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The effect of eugenol on oral mucous membranes.

Eugenol, in the 100 percent concentration in commercial use, was applied to a circumscribed area, 3 mm in diameter, of rat labial mucosa for 1 minute. Reaction periods of 15 minutes, 1, 2, 4 and 6 hours were then permitted. Using routine histological procedures for processing the experimental tissues, it was observed that eugenol caused denaturation of cytoplasmic proteins and loss of staining capacity of epithelium, loss of cell boundaries, swelling and cell necrosis. In addition, vesicle formation, edema in the corium, and striated muscle dissolution were observed.

Administration, Topical↗

Binding of eugenol and o-ethoxybenzoic acid to bovine serum albumin.

The binding constants (log K) of eugenol, o-ethoxy-benzoic acid, and their analogues, plus other organic compounds widely used in dentistry with bovine serum albumin, were examined with respect to the partition coefficients of these compounds in octanol-water (log P). Linear relationships between log K and log P values were obtained with high relative coefficients. Eugenol and o-ethoxybenzoic acid showed a relatively large log K value.

Alcohols↗

Effect of eugenol on constrictor responses in blood vessels of the rabbit ear.

Aqueous solutions of eugenol depressed vasoconstrictor responses to exogenous norepinephrine (NE), histamine, and peri-arterial sympathetic nerve stimulation in the isolated central artery of the rabbit ear and in the isolated perfused whole rabbit ear. The depression was dose- and time-dependent, and was slowly reversible. Eugenol appeared to act as an inhibitor of smooth muscle contractility.

Animals↗

Antimicrobial effect of trans-cinnamaldehyde, (-)-perillaldehyde, (-)-citronellal, citral, eugenol and carvacrol on airborne microbes using an airwasher.

Citral, trans-cinnamaldehyde, (-)-perillaldehyde, (-)-citronellal, eugenol and carvacrol were tested for their influence on microbial count in air by vaporizing with an air washer. The highest antibacterial activity was observed when (-)-perillaldehyde was sprayed. The average reduce of germ count was 53%. On the other hand, the antimicrobial activity of eugenol was the lowest of these six compounds. The average reduction of germ count was 13%. When water without volatile compounds was sprayed, the colony forming units increased. These results suggest the utility of selected aroma-compounds for the control of bacteria in the room.

Acrolein↗

A simple in vito cytotoxicity test using the MTT (3-(4,5)-dimethylthiazol-2-yl)-2,5-diphenyl tetrazolium bromide) colorimetric assay: analysis of eugenol toxicity on dental pulp cells (RPC-C2A).

A simple colorimetric assay using MTT has been developed to monitor mammalian cell survival and proliferation in vitro. In this study we used a clonal fibroblastic cell line (RPC-C2A) from, rat incisal dental pulp to examine the effectiveness of the colorimetric assay to test for the toxicity of eugenol, which is frequently used to treat inflammed dental pulp. A technical problem encountered was the insolubility of MTT formazan, produced by the activity of mitochondria dehydrogenases. Dimethyl sulfoxide (DMSO) seemed to be the best solvent. Doses of eugenol causing a 50% inhibition in the colorimetric assay were calculated as 0.6 mM and 1 mM for cells in the growing phase and for cells at confluence, respectively. These values exist in the concentration range reported in the previous studies. Although the correlation between spectrophotometric absorbance and cell number was not completely linear, this method could be used effectively as a simple preliminary assay to test for the toxicity of dental drugs and materials.

Cell Survival↗

The pharmacologic and toxicological properties of zinc oxide-eugenol.

An explanation of the therapeutic effects of zinc oxide-eugenol when placed in contact with intact or carious dentin, and the toxic effects of zinc oxide-eugenol when placed in contact with soft tissue or tissue cultures is presented to allow for the rational, safe, and effective use of the material.

Animals↗

[Factors affecting the setting time of zinc oxide-eugenol impression materials--the influence of humidity and temperature to the reaction velocity].

Zinc oxide-eugenol paste are widely used in clinical dentistry, principally for impression of non-undercut edentulous ridges, or bite taking materials. However it has been realized by those who use these paste that different products, direction for mixing, or different conditions for mixing, have different characteristics. An experiment have been made to observe the influence of different conditions for mixing to the setting time. Zinc oxide-eugenol impression pastes were mixed in accordance with the manufacturer's instruction when supplied. The condition for mixing was at temperature of 15 +/- 1, 20 +/- 1, 25 +/- 1, 30 +/- 1 degrees C and at humidity of 40 +/- 5, 70 +/- 5, 90 +/- 5%. The setting time (a initial setting time, a final setting time) was defined in the A.D.A. specification No. 16. The following results were obtained. 1. A higher temperature and humidity shortened the initial setting time of all paste. 2. A higher temperature and humidity shortened slightly the time interval between a initial and a final setting time of all paste. 3. In clinical use, sample C is better than other ones, so that a setting time of the sample is property for impression making.

Dental Impression Materials↗

Metabolism of alkenebenzene derivatives in the rat. II. Eugenol and isoeugenol methyl ethers.

