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

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

Research output: Contribution to journal › Article › peer-review

2 Citations (Scopus)

Abstract

Caffeic acid ß-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 language	English
Pages (from-to)	476-480
Number of pages	5
Journal	Bioscience, Biotechnology and Biochemistry
Volume	85
Issue number	3
DOIs	https://doi.org/10.1093/bbb/zbaa077
Publication status	Published - 2021 Mar 1

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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10.1093/bbb/zbaa077

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

abstract = "Caffeic acid {\ss}-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",

author = "Riichi Hashimoto and Hiyori Iai and Rie Fujita and Kengo Hanaya and Shuhei Higashibayashi and Hiroyoshi Inoue and Takeshi Sugai",

note = "Funding Information: This work was supported by JSPS KAKENHI (19K05849) for T.S. and is gratefully acknowledged. This work was also supported by Global Science Campus, Japan Science and Technology Agency for H.I. (Inoue) and H.I. (Iai) thanks for the participation of this program. Publisher Copyright: {\textcopyright} The Author(s) 2021.",

year = "2021",

month = mar,

day = "1",

doi = "10.1093/bbb/zbaa077",

language = "English",

volume = "85",

pages = "476--480",

journal = "Bioscience, Biotechnology and Biochemistry",

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publisher = "Japan Society for Bioscience Biotechnology and Agrochemistry",

number = "3",

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TY - JOUR

T1 - Chemoenzymatic semisynthesis of caffeic acid β-phenethyl ester, an antioxidative component in propolis, from raw coffee bean extract

AU - Hashimoto, Riichi

AU - Iai, Hiyori

AU - Fujita, Rie

AU - Hanaya, Kengo

AU - Higashibayashi, Shuhei

AU - Inoue, Hiroyoshi

AU - Sugai, Takeshi

N1 - Funding Information: This work was supported by JSPS KAKENHI (19K05849) for T.S. and is gratefully acknowledged. This work was also supported by Global Science Campus, Japan Science and Technology Agency for H.I. (Inoue) and H.I. (Iai) thanks for the participation of this program. Publisher Copyright: © The Author(s) 2021.

PY - 2021/3/1

Y1 - 2021/3/1

N2 - Caffeic acid ß-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.

AB - Caffeic acid ß-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.

KW - caffeic acid

KW - catechol

KW - chlorogenic acid

KW - cinnamate ester

KW - lipase-catalyzed deacetylation

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U2 - 10.1093/bbb/zbaa077

DO - 10.1093/bbb/zbaa077

M3 - Article

C2 - 33624772

AN - SCOPUS:85101949050

SN - 0916-8451

VL - 85

SP - 476

EP - 480

JO - Bioscience, Biotechnology and Biochemistry

JF - Bioscience, Biotechnology and Biochemistry

IS - 3

ER -

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

Abstract

Keywords

ASJC Scopus subject areas

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