Synthesis of trilobatin from naringin via prunin as the key intermediate: Acidic hydrolysis of the α-rhamnosidic linkage in naringin under improved conditions

Kazuki Kurahayashi; Kengo Hanaya; Shuhei Higashibayashi; Takeshi Sugai

doi:10.1080/09168451.2018.1482455

Synthesis of trilobatin from naringin via prunin as the key intermediate: Acidic hydrolysis of the α-rhamnosidic linkage in naringin under improved conditions

Kazuki Kurahayashi, Kengo Hanaya, Shuhei Higashibayashi, Takeshi Sugai

School of Pharmaceutical Sciences

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

4 Citations (Scopus)

Abstract

Trilobatin [4-(β-D-glucopyranosyloxy)-2,4”,6-trihydroxydihydrochalcone] was synthesized from commercially available naringin in three steps with an overall yield of 30%. The key step was the acid-catalyzed site-selective hydrolysis of terminal α-rhamnopyranosidic linkage in neohesperidose involved in naringin under controlled conditions, by applying a high-pressure steam sterilizer.

Original language	English
Pages (from-to)	1463-1467
Number of pages	5
Journal	Bioscience, Biotechnology and Biochemistry
Volume	82
Issue number	9
DOIs	https://doi.org/10.1080/09168451.2018.1482455
Publication status	Published - 2018

Keywords

Dihydrochalcone glycoside
Naringin
Site-selective hydrolysis
Trilobatin

ASJC Scopus subject areas

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

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Synthesis of trilobatin from naringin via prunin as the key intermediate : Acidic hydrolysis of the α-rhamnosidic linkage in naringin under improved conditions. / Kurahayashi, Kazuki; Hanaya, Kengo ; Higashibayashi, Shuhei ; Sugai, Takeshi.

In: Bioscience, Biotechnology and Biochemistry, Vol. 82, No. 9, 2018, p. 1463-1467.

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

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abstract = "Trilobatin [4-(β-D-glucopyranosyloxy)-2,4”,6-trihydroxydihydrochalcone] was synthesized from commercially available naringin in three steps with an overall yield of 30%. The key step was the acid-catalyzed site-selective hydrolysis of terminal α-rhamnopyranosidic linkage in neohesperidose involved in naringin under controlled conditions, by applying a high-pressure steam sterilizer.",

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