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1.
Chem Pharm Bull (Tokyo) ; 54(12): 1694-704, 2006 Dec.
Artículo en Inglés | MEDLINE | ID: mdl-17139105

RESUMEN

The MeOH extract of the fruits of Bupleurum rotundifolium showed inhibitory activity against human gastric adenocarcinoma (MK-1) cell growth. Bioactivity-guided fractionation of the MeOH extract led to the isolation of four new triglycosides of 13beta,28-epoxy oleanane-type triterpenes, named rotundiosides O, Q, S and T; 12 new glycosides of oleanane-type triterpenes, named rotundiosides J-N, P, R, U-Y, and others; echinocystic acid 3-O-sulfate; and three known oleanane-type triterpene glycosides, rotundiosides A, F and G. The structures of the new isolates were determined based on chemical and spectroscopic evidence. The GI(50) of isolates against MK-1, HeLa and B16F10 cell lines are reported.


Asunto(s)
Bupleurum/química , Frutas/química , Glicósidos/química , Glicósidos/farmacología , Triterpenos/química , Triterpenos/farmacología , Antineoplásicos Fitogénicos/química , Antineoplásicos Fitogénicos/farmacología , Línea Celular Tumoral , Humanos , Estructura Molecular , Relación Estructura-Actividad
2.
Biol Pharm Bull ; 28(1): 173-5, 2005 Jan.
Artículo en Inglés | MEDLINE | ID: mdl-15635187

RESUMEN

The antiproliferative constituents in the MeOH extract from the aerial parts of Centella asiatica were investigated. Activity-guided fractionation of MeOH extract resulted in the isolation of ursolic acid lactone, ursolic acid, pomolic acid, 2alpha,3alpha-dihydroxyurs-12-en-28-oic acid, 3-epimaslinic acid, asiatic acid, corosolic acid, and rosmarinic acid. Antiproliferative activity of the isolated compounds against human gastric adenocarcinoma (MK-1), human uterine carcinoma (HeLa), and murine melanoma (B16F10) cells was estimated.


Asunto(s)
Proliferación Celular/efectos de los fármacos , Centella , Cinamatos/farmacología , Inhibidores de Crecimiento/farmacología , Triterpenos/farmacología , Apiaceae , Cinamatos/química , Cinamatos/aislamiento & purificación , Depsidos , Inhibidores de Crecimiento/química , Inhibidores de Crecimiento/aislamiento & purificación , Células HeLa , Humanos , Extractos Vegetales/química , Extractos Vegetales/aislamiento & purificación , Extractos Vegetales/farmacología , Triterpenos/química , Triterpenos/aislamiento & purificación , Ácido Rosmarínico
3.
Bioorg Med Chem ; 13(2): 443-8, 2005 Jan 17.
Artículo en Inglés | MEDLINE | ID: mdl-15598565

RESUMEN

(+)-1(R)-Coclaurine (1) and (-)-1(S)-norcoclaurine (3), together with quercetin 3-O-beta-D-glucuronide (4), were isolated from the leaves of Nelumbo nucifera (Nymphaceae), and identified as anti-HIV principles. Compounds 1 and 3 demonstrated potent anti-HIV activity with EC50 values of 0.8 and <0.8 microg/mL, respectively, and therapeutic index (TI) values of >125 and >25, respectively. Compound 4 was less potent (EC50 2 microg/mL). In a structure-activity relationship study, other benzylisoquinoline, aporphine, and bisbenzylisoquinoline alkaloids, including liensinine (14), negferine (15), and isoliensinine (16), which were previously isolated from the leaves and embryo of Nelumbo nucifera, were evaluated for anti-HIV activity. Compounds 14-16 showed potent anti-HIV activities with EC50 values of <0.8 microg/mL and TI values of >9.9, >8.6, and >6.5, respectively. Nuciferine (12), an aporphine alkaloid, had an EC50 value of 0.8 microg/mL and TI of 36. In addition, synthetic coclaurine analogs were also evaluated. Compounds 1, 3, 12, and 14-16 can serve as new leads for further development of anti-AIDS agents.


