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

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 degradat...

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Bibliographic Details
Published in:Bioscience, Biotechnology, and Biochemistry
Main Authors: Hashimoto, Riichi, Iai, Hiyori, Fujita, Rie, Hanaya, Kengo, Higashibayashi, Shuhei, Inoue, Hiroyoshi, Sugai, Takeshi
Other Authors: Japan Society for the Promotion of Science
Format: Article in Journal/Newspaper
Language:English
Published: Oxford University Press (OUP) 2020
Subjects:
Organic Chemistry
Molecular Biology
Applied Microbiology and Biotechnology
General Medicine
Biochemistry
Analytical Chemistry
Biotechnology
Antarc*
Antarctica
Online Access:http://dx.doi.org/10.1093/bbb/zbaa077
http://academic.oup.com/bbb/article-pdf/85/3/476/36660781/zbaa077.pdf
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Summary: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.

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