JOURNAL OF CHILEAN CHEMICAL SOCIETY

Vol 63 No 4 (2018): Journal of the Chilean Chemical Society
Original Research Papers

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

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  • Eillen Torres,
  • Apolinaria García,
  • Mario Aranda,
  • Vania Saéz,
  • Felipe Zúñiga,
  • Julio Alarcón,
  • Marcia Avello,
  • Edgar Pastene
Eillen Torres
Laboratory of Bacterial Pathogenicity, Department of Microbiology, Faculty of Biological Sciences, University of Concepción
Apolinaria García
Laboratory of Bacterial Pathogenicity, Department of Microbiology, Faculty of Biological Sciences, University of Concepción
Mario Aranda
Laboratory of Mass Spectrometry, Department of Science and Food Technology, Faculty of Pharmacy, University of Concepción
Vania Saéz
Department of Instrumental Analysis, Faculty of Pharmacy, University of Concepción
Felipe Zúñiga
Department of Clinical Chemistry and Immunology, Faculty of Pharmacy, University of Concepción
Julio Alarcón
Laboratory of Synthesis and Natural Products, Department of Basic Sciences, Faculty of Sciences, University of Bío-Bío
Marcia Avello
Laboratory of Pharmacognosy, Department of Pharmacy, Faculty of Pharmacy, University of Concepción
Edgar Pastene
Laboratory of Pharmacognosy, Department of Pharmacy, Faculty of Pharmacy, University of Concepción
Published January 9, 2019
Keywords
  • Centrifugal Partition Chromatography,
  • Helicobacter pylori,
  • avocado,
  • proanthocyanidins,
  • IL-8
How to Cite
Torres, E., García, A., Aranda, M., Saéz, V., Zúñiga, F., Alarcón, J., Avello, M., & Pastene, E. (2019). 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. Journal of the Chilean Chemical Society, 63(4). Retrieved from https://jcchems.com/index.php/JCCHEMS/article/view/920

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Abstract

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.

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