Dehydrodiisoeugenol, an isoeugenol dimer, inhibits lipopolysaccharide-stimulated nuclear factor kappa B activation and cyclooxygenase-2 expression in macrophages
Section snippets
Reagents
Isoeugenol and eugenol were purchased from Tokyo Kasei (Tokyo, Japan). Dehydrodiisoeugenol was synthesized from isoeugenol monomers by the FeCl3-catalyzed coupling reaction described previously [4]. α-Diisoeugenol was synthesized from isoeugenol monomers by use of the trifluoroacetic acid-catalyzed α-configurational coupling reaction described earlier [4]. bis-Eugenol was synthesized from eugenol monomers by the CuCl(OH)-catalyzed ortho coupling reaction described previously [3]. The chemical
Results and discussion
Many previous studies demonstrated that COX-2 plays important roles in inflammation and mutagenesis [11], [12], [13]. Recently, we demonstrated that bis-eugenol significantly inhibited LPS-stimulated NF-κB activation and expression of inflammatory cytokines in macrophages [5]. This result suggested that other dimer compounds of o-methoxyphenols might also have anti-inflammatory activity. Therefore, we first examined by using the Northern blot assay whether various o-methoxyphenol compounds (
Acknowledgment
This work was supported by a Grant-in-Aid for scientific research (No. 15592133) from the Ministry of Education, Science, and Culture of Japan.
References (29)
- et al.
Biochem. Pharmacol.
(2003) - et al.
J. Biol. Chem.
(1996) - et al.
Arch. Biochem. Biophys.
(1993) - et al.
FEBS Lett.
(1997) - et al.
J. Biol. Chem.
(1994) - et al.
Anal. Biochem.
(1985) - et al.
Immunobiology
(1993) - et al.
J. Biol. Chem.
(2002) - et al.
Toxicology
(2002) - et al.
Free Radic. Biol. Med.
(2000)
Chem. Res. Toxicol.
Jpn. J. Pharmacol.
Anticancer Res.
Anticancer Res.
Cited by (85)
The effect of natural products on inflammatory cytokines production and secretion
2023, Phytomedicine PlusBoth eugenol and biseugenol treatments reduced lung alterations in an experimental model of elastase-induced pulmonary emphysema
2023, Pharmacological Research - Modern Chinese MedicineNatural therapeutics and nutraceuticals for lung diseases: Traditional significance, phytochemistry, and pharmacology
2022, Biomedicine and PharmacotherapyEugenol disrupts Plasmodium falciparum intracellular development during the erythrocytic cycle and protects against cerebral malaria
2021, Biochimica et Biophysica Acta - General SubjectsCitation Excerpt :Essential oils from plants have been widely used for different purposes in medicine because of their analgesic, anti-inflammatory, antioxidant, fungicide, or antitumor activities [14]. Eugenol, a phenylpropene from clove oil, has potential analgesic, anti-inflammatory, antioxidant and anti-cancer properties and it has been shown to be efficient against microorganisms [15,16]. Eugenol derivatives protect the host from visceral leishmaniasis by inducing an immunomodulatory response characterized by an increase in the Th1 response and generation of nitric oxide [17].
The anti-inflammatory and anti-oxidative actions of eugenol improve lipopolysaccharide-induced lung injury
2019, Respiratory Physiology and NeurobiologyCitation Excerpt :The anti-inflammatory action of eugenol in this model can be explained by its effect on TNF-α levels and NF-κB activation (Magalhães et al., 2010), as well as on inflammatory cytokine release, as supported by IL-1β and IL-6 levels observed in the present study. These results reproduce in vivo the preventive effect of eugenol on NF-κB activation, inflammatory cytokine release, and COX-2 expression observed on LPS-stimulated macrophages in culture (Murakami et al., 2003, 2005). Our data also support in vivo previous observation in human macrophages, demonstrating that eugenol down-regulates IL-1 protein level and TNF-α induced by LPS (Lee et al., 2007).