One-step purification of two semi-synthetic epicatechin adducts prepared from avocado peels procyanidins by centrifugal partition chromatography and evaluation of their anti-inflammatory effects on adenocarcinoma gastric cells infected with helicobacter pylori

• Autores: Eillen Torres, Apolinaria García, Mario Aranda-Bustos, Vania Sáez, Felipe Zuñiga, Julio Alarcón, Marcia Avello L, Edgar Pastene
• Localización: Journal of the Chilean Chemical Society (Boletín de la Sociedad Chilena de Química), ISSN-e 0717-6309, ISSN 0366-1644, Vol. 63, Nº. 4, 2018, págs. 4222-4228
• Idioma: inglés
• Enlaces
  • Texto completo
• Resumen

  • Avocado peels were used to extract proanthocyanidins (PACs) as starting material to prepare semi-synthetic derivatives of epicatechin by nucleophilic attack with pyrogallol and resorcinol. One-step isolation of both semi-synthetic derivatives was successfully performed through centrifugal partition chromatography (CPC), and identified by TLC and LC-MS/MS. The effect upon adherence of Helicobacter pylori ATCC 43504 to AGS cells and the subsequent induction of pro-inflammatory IL-8 release was tested for these two semi-synthetic derivatives. Bacterial adherence and IL-8 synthesis was evaluated using AGS cells con-infected with FITC-labeled H. pylori. Concentration of 700 μg/mL of epicatechin-pyrogallol and epicatechin-resorcinol decreased H. pylori adherence to AGS cells to less than 20% and reduced IL-8 production to less than 10%. In conclusion, semi-synthetic adducts prepared from avocado PACs reduce significantly the adherence and IL-8 production in H. pylori-infected AGS cells.