TY - JOUR
T1 - Lipase-catalysed esters synthesis of cafestol and kahweol
AU - Novaes, Fábio Junior Moreira
AU - Itabaiana Junior, Ivaldo
AU - Sutili, Felipe Korbus
AU - Marriott, Philip John
AU - Bizzo, Humberto Ribeiro
AU - Aquino Neto, Francisco Radler de
AU - Souza, Rodrigo Octávio Mendonça Alves de
AU - Rezende, Claudia Moraes
PY - 2018/9/1
Y1 - 2018/9/1
N2 - 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.
AB - 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.
KW - Cafestol
KW - Cafestol ester
KW - Coffee diterpenes
KW - Ester synthesis
KW - Kahweol
KW - Kahweol ester
KW - Lipase catalyst
KW - Preparative scale isolation
UR - http://www.scopus.com/inward/record.url?scp=85044589636&partnerID=8YFLogxK
U2 - 10.1016/j.foodchem.2018.03.111
DO - 10.1016/j.foodchem.2018.03.111
M3 - Article
AN - SCOPUS:85044589636
SN - 0308-8146
VL - 259
SP - 226
EP - 233
JO - Food Chemistry
JF - Food Chemistry
ER -