Disease relevance of eugenol

• 4-Allyl-2-methoxyphenol (eugenol) was tested for its ability to inhibit proliferation of melanoma cells [1].
• The expressed enzyme in Escherichia coli displayed high P-ST activity towards phenolic odorants such as eugenol and guaiacol, and it showed a high N-hydroxy-2-acetylaminofluorene sulphation activity in comparison with the rat ST1C1 enzyme [2].
• When a series of nine alkenylbenzenes were administered to preweanling male mice, safrole, estragole and methyleugenol induced a significant incidence of hepatic carcinomas, while eugenol, anethole, elemicin, myristicin, dill apiol and parsley apiol did not (Miller et al., Cancer Res., 43, 1124-1134, 1983) [3].
• The genes ehyAB, encoding eugenol hydroxylase of Pseudomonas sp. strain HR199, and azu, encoding the potential physiological electron acceptor of this enzyme, were shown to be unsuitable for establishing eugenol bioconversion in E. coli XL1-Blue [4].
• In broth media at 20 degrees C, 5 mM eugenol or 30 mM cinnamaldehyde was bactericidal (>1-log reduction in the number of CFU per milliliter in 1 h) to Listeria monocytogenes [5].

Psychiatry related information on eugenol

• The association between the odor of eugenol and dental fear and anxiety could be explained by the fact that eugenates (eugenol-containing cements) are often used in potentially painful restorative dentistry on vital teeth [6].
• These results suggest that eugenol may act by blocking Abeta-induced-Ca(2+) intake and provide a strong case for further pursuit of the therapeutic and prophylactic potentials of RAG and its active principles for the management of Alzheimer's disease [7].
• In doing this, the psychometric properties of odor quality in the case of eugenol and citral are investigated using both discrimination (experiment 1) and scaling (experiment 2) [8].
• Antioxidants such as eugenol and maltol may play an important role in the pharmaceutical activities of natural plant extracts used for aromatherapy [9].

High impact information on eugenol

• Petunia (Petunia hybrida cv. Mitchell) flowers, which emit large amounts of isoeugenol, possess an enzyme homologous to the basil eugenol-forming enzyme that also uses coniferyl acetate and NADPH as substrates but catalyzes the formation of isoeugenol [10].
• We show here that glandular trichomes of sweet basil (Ocimum basilicum), which synthesize and accumulate phenylpropenes, possess an enzyme that can use coniferyl acetate and NADPH to form eugenol [10].
• Transient transfection assays and electrophoretic mobility shift assays showed that eugenol inhibits the transcriptional activity of E2F1 [1].
• Examination of the mechanism of the antiproliferative action of eugenol in the human malignant melanoma cell line, WM1205Lu, showed that it arrests cells in the S phase of the cell cycle [1].
• These results indicate that deregulation of E2F1 may be a key factor in eugenol-mediated melanoma growth inhibition both in vitro and in vivo [1].

Chemical compound and disease context of eugenol

• Resting cells of the corresponding recombinant strain E. coli XL1-Blue(pSKvaomPcalAmcalB) converted eugenol to ferulic acid with a molar yield of 91% within 15 h on a 50-ml scale, reaching a ferulic acid concentration of 8.6 g liter(-1) [4].
• Highly efficient biotransformation of eugenol to ferulic acid and further conversion to vanillin in recombinant strains of Escherichia coli [4].
• The gene loci ehyAB, calA, and calB, encoding eugenol hydroxylase, coniferyl alcohol dehydrogenase, and coniferyl aldehyde dehydrogenase, respectively, which are involved in the first steps of eugenol catabolism in Pseudomonas sp. strain HR199, were amplified by PCR and combined to construct a catabolic gene cassette [11].
• These results confirm the validity of fluorination and/or removal of the 2-propenyl moiety in reducing the toxicity and recombinagenicity of methyl eugenol derivatives [12].
• Fragrances such as eugenol (4-allyl-2-methoxyphenol) and isoeugenol (2-methoxy-4-propenylphenol), naturally found in reasonable quantities in the essential oils of different spices, are not only common causes of contact dermatitis but also known for their antiproliferative actions [13].

