Obtención de 16 -Dehidroprogesterona a partir de solasodina de frutos maduros de Solanum mammosum
DOI:
https://doi.org/10.17533/udea.vitae.685Abstract
A partir de los frutos maduros de Solanum mammosum, conocido en Colombia con el nombre común de <> ó <>. Y mediante un proceso de extracción con etanoly precipitación con amoniaco se obtuvo la fracción de glicoalcaloides (mezcla de los compuestos 1 y 2, figura 1), con un rendimiento del 4.8%, el cual es superior al reportado por otros estudios en el género Solanum. Un ensayo de hidrólisis ácida de esta fracción produjo una mezcla de solasodina y 3.5-solasodieno (compuestos 3 y 4) en proporción 98:2. Una porción de solasodina (400 mg) se sometió a reflujo con anhídrido acético y piridina, y se obtuvo el correspondiente derivado O,N-diacetilsolasodina, el cual a su vez se sometió a reflujo para producir su isomerización. El producto se oxidó con Cro3, y finalmente se elimino la cadena aciloxílica mediante reflujo con ácido acético glacial para obtener el acetato de 16-dehidropregnenolona. Este producto se hidrolizó con HCI formándose el respectivo derivado con un grupo hidroxilo en el C-3, el cual se oxido con PCC para obtener finalmente la 16-dehidroprogesterona (148.5mg). Todos los productos naturales, los de hidrólisis y los de degradación química se identifica por técnicas espectrales UV. IR. RMN-1H y Espectrometría de Masas (EM).Downloads
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