| Revista: | Electronic journal of biotechnology |
| Base de datos: | PERIÓDICA |
| Número de sistema: | 000336251 |
| ISSN: | 0717-3458 |
| Autores: | Carvajal, Marcela1 Espinoza, Luis1 Caggia, Silvia2 Cardile, Venera2 Garbarino, Juan A1 Peña Cortés, Hugo3 Russo, Alessandra4 |
| Instituciones: | 1Universidad Técnica Federico Santa María, Departamento de Química, Valparaíso. Chile 2Universita di Catania, Dipartimento di Scienze Fisiologiche, Catania, Sicilia. Italia 3Universidad Técnica Federico Santa María, Centro de Biotecnología "D. Alkalay L.", Valparaíso. Chile 4Universita di Catania, Dipartimento di Chimica Biologica, Chimica Medica e Biologia Moleculare, Catania, Sicilia. Italia |
| Año: | 2011 |
| Periodo: | Mar |
| Volumen: | 14 |
| Número: | 2 |
| País: | Chile |
| Idioma: | Inglés |
| Tipo de documento: | Artículo |
| Enfoque: | Experimental, aplicado |
| Resumen en inglés | Background: Several studies have shown that (-)-Jasmonic acid, (+)-7-iso-Jasmonic acid and its methyl ester, methyl jasmonate, have anti-cancer activity in vitro and in vivo, exhibiting selective cytotoxicity towards cancer cells. The degree of activity of these molecules is strongly related to their stereochemistry. The biotransformation of known compounds, natural or synthesized, related to interesting biological activities, generates new molecules displaying new improved properties compared with the original ones, increasing its value and providing new more effective products. Therefore, based on the above rationales and observations, in this work a biotransformation protocol to modify the chemical structure of the plant hormone jasmonic acid by using the fungus Gibberella fujikuroi was established. Results: The three jasmonic acid derivatives obtained, 3(S)-Hydroxy-2(R)-(2Z-pentenyl)-cyclopentane-1(R)-acetic acid (1), 3(R)-Hydroxy-2(R)-(2Z-pentenyl)-cyclopentane-1(R)-acetic acid (2), 3-Hydroxy-2(S)-(2Z-pentenyl)-cyclopentane-1(S)-acetic acid (3), were tested for cell-growth inhibition activity towards the human cancer epithelial cell line, the oral squamous carcinoma cells (KB). The results obtained show that jasmonic acid derivatives (1-3) are active on human cancer cells examined in different concentration ranges, with IC50 value less than of 25 μM. The compound 3, with the same molecular structure of compounds 1 and 2, but with different stereochemistry, was more active confirming that the activity of jasmonate compounds is related to their stereochemistry and to substituents in the cyclopentane ring. In this study, we also tested the potential proapoptotic activity of compound 3, and our data suggest that it, as other jasmonate compounds, is able to trigger apoptotic death in cancer cells. This event may be correlated at an elevation of reactive oxygen species (ROS). Administration of N-acetylcysteine (NAC) prevented compound 3 cytotoxicity. Conclus |
| Disciplinas: | Medicina, Química |
| Palabras clave: | Bioquímica, Biotecnología, Acido jasmónico, Hidroxilación, Apoptosis, Células cancerosas, Biotransformación |
| Keyword: | Medicine, Chemistry, Biochemistry, Biotechnology, Jasmonic acid, Hydroxylation, Apoptosis, Cancer cells, Biotransformation |
| Texto completo: | Texto completo (Ver PDF) |
