Yezo’otogirins D–H, Acylphloroglucinols and Meroterpenes from <i>Hypericum yezoense</i>

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  • Tanaka Naonobu
    Graduate School of Pharmaceutical Sciences, Hokkaido University Graduate School of Pharmaceutical Sciences, Tokushima University
  • Tsuji Eri
    Graduate School of Pharmaceutical Sciences, Hokkaido University
  • Kashiwada Yoshiki
    Graduate School of Pharmaceutical Sciences, Tokushima University
  • Kobayashi Jun’ichi
    Graduate School of Pharmaceutical Sciences, Hokkaido University

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  • Yezo'otogirins D-H, Acylphloroglucinols and Meroterpenes from Hypericum yezoense

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Abstract

Investigation of the methanolic extract from the aerial parts of Hypericum yezoense resulted in the isolation of three new acylphloroglucinols, yezo’otogirins D–F (1–3), and two new meroterpenes, yezo’otogirins G (4) and H (5). The structures of 1–5 were assigned on the basis of spectroscopic data. Yezo’otogirin D (1) is an acylphloroglucinol with a monoterpene moiety linked through an ether bond, while yezo’otogirins E (2) and F (3) are polyprenylated acylphloroglucinols possessing a tricyclic core. Yezo’otogirins G (4) and H (5) are linear meroterpenes with an enolized β-diketone moiety. Yezo’otogirin E (2) exhibited antimicrobial activity against Escherichia coli and Staphylococcus aureus.

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