| Name | cytochrome P450 (protein family or complex) |
|---|---|
| Synonyms | cytochrome P450; cytochrome P 450; CYP450; CYP 450 |
| Name | eugenol |
|---|---|
| CAS | 2-methoxy-4-(2-propen-1-yl)phenol |
| PubMed | Abstract | RScore(About this table) | |
|---|---|---|---|
| 7786311 | Kumaravelu P, Dakshinamoorthy DP, Subramaniam S, Devaraj H, Devaraj NS: Effect of eugenol on drug-metabolizing enzymes of carbon tetrachloride-intoxicated rat liver. Biochem Pharmacol. 1995 May 26;49(11):1703-7. An overall decrease in drug-metabolizing enzymes, namely -cytochrome c reductase, -cytochrome reductase, hydroxylase, 7-ethoxy -O-deethylase, UDP-glucuronyltransferase and glutathione-S-transferase, was observed with CCl4 intoxication, with a subsequent decrease in cytochrome P450 and cytochrome b5 content. |
1(0,0,0,1) | Details |
| 18505250 | Podobnik B, Stojan J, Lah L, Krasevec N, Seliskar M, Rizner TL, Rozman D, Komel R: CYP53A15 of Cochliobolus lunatus, a target for natural antifungal compounds. J Med Chem. 2008 Jun 26;51(12):3480-6. A novel cytochrome P450, CYP53A15, was identified in the pathogenic filamentous ascomycete Cochliobolus lunatus. |
1(0,0,0,1) | Details |
| 15914212 | Rietjens IM, Boersma MG, van der Woude H, Jeurissen SM, Schutte ME, Alink GM: Flavonoids and alkenylbenzenes: mechanisms of mutagenic action and carcinogenic risk. Mutat Res. 2005 Jul 1;574(1-2):124-38. Epub 2005 Mar 31. Identification of the cytochrome P450 isoenzymes involved in bioactivation of the alkenylbenzenes identifies the groups within the population possibly at increased risk, due to life style factors or genetic polymorphisms leading to rapid metaboliser phenotypes. |
1(0,0,0,1) | Details |
| 8406240 | Rompelberg CJ, Verhagen H, van Bladeren PJ: Effects of the naturally occurring alkenylbenzenes eugenol and trans-anethole on drug-metabolizing enzymes in the rat liver. Food Chem Toxicol. 1993 Sep;31(9):637-45. |
0(0,0,0,0) | Details |
| 7578916 | Thompson DC, Perera K, Krol ES, Bolton JL: o-Methoxy-4-alkylphenols that form methides of intermediate reactivity are the most toxic in rat liver slices. Chem Res Toxicol. 1995 Apr-May;8(3):323-7. The derivatives of 4-alkyl- studied were 4-methyl- (creosol), 4-ethyl-, 4-propyl-, 4-isopropyl-, (eugenol), as well as 4-allyl-2,6-dimethoxyphenol. The data were correlated with previous microsomal experiments which showed that all of the 4-alkyl-2-methoxyphenols were converted to methides (QMs; 4-methylene-2,5-cyclohexadien-1-ones) via a cytochrome P450-catalyzed process [Bolton, J. |
1(0,0,0,1) | Details |
| 8574354 | Nagababu E, Sesikeran B, Lakshmaiah N: The protective effects of eugenol on carbon tetrachloride induced hepatotoxicity in rats. Free Radic Res. 1995 Dec;23(6):617-27. |
0(0,0,0,0) | Details |
| 8205227 | Nagababu E, Lakshmaiah N: Inhibition of microsomal lipid peroxidation and monooxygenase activities by eugenol. Free Radic Res. 1994 Apr;20(4):253-66. Eugenol significantly protected against the degradation of cytochrome P-450 during lipid peroxidation with all the systems tested. |
87(1,1,2,2) | Details |
| 11312644 | Sieben S, Hertl M, Al Masaoudi T, Merk HF, Blomeke B: Characterization of T cell responses to fragrances. Toxicol Appl Pharmacol. 2001 May 1;172(3):172-8. Interestingly, stimulation of eugenol and was increased in the presence of antigen-modified human liver microsomes (CYP450) or recombinant CYP1A1 in five of seven cases. |
81(1,1,1,1) | Details |
| 20013178 | Nagababu E, Rifkind JM, Boindala S, Nakka L: Assessment of antioxidant activity of eugenol in vitro and in vivo. Methods Mol Biol. 2010;610:165-80. Eugenol significantly inhibited the rise in SGOT activity and cell necrosis without protecting the endoplasmic reticulum (ER) damage as assessed by its failure to prevent a decrease in cytochrome p450 and G-6-phosphatase activity. |
81(1,1,1,1) | Details |