Asunto(s)
Alcaloides/química , Fármacos Anti-VIH/química , Isoquinolinas/química , Nelumbo/química , Quercetina/análogos & derivados , Quercetina/química , Tetrahidroisoquinolinas/química , Alcaloides/aislamiento & purificación , Alcaloides/farmacología , Animales , Fármacos Anti-VIH/aislamiento & purificación , Fármacos Anti-VIH/farmacología , Línea Celular , VIH-1/efectos de los fármacos , Isoquinolinas/farmacología , Estructura Molecular , Hojas de la Planta/química , Quercetina/farmacología , Relación Estructura-Actividad , Tetrahidroisoquinolinas/farmacología
4.
Chem Pharm Bull (Tokyo) ; 51(4): 365-72, 2003 Apr.
Artículo en Inglés | MEDLINE | ID: mdl-12672986

RESUMEN

The MeOH extract of the fruits of Bupleurum rotundifolium showed inhibitory activity against human gastric adenocarcinoma (MK-1) cell growth (GI(50): 6.25 microg/ml). From this extract, 10 new ursane-type triterpene glycosides viz. three 3-O-triosides (called rotundifoliosides A, I, and J) of 13beta,28-epoxy-3beta,16alpha-dihydroxyurs-11-ene, two (G and H) of 13beta,28-epoxy-3beta,16alpha,23-trihydroxyurs-11-ene, two (E and F) of 13beta,28-epoxy-3beta,16alpha,21beta-trihydroxyurs-11-ene, two (B and C) of 3beta,11alpha,16alpha,28-tetrahydroxyurs-12-ene, and one (D) of 3beta,11alpha,28-trihydroxy-15alpha,16alpha-epoxyurs-12-ene were isolated in addition to 16 new oleanane-type triterpene glycosides (rotundiosides J-Y), echinocystic acid 3-O-sulfate and 3 known oleanane-type triterpene glycosides (rotundiosides A, F and G). The isolation, structures and antiproliferative activity of the new ursane-type triterpene glycosides against MK-1, human uterus carcinoma (HeLa), and murine melanoma (B16F10) cell lines are described with some comments on the structural requirements for their activity.


Asunto(s)
Bupleurum , Frutas , Inhibidores de Crecimiento/farmacología , Ácido Oleanólico/análogos & derivados , Ácido Oleanólico/farmacología , Saponinas/farmacología , Animales , Apiaceae , Inhibidores de Crecimiento/química , Inhibidores de Crecimiento/aislamiento & purificación , Humanos , Ratones , Ácido Oleanólico/química , Ácido Oleanólico/aislamiento & purificación , Extractos Vegetales/química , Extractos Vegetales/aislamiento & purificación , Extractos Vegetales/farmacología , Saponinas/química , Saponinas/aislamiento & purificación , Células Tumorales Cultivadas/efectos de los fármacos , Células Tumorales Cultivadas/fisiología
5.
Phytochemistry ; 62(4): 643-6, 2003 Feb.
Artículo en Inglés | MEDLINE | ID: mdl-12560040

RESUMEN

Two polyacetylene glycosides, lobetyol 9-O-glc(6)-(1)rha (pratialin-A) and lobetyol 9-O-glc(6)-(1)glc(6)-(1)glc (pratialin-B), were isolated from Pratia nummularia (Campanulaceae) callus and hairy root cultures and their chemical structures were determined by analysis of spectroscopic data. From the methanol extract of the hairy root cultures, together with the known polyacetylene constituents lobetyol, lobetyolin, and lobetyolinin, tryptophan was also isolated. This report is the first example of the isolation and structure elucidation of rutinoside (pratialin-A) and triglucoside (pratialin-B) derivatives of polyacetylene constituents.


Asunto(s)
Acetileno/análogos & derivados , Acetileno/química , Campanulaceae/química , Disacáridos/aislamiento & purificación , Alcoholes Grasos/aislamiento & purificación , Glicósidos/aislamiento & purificación , Polímeros/química , Trisacáridos/aislamiento & purificación , Disacáridos/química , Alcoholes Grasos/química , Glicósidos/química , Espectroscopía de Resonancia Magnética , Estructura Molecular , Raíces de Plantas/química , Poliinos , Tailandia , Trisacáridos/química
6.
J Nat Prod ; 65(11): 1582-7, 2002 Nov.
Artículo en Inglés | MEDLINE | ID: mdl-12444680

RESUMEN

Production and accumulation of catechin dimer quinones during tea fermentation were chemically confirmed for the first time by trapping as phenazine derivatives. Direct treatment of the fermented tea leaves with o-phenylenediamine yielded five phenazine derivatives (8-12) of o-quinones of an epigallocatechin dimer and its galloyl esters (13-16), in which two flavan units were linked at the B-rings through a C-C bond. Atrop isomerism of the biphenyl bonds was shown to be the R configuration, suggesting that the o-quinone dimers were generated by stereoselective coupling of monomeric quinones. The total concentration of the phenazine derivatives in the o-phenylenediamine-treated tea leaves was higher than that of theaflavins. In contrast, phenazine derivatives of monomeric quinones of epigallocatechin were not isolated. When the fermented tea leaves were heated, the quinone dimers were converted to theasinensins, which are constituents of black tea, suggesting that theasinensins are generated by reduction of the quinone dimers during the heating and drying steps in black tea manufacturing.


