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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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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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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