Identification of a New Naphthalene and Its Derivatives from the Bulb of Eleutherine americana with Inhibitory Activity on Lipopolysaccharide-Induced Nitric Oxide Production

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  • Han Ah-Reum
    College of Pharmacy and the Center for Cell Signaling & Drug Discovery Research, Ewha Womans University
  • Min Hye-Young
    College of Pharmacy and the Center for Cell Signaling & Drug Discovery Research, Ewha Womans University
  • Nam Joo-Won
    College of Pharmacy and the Center for Cell Signaling & Drug Discovery Research, Ewha Womans University
  • Lee Na-Youn
    College of Pharmacy and the Center for Cell Signaling & Drug Discovery Research, Ewha Womans University
  • Wiryawan Adam
    Faculty of Sciences, Brawijaya University
  • Suprapto Wahyu
    Batu Herba Medica Centre
  • Lee Sang Kook
    College of Pharmacy and the Center for Cell Signaling & Drug Discovery Research, Ewha Womans University
  • Lee Kang Ro
    College of Pharmacy, Sungkyunkwan University
  • Seo Eun-Kyoung
    College of Pharmacy and the Center for Cell Signaling & Drug Discovery Research, Ewha Womans University

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A new naphthoquinone, (−)-3-[2-(acetyloxy)propyl]-2-hydroxy-8-methoxy-1,4-naphthoquinone (1) was isolated from the bulb of Eleutherine americana MERR. et HEYNE (Iridaceae) together with two known compounds, eleutherinol (6) and 1,5-dihydroxy-3-methylanthraquinone (7) which were found in this species for the first time. The other known compounds, (−)-isoeleutherin (2), (+)-eleutherin (3), (−)-hongconin (4), and (+)-dihydroeleutherinol (5) which were reported previously from this species, were also isolated in the present study. Compounds 2—6 exhibited potent inhibitory activity on nitric oxide production in RAW 264.7 lipopolysaccharide-activated mouse macrophage cells with IC50 values of 7.7, 11.4, 19.8, 21.7, and 34.4 μM, respectively, whereas the other two compounds, 1 and 7, were inactive. The structure of compound 1 was elucidated by spectroscopic data analysis including 1D and 2D NMR experiments.

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