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1.
J Enzyme Inhib Med Chem ; 35(1): 1372-1378, 2020 Dec.
Artículo en Inglés | MEDLINE | ID: mdl-32571102

RESUMEN

Gut microbial ß-glucuronidase (GUS) is a potential therapeutic target to reduce gastrointestinal toxicity caused by irinotecan. In this study, the inhibitory effects of 17 natural cinnamic acid derivatives on Escherichia coli GUS (EcGUS) were characterised. Seven compounds, including caffeic acid ethyl ester (CAEE), had a stronger inhibitory effect (IC50 = 3.2-22.2 µM) on EcGUS than the positive control, D-glucaric acid-1,4-lactone. Inhibition kinetic analysis revealed that CAEE acted as a competitive inhibitor. The results of molecular docking analysis suggested that CAEE bound to the active site of EcGUS through interactions with Asp163, Tyr468, and Glu504. In addition, structure-activity relationship analysis revealed that the presence of a hydrogen atom at R1 and bulky groups at R9 in cinnamic acid derivatives was essential for EcGUS inhibition. These data are useful to design more potent cinnamic acid-type inhibitors of EcGUS.

3.
Molecules ; 23(12)2018 Nov 22.
Artículo en Inglés | MEDLINE | ID: mdl-30467293

RESUMEN

Cytisine-pterocarpan-derived compounds were biomimetically synthesized with (-)-cytisine and (-)-maackiain via a N,N-4-dimethyl-4-aminopyridine (DMAP)-mediated synthetic strategy in a mild manner. In the present study, tonkinensine B (4) was elaborated in good and high yields with the optimized reaction conditions. The in vitro cytotoxicity of compound 4 was evaluated against breast cancer cell lines and showed that 4 had a better cytotoxicity against MDA-MB-231 cells (IC50 = 19.2 µM). Depending on the research on cytotoxicities of 4 against RAW 264.7 and BV2 cells, it was suggested that 4 produced low cytotoxic effects on the central nervous system. Further study indicated that 4 demonstrated cytotoxic activity against MDA-MB-231 cells and the cytotoxic activity was induced by apoptosis. The results implied that the apoptosis might be induced by mitochondrion-mediated apoptosis via regulating the ratio of Bax/Bcl-2 and promoting the release of cytochrome c from the mitochondrion to the cytoplasm in MDA-MB-231 cells.


Asunto(s)
Neoplasias de la Mama/metabolismo , Citocromos c/metabolismo , Compuestos Heterocíclicos con 2 Anillos/síntesis química , Compuestos Heterocíclicos con 2 Anillos/farmacología , Mitocondrias/metabolismo , Alcaloides/química , Animales , Azocinas/química , Mimetismo Biológico , Neoplasias de la Mama/tratamiento farmacológico , Línea Celular Tumoral , Proliferación Celular/efectos de los fármacos , Supervivencia Celular/efectos de los fármacos , Femenino , Compuestos Heterocíclicos con 2 Anillos/química , Humanos , Células MCF-7 , Ratones , Estructura Molecular , Proteínas Proto-Oncogénicas c-bcl-2/metabolismo , Pterocarpanos/química , Quinolizinas/química , Células RAW 264.7 , Proteína X Asociada a bcl-2/metabolismo
4.
Food Res Int ; 99(Pt 1): 755-761, 2017 09.
Artículo en Inglés | MEDLINE | ID: mdl-28784541

RESUMEN

The baobab (Adansonia digitata L.) is a magnificent tree revered throughout Africa and is becoming recognized for its high nutritional and medicinal values. Despite numerous reports on the pharmacological potential, little is known about its chemical compositions. In this study, four hydroxycinnamic acid glycosides (1-4), six iridoid glycosides (5-10), and three phenylethanoid glycosides (11-13) were isolated from the dried baobab fruit pulp. Their structures were determined by means of spectroscopic analyses, including HRMS, 1H and 13C NMR and 2D experiments (COSY, HSQC, HMBC, and ROESY). All 13 compounds isolated were reported for the first time in the genus of Adansonia. An ultra high-performance liquid chromatography high-resolution accurate-mass mass spectrometry (UHPLC HRAM MS) method was used to conduct further investigation of the chemical compositions of the hydro-alcohol baobab fruit pulp extract. Hydroxycinnamic acid glycosides, iridoid glycosides and phenylethanoid glycosides were found to be the main components in baobab fruit pulp.


