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

doi:10.1016/j.foodchem.2018.03.111

Lipase-catalysed esters synthesis of cafestol and kahweol

Food Chem. 2018 Sep 1:259:226-233. doi: 10.1016/j.foodchem.2018.03.111. Epub 2018 Mar 27.

Authors

Fábio Junior Moreira Novaes¹, Ivaldo Itabaiana Junior², Felipe Korbus Sutili³, Philip John Marriott⁴, Humberto Ribeiro Bizzo⁵, Francisco Radler de Aquino Neto⁶, Rodrigo Octávio Mendonça Alves de Souza⁷, Claudia Moraes Rezende⁸

Affiliations

¹ Universidade Federal do Rio de Janeiro, Instituto de Química, Laboratório de Análise de Aromas, Avenida Athos da Silveira Ramos, 149, Bloco A, Sala 626, Rio de Janeiro, RJ 21941-895, Brazil; Universidade Federal do Rio de Janeiro, Instituto de Química, LADETEC, Avenida Horacio Macedo, 1281, Rio de Janeiro, RJ 21941-598, Brazil. Electronic address: fabiojmnovaes@yahoo.com.br.
² Universidade Federal do Rio de Janeiro, Escola de Química, Departamento de Engenharia Bioquímica, Avenida Athos da Silveira Ramos, Bloco E, Sala E203, Rio de Janeiro, RJ 21941-909, Brazil. Electronic address: ivaldo@eq.ufrj.br.
³ Universidade Estadual Paulista - Campus Botucatu, Departamento de Engenharia de Bioprocessos e Biotecnologia, Rua José Barbosa de Barros, 1780, Lageado, SP 18610 307, Brazil. Electronic address: felipe.sutili@fca.unesp.br.
⁴ Australian Centre for Research on Separation Science, School of Chemistry, Monash University, Wellington Road, Clayton, Victoria 3800, Australia. Electronic address: philip.marriott@monash.edu.
⁵ Embrapa Agroindústria de Alimentos, Avenida das Américas, 29501, Rio de Janeiro, RJ 23020-470, Brazil. Electronic address: humberto.bizzo@embrapa.br.
⁶ Universidade Federal do Rio de Janeiro, Instituto de Química, LADETEC, Avenida Horacio Macedo, 1281, Rio de Janeiro, RJ 21941-598, Brazil. Electronic address: radler@iq.ufrj.br.
⁷ Universidade Federal do Rio de Janeiro, Instituto de Química, Laboratório de Biocatálise e Síntese Orgânica, Avenida Athos da Silveira Ramos, 149, Rio de Janeiro, RJ 21941-895, Brazil. Electronic address: rodrigosouza@iq.ufrj.br.
⁸ Universidade Federal do Rio de Janeiro, Instituto de Química, Laboratório de Análise de Aromas, Avenida Athos da Silveira Ramos, 149, Bloco A, Sala 626, Rio de Janeiro, RJ 21941-895, Brazil. Electronic address: crezende@iq.ufrj.br.

PMID: 29680048
DOI: 10.1016/j.foodchem.2018.03.111

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-C_14:0-C_20:0, C_18:1, C_18:2 and C_18:3.

Keywords: Cafestol; Cafestol ester; Coffee diterpenes; Ester synthesis; Kahweol; Kahweol ester; Lipase catalyst; Preparative scale isolation.

MeSH terms

Biocatalysis
Chromatography, Gas
Chromatography, High Pressure Liquid
Coffee / chemistry
Coffee / metabolism
Diterpenes / chemistry
Diterpenes / metabolism*
Esters / analysis
Esters / metabolism*
Lipase / metabolism*

Substances

Coffee
Diterpenes
Esters
kahweol
cafestol
Lipase