Protein Information

Name cyclooxygenase 2
Synonyms COX 2; COX2; PHS2; PGG/HS; Cyclooxygenase 2; Cyclooxygenase 2b; Cycloxygenase 2; PGH synthase 2…

Compound Information

Name eugenol
CAS 2-methoxy-4-(2-propen-1-yl)phenol

Reference List

PubMed Abstract RScore(About this table)
17436566 Fujisawa S, Ishihara M, Murakami Y, Atsumi T, Kadoma Y, Yokoe I: Predicting the biological activities of 2-methoxyphenol antioxidants: effects of dimers. In Vivo. 2007 Mar-Apr;21(2):181-8.

Selective cyclooxygenase (COX)-2 inhibitors have attracted much attention in relation to the design of non-steroidal anti-inflammatory agents (NSAIDs).
Results: Cytotoxicity declined in the order of curcumin > dehydrodiisoeugenol > isoeugenol > bis-MMP > eugenol > ferulic acid > 2-methoxy-4-methylphenol (MMP) > bis-eugenol > bis-ferulic acid.
1(0,0,0,1) Details
15461561 Aggarwal BB, Takada Y, Oommen OV: From chemoprevention to chemotherapy: common targets and common goals. Expert Opin Investig Drugs. 2004 Oct;13(10):1327-38.

These targets include the activation of apoptosis; suppression of growth factor expression or signalling; downregulation of antiapoptotic proteins; suppression of phosphatidylinositol-3'-kinase/Akt, NF-kappaB, Janus kinase-signal transducer and activator of transcription and activator protein-1 signalling pathways; and downregulation of angiogenesis through inhibition of vascular endothelial growth factor expression, cyclooxygenase-2, matrix metalloproteinase-9, urokinase-type plasminogen activator, adhesion molecules and cyclin D1.
These phytochemicals include genistein, resveratrol, dially sulfide, S-ally cysteine, allicin, lycopene, capsaicin, curcumin, 6-gingerol, ellagic acid, ursolic acid, betulinic acid, flavopiridol, silymarin, anethol, catechins and eugenol.
1(0,0,0,1) Details
12757841 Kim SS, Oh OJ, Min HY, Park EJ, Kim Y, Park HJ, Nam Han Y, Lee SK: Eugenol suppresses cyclooxygenase-2 expression in lipopolysaccharide-stimulated mouse macrophage RAW264.7 cells. Life Sci. 2003 Jun 6;73(3):337-48.
163(2,2,2,3) Details
17889685 Lee YY, Yang SF, Ho WH, Lee YH, Hung SL: Eugenol modulates cyclooxygenase-2 expression through the activation of nuclear factor kappa B in human osteoblasts. J Endod. 2007 Oct;33(10):1177-82. Epub 2007 Jul 12.
162(2,2,2,2) Details
16101137 Okada N, Hirata A, Murakami Y, Shoji M, Sakagami H, Fujisawa S: Induction of cytotoxicity and apoptosis and inhibition of cyclooxygenase-2 gene expression by eugenol-related compounds. Anticancer Res. 2005 Sep-Oct;25(5):3263-9.
87(1,1,2,2) Details
17509409 Lee YY, Hung SL, Pai SF, Lee YH, Yang SF: Eugenol suppressed the expression of lipopolysaccharide-induced proinflammatory mediators in human macrophages. J Endod. 2007 Jun;33(6):698-702. Epub 2007 Apr 2.

Consistent with downregulation of bone-resorbing mediators, eugenol suppressed the messenger RNA expression of LPS-induced IL-1beta, TNF-alpha, and cyclooxygenase-2 in macrophages.
81(1,1,1,1) Details
16707845 Li W, Tsubouchi R, Qiao S, Haneda M, Murakami K, Yoshino M: Inhibitory action of eugenol compounds on the production of nitric oxide in RAW264.7 macrophages. Biomed Res. 2006 Apr;27(2):69-74.

LPS-dependent expression of cyclooxygenase-2 (COX-2) protein was also inhibited markedly by isoeugenol, and less effectively by eugenol.
81(1,1,1,1) Details
20075264 Magalhaes CB, Riva DR, Depaula LJ, Brando-Lima AC, Koatz VL, Leal-Cardoso JH, Zin WA, Faffe DS: In vivo anti-inflammatory action of eugenol on lipopolysaccharide-induced lung injury. J Appl Physiol. 2010 Jan 14.

Eugenol, a methoxyphenol component of clover oil, suppresses cyclooxygenase-2 expression, while eugenol dimers prevent nuclear factor kappa B activation and inflammatory cytokine expression in lipopolysaccharide-stimulated macrophages.
81(1,1,1,1) Details
10782484 Kelm MA, Nair MG, Strasburg GM, DeWitt DL: Antioxidant and cyclooxygenase inhibitory phenolic compounds from Ocimum sanctum Linn. Phytomedicine. 2000 Mar;7(1):7-13.

Eugenol and compounds 1, 2, 5, and 6 demonstrated cyclooxygenase-2 inhibitory activity at slightly higher levels when assayed at 1000-microM concentrations.
31(0,1,1,1) Details
12615477 Huang FM, Chou MY, Chang YC: Induction of cyclooxygenase-2 mRNA and protein expression by epoxy resin and zinc oxide-eugenol based root canal sealers in human osteoblastic cells. Biomaterials. 2003 May;24(11):1869-75.
7(0,0,1,2) Details
17465205 Murakami Y, Hirata A, Ito S, Shoji M, Tanaka S, Yasui T, Machino M, Fujisawa S: Re-evaluation of cyclooxygenase-2-inhibiting activity of vanillin and guaiacol in macrophages stimulated with lipopolysaccharide. Anticancer Res. 2007 Mar-Apr;27(2):801-7.

