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

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2 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 languageEnglish
Pages (from-to)1463-1467
Number of pages5
JournalBioscience, Biotechnology and Biochemistry
Volume82
Issue number9
DOIs
Publication statusPublished - 2018 Jan 1

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Hydrolysis
Sterilizers
2,4-Dichlorophenoxyacetic Acid
Steam
Pressure
Acids
prunin
naringin
trilobatin

Keywords

  • Dihydrochalcone glycoside
  • Naringin
  • Site-selective hydrolysis
  • Trilobatin

ASJC Scopus subject areas

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

Cite this

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title = "Synthesis of trilobatin from naringin via prunin as the key intermediate: Acidic hydrolysis of the α-rhamnosidic linkage in naringin under improved conditions",
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.",
keywords = "Dihydrochalcone glycoside, Naringin, Site-selective hydrolysis, Trilobatin",
author = "Kazuki Kurahayashi and Kengo Hanaya and Shuhei Higashibayashi and Takeshi Sugai",
year = "2018",
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doi = "10.1080/09168451.2018.1482455",
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T1 - Synthesis of trilobatin from naringin via prunin as the key intermediate

T2 - Acidic hydrolysis of the α-rhamnosidic linkage in naringin under improved conditions

AU - Kurahayashi, Kazuki

AU - Hanaya, Kengo

AU - Higashibayashi, Shuhei

AU - Sugai, Takeshi

PY - 2018/1/1

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N2 - 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.

AB - 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.

KW - Dihydrochalcone glycoside

KW - Naringin

KW - Site-selective hydrolysis

KW - Trilobatin

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