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PubMed1976

[Zinc oxide-eugenol as dental material (1)].

Zinc oxide-eugenol cements are considerably better tolerated by tissue than other dental materials. As they alleviate pain and are bacteriostatic and antiseptic, they are well tolerated by patients. The cements are good insulators and possess better sealing properties than zinc phosphate cements. Because of their poor mechanic properties, the conventional zinc oxide-eugenol cements are mainly used as temporary fixing contents and filling materials, for gingival dressings and together with filling materials as impression materials. Recently, reinforced zinc oxide-eugenol cements and cements containing ethoxy benzoic acid (EBA) have been developed. These new cements have considerably better mechanic properties and are therefore used for cement bases, indirect capping, long-term temporary fillings and in selected cases as definite fixing cements.

Animals↗
PubMedDate not supplied

Effect of eugenol-containing temporary cements on bond strength of composite to dentin.

The effect of temporary materials on shear bond strength of composite to dentin was investigated. Sixty previously impacted (caries-free) human third molars were embedded and sectioned horizontally at the pulp chamber and at the half of the crown. The samples were covered with ZOE, Temp Bond (eugenol-containing), Fermit, (temporary resin material, used without cementing) and Provicol, (eugenol-free, calcium hydroxide-containing). All specimens were stored in saline for 10 days. After mechanical cleaning the dentin was pretreated with a dentin bonding agent (Syntac), and the composite columns were applied. Debonding was performed using a Zwick Universal Testing Machine (cross-head speed 1.5 mm/min). The mode of failure was noted using a light microscope, and the thickness of the dentin at the composite/dentin interface was measured. The median shear bond strength values for the treated and control samples were: ZOE 7.46 MPa, Temp Bond 10.22 MPa, Fermit 6.49 MPa, Provicol 8.43 MPa, and control 10.06 MPa. No two groups were significantly different at the 0.05 level (one-way ANOVA and Scheffé test). In all groups the predominant mode of failure was adhesive and there was a slight tendency towards lower shear bond strength values at lower values for the thickness of the dentin. Under the conditions described the use of eugenol-containing temporary cements had no adverse effect on shear bond strength of a dual-curing composite luting cement to dentin.

Analysis of Variance↗
PubMed2003

Selective alpha-glucosylation of eugenol by alpha-glucosyl transfer enzyme of Xanthomonas campestris WU-9701.

For one-step enzymatic synthesis of eugenyl alpha-glucoside as a promising pro-drug for a hair restorer and a derivative of spices, selective alpha-glucosylation of eugenol was carried out using the alpha-glucosyl transfer enzyme of Xanthomonas campestris WU-9701. When 130 micromol eugenol and crude enzyme showing 1.0 unit of alpha-glucosyl transfer activity were shaken in 2 ml of 10 mM H3BO3-NaOH-KCl buffer (pH 8.0) containing 1.2 M maltose as a glucosyl donor at 40 degrees C, only one form of eugenyl glucoside was selectively obtained as a product and identified as eugenyl alpha-D-glucopyranoside (alpha-EG) by 13C-NMR, 1H-NMR, and two-dimensional heteronuclear multiple-bond coherence analyses. In the reaction, no other glucosylated products such as maltotriose or eugenyl maltoside were detected in the reaction mixture. The reaction at 40 degrees C for 48 h under the above conditions yielded 68 mumol alpha-EG in 2 ml suspension, and the maximum molar conversion yield based on the amount of eugenol supplied reached 52%.

Journal Article↗
PubMed2005

IR/UV and UV/UV double-resonance study of guaiacol and eugenol dimers.

Guaiacol (2-methoxyphenol) and eugenol (4-allyl-2-methoxyphenol) molecules are biologically active phenol derivatives with an intramolecular -OH...OCH3 hydrogen bond (H bond). Pulsed supersonic expansions of mixtures of either of the two molecules with He yield weakly bound homodimers as well as other higher-order complexes. A number of complementary and powerful laser spectroscopic techniques, including UV-UV and IR-UV double resonances, have been employed to interrogate the species formed in the expansion in order to get information on their structures and spectroscopic properties. The interpretation of the spectra of eugenol dimer is complex and required a previous investigation on a similar but simpler molecule both to gain insight into the possible structures and support the conclusions. Guaiacol (2-methoxyphenol) has been used for that purpose. The combination of the broad laser study combined with ab initio calculations at the Becke 3 Lee-Yang-Parr/6-31+Gd level has provided the isomer structures, the potential-energy wells, and shed light on the inter- and intramolecular interactions involved. Guaiacol homodimer has been shown to have a single isomer whereas eugenol dimer has at least two. The comparison between the computed geometries of the dimers, their respective energies, and the vibrational normal modes permits the identification of the spectra.