1. The metabolites of 3,4-dimethoxyallylbenzene (eugenol methyl ether) and 3,4-dimethoxypropenylbenzene (isoeugenol methyl ether) in the rat were identified and quantitatively determined by g.l.c. and g.l.c.-mass spectrometry. 2. The major metabolic reactions of 3,4-dimethoxyallylbenzene were oxidation of the allylic side chain to 2-hydroxy-3-(3,4-dimethoxyphenyl)-propionic acid, 3,4-dimethoxybenzoic acid and 3,4-dimethoxycinnamic acid, the two latter being largely excreted as their glycine conjugates. The formation of the hydroxy acid presumably involved epoxidation of the double bond and subsequent hydration to the diol whereas the formation of 3,4-dimethoxycinnamic acid and 3,4-dimethoxybenzoic acid involved migration of the double bond and the formation of cinnamoyl intermediates. Other reactions were O-demethylation to 4-hydroxy-3-methoxyallylbenzene (eugenol) and 3-hydroxy-4-methoxyallylbenzene in equal amounts, oxidation to 1-(3,4-dimethoxyphenyl)-2-propen-1-ol, hydroxylation of the benzene ring to a hydroxy-3,4-dimethoxyallylbenzene and oxidation to 3,4-dimethoxyphenylacetic acid. The formation of 1-(3,4-dihydroxyphenyl)propane was found to be carried out by the rat intestinal micro-organisms. A total of at least 63% but as much as 95% dose was accounted for. 3. The major metabolic pathway of 3,4-dimethoxypropenylbenzene was via the cinnamoyl derivatives, leading to the formation of 4-hydroxy-3-methoxycinnamic acid (ferulic acid), 3,4-dimethoxycinnamic acid and 3,4-dimethoxybenzoic acid, the two latter being excreted largely as their glycine conjugates. Other reactions were O-demethylation to 4-hydroxy-3-methoxypropenylbenzene (isoeugenol) and 3-hydroxy-4-methoxypropenylbenzene in equal amounts, and oxidation to 3,4-dimethoxyphenylacetic acid and 4-hydroxy-3-methoxyphenylacetone. Epoxidation of the side chain appeared to be a minor metabolic reaction with the propenyl derivative. 4. The biliary metabolites of 3,4-dimethoxyallylbenzene and 3,4-dimethoxypropenylbenzene were identified and most of the urinary metabolites were also found in the bile.

Animals↗

Effects of visible light irradiation on eugenol-treated oral mucosa.

The purpose of this study was to evaluate the histopathological effects of eugenol (EUG) and iso-eugenol (IsoEUG)--with or without visible light (VL) irradiation--on oral mucous membranes. Oral mucous membranes of mice were applied with three agents, EUG, IsoEUG, and aceton (as the control) in the absence or presence of VL irradiation. VL irradiation resulted in more tissue damage for EUG- or IsoEUG-treated mucosa compared to corresponding compounds without VL irradiation, and that damage under IsoEUG treatment was greater than that under EUG treatment. Necrosis, but not apoptosis, was preferentially expressed in EUG- or IsoEUG-treated mucous membranes in the presence of VL irradiation.

Animals↗

Effect of short-term treatment of eugenol on the seminal vesicles of adult albino rats.

The structure and biochemical content of adult albino rat seminal vesicles, were studied, after administration of two different doses of eugenol for 10 days (0.2 and 0.3 mg/kg/day, i.m.). Marked decreases in the concentrations of nucleic acids, fructose and total protein as well as RNA/DNA ratio (61%) and protein/DNA ratio (27%) were observed. A remarkable increase in phospholipid concentration was noted with a corresponding decrease in neutral lipids. Histologically, eugenol treated animals showed degeneration of the secretory columnar cells and well developed myofibrillar connective tissues when compared to control animals.

Animals↗

Pre- and postsynaptic effects of eugenol and related compounds on Helix pomatia L. neurons.

We showed how eugenol blocks the synaptic transmission and gave a possible interpretation how it inhibits the excitation-contraction coupling that several authors described previously. Eugenol acts both in the pre- and postsynaptic side of the neurons. It blocks the Ca2+-currents, decreases the membrane potential of the neurons, increases the inward resistance and decreases the GABA, ACh and glutamate evoked excitatory responses in submillimolar concentration.

Acetylcholine↗

Retention of posts luted with phosphate monomer-based composite cement in canals obturated using a eugenol sealer.

