Chemoenzymatic semisynthesis of caffeic acid β-phenethyl ester, an antioxidative component in propolis, from raw coffee bean extract

Riichi Hashimoto; Hiyori Iai; Rie Fujita; Kengo Hanaya; Shuhei Higashibayashi; Hiroyoshi Inoue; Takeshi Sugai

doi:10.1093/bbb/zbaa077

Chemoenzymatic semisynthesis of caffeic acid β-phenethyl ester, an antioxidative component in propolis, from raw coffee bean extract

Biosci Biotechnol Biochem. 2021 Feb 24;85(3):476-480. doi: 10.1093/bbb/zbaa077.

Authors

Riichi Hashimoto¹, Hiyori Iai², Rie Fujita¹, Kengo Hanaya¹, Shuhei Higashibayashi¹, Hiroyoshi Inoue³, Takeshi Sugai¹

Affiliations

¹ Department of Pharmaceutical Sciences, Faculty of Pharmacy, Keio University, Shibakoen, Minato-ku, Tokyo, Japan.
² Yokohama Science Frontier High School, 6 Ono-cho, Tsurumi-ku, Yokohama, Japan.
³ Department of Chemistry, School of Medicine, Keio University, Hiyoshi, Kohoku-ku, Yokohama, Japan.

PMID: 33624772
DOI: 10.1093/bbb/zbaa077

Abstract

Caffeic acid β-phenethyl ester (CAPE), an antioxidative bioactive catechol isolated from propolis, was semisynthesized from chlorogenic acid and related compounds in an extract of raw (unroasted) Robusta coffee (Coffea canephora) beans in 5 steps and a total yield of 31%. Oxidative degradation of the intermediates and target molecule was prevented by alkaline hydrolysis of the chlorogenic acids in the presence of sodium dithionite (Na2S2O4) and deprotection of the catecholic diacetate precursor by Candida antarctica lipase B-mediated transesterification as the final step.

Keywords: caffeic acid; catechol; chlorogenic acid; cinnamate ester; lipase-catalyzed deacetylation.

MeSH terms

Antioxidants / chemical synthesis*
Caffeic Acids / chemical synthesis*
Coffea / chemistry*
Esterification
Phenylethyl Alcohol / analogs & derivatives*
Phenylethyl Alcohol / chemical synthesis
Plant Extracts / chemical synthesis*
Propolis / chemistry*

Substances

Antioxidants
Caffeic Acids
Plant Extracts
Propolis
caffeic acid phenethyl ester
Phenylethyl Alcohol