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

Research output: Contribution to journalArticlepeer-review

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.

Original languageEnglish
Pages (from-to)476-480
Number of pages5
JournalBioscience, Biotechnology, and Biochemistry
Volume85
Issue number3
DOIs
Publication statusPublished - 2021 Feb 24

Keywords

  • caffeic acid
  • catechol
  • chlorogenic acid
  • cinnamate ester
  • lipase-catalyzed deacetylation

ASJC Scopus subject areas

  • Biotechnology
  • Analytical Chemistry
  • Biochemistry
  • Applied Microbiology and Biotechnology
  • Molecular Biology
  • Organic Chemistry

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