Dehydrodiisoeugenol, an isoeugenol dimer, inhibits lipopolysaccharide-stimulated nuclear factor kappa B activation and cyclooxygenase-2 expression in macrophages

Murakami, Yukio; Shoji, Masao; Hirata, Atsushi; Tanaka, Shoji; Yokoe, Ichiro; Fujisawa, Seiichiro

doi:10.1016/j.abb.2004.11.013

Cited by 81 publications

(66 citation statements)

References 22 publications

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“…The mechanism of analgesic effect of CL in acetic acid induced writhing could probably be due to blockade of the effect or the release of endogenous substances that excite pain nerve endings similar to that of indomethacin and other NSAIDs. 36,37…”

Section: Discussionmentioning

confidence: 99%

Antinociceptive effects of purified Curcuma longa in mice

Sharma¹,

Rauniar

2016

Int J Basic Clin Pharmacol

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Section: Discussionmentioning

confidence: 99%

Antinociceptive effects of purified Curcuma longa in mice

Sharma¹,

Rauniar

2016

Int J Basic Clin Pharmacol

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“…Recently, there has been growing research interest in the synthesis of new anti-inflammatory compounds derived from eugenol and isoeugenol, two active components of clover oil, due to their antifungicidal, antibacterial, anti-oxidant and anti-inflammatory properties (5)(6)(7)(8). Previous studies have shown that several isoeugenolderived compounds, including dehydrodiisoeugenol, demethyldiisoeugenol, and o-diisoeugenol, have valuable cytoprotective and anti-inflammatory effects (5,(9)(10)(11). We have also developed some novel derivatives, such as eugenolol, isoeugenolol and isoeugenodilol, and demonstrated their pleiotropic effects including vasodilatory, antioxidant, tracheal relaxant, and -or~-adrenoceptor blockade properties (12)(13)(14).…”

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confidence: 99%

Eugenolol and Glyceryl-Isoeugenol Suppress LPS-Induced INOS Expression by Down-Regulating NF-κB and AP-1 through Inhibition of Mapks and AKT/IκBα Signaling Pathways in Macrophages

Yeh

Hsu

Hong

et al. 2011

Int J Immunopathol Pharmacol

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Eugenol and isoeugenol, two components of clover oil, have been reported to possess several biomedical properties, such as anti-inflammatory, antimicrobial and antioxidant effects. This study aims to examine the anti-inflammatory effects of eugenol, isoeugenol and four of their derivatives on expression of inducible nitric oxide synthase (iNOS) activated by lipopolysaccharide (LPS) in mouse macrophages (RAW 264.7), and to investigate molecular mechanisms underlying these effects. We found that two derivatives, eugenolol and glyceryl-isoeugenol, had potent inhibitory effects on LPS-induced up regulation of nitrite levels, iNOS protein and iNOS mRNA. In addition, they both suppressed the release of tumor necrosis factor-a (TNF-a) and Interleukin-If (IL-l~) induced by LPS. Moreover, they both attenuated the DNA binding of NF-KB and AP-l, phosphorylation of inhibitory KBa (IKBa), and nuclear translocation of p65 protein induced by LPS. Finally, we demonstrated that glyceryl-isoeugenol suppressed the phosphorylation of ERKl/2, JNK and p38 MAPK, whereas eugenolol suppressed the phosphorylation of ERKl/2 and p38 MAPK. Taken together, these results suggest that that eugenolol and glyceryl-isoeugenol suppress LPS-induced iNOS expression by down-regulating NF-KB and AP-l through inhibition ofMAPKs and AktlIKBa signaling pathways. Thus, this study implies that eugenolol and glyceryl-isoeugenol may provide therapeutic benefits for inflammatory diseases.An expanding body of literature indicates that inducible nitric oxide synthase (iNOS) is a key mediator activated by the inflammatory process and can produce a large amount of NO, causing detrimental effects in patients with chronic inflammation (1-2). Macrophage is one of the most important cells contributing to NO production during inflammatory responses. Expression of the iNOS in macrophages is regulated by many transcriptional factors, including nuclear factor-KB (NF-KB), activator protein-l (AP-l), interferon regulatory factor 1 (IRF1) and signal transducer and activator of transcription I (STATl). In particular,

