by spectroscopic methods including 1D and 2D NMR (1H, 13C, COSY, HSQC, and HMBC) and high resolution mass spectrometry (HRESIMS). Compounds 1-3 showed moderate inhibitory activities in vitro against two cultured tumor cell lines, Hela and SMMC7721, with IC50 values of 32.42-62.90 µM. Only compound 1 had in vitro cytotoxic activity against Bcap37 cells, with the IC50 value of 90.61 µM.


Asunto(s)
Antineoplásicos Fitogénicos/farmacología , Aporfinas/farmacología , Medicamentos Herbarios Chinos/farmacología , Hernandiaceae/química , Antineoplásicos Fitogénicos/química , Antineoplásicos Fitogénicos/aislamiento & purificación , Aporfinas/química , Aporfinas/aislamiento & purificación , Proliferación Celular/efectos de los fármacos , China , Relación Dosis-Respuesta a Droga , Ensayos de Selección de Medicamentos Antitumorales , Medicamentos Herbarios Chinos/química , Medicamentos Herbarios Chinos/aislamiento & purificación , Humanos , Medicina Tradicional China , Estructura Molecular , Relación Estructura-Actividad , Células Tumorales Cultivadas
7.
Mini Rev Med Chem ; 18(19): 1590-1602, 2018.
Artículo en Inglés | MEDLINE | ID: mdl-29692245

RESUMEN

Aporphine alkaloids, characterized by a heterocyclic aromatic basic skeleton, are known from different organisms and exhibit various biological activities: anti-tumor, anti-viral, anti-microbial, anti-inflammatory etc. The review gives information which provides an overview of the latest progress in the structural diversity and the biological activity of the aporphine alkaloids with their derivatives isolated from natural resource in recent years. Additionally, the synthetic approaches of aporphine alkaloids have also been reviewed.


Asunto(s)
Alcaloides/farmacología , Aporfinas/farmacología , Alcaloides/síntesis química , Alcaloides/química , Antiinfecciosos/síntesis química , Antiinfecciosos/química , Antiinfecciosos/farmacología , Antineoplásicos/síntesis química , Antineoplásicos/química , Antineoplásicos/farmacología , Aporfinas/síntesis química , Aporfinas/química , Isomerismo , Estructura Molecular
8.
Mini Rev Med Chem ; 18(13): 1072-1094, 2018.
Artículo en Inglés | MEDLINE | ID: mdl-29512458

RESUMEN

Recently, the marine-derived Aspergillus present as producers of a large number of structurally novel secondary metabolites. Some of these metabolites have shown antitumor, antimicrobial, anti-inflammatory, antioxidant and enzymatic activities, and may be promising resources for new therapeutic drugs. This review sums up 232 new bioactive metabolites from the marine-derived Aspergillus with classification through their biological activities and chemical structures in 2006-2016. Besides, structure-activity relationships of some compounds are explored.


Asunto(s)
Antiinfecciosos/química , Antioxidantes/química , Aspergillus/química , Terpenos/química , Acetilcolinesterasa/química , Acetilcolinesterasa/metabolismo , Antiinfecciosos/aislamiento & purificación , Antiinfecciosos/farmacología , Antioxidantes/aislamiento & purificación , Aspergillus/metabolismo , Supervivencia Celular/efectos de los fármacos , Bacterias Gramnegativas/efectos de los fármacos , Bacterias Grampositivas/efectos de los fármacos , Humanos , Agua de Mar/microbiología , Terpenos/aislamiento & purificación
9.
Chem Biodivers ; 14(7)2017 Jul.
Artículo en Inglés | MEDLINE | ID: mdl-28434194

RESUMEN

Bioassay-guided phytochemical investigation of the stalks of Microtropis triflora Merr. & F.L. Freeman led to the isolation of ten triterpenes 1 - 10, including one novel compound 3,24-epoxy-2α,24-dihydroxyfriedelan-29-oic acid (1). Their chemical structures were identified on the basis of spectroscopic analysis, including HR-ESI mass spectrometry, 1D- and 2D-NMR (1 H, 13 C, 1 H,1 H-COSY, HSQC, HMBC, and NOESY), and by comparison with the data reported. The cytotoxicities of compounds 1 - 10 against a panel of cultured human tumor cell lines (Bcap37, SMMC7721, HeLa, CNE) were evaluated. The new compound 1 showed moderate anti-tumor activities with IC50 values of 39.22, 29.24, 23.28, and 68.81 µm/ml, respectively. These results might be helpful for explaining the use of M. triflora in traditional medicine. Triterpenes are characteristic of Microtropis genus and could be useful as potential chemotaxonomic markers.


