Structures of Epicatechin Gallate Trimer and Tetramer Produced by Enzymatic Oxidation

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During black tea production, catechins and their galloyl esters are enzymatically oxidized to generate a complex mixture of black tea polyphenols. The role of galloyl ester groups in this process has yet to be determined. Enzymatic oxidation of epicatechin 3-O-gallate (1) yielded two new oxidation products, theaflavate C and bistheaflavate A, along with theaflavate A (2), a known dimer of 1 generated by coupling of the B-ring with the galloyl group. Theaflavate C is a trimer of 1 and possesses two benzotropolone moieties generated by the oxidative coupling of the galloyl groups with the catechol B-rings. Bistheaflavate A was found to be a tetramer produced by intermolecular coupling of two benzotropolone moieties of 2. From the structures of the products, it was deduced that oxidative coupling of galloyl groups resulted in extension of the molecular size of the products in catechin oxidation.

During black tea production, catechins and their galloyl esters are enzymatically oxidized to generate a complex mixture of black tea polyphenols. The role of galloyl ester groups in this process has yet to be determined. Enzymatic oxidation of epicatechin 3-<i>O</i>-gallate (1) yielded two new oxidation products, theaflavate C and bistheaflavate A, along with theaflavate A (2), a known dimer of 1 generated by coupling of the B-ring with the galloyl group. Theaflavate C is a trimer of 1 and possesses two benzotropolone moieties generated by the oxidative coupling of the galloyl groups with the catechol B-rings. Bistheaflavate A was found to be a tetramer produced by intermolecular coupling of two benzotropolone moieties of 2. From the structures of the products, it was deduced that oxidative coupling of galloyl groups resulted in extension of the molecular size of the products in catechin oxidation.

収録刊行物

  • Chemical & pharmaceutical bulletin

    Chemical & pharmaceutical bulletin 55(12), 1768-1772, 2007-12-01

    公益社団法人日本薬学会

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各種コード

  • NII論文ID(NAID)
    110006532125
  • NII書誌ID(NCID)
    AA00602100
  • 本文言語コード
    ENG
  • 資料種別
    NOT
  • ISSN
    00092363
  • NDL 記事登録ID
    9274186
  • NDL 雑誌分類
    ZS51(科学技術--薬学) // ZP1(科学技術--化学・化学工業)
  • NDL 請求記号
    Z53-D167
  • データ提供元
    CJP書誌  CJP引用  NDL  NII-ELS  IR  J-STAGE 
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