Semisynthesis of prunetin, a bioactive O-methylated isoflavone from naringenin, by the sequential deacetylation of chalcone intermediates and oxidative rearrangement

Takeshi Sugai; Kengo Hanaya; Shuhei Higashibayashi

doi:10.1093/bbb/zbaa021

Semisynthesis of prunetin, a bioactive O-methylated isoflavone from naringenin, by the sequential deacetylation of chalcone intermediates and oxidative rearrangement

Takeshi Sugai, Kengo Hanaya, Shuhei Higashibayashi

School of Pharmaceutical Sciences

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

Abstract

Prunetin (4′,5-dihydroxy-7-methoxyisoflavone) was semisynthesized in 8 steps from readily available naringenin in 26% total yield. The key reaction was chemoenzymatic sequential deacetylation to 6′-acetoxy-2′,4″-dihydroxy-4′-methoxychalcone, the in situ-formed precursor for thallium(III) nitrate-mediated oxidative rearrangement.

Original language	English
Pages (from-to)	143-147
Number of pages	5
Journal	Bioscience, Biotechnology and Biochemistry
Volume	85
Issue number	1
DOIs	https://doi.org/10.1093/bbb/zbaa021
Publication status	Published - 2021 Jan 1

Keywords

O-methylated isoflavone
chalcone
deacetylation
naringenin
oxidative rearrangement

ASJC Scopus subject areas

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

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10.1093/bbb/zbaa021

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Semisynthesis of prunetin, a bioactive O-methylated isoflavone from naringenin, by the sequential deacetylation of chalcone intermediates and oxidative rearrangement. / Sugai, Takeshi ; Hanaya, Kengo ; Higashibayashi, Shuhei.

In: Bioscience, Biotechnology and Biochemistry, Vol. 85, No. 1, 01.01.2021, p. 143-147.

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

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abstract = "Prunetin (4′,5-dihydroxy-7-methoxyisoflavone) was semisynthesized in 8 steps from readily available naringenin in 26% total yield. The key reaction was chemoenzymatic sequential deacetylation to 6′-acetoxy-2′,4″-dihydroxy-4′-methoxychalcone, the in situ-formed precursor for thallium(III) nitrate-mediated oxidative rearrangement. ",

keywords = "O-methylated isoflavone, chalcone, deacetylation, naringenin, oxidative rearrangement",

author = "Takeshi Sugai and Kengo Hanaya and Shuhei Higashibayashi",

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AU - Hanaya, Kengo

AU - Higashibayashi, Shuhei

N1 - Funding Information: This work was supported by JSPS KAKENHI (19K05849) to T.S. and is gratefully acknowledged with thanks. Publisher Copyright: © The Author(s) 2021. Published by Oxford University Press on behalf of Japan Society for Bioscience, Biotechnology, and Agrochemistry. All rights reserved.

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N2 - Prunetin (4′,5-dihydroxy-7-methoxyisoflavone) was semisynthesized in 8 steps from readily available naringenin in 26% total yield. The key reaction was chemoenzymatic sequential deacetylation to 6′-acetoxy-2′,4″-dihydroxy-4′-methoxychalcone, the in situ-formed precursor for thallium(III) nitrate-mediated oxidative rearrangement.

AB - Prunetin (4′,5-dihydroxy-7-methoxyisoflavone) was semisynthesized in 8 steps from readily available naringenin in 26% total yield. The key reaction was chemoenzymatic sequential deacetylation to 6′-acetoxy-2′,4″-dihydroxy-4′-methoxychalcone, the in situ-formed precursor for thallium(III) nitrate-mediated oxidative rearrangement.

KW - O-methylated isoflavone

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KW - deacetylation

KW - naringenin

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Semisynthesis of prunetin, a bioactive O-methylated isoflavone from naringenin, by the sequential deacetylation of chalcone intermediates and oxidative rearrangement

Abstract

Keywords

ASJC Scopus subject areas

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