Asunto(s)
Camellia sinensis/química , Catequina/análogos & derivados , Catequina/química , Catequina/metabolismo , Fenazinas/química , Té/química , Té/metabolismo , Catequina/aislamiento & purificación , Cromatografía Líquida de Alta Presión , Fermentación , Hidrólisis , Japón , Metilación , Conformación Molecular , Estructura Molecular , Resonancia Magnética Nuclear Biomolecular , Oxidación-Reducción , Hojas de la Planta/química , Plantas Medicinales/química , Quinonas/química , Quinonas/metabolismo
7.
Chem Pharm Bull (Tokyo) ; 50(8): 1035-40, 2002 Aug.
Artículo en Inglés | MEDLINE | ID: mdl-12192133

RESUMEN

A further investigation of the leaves and stems of Saprosma scortechinii afforded 13 compounds, of which 10 are new compounds. These were elucidated as the bis-iridoid glucosides, saprosmosides G (1) and H (2), the iridoid glucoside, 6-O-epi-acetylscandoside (3), and the anthraquinones, 1-methoxy-3-hydroxy-2-carbomethoxy-9,10-anthraquinone (4), 1-methoxy-3-hydroxy-2-carbomethoxy-9,10-anthraquinone 3-O-beta-primeveroside (5), 1,3-dihydroxy-2-carbomethoxy-9,10-anthraquinone 3-O-beta-primeveroside (6), 1,3,6-trihydroxy-2-methoxymethyl-9,10-anthraquinone (7), 1-methoxy-3,6-dihydroxy-2-hydroxymethyl-9,10-anthraquinone (8), 1,3,6-trihydroxy-2-hydroxymethyl-9,10-anthraquinone 3-O-beta-primeveroside (9), and 3,6-dihydroxy-2-hydroxymethyl-9,10-anthraquinone (10). Structure assignments for all compounds were established by means of mass and NMR spectroscopies, chemical methods, and comparison with published data. The new anthraquinones were derivatives of munjistin and lucidin.


Asunto(s)
Antraquinonas/aislamiento & purificación , Iridoides/aislamiento & purificación , Rubiaceae , Antraquinonas/química , Iridoides/química , Malasia , Extractos Vegetales/química , Extractos Vegetales/aislamiento & purificación , Hojas de la Planta/química , Tallos de la Planta/química , Plantas Medicinales/química , Rubiaceae/química
8.
J Nat Prod ; 65(5): 656-60, 2002 May.
Artículo en Inglés | MEDLINE | ID: mdl-12027736

RESUMEN

Six new sulfur-containing bis-iridoid glucosides, saprosmosides A-F (1-6), were isolated from the leaves of Saprosma scortechinii. From the stems of this same plant, two new iridoid glucosides, 3,4-dihydro-3-methoxypaederoside (8) and 10-O-benzoyldeacetylasperulosidic acid (12), were isolated. Their structures were elucidated by means of chemical, NMR, and mass spectroscopic methods. Additionally, 11 known iridoid glucosides were isolated and characterized as deacetylasperuloside, asperuloside, paederoside (7), deacetylasperulosidic acid (9), scandoside, asperulosidic acid, 10-acetylscandoside, paederosidic acid (10), 6-epi-paederosidic acid (11), methylpaederosidate, and monotropein. The structures of the new bis-iridoid glucosides were formed by intermolecular esterification between the glucose and carboxyl groups of three monomeric iridoid glucosides (7, 9, and 10).


Asunto(s)
Glucósidos/aislamiento & purificación , Plantas/química , Piranos/aislamiento & purificación , Rubiaceae/química , Azufre/química , Glucósidos/química , Hidrólisis , Iridoides , Malasia , Estructura Molecular , Resonancia Magnética Nuclear Biomolecular , Hojas de la Planta/química , Tallos de la Planta/química , Piranos/química , Espectroscopía Infrarroja por Transformada de Fourier , Estereoisomerismo
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