Cyclooxygenase-2 inhibitory phenylbutenoids from the rhizomes of Zingiber cassumunar

Ah Reum Han; Moon Sun Kim; Yeon Hee Jeong; Sang Kook Lee; Eun Kyoung Seo

doi:10.1248/cpb.53.1466

Cyclooxygenase-2 inhibitory phenylbutenoids from the rhizomes of Zingiber cassumunar

Ah Reum Han, Moon Sun Kim, Yeon Hee Jeong, Sang Kook Lee, Eun Kyoung Seo

Department of Pharmaceutical Sciences

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

56 Scopus citations

Abstract

Phenylbutenoids 1-6 isolated previously from the CHCl₃ extracts of the rhizomes of Zingiber cassumunar, were evaluated for their cyclooxygenase-2 (COX-2) inhibitory activity along with a new isolate, 7 from the n-BuOH extracts of this plant. The COX-2 inhibitory assay was performed by measuring prostaglandin E₂ production in lipopolysaccharide- stimulated mouse macrophage RAW 264.7 cells. Two phenylbutenoid dimers, 1 and 2, exhibited considerable activity with IC₅₀ values of 2.71 and 3.64 μM. Two phenylbutenoid monomers, 3 and 4, showed moderate activity (IC ₅₀ 14.97, 20.68 μM, respectively). The other three phenylbutenoids, 5-7, were found to be inactive. Compound 7 was elucidated as a new phenylbutenoid glycoside, namely, (E)-4-(3,4-dimethoxyphenyl) but-3-en-1-O-β-D-glucopyranoside by spectral analysis including various 1D- and 2D-NMR experiments.

Original language	English
Pages (from-to)	1466-1468
Number of pages	3
Journal	Chemical and Pharmaceutical Bulletin
Volume	53
Issue number	11
DOIs	https://doi.org/10.1248/cpb.53.1466
State	Published - Nov 2005

Keywords

(E)-4-(3,4-dimethoxyphenyl)but-3-en-1-O-β-D-glucopyranoside
Cyclooxygenase-2
Phenylbutenoid dimer
Zingiber cassumunar
Zingiberaceae

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@article{983c439f2fec4305b20256c80c4a70c2,

title = "Cyclooxygenase-2 inhibitory phenylbutenoids from the rhizomes of Zingiber cassumunar",

abstract = "Phenylbutenoids 1-6 isolated previously from the CHCl3 extracts of the rhizomes of Zingiber cassumunar, were evaluated for their cyclooxygenase-2 (COX-2) inhibitory activity along with a new isolate, 7 from the n-BuOH extracts of this plant. The COX-2 inhibitory assay was performed by measuring prostaglandin E2 production in lipopolysaccharide- stimulated mouse macrophage RAW 264.7 cells. Two phenylbutenoid dimers, 1 and 2, exhibited considerable activity with IC50 values of 2.71 and 3.64 μM. Two phenylbutenoid monomers, 3 and 4, showed moderate activity (IC 50 14.97, 20.68 μM, respectively). The other three phenylbutenoids, 5-7, were found to be inactive. Compound 7 was elucidated as a new phenylbutenoid glycoside, namely, (E)-4-(3,4-dimethoxyphenyl) but-3-en-1-O-β-D-glucopyranoside by spectral analysis including various 1D- and 2D-NMR experiments.",

keywords = "(E)-4-(3,4-dimethoxyphenyl)but-3-en-1-O-β-D-glucopyranoside, Cyclooxygenase-2, Phenylbutenoid dimer, Zingiber cassumunar, Zingiberaceae",

author = "Han, {Ah Reum} and Kim, {Moon Sun} and Jeong, {Yeon Hee} and Lee, {Sang Kook} and Seo, {Eun Kyoung}",

year = "2005",

month = nov,

doi = "10.1248/cpb.53.1466",

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pages = "1466--1468",

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T1 - Cyclooxygenase-2 inhibitory phenylbutenoids from the rhizomes of Zingiber cassumunar

AU - Han, Ah Reum

AU - Kim, Moon Sun

AU - Jeong, Yeon Hee

AU - Lee, Sang Kook

AU - Seo, Eun Kyoung

PY - 2005/11

Y1 - 2005/11

N2 - Phenylbutenoids 1-6 isolated previously from the CHCl3 extracts of the rhizomes of Zingiber cassumunar, were evaluated for their cyclooxygenase-2 (COX-2) inhibitory activity along with a new isolate, 7 from the n-BuOH extracts of this plant. The COX-2 inhibitory assay was performed by measuring prostaglandin E2 production in lipopolysaccharide- stimulated mouse macrophage RAW 264.7 cells. Two phenylbutenoid dimers, 1 and 2, exhibited considerable activity with IC50 values of 2.71 and 3.64 μM. Two phenylbutenoid monomers, 3 and 4, showed moderate activity (IC 50 14.97, 20.68 μM, respectively). The other three phenylbutenoids, 5-7, were found to be inactive. Compound 7 was elucidated as a new phenylbutenoid glycoside, namely, (E)-4-(3,4-dimethoxyphenyl) but-3-en-1-O-β-D-glucopyranoside by spectral analysis including various 1D- and 2D-NMR experiments.

AB - Phenylbutenoids 1-6 isolated previously from the CHCl3 extracts of the rhizomes of Zingiber cassumunar, were evaluated for their cyclooxygenase-2 (COX-2) inhibitory activity along with a new isolate, 7 from the n-BuOH extracts of this plant. The COX-2 inhibitory assay was performed by measuring prostaglandin E2 production in lipopolysaccharide- stimulated mouse macrophage RAW 264.7 cells. Two phenylbutenoid dimers, 1 and 2, exhibited considerable activity with IC50 values of 2.71 and 3.64 μM. Two phenylbutenoid monomers, 3 and 4, showed moderate activity (IC 50 14.97, 20.68 μM, respectively). The other three phenylbutenoids, 5-7, were found to be inactive. Compound 7 was elucidated as a new phenylbutenoid glycoside, namely, (E)-4-(3,4-dimethoxyphenyl) but-3-en-1-O-β-D-glucopyranoside by spectral analysis including various 1D- and 2D-NMR experiments.

KW - (E)-4-(3,4-dimethoxyphenyl)but-3-en-1-O-β-D-glucopyranoside

KW - Cyclooxygenase-2

KW - Phenylbutenoid dimer

KW - Zingiber cassumunar

KW - Zingiberaceae

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AN - SCOPUS:27744555241

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JO - Chemical and Pharmaceutical Bulletin

JF - Chemical and Pharmaceutical Bulletin

IS - 11

ER -

Cyclooxygenase-2 inhibitory phenylbutenoids from the rhizomes of Zingiber cassumunar

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