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

Author:

Hashimoto Riichi1,Iai Hiyori2,Fujita Rie1,Hanaya Kengo1,Higashibayashi Shuhei1,Inoue Hiroyoshi3,Sugai Takeshi1ORCID

Affiliation:

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

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 (Na2S2O4) and deprotection of the catecholic diacetate precursor by Candida antarctica lipase B-mediated transesterification as the final step.

Funder

Japan Society for the Promotion of Science

Publisher

Oxford University Press (OUP)

Subject

Organic Chemistry,Molecular Biology,Applied Microbiology and Biotechnology,General Medicine,Biochemistry,Analytical Chemistry,Biotechnology

Reference29 articles.

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5. Synthesis of 4-nitrophenyl caffeate and its use in assays of caffeoyl esterases;Chyba;Anal Biochem,2014

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