Lipase-catalysed esters synthesis of cafestol and kahweol

Fábio Junior Moreira Novaes, Ivaldo Itabaiana Junior, Felipe Korbus Sutili, Philip John Marriott, Humberto Ribeiro Bizzo, Francisco Radler de Aquino Neto, Rodrigo Octávio Mendonça Alves de Souza, Claudia Moraes Rezende

Research output: Contribution to journalArticleResearchpeer-review

Abstract

Cafestol and kahweol (C&K), two coffee diterpene alcohols with structural similarity which exhibit anticarcinogenic effects, were isolated from green coffee Arabica beans, followed by their lipase-catalysed esterification and purification by preparative high-performance liquid chromatography (HPLC). The isolation and enzymatic synthesis parameters of C&K esters were studied, with the latter optimised by a Central Composite Design; both procedures were monitored by gas chromatography. Scale up and improved isolation conditions resulted in 1.29 g of C&K, with 98% purity from 300 g of green Arabica beans. The highest C&K ester yields were observed using an alcohol:fatty acid molar ratio of 1:5, 73.3 mg mL−1 of CAL-B enzyme, 70 °C and 240 rpm for 3 days in toluene, leading to 85–88% conversion among a variety of tested C&K esters, including n-C14:0-C20:0, C18:1, C18:2 and C18:3.

Original languageEnglish
Pages (from-to)226-233
Number of pages8
JournalFood Chemistry
Volume259
DOIs
Publication statusPublished - 1 Sep 2018

Keywords

  • Cafestol
  • Cafestol ester
  • Coffee diterpenes
  • Ester synthesis
  • Kahweol
  • Kahweol ester
  • Lipase catalyst
  • Preparative scale isolation

Cite this

Novaes, F. J. M., Itabaiana Junior, I., Sutili, F. K., Marriott, P. J., Bizzo, H. R., Aquino Neto, F. R. D., ... Rezende, C. M. (2018). Lipase-catalysed esters synthesis of cafestol and kahweol. Food Chemistry, 259, 226-233. https://doi.org/10.1016/j.foodchem.2018.03.111