Revised Structures of Gambiriins A1, A2, B1, and B2, Chalcane-Flavan Dimers from Gambir (Uncaria gambir Extract)

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  • Taniguchi Shoko
    Pharmaceutical Sciences, Okayama University Graduate School of Medicine, Dentistry and Pharmaceutical Sciences
  • Kuroda Kayo
    Pharmaceutical Sciences, Okayama University Graduate School of Medicine, Dentistry and Pharmaceutical Sciences
  • Doi Kou-ichi
    Taiko Pharmaceutical Co., Ltd.
  • Tanabe Masahiro
    Taiko Pharmaceutical Co., Ltd.
  • Shibata Takashi
    Taiko Pharmaceutical Co., Ltd.
  • Yoshida Takashi
    Pharmaceutical Sciences, Okayama University Graduate School of Medicine, Dentistry and Pharmaceutical Sciences
  • Hatano Tsutomu
    Pharmaceutical Sciences, Okayama University Graduate School of Medicine, Dentistry and Pharmaceutical Sciences

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Abstract

Gambir, the aqueous extract from Uncaria gambir (Rubiaceae), has been used as an astringent medicine in Asian countries. Investigation of the constituents in the extract led to the isolation of four chalcane-flavan dimers, gambiriin A1 (6), A2 (7), B1 (8), and B2 (9), in addition to (+)-catechin (1), (+)-epicatechin (2), and dimeric proanthocyanidins, procyanidin B1 (3), procyanidin B3 (4), and gambiriin C (5). The spectroscopic and chemical data obtained in the present study indicated that their previously proposed structures 6a, 7a, 8a, and 9a should be revised to 6, 7, 8, and 9, respectively.

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