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Research ArticleArticle

Incensole Acetate, a Novel Anti-Inflammatory Compound Isolated from Boswellia Resin, Inhibits Nuclear Factor-κB Activation

Arieh Moussaieff, Esther Shohami, Yoel Kashman, Ester Fride, M. Lienhard Schmitz, Florian Renner, Bernd L. Fiebich, Eduardo Munoz, Yinon Ben-Neriah and Raphael Mechoulam
Molecular Pharmacology December 2007, 72 (6) 1657-1664; DOI: https://doi.org/10.1124/mol.107.038810
Arieh Moussaieff
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Esther Shohami
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Yoel Kashman
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Ester Fride
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M. Lienhard Schmitz
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Florian Renner
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Bernd L. Fiebich
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Eduardo Munoz
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Yinon Ben-Neriah
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Raphael Mechoulam
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Abstract

Boswellia resin is a major anti-inflammatory agent in herbal medical tradition, as well as a common food supplement. Its anti-inflammatory activity has been attributed to boswellic acid and its derivatives. Here, we re-examined the anti-inflammatory effect of the resin, using inhibitor of nuclear factor-κBα (IκBα) degradation in tumor necrosis factor (TNF) α-stimulated HeLa cells for a bioassay-guided fractionation. We thus isolated two novel nuclear factor-κB (NF-κB) inhibitors from the resin, their structures elucidated as incensole acetate (IA) and its nonacetylated form, incensole (IN). IA inhibited TAK/TAB-mediated IκB kinase (IKK) activation loop phosphorylation, resulting in the inhibition of cytokine and lipopolysaccharide-mediated NF-κB activation. It had no effect on IKK activity in vitro, and it did not suppress IκBα phosphorylation in costimulated T-cells, indicating that the kinase inhibition is neither direct nor does it affect all NF-κB activation pathways. The inhibitory effect seems specific; IA did not interfere with TNFα-induced activation of c-Jun N-terminal kinase (JNK) and p38 mitogen-activated protein kinase. IA treatment had a robust anti-inflammatory effect in a mouse inflamed paw model. Cembrenoid diterpenoids, specifically IA and its derivatives, may thus constitute a potential novel group of NF-κB inhibitors, originating from an ancient anti-inflammatory herbal remedy.

Footnotes

  • This work was supported by a EC 5th framework consortium grant number QLK3-CT-2000-00-463 (Anti-Inflammatory Natural Products consortium), and by the Miriam and Sheldon Adelson program in Neural Repair and Rehabilitation for support (to R.M.).

  • Article, publication date, and citation information can be found at http://molpharm.aspetjournals.org.

  • doi:10.1124/mol.107.038810.

  • ABBREVIATIONS: NF-κB, nuclear factor κB; IκB, inhibitor of nuclear factor-κB; IKK, IκB kinase; TAK, transforming growth factor β-activated kinase; TAB, transforming growth factor β-activated kinase-binding protein; IA, incensole acetate; IN, incensole; PE, petroleum ether; HPLC, high-performance liquid chromatography; GC-MS, gas chromatograph-mass spectrometry; LTR, long-terminal repeat; TNFα, tumor necrosis factor-α; PBS, phosphate-buffered saline; PMA, phorbol 12-myristate 13-acetate; NP-40, Nonidet P-40; WB, Western blotting; GST, glutathione transferase; JNK, C-Jun N-terminal kinase; MAPK, mitogen-activated protein kinase; WB, Western blotting.

  • ↵ Embedded Image The online version of this article (available at http://molpharm.aspetjournals.org) contains supplemental material.

    • Received June 6, 2007.
    • Accepted September 6, 2007.
  • The American Society for Pharmacology and Experimental Therapeutics
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Molecular Pharmacology: 72 (6)
Molecular Pharmacology
Vol. 72, Issue 6
1 Dec 2007
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Research ArticleArticle

Incensole Acetate, a Novel Anti-Inflammatory Compound Isolated from Boswellia Resin, Inhibits Nuclear Factor-κB Activation

Arieh Moussaieff, Esther Shohami, Yoel Kashman, Ester Fride, M. Lienhard Schmitz, Florian Renner, Bernd L. Fiebich, Eduardo Munoz, Yinon Ben-Neriah and Raphael Mechoulam
Molecular Pharmacology December 1, 2007, 72 (6) 1657-1664; DOI: https://doi.org/10.1124/mol.107.038810

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Research ArticleArticle

Incensole Acetate, a Novel Anti-Inflammatory Compound Isolated from Boswellia Resin, Inhibits Nuclear Factor-κB Activation

Arieh Moussaieff, Esther Shohami, Yoel Kashman, Ester Fride, M. Lienhard Schmitz, Florian Renner, Bernd L. Fiebich, Eduardo Munoz, Yinon Ben-Neriah and Raphael Mechoulam
Molecular Pharmacology December 1, 2007, 72 (6) 1657-1664; DOI: https://doi.org/10.1124/mol.107.038810
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