Asunto(s)
Adansonia/química , Frutas/química , Glicósidos/análisis , Glicósidos Iridoides/análisis , Extractos Vegetales/química , Ácidos Cumáricos/análisis , Alcohol Feniletílico/análisis
5.
Magn Reson Chem ; 55(3): 210-213, 2017 Mar.
Artículo en Inglés | MEDLINE | ID: mdl-27396835

RESUMEN

The structure of a novel compound from Adansonia digitata has been elucidated, and its 1 H and 13 C NMR spectra have been assigned employing a variety of one-dimensional and two-dimensional NMR techniques without degradative chemistry. The Advanced Chemistry Development ACD/Structure Elucidator software was important for determining part of this structure that contained a fused bicyclic system with very few hydrogen atoms, which in turn, exhibited essentially no discriminating HMBC connectivities throughout that portion of the molecule. Copyright © 2016 John Wiley & Sons, Ltd.

6.
Molecules ; 19(2): 2042-8, 2014 Feb 13.
Artículo en Inglés | MEDLINE | ID: mdl-24531219

RESUMEN

A new coumarin, edgeworic acid (1), was isolated from the flower buds of Edgeworthia chrysantha, together with the five known coumarins umbelliferone (2), 5,7-dimethoxycoumarin (3), daphnoretin (4), edgeworoside C (5), and edgeworoside A (6). Their structures were established on the basis of spectral data, particularly by the use of 1D NMR and several 2D shift-correlated NMR pulse sequences (1H-1H COSY, HSQC and HMBC), in combination with acetylation reactions.


Asunto(s)
Cumarinas/química , Flores/química , Thymelaeaceae/química , Acetilación , Cumarinas/aislamiento & purificación , Espectroscopía de Resonancia Magnética , Estructura Molecular , Monosacáridos/química , Monosacáridos/aislamiento & purificación , Raíces de Plantas/química , Umbeliferonas/química , Umbeliferonas/aislamiento & purificación
7.
J Sep Sci ; 36(18): 3101-6, 2013 Sep.
Artículo en Inglés | MEDLINE | ID: mdl-23857918

RESUMEN

This paper extends the research of the utilization of borate coordination complexes in chiral separation by counter-current chromatography (CCC). Racemic propafenone was successfully enantioseparated by CCC with di-n-butyl l-tartrate combined with boric acid as the chiral selector. The two-phase solvent system was composed of chloroform/ 0.05 mol/L acetate buffer pH 3.4 containing 0.10 mol/L boric acid (1:1, v/v), in which 0.10 mol/L di-n-butyl l-tartrate was added in the organic phase. The influence of factors in the enantioseparation of propafenone were investigated and optimized. A total of 92 mg of racemic propafenone was completely enantioseparated using high-speed CCC in a single run, yielding 40-42 mg of (R)- and (S)-propafenone enantiomers with an HPLC purity over 90-95%. The recovery for propafenone enantiomers from fractions of CCC was in the range of 85-90%.


Asunto(s)
Ácidos Bóricos/química , Propafenona/aislamiento & purificación , Tartratos/química , Distribución en Contracorriente , Extracción Líquido-Líquido , Estructura Molecular , Propafenona/química , Estereoisomerismo
8.
Nat Prod Res ; 27(8): 750-2, 2013 Apr.
Artículo en Inglés | MEDLINE | ID: mdl-22720714

RESUMEN

The phytochemical investigation of extracts from the root barks of Lycium chinense yielded a new furolactone-type lignan, lyciumin (1). Its structure and absolute configurations were established on the basis of spectral data, particularly by the use of 1D NMR, 2D shift-correlated NMR pulse sequences ((1)H-(1)H COSY, HSQC, HMBC and ROESY) and CD spectra.


Asunto(s)
Lignanos/aislamiento & purificación , Lycium/química , Medicamentos Herbarios Chinos/química , Lignanos/química , Corteza de la Planta/química , Raíces de Plantas/química
9.
Nat Prod Commun ; 7(10): 1357-8, 2012 Oct.
Artículo en Inglés | MEDLINE | ID: mdl-23157009

RESUMEN

A new norlignan glycoside, named iso-agatharesinoside (2), and its aglycone, iso-agatharesinol (1), were isolated from the tuberous roots of Asparagus cochinchinensis. Their structures were established on the basis of spectral data, particularly by the use of 1D NMR and several 2D shift-correlated NMR pulse sequences (1H-1H COSY, HSQC, HMBC and ROESY).