PURPOSE: To examine the effect post-obturation sequencing had on retention of endodontic posts luted with a phosphate monomer-based resin cement into canals previously obturated using a eugenol-based sealer. MATERIALS AND METHODS: 64 single-rooted teeth were decoronated, and root canals were filed, cleaned, and shaped with a size 5 Gates Glidden drill and 0.12 taper rotary instrumentation. Teeth were then divided into 4 groups of 16 specimens each. Group 1 was not obturated, and served as a control. The other three groups were obturated with gutta percha and a eugenol-based sealer. Post space preparation and post cementation were completed at three different post-obturation intervals - immediate (Group 2), 1 week (Group 3), and 4 weeks (Group 4). Ten-mm deep post spaces were prepared with a size 6 Gates Glidden drill, and size 5 Paraposts were cemented with Panavia 21 OP. Following 48-hour of storage, specimens were mounted in PVC pipe with acrylic, and the posts were removed in tensile mode using a universal testing machine at 1 mm min(-1), with data recorded in kilograms. RESULTS: Group 1 (controls) mean = 61.80, SD = 16.21; Group 2 (immediate) mean = 38.70, SD = 12.97; Group 3 (1 week) mean = 43.15, SD = 14.66; Group 4 (4 weeks) mean = 18.82, SD = 8.00. Using ANOVA and Bonferroni tests, Group 1 demonstrated significantly greater mean retention strength values than Groups 2 and 3 (P < 0.05), which in turn had significantly greater mean retention strength values than Group 4 (P < 0.05).

Analysis of Variance↗

[Metabolic activation of a natural promutagen, eugenol, by replicative cultures of adult rat liver epithelial cells].

The metabolism of eugenol via the epoxide-diol pathway has been characterized by the incubation of this compound in replicative cultures of epithelial cells from sexed rat liver. It is a naturally occuring compound which has been found as the second metabolite of a known hepatocancerogen: safrole. Eugenol did not appear as a mutagen while epoxyeugenol was mutagenic using the Ames Test.

Animals↗

Inhibition of aflatoxin production & growth of Aspergillus flavus by eugenol & onion & garlic extracts.

Efficacy of natural non-toxic materials including extracts of onion and garlic as well as eugenol was tested against aflatoxin production by A. flavus in liquid SMKY medium and in maize grains. Maximum inhibition in the mycelial growth occurred with garlic extract (61.94%), whereas inhibition of aflatoxin production was highest (60.44%) due to onion extract. Eugenol was most suitable for inhibiting aflatoxin production (60.35%) on maize grains.

Aflatoxins↗

Therapeutic uses of Ocimum sanctum Linn (Tulsi) with a note on eugenol and its pharmacological actions: a short review.

The medicinal plants are widely used by the traditional medical practitioners for curing various diseases in their day to day practice. In traditional systems of medicine, different parts (leaves, stem, flower, root, seeds and even whole plant) of Ocimum sanctum Linn (known as Tulsi in Hindi), a small herb seen throughout India, have been recommended for the treatment of bronchitis, bronchial asthma, malaria, diarrhea, dysentery, skin diseases, arthritis, painful eye diseases, chronic fever, insect bite etc. The Ocimum sanctum L. has also been suggested to possess antifertility, anticancer, antidiabetic, antifungal, antimicrobial, hepatoprotective, cardioprotective, antiemetic, antispasmodic, analgesic, adaptogenic and diaphoretic actions. Eugenol (1-hydroxy-2-methoxy-4-allylbenzene), the active constituent present in Ocimum sanctum L., has been found to be largely responsible for the therapeutic potentials of Tulsi. Although because of its great therapeutic potentials and wide occurrence in India the practitioners of traditional systems of medicine have been using Ocimum sanctum L. for curing various ailments, a rational approach to this traditional medical practice with modern system of medicine is, however, not much available. In order to establish the therapeutic uses of Ocimum sanctum L. in modern medicine, in last few decades several Indian scientists and researchers have studied the pharmacological effects of steam distilled, petroleum ether and benzene extracts of various parts of Tulsi plant and eugenol on immune system, reproductive system, central nervous system, cardiovascular system, gastric system, urinary system and blood biochemistry and have described the therapeutic significance of Tulsi in management of various ailments. These pharmacological studies have established a scientific basis for therapeutic uses of this plant.

Animals↗

[Case of cutaneous necrosis in African clawed frogs Xenopus laevis after the topical application of eugenol].

Case of cutaneous necrosis in African Clawed frogs Xenopus laevis after the topical application of eugenol. African Clawed frogs showed necrotic cutaneous lesions after a topical application of high concentrations of eugenol, an analgesic and anesthetic agent. Microscopically, ulceration of the epidermis, a loss of mucous and serous glands as well as an infiltration of inflammatory cells were observed.

Administration, Topical↗

Antimicrobial efficacy of iodoformized zinc oxide-eugenol sealer on micro-organisms of root canal.

Iodoformized zinc oxide-eugenol was tested for its antibacterial effect against the aerobic and anaerobic bacteria obtained from the root canals of deciduous teeth; the bacteria were staph aureus, strep viridans, strep faecalis, bacteroides melaninogenicus and also mixed culture obtained from infected non-vital anterior teeth. The sensitivity was checked on BHI- agar plates employing well-method. Iodoformized zinc oxide eugenol paste was found to be effective for both the aerobic and anaerobic bacteria of the root canals of deciduous teeth with maximum sustaining period of 10 days; staphylococcus aureus was found to be the most susceptible, while Streptococcus faecalis the most resistant.

Bacteria↗