Chemoenzymatic semisynthesis of caffeic acid β-phenethyl ester, an antioxidative component in propolis, from raw coffee bean extract. Issue 3 (31st December 2020)

• Record Type: Journal Article
• Authors: Hashimoto, Riichi; Iai, Hiyori; Fujita, Rie; Hanaya, Kengo; Higashibayashi, Shuhei; Inoue, Hiroyoshi; Sugai, Takeshi
• Is Part Of: Bioscience, biotechnology, and biochemistry. Volume 85:Issue 3(2021)
• Page Start: 476
• Page End: 480
• Publication Date: 2020-12-31
• Subjects: catechol -- cinnamate ester -- chlorogenic acid -- caffeic acid -- lipase-catalyzed deacetylation; Biotechnology -- Periodicals; Biochemistry -- Periodicals; 660.6
• DOI: 10.1093/bbb/zbaa077
• Languages: English
• ISSNs: 0916-8451

Abstract

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 (Na2 S2 O4 ) and deprotection of the catecholic diacetate precursor by Candida antarctica lipase B-mediated transesterification as the final step. Graphical Abstract: