Identification of a new naphthalene and its derivatives from the bulb of Eleutherine americana with inhibitory activity on lipopolysaccharide-induced nitric oxide production

Ah Reum Han; Hye Young Min; Joo Won Nam; Na Youn Lee; Adam Wiryawan; Wahyu Suprapto; Sang Kook Lee; Kang Ro Lee; Eun Kyoung Seo

doi:10.1248/cpb.56.1314

Identification of a new naphthalene and its derivatives from the bulb of Eleutherine americana with inhibitory activity on lipopolysaccharide-induced nitric oxide production

Ah Reum Han, Hye Young Min, Joo Won Nam, Na Youn Lee, Adam Wiryawan, Wahyu Suprapto, Sang Kook Lee, Kang Ro Lee, Eun Kyoung Seo

Department of Pharmaceutical Sciences

Research output: Contribution to journal › Article › peer-review

33 Scopus citations

Abstract

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.

Original language	English
Pages (from-to)	1314-1316
Number of pages	3
Journal	Chemical and Pharmaceutical Bulletin
Volume	56
Issue number	9
DOIs	https://doi.org/10.1248/cpb.56.1314
State	Published - Sep 2008

Keywords

Eleutherine Americana
Iridaceae
Naphthoquinone
Nitric oxide inhibitor

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10.1248/cpb.56.1314

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Han, A. R., Min, H. Y., Nam, J. W., Lee, N. Y., Wiryawan, A., Suprapto, W., Lee, S. K., Lee, K. R., & Seo, E. K. (2008). Identification of a new naphthalene and its derivatives from the bulb of Eleutherine americana with inhibitory activity on lipopolysaccharide-induced nitric oxide production. Chemical and Pharmaceutical Bulletin, 56(9), 1314-1316. https://doi.org/10.1248/cpb.56.1314

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title = "Identification of a new naphthalene and its derivatives from the bulb of Eleutherine americana with inhibitory activity on lipopolysaccharide-induced nitric oxide production",

abstract = "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.",

keywords = "Eleutherine Americana, Iridaceae, Naphthoquinone, Nitric oxide inhibitor",

author = "Han, {Ah Reum} and Min, {Hye Young} and Nam, {Joo Won} and Lee, {Na Youn} and Adam Wiryawan and Wahyu Suprapto and Lee, {Sang Kook} and Lee, {Kang Ro} and Seo, {Eun Kyoung}",

year = "2008",

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language = "English",

volume = "56",

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Han, AR, Min, HY, Nam, JW, Lee, NY, Wiryawan, A, Suprapto, W, Lee, SK, Lee, KR & Seo, EK 2008, 'Identification of a new naphthalene and its derivatives from the bulb of Eleutherine americana with inhibitory activity on lipopolysaccharide-induced nitric oxide production', Chemical and Pharmaceutical Bulletin, vol. 56, no. 9, pp. 1314-1316. https://doi.org/10.1248/cpb.56.1314

Identification of a new naphthalene and its derivatives from the bulb of Eleutherine americana with inhibitory activity on lipopolysaccharide-induced nitric oxide production. / Han, Ah Reum; Min, Hye Young; Nam, Joo Won et al.
In: Chemical and Pharmaceutical Bulletin, Vol. 56, No. 9, 09.2008, p. 1314-1316.

Research output: Contribution to journal › Article › peer-review

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AU - Han, Ah Reum

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AU - Lee, Na Youn

AU - Wiryawan, Adam

AU - Suprapto, Wahyu

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AU - Lee, Kang Ro

AU - Seo, Eun Kyoung

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N2 - 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.

AB - 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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AN - SCOPUS:51349083750

SN - 0009-2363

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JO - Chemical and Pharmaceutical Bulletin

JF - Chemical and Pharmaceutical Bulletin

IS - 9

ER -

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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