Lipase-catalysed esters synthesis of cafestol and kahweol.

Authors :: Novaes FJM
Itabaiana Junior I
Sutili FK
Marriott PJ
Bizzo HR
Aquino Neto FR
Souza ROMA
Rezende CM
Source :: Food chemistry [Food Chem] 2018 Sep 01; Vol. 259, pp. 226-233. Date of Electronic Publication: 2018 Mar 27.
Publication Year :: 2018
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 <superscript>-1</superscript> 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-C <subscript>14:0</subscript> -C <subscript>20:0</subscript> , C <subscript>18:1</subscript> , C <subscript>18:2</subscript> and C <subscript>18:3</subscript> .<br /> (Copyright © 2018. Published by Elsevier Ltd.)