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).
2(0,0,0,2) Details
15639233 Murakami Y, Shoji M, Hirata A, Tanaka S, Yokoe I, Fujisawa S: Dehydrodiisoeugenol, an isoeugenol dimer, inhibits lipopolysaccharide-stimulated nuclear factor kappa B activation and cyclooxygenase-2 expression in macrophages. Arch Biochem Biophys. 2005 Feb 15;434(2):326-32.

o-Methoxyphenols such as eugenol and isoeugenol exhibit anti-oxidant and anti-inflammatory activities, but at higher concentrations act as oxidants and potent allergens.
2(0,0,0,2) Details
12969226 Tang DW, Lin SC, Chang KW, Chi CW, Chang CS, Liu TY: Elevated expression of cyclooxygenase (COX)-2 in oral squamous cell carcinoma--evidence for COX-2 induction by areca quid ingredients in oral keratinocytes. J Oral Pathol Med. 2003 Oct;32(9):522-9.

2(0,0,0,2) Details
15934011 Huang FM, Chou LS, Chou MY, Chang YC: Protective effect of NAC on formaldehyde-containing-ZOE-based root-canal-sealers-induced cyclooxygenase-2 expression and cytotoxicity in human osteoblastic cells. J Biomed Mater Res B Appl Biomater. 2005 Aug;74(2):768-73.

2(0,0,0,2) Details
12444669 Huss U, Ringbom T, Perera P, Bohlin L, Vasange M: Screening of ubiquitous plant constituents for COX-2 inhibition with a scintillation proximity based assay. J Nat Prod. 2002 Nov;65(11):1517-21.

A rapid semi-homogeneous cyclooxygenase-2 (COX-2) enzymatic assay using scintillation proximity assay (SPA) technology was developed, and 49 ubiquitous plant secondary metabolites were screened for inhibition of COX-2-catalyzed prostaglandin E (2) (PGE (2)) biosynthesis.
Of these 49 plant metabolites, eugenol, pyrogallol, and cinnamaldehyde (with IC (50) values of 129, 144, and 245 microM, respectively) were found to inhibit COX-2.
1(0,0,0,1) Details
19671757 Koeberle A, Northoff H, Werz O: Curcumin blocks prostaglandin E2 biosynthesis through direct inhibition of the microsomal prostaglandin E2 synthase-1. Mol Cancer Ther. 2009 Aug;8(8):2348-55. Epub 2009 Aug 11.

Cyclooxygenase (COX)-2 and microsomal PGE (2) synthase-1, which are overexpressed in many cancers, are functionally coupled and thus produce massive PGE (2) in various tumors.
Closely related polyphenols (e.g., resveratrol, coniferyl alcohol, eugenol, rosmarinic acid) failed in this respect, and isolated ovine COX-1 and human recombinant COX-2 were not inhibited by curcumin up to 30 micromol/L.
1(0,0,0,1) Details
15488631 Dorai T, Aggarwal BB: Role of chemopreventive agents in cancer therapy. Cancer Lett. 2004 Nov 25;215(2):129-40.

Phytochemicals derived from such fruits and vegetables, referred to as chemopreventive agents include genistein, resveratrol, diallyl sulfide, S-allyl cysteine, allicin, lycopene, capsaicin, curcumin, 6-gingerol, ellagic acid, ursolic acid, silymarin, anethol, catechins and eugenol.
Because these agents have been shown to suppress cancer cell proliferation, inhibit growth factor signaling pathways, induce apoptosis, inhibit NF-kappaB, AP-1 and JAK-STAT activation pathways, inhibit angiogenesis, suppress the expression of anti-apoptotic proteins, inhibit cyclooxygenase-2, they may have untapped therapeutic value.
1(0,0,0,1) Details
20036707 Yogalakshmi B, Viswanathan P, Anuradha CV: Investigation of antioxidant, anti-inflammatory and DNA-protective properties of eugenol in thioacetamide-induced liver injury in rats. Toxicology. 2010 Feb 9;268(3):204-12. Epub 2009 Dec 29.

Expression of cyclooxygenase-2 (COX-2) and the extent of DNA damage were analyzed using immunoblotting and comet assay, respectively.
1(0,0,0,1) Details
18507010 Murakami Y, Ishii H, Takada N, Tanaka S, Machino M, Ito S, Fujisawa S: Comparative anti-inflammatory activities of curcumin and tetrahydrocurcumin based on the phenolic O-H bond dissociation enthalpy, ionization potential and quantum chemical descriptor. Anticancer Res. 2008 Mar-Apr;28(2A):699-707.

Cyclooxygenase-2 (COX-2) inhibition in lipopolysaccharide (LPS)- or Porphyromonas gingivalis fimbria-stimulated RAW 264.7 cells was investigated using Northern blot analysis.
The calculated chemical hardness (eta) for curcumin was clearly smaller, whereas its electronegativity (chi) and electrophilicity (omega) were clearly greater than the corresponding values for the curcumin-related compounds tetrahydrocurcumin, isoeugenol and eugenol.
1(0,0,0,1) Details
16309195 Atsumi T, Murakami Y, Shibuya K, Tonosaki K, Fujisawa S: Induction of cytotoxicity and apoptosis and inhibition of cyclooxygenase-2 gene expression, by curcumin and its analog, alpha-diisoeugenol. Anticancer Res. 2005 Nov-Dec;25(6B):4029-36.

1(0,0,0,1) Details