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La migrastatina y las dorrigocinas son metabolitos de derivación de la isomigrastatina
Jianhua Ju1, Si-Kyu Lim, Hui Jiang
1Division of Pharmaceutical Sciences and Department of Chemistry, University of Wisconsin-Madison, Madison, WI 53705, USA.
Journal of the American Chemical Society
|February 11, 2005
Resumen
Streptomyces platensis produce iso-migrastatin (4), que se convierte en otros compuestos (1-3, 5). Este estudio identifica a la iso-migrastatina como el único producto natural, mientras que otros son metabolitos de derivación formados a través de un reordenamiento mediado por agua.
Área de la Ciencia:
- Microbiología Microbiología.
- Química de Productos Naturales Química de Productos Naturales
- La bioquímica es la bioquímica.
Sus antecedentes:
- Streptomyces platensis NRRL18993 generalmente produce migrastatina, dorrigocina A, dorrigocina B y 13-epi-dorrigocina A. También se encuentra en el género Streptomyces.
- La suplementación con resina XAD-16 altera el resultado de la fermentación, lo que lleva a la producción exclusiva de iso-migrastatina.
Objetivo del estudio:
- Para identificar el verdadero producto natural biosintetizado por S. platensis.
- Para aclarar la relación entre iso-migrastatin y otros compuestos relacionados.
- Para determinar el mecanismo de interconversión entre estos compuestos.
Principales métodos:
- Fermentación de Streptomyces platensis con y sin resina XAD-16.
- Estudios de estabilidad in vitro en soluciones acuosas.
- Análisis estereoquímico de los compuestos.
- Estudios de etiquetado de isótopos utilizando H218O para investigar el mecanismo de reordenamiento.
Principales resultados:
- La fermentación con resina XAD-16 produce exclusivamente iso-migrastatina (4).
- Los compuestos 1, 2, 3 y 5 fueron estables en solución acuosa, mientras que 4 se convirtió rápidamente a ellos.
- La isomigrastatina (4) fue identificada como el único producto natural de buena fe, con 1, 2, 3 y 5 identificados como sus metabolitos de derivación.
- Se estableció la estereoquímica de los compuestos 2-5 con la excepción de C-11 en 3 y 4.
- Se propuso un mecanismo para el reordenamiento regio- y estereospecífico mediado por H2O de 4 a 1, 2, 3 y 5 y fue apoyado por la incorporación de 18O.
Conclusiones:
- Iso-migrastatin (4) es el producto natural primario sintetizado por S. platensis.
- Los otros compuestos identificados (1, 2, 3, 5) se derivan de la iso-migrastatina a través de un proceso de reordenamiento mediado por agua.
- Este estudio aclara la vía biosintética y la interconversión de estos importantes metabolitos microbianos.
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