Asunto(s)
Antineoplásicos Fitogénicos/aislamiento & purificación , Celastraceae/química , Triterpenos/aislamiento & purificación , Antineoplásicos Fitogénicos/química , Antineoplásicos Fitogénicos/farmacología , Línea Celular Tumoral , Citotoxinas/aislamiento & purificación , Humanos , Espectroscopía de Resonancia Magnética , Estructura Molecular , Fitoquímicos/aislamiento & purificación , Prohibitinas , Espectrometría de Masa por Ionización de Electrospray , Triterpenos/química , Triterpenos/farmacología
10.
Chem Biodivers ; 14(1)2017 Jan.
Artículo en Inglés | MEDLINE | ID: mdl-27585089

RESUMEN

An unusual tetrahydrofuran lignin, zanthplanispine (1), together with 14 known lignans (2 - 15) were isolated from the AcOEt-soluble fraction from the MeOH extract of Z. planispinum roots. The structures of 1 was elucidated on the basis of 1D- and 2D-NMR experiments as well as HR-ESI-MS analysis. The known compounds were identified by the comparison of their NMR data with previously reported in the literatures. Bioassay showed that compounds 1 - 4 could inhibit nitric oxide (NO) production in lipopolysaccharide (LPS) stimulated RAW 264.7 cells. In particular, compound 1 showed significant inhibitory activity with an IC50 value of 36.8 µm.


Asunto(s)
Lignanos/química , Zanthoxylum/química , Animales , Antiinflamatorios/química , Antiinflamatorios/aislamiento & purificación , Antiinflamatorios/farmacología , Furanos , Concentración 50 Inhibidora , Lignanos/aislamiento & purificación , Lignanos/farmacología , Ratones , Óxido Nítrico/antagonistas & inhibidores , Extractos Vegetales/química , Raíces de Plantas/química , Células RAW 264.7
11.
Phytochemistry ; 122: 294-300, 2016 Feb.
Artículo en Inglés | MEDLINE | ID: mdl-26790964

RESUMEN

Phytochemical investigation of the aerial parts of Chimonanthus salicifolius resulted in the isolation of two sesquiterpenoids, 8α-hydroxy-T-muurolol and (1α,6ß,7ß)-cadinane-4-en-8α,10α-diol, together with 13 known compounds. The 15 structures were established by means of 1D and 2D NMR spectroscopy. The relative and absolute configurations of 8α-hydroxy-T-muurolol and 8α,11-elemodiol were achieved by NOESY experiments and X-ray crystallography using CuKα radiation. 8α-hydroxy-T-muurolol and (1α,6ß,7ß)-cadinane-4-en-8α,10α-diol showed immunosuppressive activities in a dose-dependent manner.


Asunto(s)
Calycanthaceae/química , Sesquiterpenos/química , Terpenos/química , Cristalografía por Rayos X , Resonancia Magnética Nuclear Biomolecular , Sesquiterpenos Policíclicos , Estereoisomerismo
12.
Mini Rev Med Chem ; 14(4): 370-91, 2014 Apr.
Artículo en Inglés | MEDLINE | ID: mdl-24552269

RESUMEN

In recent years, mangrove endophytic fungi are increasingly attracting attention of the pharmaceutical community as they produce a wide variety of metabolites that are structurally unique and pharmacologically active. Previous chemical investigation of mangrove fungi resulted in the discovery of various bioactive secondary metabolites including terpenes, chromones, coumarins, polyketides, alkaloids and peptides with diverse structural features. The present report reviews the papers, which have appeared in the literature till now, concerning the isolation, structural elucidation, and biological activities of the secondary metabolites from mangrove endophytic fungi.


