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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2020
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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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croxfordunivpr:10.1093/bbb/zbaa077 2023-05-15T14:10:41+02:00 Chemoenzymatic semisynthesis of caffeic acid β-phenethyl ester, an antioxidative component in propolis, from raw coffee bean extract Hashimoto, Riichi Iai, Hiyori Fujita, Rie Hanaya, Kengo Higashibayashi, Shuhei Inoue, Hiroyoshi Sugai, Takeshi Japan Society for the Promotion of Science 2020 http://dx.doi.org/10.1093/bbb/zbaa077 http://academic.oup.com/bbb/article-pdf/85/3/476/36660781/zbaa077.pdf en eng Oxford University Press (OUP) https://academic.oup.com/journals/pages/open_access/funder_policies/chorus/standard_publication_model Bioscience, Biotechnology, and Biochemistry volume 85, issue 3, page 476-480 ISSN 1347-6947 Organic Chemistry Molecular Biology Applied Microbiology and Biotechnology General Medicine Biochemistry Analytical Chemistry Biotechnology journal-article 2020 croxfordunivpr https://doi.org/10.1093/bbb/zbaa077 2022-04-15T06:22:24Z 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. Article in Journal/Newspaper Antarc* Antarctica Oxford University Press (via Crossref) Bioscience, Biotechnology, and Biochemistry 85 3 476 480 |
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Oxford University Press (via Crossref) |
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English |
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Organic Chemistry Molecular Biology Applied Microbiology and Biotechnology General Medicine Biochemistry Analytical Chemistry Biotechnology |
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Organic Chemistry Molecular Biology Applied Microbiology and Biotechnology General Medicine Biochemistry Analytical Chemistry Biotechnology Hashimoto, Riichi Iai, Hiyori Fujita, Rie Hanaya, Kengo Higashibayashi, Shuhei Inoue, Hiroyoshi Sugai, Takeshi Chemoenzymatic semisynthesis of caffeic acid β-phenethyl ester, an antioxidative component in propolis, from raw coffee bean extract |
topic_facet |
Organic Chemistry Molecular Biology Applied Microbiology and Biotechnology General Medicine Biochemistry Analytical Chemistry Biotechnology |
description |
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. |
author2 |
Japan Society for the Promotion of Science |
format |
Article in Journal/Newspaper |
author |
Hashimoto, Riichi Iai, Hiyori Fujita, Rie Hanaya, Kengo Higashibayashi, Shuhei Inoue, Hiroyoshi Sugai, Takeshi |
author_facet |
Hashimoto, Riichi Iai, Hiyori Fujita, Rie Hanaya, Kengo Higashibayashi, Shuhei Inoue, Hiroyoshi Sugai, Takeshi |
author_sort |
Hashimoto, Riichi |
title |
Chemoenzymatic semisynthesis of caffeic acid β-phenethyl ester, an antioxidative component in propolis, from raw coffee bean extract |
title_short |
Chemoenzymatic semisynthesis of caffeic acid β-phenethyl ester, an antioxidative component in propolis, from raw coffee bean extract |
title_full |
Chemoenzymatic semisynthesis of caffeic acid β-phenethyl ester, an antioxidative component in propolis, from raw coffee bean extract |
title_fullStr |
Chemoenzymatic semisynthesis of caffeic acid β-phenethyl ester, an antioxidative component in propolis, from raw coffee bean extract |
title_full_unstemmed |
Chemoenzymatic semisynthesis of caffeic acid β-phenethyl ester, an antioxidative component in propolis, from raw coffee bean extract |
title_sort |
chemoenzymatic semisynthesis of caffeic acid β-phenethyl ester, an antioxidative component in propolis, from raw coffee bean extract |
publisher |
Oxford University Press (OUP) |
publishDate |
2020 |
url |
http://dx.doi.org/10.1093/bbb/zbaa077 http://academic.oup.com/bbb/article-pdf/85/3/476/36660781/zbaa077.pdf |
genre |
Antarc* Antarctica |
genre_facet |
Antarc* Antarctica |
op_source |
Bioscience, Biotechnology, and Biochemistry volume 85, issue 3, page 476-480 ISSN 1347-6947 |
op_rights |
https://academic.oup.com/journals/pages/open_access/funder_policies/chorus/standard_publication_model |
op_doi |
https://doi.org/10.1093/bbb/zbaa077 |
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Bioscience, Biotechnology, and Biochemistry |
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85 |
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3 |
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476 |
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480 |
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1766282764507676672 |