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https://doi.org/10.18502/espoch.v3i1.14418

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authors

  • E. R. Ocaña

    E. R. Ocaña

    Departamento de Química, Universidad Técnica Particular de Loja, Loja, Ecuador
  • M. J. Suárez

    M. J. Suárez

    Departamento de Química, Universidad Técnica Particular de Loja, Loja, Ecuador
  • G. Gilardoni

    G. Gilardoni

    Departamento de Química, Universidad Técnica Particular de Loja, Loja, Ecuador
  • O. G. Malagón

    O. G. Malagón

    Departamento de Química, Universidad Técnica Particular de Loja, Loja, Ecuador
    http://orcid.org/0000-0001-7946-7858

Published Date

  • Nov 9, 2023

Semi-synthetic Derivatives of Limonin A: Synthesis Using Basic Hydrolysis and Reduction with NaBH4

ESPOCH Congresses: The Ecuadorian Journal of S.T.E.A.M. / Volume 3 Issue 1 / Pages 109–120

Abstract

Limonin A (L-A) was obtained from seeds of Citrus sinensis that were dried, grounded, and extracted using Soxhlet equipment. Initially, 100% hexane was used to eliminate fats, and finally, 100% dichloromethane was used in order to concentrate and isolate the compound. L-A recrystallization was performed using acetic acid. The purified fraction was identified as limonin according to spectral nuclear magnetic resonance (NMR) data. Two reactions were performed from L-A: Basic hydrolysis that acted on the A’ lactone ring producing a sodium salt of the lactone, and reduction with NaBH4 to reduce the carbonyl of carbon C-7 and generate the corresponding alcohol limonol. The structural modification of abundant secondary metabolites can become a source of new products with biological activity, useful in the pharmaceutical, cosmetic, and agrochemical industries of natural origin.


Keywords: limonin, semisynthetic derivates, bioactive compounds, non-timber forest products.


Resumen


La limonina A (L-A) se obtuvo a partir de semillas de Citrus sinensis, que fueron secadas, molidas y extraídas en equipo Soxhlet, utilizando inicialmente hexano al 100% para eliminar grasas y finalmente diclorometano al 100% para concentrar y aislar el compuesto. La re cristalización de la L-A se realizó utilizando ácido acético. La fracción purificada se identificó como limonina, acorde a los datos espectrales de RMN (Resonancia Magnética Nuclear). A partir de la Limonina A se realizaron dos reacciones: Hidrólisis básica que actuó sobre el anillo de lactona A’ produciendo la sal sódica de lactona y reducción con NaBH4 para reducir el carbonilo del carbono C-7 y generar el correspondiente alcohol limonol. La modificación estructural de metabolitos secundarios abundantes puede convertirse en una fuente para generar nuevos productos con actividad biológica, útiles en las industrias farmacéutica, cosmética y agroquímica de origen natural.


Palabras Clave: Limonina; derivados semisintéticos, compuestos bioactivos, productos forestales no maderables.

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