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“…1,2) In addition, eugenol and related compounds exhibit anti-inflammatory activities, e.g. inhibition of lipopolysaccharide (LPS)-stimulated nuclear factor-kappa B (NF-κB) activation, cytokine release and cyclooxygenase-2 (COX-2) expression by macrophages in vitro 3) and inhibition of 5-lipoxygenase activity in polymorphonuclear cells. 4) However, despite the anti-inflammatory effects of eugenol described previously, there is only one report of it exhibiting antirheumatic effects in a model of adjuvant arthritis.…”

mentioning

confidence: 99%

Anti-arthritic Effect of Eugenol on Collagen-Induced Arthritis Experimental Model

Grespan

Paludo

Lemos

et al. 2012

Biological & Pharmaceutical Bulletin

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This study was designed to test the efficacy of eugenol, a compound obtained from the essential oil of cloves (Syzygium aromaticum) in collagen-induced arthritis (CIA), a well characterized murine model of rheumatoid arthritis. Macroscopic clinical evidence of CIA manifests first as periarticular erythema and edema in the hind paws. Treatment with eugenol starting at the onset of arthritis (day 25) ameliorated these clinical signs of CIA. Furthermore, eugenol inhibited mononuclear cell infiltration into the knee joints of arthritic mice and also lowered the levels of cytokines (tumor necrosis factor (TNF)-α, interferon (IFN)-γ and tumor growth factor (TGF)-β) within the ankle joints. Eugenol treatment did not affect the in vitro cell viability as assessed using the 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) assay. Therefore, eugenol ameliorates experimental arthritis and could be useful as a beneficial supplement in treating human arthritis.Key words eugenol; collagen-induced arthritis; inflammation; cytokine; mononuclear cell Eugenol (4-allyl-2-methoxyphenol) is the major component in the essential oil of many aromatic plants, including clove (Zyzygium aromaticum) and it is known to possess antioxidant, analgesic and neuroprotective properties among others.1,2) In addition, eugenol and related compounds exhibit anti-inflammatory activities, e.g. inhibition of lipopolysaccharide (LPS)-stimulated nuclear factor-kappa B (NF-κB) activation, cytokine release and cyclooxygenase-2 (COX-2) expression by macrophages in vitro 3) and inhibition of 5-lipoxygenase activity in polymorphonuclear cells. 4) However, despite the anti-inflammatory effects of eugenol described previously, there is only one report of it exhibiting antirheumatic effects in a model of adjuvant arthritis. 5)This new therapeutic strategy involving natural products has been devised because the anti-inflammatory and immunosuppressive drugs currently available cause many side effects and show limited efficacy in the treatment of rheumatoid arthritis.Collagen-induced arthritis (CIA) is used as an experimental model that resembles human rheumatoid arthritis. Both T cell and B cell responses to the autoantigen as well as the production of cytokines by systemic and tissue-specific cell populations are critical for the development (and eventual diminution) of the autoimmune response to CII and to the pathology in CIA.6) Due to the paucity of information on the effect of eugenol on experimental models of arthritis, this study was undertaken to investigate the efficacy of eugenol on CIA model.

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Dehydrodiisoeugenol, an isoeugenol dimer, inhibits lipopolysaccharide-stimulated nuclear factor kappa B activation and cyclooxygenase-2 expression in macrophages

Cited by 81 publications

References 22 publications

Antinociceptive effects of purified Curcuma longa in mice

Antinociceptive effects of purified Curcuma longa in mice

Eugenolol and Glyceryl-Isoeugenol Suppress LPS-Induced INOS Expression by Down-Regulating NF-κB and AP-1 through Inhibition of Mapks and AKT/IκBα Signaling Pathways in Macrophages

Anti-arthritic Effect of Eugenol on Collagen-Induced Arthritis Experimental Model

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