Biomimetic one-pot preparation of a black tea polyphenol theasinensin A from epigallocatechin gallate by treatment with copper(2) chloride and ascorbic acid

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  • Shii Takuya
    Graduate School of Biomedical Sciences, Nagasaki University
  • Miyamoto Makoto
    Graduate School of Biomedical Sciences, Nagasaki University
  • Matsuo Yosuke
    Graduate School of Biomedical Sciences, Nagasaki University
  • Tanaka Takashi
    Graduate School of Biomedical Sciences, Nagasaki University
  • Kouno Isao
    Graduate School of Biomedical Sciences, Nagasaki University

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  • Biomimetic One-Pot Preparation of a Black Tea Polyphenol Theasinensin A from Epigallocatechin Gallate by Treatment with Copper(II) Chloride and Ascorbic Acid

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Chromatographic separation of black tea polyphenols is too difficult to supply sufficient quantities of pure compounds for biological experiments. Thus, facile methods to prepare black tea constituents were desired. Treatment of epigallocatechin gallate with copper(II) chloride efficiently afforded an unstable quinone dimer, dehydrotheasinensin A, and subsequent treatment with ascorbic acid stereoselectively yielded theasinensin A. The latter is a dimer with an R-biphenyl bond, one of the major polyphenols found in black tea. The method is simpler and more effective than enzymatic preparation.

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