Biological context of eugenol

• Flow cytometry coupled with biochemical analyses demonstrated that eugenol induced apoptosis. cDNA array analysis showed that eugenol caused deregulation of the E2F family of transcription factors [1].
• Sweet basil (Ocimum basilicum) peltate glandular trichomes produce a variety of small molecular weight phenylpropanoids, such as eugenol, caffeic acid, and rosmarinic acid, that result from meta hydroxylation reactions [14].
• We propose that the formation of this DNA damage may contribute to the observed toxic properties of eugenol [15].
• Eugenol also inhibited lipid peroxidation [16].
• Cells of R. eutropha H16(pBBR1-JO2ehyABcalAcalB) from the late-exponential growth phase were used as biocatalysts for the biotransformation of eugenol to ferulic acid [11].

Anatomical context of eugenol

• Finally, the oxidation products of eugenol/peroxidase were observed to be highly cytotoxic using isolated rat hepatocytes as target cells [17].
• The DNA adducts formed in HL-60 cells treated with eugenol were the same as those formed by in vitro peroxidase activation [15].
• An analysis of the release and the diffusion through dentin of eugenol from zinc oxide-eugenol mixtures [18].
• At a concentration higher than 3 mmol/L, eugenol was cytotoxic to oral mucosal fibroblasts in a concentration- and time-dependent manner [16].
• Preventive effect of bis-eugenol, a eugenol ortho dimer, on lipopolysaccharide-stimulated nuclear factor kappa B activation and inflammatory cytokine expression in macrophages [19].

Associations of eugenol with other chemical compounds

• The eugenol phenoxyl radical was detected using fast-flow electron spin resonance [17].
• The anethole analogues eugenol and isoeugenol also blocked TNF signaling [20].
• We demonstrate here that the volatile oil constituents eugenol and methylchavicol accumulate, respectively, in the peltate glands of basil lines SW (which produces essentially only eugenol) and EMX-1 (which produces essentially only methylchavicol) [21].
• The proposed method includes two parts: a selective sorbent for ozone, that is, eugenol, and a formaldehyde amperometric biosensor mounted into a flow-through cell [22].
• In vitro activation of eugenol with either horseradish peroxidase or myeloperoxidase and H2O2 produced three DNA adducts that were inhibited by the addition of either ascorbic acid or glutathione, by 66 and 90%, respectively [15].

Gene context of eugenol

• In addition, eugenol suppressed the cyclooxygenase-2 (COX-2) gene expression in LPS-stimulated mouse macrophage cells [23].
• This result suggests that eugenol might be a plausible lead candidate for further developing the COX-2 inhibitor as an anti-inflammatory or cancer chemopreventive agent [23].
• Results suggest a potential link between the antidepressant activity of eugenol and its MAOA inhibitory activity [24].
• Metabolic activation of eugenol by myeloperoxidase and polymorphonuclear leukocytes [25].
• Eugenol treatment was not linked to ERK or JNK activation in either cell type [26].

Analytical, diagnostic and therapeutic context of eugenol

• In a B16 xenograft study, eugenol treatment produced a significant tumor growth delay (p = 0.0057), an almost 40% decrease in tumor size, and a 19% increase in the median time to end point [1].
• The other study examined the effects of 150 mg eugenol/d in capsule form, using a double-blind, placebo-controlled crossover design [27].
• This study examined these responses in the ferret in more detail, both quantitatively and in three dimensions, 12 months after pulpectomy which was followed by obturation with gutta percha and zinc oxide and eugenol sealer [28].
• The purity of several brands of eugenol was compared by using high performance liquid chromatography with a UV detector [29].
• This seems to confirm the role of odors as elicitors of emotional memories and to support the possible influence of eugenol odor on the avoidance behavior of some subjects toward dental care [6].

References