| 15781214 | Munerato MC, Sinigaglia M, Reguly ML, de Andrade HH: Genotoxic effects of eugenol, and in the wing spot test of Drosophila melanogaster. Mutat Res. 2005 Apr 4;582(1-2):87-94. Eugenol and produced a positive recombinagenic response only in the improved assay, which was related to a high CYP450-dependent activation capacity. |
32(0,1,1,2) | Details |
| 15576237 | Sakano K, Inagaki Y, Oikawa S, Hiraku Y, Kawanishi S: -mediated oxidative DNA damage induced by eugenol: possible involvement of O-demethylation. Mutat Res. 2004 Dec 31;565(1):35-44. We examined whether eugenol can induce oxidative DNA damage in the presence of cytochrome P450 using [32P]-5'-end-labeled DNA fragments obtained from human genes relevant to cancer. |
6(0,0,1,1) | Details |
| 9328175 | Gardner I, Wakazono H, Bergin P, de Waziers I, Beaune P, Kenna JG, Caldwell J: Cytochrome P450 mediated bioactivation of methyleugenol to 1'-hydroxymethyleugenol in Fischer 344 rat and human liver microsomes. Carcinogenesis. 1997 Sep;18(9):1775-83. |
4(0,0,0,4) | Details |
| 8901789 | Nanjee MN, Verhagen H, van Poppel G, Rompelberg CJ, van Bladeren PJ, Miller NE: Do dietary phytochemicals with cytochrome P-450 enzyme-inducing activity increase high-density-lipoprotein concentrations in humans?. Am J Clin Nutr. 1996 Nov;64(5):706-11. The other study examined the effects of 150 mg eugenol/d in capsule form, using a double-blind, placebo-controlled crossover design. |
3(0,0,0,3) | Details |
| 17407329 | Jeurissen SM, Punt A, Boersma MG, Bogaards JJ, Fiamegos YC, Schilter B, van Bladeren PJ, Cnubben NH, Rietjens IM: Human cytochrome p450 enzyme specificity for the bioactivation of estragole and related alkenylbenzenes. Chem Res Toxicol. 2007 May;20(5):798-806. Epub 2007 Apr 4. |
2(0,0,0,2) | Details |
| 16411663 | Jeurissen SM, Bogaards JJ, Boersma MG, ter Horst JP, Awad HM, Fiamegos YC, van Beek TA, Alink GM, Sudholter EJ, Cnubben NH, Rietjens IM: Human cytochrome p450 enzymes of importance for the bioactivation of methyleugenol to the proximate carcinogen 1'-hydroxymethyleugenol. Chem Res Toxicol. 2006 Jan;19(1):111-6. |
2(0,0,0,2) | Details |
| 7728898 | Bolton JL, Comeau E, Vukomanovic V: The influence of 4-alkyl substituents on the formation and reactivity of 2-methoxy- methides: evidence that extended pi-conjugation dramatically stabilizes the methide formed from eugenol. Chem Biol Interact. 1995 Apr 14;95(3):279-90. The effects of para-alkyl substituents on both the cytochrome P450-catalyzed oxidation of phenols to methides (QMs; 4-methylene-2,5-cyclohexadien-1-ones), and on the rates of nucleophilic additions to the QMs were investigated. |
1(0,0,0,1) | Details |
| 12428018 | Gang DR, Beuerle T, Ullmann P, Werck-Reichhart D, Pichersky E: Differential production of meta hydroxylated phenylpropanoids in sweet basil peltate glandular trichomes and leaves is controlled by the activities of specific acyltransferases and hydroxylases. Plant Physiol. 2002 Nov;130(3):1536-44. Sweet basil (Ocimum basilicum) peltate glandular trichomes produce a variety of small molecular weight phenylpropanoids, such as eugenol, and that result from meta hydroxylation reactions. Two basil cDNAs encoding isozymes of cytochrome P450 CYP98A13, which meta hydroxylates p-coumaroyl were isolated and found to be highly similar (90% identity) to the Arabidopsis homolog, CYP98A3. |
1(0,0,0,1) | Details |
| 16250655 | Cruciani G, Carosati E, De Boeck B, Ethirajulu K, Mackie C, Howe T, Vianello R: MetaSite: understanding metabolism in human cytochromes from the perspective of the chemist. J Med Chem. 2005 Nov 3;48(22):6970-9. This paper presents a new method, specifically designed for chemists, that provides the cytochrome involved and the site of metabolism for any human cytochrome P450 (CYP) mediated reaction acting on new substrates. |
1(0,0,0,1) | Details |