Asunto(s)
Productos Biológicos/química , Hongos/química , Alcaloides/química , Alcaloides/aislamiento & purificación , Alcaloides/farmacología , Animales , Apoptosis/efectos de los fármacos , Productos Biológicos/aislamiento & purificación , Productos Biológicos/farmacología , Cromonas/química , Cromonas/aislamiento & purificación , Cromonas/farmacología , Cumarinas/química , Cumarinas/aislamiento & purificación , Cumarinas/farmacología , Hongos/metabolismo , Humanos , Péptidos/química , Péptidos/aislamiento & purificación , Péptidos/farmacología , Policétidos/química , Policétidos/aislamiento & purificación , Policétidos/farmacología , Terpenos/química , Terpenos/aislamiento & purificación , Terpenos/farmacología
13.
Magn Reson Chem ; 51(7): 435-8, 2013 Jul.
Artículo en Inglés | MEDLINE | ID: mdl-23630063

RESUMEN

Complete and unambiguous (1)H and (13)C NMR chemical shift assignments for all-trans-retinal, 13-cis-retinal, 11-cis-retinal and 9-cis-retinal (1-4) have been established by means of two-dimensional COSY, HSQC, HMBC and NOESY spectroscopic experiments.


Asunto(s)
Espectroscopía de Resonancia Magnética , Retinaldehído/química , Diterpenos , Estructura Molecular
14.
Nat Prod Res ; 27(6): 568-73, 2013.
Artículo en Inglés | MEDLINE | ID: mdl-22533633

RESUMEN

The methanol extract of the tubers of Polygonum perfoliatum L. afforded a new lignan: 8-oxo-pinoresinol (1), and five known compounds 3',5-dihydroxy-3,4',5',7-tetramethoxy-flavone (2), catechin (3), quercetin (4), quercetin-3-O-ß-D-glucuronide (5) and rutin (6). Their structures were established by MS, one- and two-dimensional NMR experiments. Compound 1 showed cytotoxicity against human mammary carcinoma (Bcap-37), human colon carcinoma (RKO), human hepatocellular carcinoma (SMMC-7721), human prostate carcinoma (PC3) and human erythroleukaemia (K562) cells.


Asunto(s)
Antineoplásicos/química , Antineoplásicos/farmacología , Lignanos/química , Lignanos/farmacología , Polygonum/química , Línea Celular Tumoral , Supervivencia Celular/efectos de los fármacos , Flavonas/química , Humanos , Extractos Vegetales/química , Extractos Vegetales/farmacología , Quercetina/análogos & derivados , Quercetina/química
15.
Yao Xue Xue Bao ; 47(5): 619-23, 2012 May.
Artículo en Chino | MEDLINE | ID: mdl-22812006

RESUMEN

An unusual novel C27-steroidal glycoside sulfate was isolated from the underground organs of Liriope graminifolia (Linn.) Baker with three known compounds. Their chemical structures were determined by spectral analysis, including HR-MS, 1D and 2D NMR as (25S)-ruscogenin 1-sulfate-3-O-alpha-L-rhamnopyranoside (1), (25S)-ruscogenin 1-O-beta-D-xylopyranosyl-3-O-alpha-L-rhamnopyranoside (2), hesperidin (3), and 4', 7-dihydroxy-5-methoxyflavanone (4). Compound 1 has cytotoxic activities against K562 and HL60 cells with IC50 values of 18.6 microg x mL(-1) and 16.5 microg x mL(-1), respectively.


Asunto(s)
Antineoplásicos Fitogénicos/aislamiento & purificación , Medicamentos Herbarios Chinos/aislamiento & purificación , Glicósidos/aislamiento & purificación , Liriope (Planta)/química , Espirostanos/aislamiento & purificación , Antineoplásicos Fitogénicos/química , Antineoplásicos Fitogénicos/farmacología , Proliferación Celular/efectos de los fármacos , Medicamentos Herbarios Chinos/química , Medicamentos Herbarios Chinos/farmacología , Glicósidos/química , Glicósidos/farmacología , Células HL-60 , Hesperidina/química , Hesperidina/aislamiento & purificación , Hesperidina/farmacología , Humanos , Concentración 50 Inhibidora , Células K562 , Tubérculos de la Planta/química , Plantas Medicinales/química , Espirostanos/química , Espirostanos/farmacología
16.
J Asian Nat Prod Res ; 13(3): 260-4, 2011 Mar.
Artículo en Inglés | MEDLINE | ID: mdl-21409689

RESUMEN

A new abietane diterpenoid, (3S,16R)-12,16-epoxy-3,6,11,14,17-pentahydroxy-17(15 â†’ 16)-abeo-5,8,11,13-abietatetraen-7-one (1), was isolated from the stems of Clerodendrum kaichianum Hsu, together with four known diterpenoids. The structures of the isolated compounds were assigned on the basis of their NMR spectra including 2D NMR techniques such as COSY, HMQC, and HMBC experiments, and were compared with those of the literature data. This new compound showed significant cytotoxicity against the HL-60 and A-549 tumor cell lines.


