| [PMID]: | 20533166 |
| [Au] Autor: | Vouffo B; Dongo E; Facey P; Thorn A; Sheldrick G; Maier A; Fiebig HH; Laatsch H |
| [Ad] Dirección: | Department of Organic and Biomolecular Chemistry, University of Göttingen, Göttingen, Germany. |
| [Ti] Título: | Antiarol cinnamate and africanoside, a cinnamoyl triterpene and a hydroperoxy-cardenolide from the stem bark of Antiaris africana. |
| [So] Fuente: | Planta Med;76(15):1717-23, 2010 Oct. |
| [Is] ISSN: | 1439-0221 |
| [Cp] País de publicación: | Germany |
| [La] Idioma: | eng |
| [Ab] Resumen: | From the methanol extract of the stem bark of the African tree Antiaris africana Engler, two new bioactive metabolites were isolated, namely, the α-amyrin derivative 1ß,11α-dihydroxy-3ß-cinnamoyl-α-amyrin (antiarol cinnamate, 1) and a cardiac glycoside, 3ß-O-(α-L-rhamnopyranosyl)-14ß-hydroperoxy-5ß-hydroxy-19-oxo-17ß-card-20(22)-enolide (africanoside, 2a), together with the known compounds ß-amyrin and its acetate, ß-sitosterol and its 3-O-ß-D-glucopyranoside, friedelin, ursolic and oleanolic acid, 19-norperiplogenin, strophanthidol, strophanthidinic acid, periplogenin (3a), 3-epiperiplogenin, strophanthidin (3b) and 3,3'-dimethoxy-4'-O-ß-D-xylopyronosyl-ellagic acid. Their structures were established on the basis of their spectroscopic data and by chemical methods, while 3a was additionally confirmed by X-ray crystal structure analysis. The aglycone moiety possessing a hydroperoxy group was found for the first time in cardenolides. Compounds 1 and 2a showed no activity against bacteria, fungi, and microalgae; however, the crude extract exhibited a high toxicity against Artemia salina and a selective antitumor activity against human tumor cell lines. Africanoside (2a) effected a concentration-dependent inhibition of tumor cell growth with a mean IC(50) value of 5.3 nM. |
| [Mh] Términos MeSH primario: |
Antiaris/química Glicósidos Cardíacos/farmacología Cinamatos/farmacología Citostáticos/farmacología Triterpenos/farmacología
|
| [Mh] Términos MeSH secundario: |
Animales Artemia/efectos de drogas Glicósidos Cardíacos/química Glicósidos Cardíacos/aislamiento & purificación Línea Celular Tumoral Cinamatos/química Cinamatos/aislamiento & purificación Cristalografía por Rayos X Citostáticos/química Citostáticos/aislamiento & purificación Humanos Pruebas de Sensibilidad Microbiana Resonancia Magnética Nuclear Biomolecular Corteza de la Planta/química Extractos Vegetales/química Extractos Vegetales/aislamiento & purificación Extractos Vegetales/farmacología Tallos de la Planta/química Triterpenos/química Triterpenos/aislamiento & purificación
|
| [Pt] Tipo de publicación: | JOURNAL ARTICLE; RESEARCH SUPPORT, NON-U.S. GOV'T |
[Nm] Nombre de substancia:
| 0 (11alpha-dihydroxy-3beta-cinnamoyl-alpha-amyrin); 0 (3beta-O-(alpha-L-rhamnopyranosyl)-14beta-hydroperoxy-5beta-hydroxy-19-oxo-17beta-card-20(22)-enolide); 0 (Cardiac Glycosides); 0 (Cinnamates); 0 (Cytostatic Agents); 0 (Plant Extracts); 0 (Triterpenes) |
| [Em] Mes de ingreso: | 1104 |
| [Sb] Subgrupo de revista: | IM |
| [Da] Fecha de ingreso para procesamiento: | 101025 |
| [St] Status: | MEDLINE |
| [do] DOI: | 10.1055/s-0030-1249958 |