Asunto(s)
Asparagus (Planta)/química , Lignanos/química , Hidrólisis , Lignanos/aislamiento & purificación , Espectroscopía de Resonancia Magnética , Modelos Moleculares , Raíces de Plantas/química , Espectrometría de Masa por Ionización de Electrospray
10.
Nat Prod Res ; 26(19): 1782-6, 2012.
Artículo en Inglés | MEDLINE | ID: mdl-21923631

RESUMEN

The phytochemical investigation of extracts from the radix of Angelica sinensis yielded a new phthalide dimer, 3,3'Z-6.7',7.6'-diligustilide, along with a known dimer, levistolide A. Their structures were established on the basis of spectral data, particularly using 1D-NMR and several 2D shift-correlated NMR pulse sequences (¹H-¹H COSY, HSQC, HMBC and NOESY).


Asunto(s)
Angelica sinensis/química , Benzofuranos/química , Dimerización , Espectroscopía de Resonancia Magnética , Estructura Molecular , Plantas Medicinales/química
11.
Nat Prod Commun ; 4(6): 813-8, 2009 Jun.
Artículo en Inglés | MEDLINE | ID: mdl-19634328

RESUMEN

A simple, sensitive and specific high-performance liquid chromatography-UV (HPLC-UV) method has been developed to simultaneously quantify the eight major bioactive phenolic compounds in Chinese propolis, namely caffeic acid, isoferulic acid, 3,4-dimethoxycinnamic acid, pinobanksin 5-methyl ether, pinocembrin, benzyl caffeate, chrysin and galangin. This HPLC assay was performed on an Agilent Zorbax Extend-C18 (250 x 4.6 mm, 5 microm) column with a gradient of methanol and 0.2% aqueous acetic acid (v/v) in 50 min, at a flow rate of 1.0 mL/min, and detected at 290 nm. All calibration curves showed good linearity (r2 > 0.999) within the test ranges. The intra- and inter-day assay precision (RSD) of eight phenolic compounds were in the range of 0.07-4.92%. The recoveries were between 98.3% and 104.8%. This assay was applied to the evaluation of nineteen samples from different origins in China. The results indicated that the developed assay could be readily utilized for the quality control of propolis.


Asunto(s)
Cromatografía Líquida de Alta Presión , Fenoles/química , Própolis/química , China , Estructura Molecular
12.
Magn Reson Chem ; 46(9): 898-902, 2008 Sep.
Artículo en Inglés | MEDLINE | ID: mdl-18615626

RESUMEN

The phytochemical investigation of extracts from the roots of Sophora tonkinensis yielded three new isoprenylated flavanones, the tonkinochromanes F (2), G (3), and H (5), along with four known compounds. Structural elucidation of the compounds were established on the basis of spectral data, particularly by the use of 1D NMR and several 2D shift-correlated NMR pulse sequences ((1)H-(1)H COSY, HSQC, HMBC, and ROESY).


Asunto(s)
Flavanonas/química , Flavonoides/química , Espectroscopía de Resonancia Magnética/métodos , Espectroscopía de Resonancia Magnética/normas , Sophora/química , Isótopos de Carbono , Flavanonas/aislamiento & purificación , Flavonoides/aislamiento & purificación , Conformación Molecular , Raíces de Plantas/química , Protones , Estándares de Referencia , Estereoisomerismo
13.
J Nat Prod ; 71(5): 873-6, 2008 May.
Artículo en Inglés | MEDLINE | ID: mdl-18321057

RESUMEN

Four new jatrophane-type diterpenoids (1-4), together with 16 known related compounds, were isolated from the Chinese medicinal plant Euphorbia helioscopia. The structures of 1-4 were determined on the basis of spectroscopic and chemical methods. Cytotoxicity of the isolated compounds against HeLa and MDA-MB-231 cells was evaluated, with only helioscopinolide A (5) and euphornin (3a) being active.


Asunto(s)
Antineoplásicos Fitogénicos/aislamiento & purificación , Antineoplásicos Fitogénicos/farmacología , Diterpenos/aislamiento & purificación , Diterpenos/farmacología , Medicamentos Herbarios Chinos/aislamiento & purificación , Medicamentos Herbarios Chinos/farmacología , Euphorbia/química , Abietanos/farmacología , Antineoplásicos Fitogénicos/química , Diterpenos/química , Ensayos de Selección de Medicamentos Antitumorales , Medicamentos Herbarios Chinos/química , Células HeLa , Humanos , Estructura Molecular
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