Biotransformation of two ent-15B-hydroxy-kaur-16-ene derivatives by Gibbewrella fujikuroi
Incubation of the fungus Gibberella fujikuroi with ent-15B-hydroxy-kaur-16-ene gave ent-11a, 15B-dihydroxy-kaur-16-ene, ent-7B,1]a,15B-trihydroxy-kaur-16-ene, ent-11a,13,15B-trihydroxy-kaur-16-ene, ent-11a,15B,19-trihydroxy-kaur-16-ene, and ent-11a,14a,15B-trihydroxy-kaur-16-ene, and a mixture of pr...
| Autores: | , , |
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| Tipo de recurso: | artículo |
| Fecha de publicación: | 1992 |
| País: | España |
| Institución: | Consejo Superior de Investigaciones Científicas (CSIC) |
| Repositorio: | DIGITAL.CSIC. Repositorio Institucional del CSIC |
| OAI Identifier: | oai:digital.csic.es:10261/21924 |
| Acceso en línea: | http://hdl.handle.net/10261/21924 |
| Access Level: | acceso abierto |
| Palabra clave: | Gibberella fujikuroi Diterpenes ent-15B-hydroxy-kaur-16-ene Candidiol Microbiological transformations |
| Sumario: | Incubation of the fungus Gibberella fujikuroi with ent-15B-hydroxy-kaur-16-ene gave ent-11a, 15B-dihydroxy-kaur-16-ene, ent-7B,1]a,15B-trihydroxy-kaur-16-ene, ent-11a,13,15B-trihydroxy-kaur-16-ene, ent-11a,15B,19-trihydroxy-kaur-16-ene, and ent-11a,14a,15B-trihydroxy-kaur-16-ene, and a mixture of products, which was resolved by acetylation to give ent-11a,14a,15B-triacetoxy-kaur-16-ene and ent-7B,15B,17-triacetoxy-11a,16a-epoxy-kaur-16-ene. The addition of candidiol (ent-15B,18-dihydroxy-kaur-16-3n3) gave ent-11a,15B,18-trihydroxy-kaur-16-ene, and a mixture of substances, which was resolved by acetulation to give ent-11B,15B,18-triacetoxy-kaur-16-ene, ent-7B,11a,15B,18-tetraacetoxy-kaur-16-ene and ent-15B,17,18-triacetoxy-11a,16a-epoxykaurane. These results confirm that the presence in ent-kaur-16-ene derivatives of a 15a-hydroxyl group inhibits oxidation at C-19 to the acid level. The biotransformation of these compounds may be useful for the synthesis of natural 11B-hydroxy-ent-kaurene analogues. |
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