Journal Article↗
PubMed1993

Reduced cytotoxicity of a root canal sealer through eugenol substitution.

The cytotoxicity of two zinc oxide root canal sealers was investigated in vitro. The sealers were freshly mixed and set for 24 and 168 h. The sealers had identical powders but different liquid components. One (Canals) used eugenol, while the other (Canals-N) used fatty acids. L929 cells were incubated for 4 and 24 h in direct contact with the materials or with an eluate of the materials. The toxicity was evaluated using the radiochromium release assay. In the direct exposure assay, both sealers were cytotoxic when freshly prepared or after 24 h of setting. After 1 wk of setting, Canals was still toxic, while Canals-N was not significantly different from the control in the 4-h assay. In the elution assay the materials showed very low cytotoxicity. Only the eluate from freshly prepared Canals was clearly cytotoxic after 24 h. The liquid of Canals-N was clearly less cytotoxic than liquid from Canals. The results showed that the cytotoxicity of a root canal sealer can be reduced by replacing eugenol with fatty acids.

Animals↗
PubMed2002

Adverse reactions associated with the use of eugenol in dentistry.

Eugenol is a material commonly used in dentistry with few reported side effects. It is not however, a bio-friendly material when in contact with oral soft tissues. It can produce both local irritative and cytotoxic effects, as well as hypersensitivity reactions. Here we report on two cases of adverse local reaction to eugenol, contained within a temporary restorative material and a temporary cementation material respectively, which illustrate these problems.

Adult↗
PubMedDate not supplied

Influence of eugenol contamination on the wetting of ground and etched dentin.

Forty third molars were sectioned parallel to the occlusal surface in order to expose superficial and deep dentin. Exposed surfaces were ground flat with 500-grit sandpaper. Contact angle measurements were performed to assess wettability using the ADSA-CD technique. Specimens were divided into two groups. Group 1 was the control group (no contamination). Group 2 served as the test group. Dentin surfaces were covered with a provisional eugenol-containing material (IRM) and were placed into a humidor at 37 degrees C for one week. The provisional material was removed. Wettability measurements of the two groups were made with water on ground dentin, with water and resin on etched dentin. Data were statistically analyzed by ANOVA, Student-Newman-Keuls multiple comparison and Student t-tests. Eugenol contamination did not affect the dentin wetting. Acid etching significantly diminished contact angle values. Dentin wetting was greater on deep dentin than on superficial dentin.

Acid Etching, Dental↗
PubMed1990

Mould growth on black table olives and prevention by sorbic acid, methyl-eugenol and spice essential oil.

Thirty-two mould strains were isolated from Turkish-style black table olives. Four of these isolates were identified as Aspergillus ochraceus, two as A. niger, 16 as Penicillium clavigerum and 10 as P. expansum. Mould growth was evaluated on olives treated with 500 ppm sorbic acid, 1000 ppm methyl-eugenol and 1500 ppm çörtük spice (Echinophora sibthorpiana Guss.) essential oil. Olives inoculated with A. parasiticus NRRL 2999 and P. clavigerum were also examined. All samples were stored at 28 degrees C, 15 degrees C and 5 degrees C for 60 days. The lower the temperature, the more time it took the mould to initiate mycelium and spore development. Most inhibition of growth was obtained using sorbic acid in all cases and especially at low temperatures, followed by methyl-eugenol and essential oil. Decreased inhibition was observed in noninoculated olives. Inhibitory effect of used agents was higher in olives inoculated with P. clavigerum than in olives inoculated with A. parasiticus.

Anesthetics↗
PubMed1999

Biotransformation of eugenol to vanillin by a mutant of Pseudomonas sp. strain HR199 constructed by disruption of the vanillin dehydrogenase (vdh) gene.

The catabolism of eugenol in Pseudomonas sp. strain HR199 (DSM7063) proceeds via coniferyl alcohol, coniferyl aldehyde, ferulic acid, vanillin, vanillate and protocatechuate, which is further degraded by the ortho-cleavage pathway. The vanillin dehydrogenase of Pseudomonas sp. strain HR199, which catalyses the NAD(+)-dependent oxidation of vanillin to vanillate, was inactivated by the insertion of omega elements into the vdh gene, which was characterized recently. Omega elements conferring resistance against kanamycin (omega Km) or gentamycin (omega Gm) were constructed by polymerase chain reaction amplification of the aminoglycoside 3'-O-phosphotransferase gene and the gentamycin-3-acetyltransferase gene, using the plasmids pSUP5011 and pBBR1MCS-5 respectively as template DNA. A 211-bp BssHII fragment of the vdh gene was substituted by omega Km or omega Gm, and the functional vdh gene was replaced by vdh omega Km or vdh omega Gm in Pseudomonas sp. strain HR199 by homologous recombination. Cells of the mutant Pseudomonas sp. strain HR vdh omega Km, pregrown on gluconate, accumulated up to 2.9 mM vanillin during incubation in mineral medium with 6.5 mM eugenol. As a result of another vanillin dehydrogenase activity (VDH-II), the accumulated vanillin was further degraded, when coniferyl aldehyde was exhausted from the medium. Characterization of the purified VDH-II revealed the identify of this enzyme with the recently characterized coniferyl-aldehyde dehydrogenase.

