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Research ArticleExperimental Studies

Re-evaluation of Cyclooxygenase-2-inhibiting Activity of Vanillin and Guaiacol in Macrophages Stimulated with Lipopolysaccharide

YUKIO MURAKAMI, ATSUSHI HIRATA, SHIGERU ITO, MASAO SHOJI, SHOJI TANAKA, TOSHIKAZU YASUI, MAMORU MACHINO and SEIICHIRO FUJISAWA
Anticancer Research March 2007, 27 (2) 801-807;
YUKIO MURAKAMI
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  • For correspondence: ymura@dent.meikai.ac.jp
ATSUSHI HIRATA
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SHIGERU ITO
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MASAO SHOJI
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SHOJI TANAKA
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TOSHIKAZU YASUI
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MAMORU MACHINO
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SEIICHIRO FUJISAWA
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Abstract

Phytophenols such as para-substituted 2-methoxyphenols exhibit antioxidant and anti-inflammatory activities, however, their biological activities are concentration-dependent, possibly due to their dual property of being both antioxidant and prooxidant. Eugenol (2-allyl-2-methoxyphenol) and isoeugenol(4-propenyl-2-methoxyphenol) did not reveal cyclooxygenase-2 (COX-2)-inhibiting activity in macrophages stimulated with lipopolysaccharide (LPS). In contrast, vanillin (2-hydroxy-3-methoxybenzaldehyde) and guaiacol (2-methoxyphenol), especially the former, inhibited LPS-stimulated nuclear factor kappa B (NF-κB) activation and cyclooxygenase (COX)-2 gene expression in cells of the RAW 264.7 murine macrophage cell line. Among the 2-methoxyphenols, vanillin demonstrated a potent anti-inflammatory activity. The phenolic O-H bond dissociation enthalpy (BDE) and molecular orbital energies (chemical hardness [eta], electronegativity [chi], and electrophilicity [omega]) were examined to clarify the mechanism responsible for inhibition of COX-2 expression. The BDE, chi, and omega values for vanillin were significantly higher than the corresponding values for the other 2-methoxyphenols. The anti-inflammatory activity of 2-methoxyphenols depended on the BDE and the phenol function was crucial for eliciting this activity. In addition, the anti-inflammatory activity depended on the chi and omega. These findings make vanillin attractive as a candidate therapeutic agent.

  • 2-Methoxyphenols
  • vanillin
  • guaiacol
  • antioxidants
  • anti-inflammatory activity
  • NF-κB
  • LPS
  • COX-2
  • macrophage

Footnotes

  • Received November 27, 2006.
  • Revision received January 29, 2007.
  • Accepted February 1, 2007.
  • Copyright© 2007 International Institute of Anticancer Research (Dr. John G. Delinassios), All rights reserved
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Anticancer Research: 27 (2)
Anticancer Research
Vol. 27, Issue 2
March-April 2007
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Re-evaluation of Cyclooxygenase-2-inhibiting Activity of Vanillin and Guaiacol in Macrophages Stimulated with Lipopolysaccharide
YUKIO MURAKAMI, ATSUSHI HIRATA, SHIGERU ITO, MASAO SHOJI, SHOJI TANAKA, TOSHIKAZU YASUI, MAMORU MACHINO, SEIICHIRO FUJISAWA
Anticancer Research Mar 2007, 27 (2) 801-807;

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Re-evaluation of Cyclooxygenase-2-inhibiting Activity of Vanillin and Guaiacol in Macrophages Stimulated with Lipopolysaccharide
YUKIO MURAKAMI, ATSUSHI HIRATA, SHIGERU ITO, MASAO SHOJI, SHOJI TANAKA, TOSHIKAZU YASUI, MAMORU MACHINO, SEIICHIRO FUJISAWA
Anticancer Research Mar 2007, 27 (2) 801-807;
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