Asunto(s)
Abietanos/química , Abietanos/aislamiento & purificación , Antineoplásicos Fitogénicos/química , Antineoplásicos Fitogénicos/aislamiento & purificación , Clerodendrum/química , Medicamentos Herbarios Chinos/química , Medicamentos Herbarios Chinos/aislamiento & purificación , Abietanos/farmacología , Antineoplásicos Fitogénicos/farmacología , Ensayos de Selección de Medicamentos Antitumorales , Medicamentos Herbarios Chinos/farmacología , Células HL-60 , Humanos , Estructura Molecular , Resonancia Magnética Nuclear Biomolecular
17.
Carbohydr Res ; 346(2): 253-8, 2011 Feb 01.
Artículo en Inglés | MEDLINE | ID: mdl-21163470

RESUMEN

Phytochemical investigation of the underground parts of Liriope graminifolia (Linn.) Baker resulted in the isolation of two new steroidal saponins lirigramosides A (1) and B (2) along with four known compounds. The structures were determined by extensive spectral analysis, including two-dimensional (2D) NMR spectroscopy and chemical methods, to be 3-O-[ß-d-xylopyranosyl-(1→3)-α-l-arabinopyranosyl-(1→2)-[α-l-rhamnopyranosyl-(1→4)]-ß-d-glucopyranosyl-(25S)-spirost-5-ene-3ß,17α-diol (1), 1-O-[α-l-rhamnopyranosyl-(1→2)-ß-d-xylopyranosyl]-(25R)-ruscogenin (2), 1-O-ß-d-xylopyranosyl-3-O-α-l-rhamnopyranosyl-(25S)-ruscogenin (3), 3-O-α-l-rhamnopyranosyl-1-O-sulfo-(25S)-ruscogenin (4), methylophiopogonanone B (5), and 5,7-dihydroxy-3-(4-methoxybenzyl)-6-methyl-chroman-4-one, (ophiopogonanone B, 6), respectively. Compound 1 has a new (25S)-spirost-5-ene-3ß,17α-diol ((25S)-pennogenin) aglycone moiety. The isolated compounds were evaluated for their cytotoxic activities against Hela and SMMC-7721 cells.


Asunto(s)
Antineoplásicos/química , Antineoplásicos/farmacología , Liliaceae/química , Saponinas/química , Saponinas/farmacología , Esteroides/química , Esteroides/farmacología , Antineoplásicos/aislamiento & purificación , Secuencia de Carbohidratos , Células HeLa , Humanos , Datos de Secuencia Molecular , Saponinas/aislamiento & purificación , Esteroides/aislamiento & purificación
19.
J Asian Nat Prod Res ; 12(4): 293-9, 2010 Apr.
Artículo en Inglés | MEDLINE | ID: mdl-20419540

RESUMEN

A profiling analysis of the total isoflavone extract of the root of Pueraria lobata (Wild.) Ohwi was performed using HPLC coupled with ESI-ion trap mass spectrometry. A total of seven isoflavones were identified according to their retention times, UV, MS data, and comparing with the literature data. Among them, two proposed new compounds were isolated and their structures were determined to be 8-C-alpha-glucofuranosyl-7,4'-dihydroxyisoflavone and 8-C-beta-glucofuranosyl-7,4'-dihydroxyisoflavone, named as neopuerarin A (7) and neopuerarin B (6), on the basis of chemical and spectral analyses.


Asunto(s)
Medicamentos Herbarios Chinos/aislamiento & purificación , Glucósidos/aislamiento & purificación , Isoflavonas/aislamiento & purificación , Pueraria/química , Cromatografía Líquida de Alta Presión , Medicamentos Herbarios Chinos/química , Glucósidos/química , Isoflavonas/química , Espectrometría de Masas , Estructura Molecular , Raíces de Plantas/química , Estereoisomerismo
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