Disease relevance of Isoeugenol

• The time-dose-response relationship for elicitation of contact dermatitis in isoeugenol allergic individuals [1].
• Evaluation of the developmental toxicity of isoeugenol in Sprague-Dawley (CD) rats [2].
• Plant-purified IEMT has K(m) values of 7 and 58 microM for eugenol and isoeugenol, respectively, and 27 microM for SAM (30, 74, and 19 microM, respectively, for the plant IEMT expressed in Escherichia coli) [3].
• In conclusion, the time until an isoeugenol allergic individual reacts in a ROAT depends on the individual sensitivity as well as the exposure concentrations; for low concentrations of the allergen or low degree of sensitivity, the allergic contact dermatitis may develop after several weeks of exposure [1].
• Hypersensitivity induced by isoeugenol was concentration dependent [4].

High impact information on Isoeugenol

• 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 [5].
• Petunia flower petals emit large amounts of isoeugenol, which has been shown to be synthesized by isoeugenol synthase (PhIGS1) from an ester of coniferyl alcohol, hypothesized to be coniferyl acetate [6].
• Dehydrozingerone and isoeugenol as inhibitors of lipid peroxidation and as free radical scavengers [7].
• Impact of the arylhydrocarbon receptor on eugenol- and isoeugenol-induced cell cycle arrest in human immortalized keratinocytes (HaCaT) [8].
• 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 [8].

Chemical compound and disease context of Isoeugenol

• Methyl isoeugenol was administered in rodent diet for a minimum of 28 consecutive days to groups of 16 male and 16 female rats (Sprague-Dawley strain) at levels of approximately 30, 100 and 300 mg/kg body weight/day [9].
• Biotransformation of isoeugenol to vanillin by Pseudomonas putida IE27 cells [10].
• It is concluded that the levels of cinnamic aldehyde and isoeugenol found in the deodorants could prove to be relevant for elicitation of contact dermatitis [11].
• Short term toxicity study in rats dosed with isoeugenol benzyl ether [12].

Biological context of Isoeugenol

• Clinical signs associated with isoeugenol exposure included dose-related evidence of sedation and aversion to treatment (rooting behavior) in all isoeugenol groups, as well as an increased incidence of piloerection at >/= 500 mg/kg/day [2].
• Freeze-thaw cycles were effective in reducing cell numbers at isoeugenol concentrations down to 25 ppm [13].
• These results indicate that isoeugenol therapy may not reverse diabetic oxidative stress in an overall sense [14].
• The administration of methyl isoeugenol in the diet did not adversely affect the growth or general health of the animals or their food intakes [9].
• DESIGN: We treated HGF and HSG cells with curcumin [1] and the related compounds biseugenol [2], eugenol [3], alpha-diisoeugenol [4], and isoeugenol [5] and measured cell survival (MTT method), ROS generation (DCFH-DA staining), and induction of early apoptosis [15].

Anatomical context of Isoeugenol

• In contrast, isoeugenol and eugenol produced cytotoxicity in hepatocytes with LC50s of approximately 200-300 microM, but did not cause UDS [16].
• Higher cytotoxic activity of isoeugenol dimers was thought to be induced by interaction with cell membranes via the lipophilic radical [17].
• A positive ROAT was observed only in patients hypersensitive to isoeugenol (P<0.001) and only in the axilla to which the deodorants containing isoeugenol had been applied (P<0.001) [18].
• Both the cytotoxic activity and the DNA synthesis inhibitory activity of these compounds against a salivary gland tumor cell line (HSG) and normal human gingival fibroblast (HGF) were decreased in the order of: dehydrodiisoeugenol, alpha-di-isoeugenol > isoeugenol > eugenol > bis-eugenol [17].

Associations of Isoeugenol with other chemical compounds

• Genotoxic effects of eugenol, isoeugenol and safrole in the wing spot test of Drosophila melanogaster [19].
• Eugenol, isoeugenol, methyleugenol, and isomethyleugenol are volatiles found in the floral scent of Clarkia breweri [3].
• Within the mix, isoeugenol (CAS 97-54-1) is an important individual allergen [20].
• The minimum inhibitory concentration (MIC) of isopanduratin A was 4 mg/l which was much lower than that of some other natural anticariogenic agents such as sanguinarine (12 mg/l), green tea extract and carvacrol (125 mg/l), thymol (250 mg/l) and isoeugenol and eucalyptol (500 mg/l) [21].
• On the other hand, poor correlations between patch test reactivity and the use test were demonstrated in another study on isoeugenol and on studies on hydroxycitronellal, formaldehyde and chromium [22].

Gene context of Isoeugenol

• Some effects of isoeugenol treatment, such as decreased activity of hepatic superoxide dismutase and glutathione reductase in diabetic rats, were unrelated to the oxidative effects of diabetes [14].
• In heart of diabetic animals, isoeugenol treatment resulted in an exacerbation of already elevated activities of catalase [14].
• Here we show that stored isoeugenol has an antagonistic effect on a mouse olfactory receptor, mOR-EG [23].
• In the present study we investigated whether the cell cycle arrest of eugenol and isoeugenol is mediated by the AhR in HaCaT cells [8].
• In contrast, isoeugenol enhanced ROS production over a wide range of concentrations (5-500 microM) [24].

Analytical, diagnostic and therapeutic context of Isoeugenol

• In this study 27 isoeugenol-sensitive patients participated in serial dilution patch tests with isoeugenol and a double-blinded Repeated Open Application Test (ROAT) using two concentrations of isoeugenol, 0.2 and 0.05% [1].
• Effects of isoeugenol on in vitro neuromuscular blockade of rat phrenic nerve-diaphragm preparations [25].
• Comparisons were made with the activity of eugenol and isoeugenol in two predictive tests for contact sensitization potential: the murine local lymph node assay and the guinea pig maximization test [26].
• Feed was withheld for 1 week immediately prior to surgery and the fish was sedated with isoeugenol (AQUI-S) at a dose rate of 10 mL/L to facilitate diagnostic imaging techniques [27].

References