Aldehyde Oxidoreductases↗
PubMed1985

Differential inhibition of A, B and C fibres in the rat vagus nerve by lidocaine, eugenol and formaldehyde.

Evoked compound-action potentials (cAP) in all three fibre types of the isolated nerve were reversibly depressed by exposure to the drugs. After 20 min exposure, lidocaine (0.5 mM) depressed the amplitude of the A and B fibre potentials significantly more than the C fibre potential. With eugenol (0.8 mM), there was no significant difference in depression of A, B and C fibre activity. With formaldehyde (4.5 mM), the latency was longer, and the C fibres were initially significantly more depressed than the A and B fibres. As dull pain from a chronically-inflamed pulp is believed to be mediated through C fibres, these results may explain the difficulties in obtaining complete local analgesia with lidocaine. They indicate that application of low concentrations of eugenol and formaldehyde to the pulp-dentine organ may have an analgesic effect on pain mediated through both A and C fibres.

Action Potentials↗
PubMed1977

The effect of eugenol on nerve transmission.

Because of its long-time use as a sedative or anodyne in dental procedures, eugenol was studied to determine its effect on evoked nerve impulse transmission. The sciatic nerve of the bullfrog was stimulated in a nerve chamber, and the compound action potential was visualized on and recorded from an oscilloscope screen. It was determined that eugenol concentrations ranging from 100 per cent to 0.01 per cent extinguished the impulse-transmission capabilities of the nerve within 3 hours. No reversal was observed within this time frame.

Action Potentials↗
PubMed1981

Capping of monkey pulps with Dycal and a Ca-eugenol cement.

Capping of 120 teeth in four monkeys was performed with Dycal or with a calcium-eugenol cement. The observation periods were 8 days or 90 days. The monkeys were killed, and the teeth were examined histologically. After 8 days, the pulp-tissue reactions were basically the same in the two groups. The tissue adjacent to the exposure site was characterized by varying amounts of necrotic tissue, inflammatory cells, and extravasated erythrocytes. Capping material and dentin chips were displaced into the pulp tissue. Particles from the capping materials were found in vessels, macrophages, and foreign body cells. After 90 days, more hard-tissue formation occurred in the Dycal group than in the Ca-eugenol cement group. The hard tissue was formed by either fibroblasts or the original odontoblasts.

Animals↗
PubMed1986

An in vitro study of the role of dentine in moderating the cytotoxicity of zinc oxide eugenol cement.

The protective role of different dentine fractions and of dentine slices in moderating the cytotoxicity of zinc oxide eugenol (ZOE) was investigated. The collagen fraction of dentine powder provided increased protection over intact powder. Slices of dentine offered greater protection probably by providing a physical barrier to the diffusion of eugenol which may also bind to the contents of the dentine tubules. With increasing thickness of the dentine slices this protection was increased. ZOE stimulated calcium release from dentine but in view of the low levels attained it is unlikely that this process has any significant effect on the protective role of dentine.

Animals↗
PubMed1981

Potentiation of genotoxicity by concurrent application of compounds found in betel quid: arecoline, eugenol, quercetin, chlorogenic acid and Mn2+.

5 components of the betel quid were examined for their clastogenic activities individually and in various combinations. They included the alkaloid, arecoline, from the betel nut (Areca catechu L.), eugenol, from the betel vine (Piper belle L.), chlorogenic acid, from tobacco leaves (Nicotiana tabacum), quercetin, from fennel seeds (Foeniculus vulgare Mill.) and the ubiquitous transition metal Mn2+. The clastogenic effects of the concurrent applications of arecoline plus eugenol, arecoline plus quercetin and arecoline plus chlorogenic acid were greater than the sum of the action of each individual component. Similarly, the combinations of arecoline, chlorogenic acid and Mn2+ induced frequencies of chromosome aberrations which exceeded the sum of the clastogenic activities of individually applied compounds or the sum of the clastogenic activities of 2 jointly applied compounds (arecoline plus Mn2+, or chlorogenic acid plus Mn2+). The clastogenic activity was estimated as the frequency of metaphase plates with at least 1 chromatid break or chromatid exchange, or the average number of chromatid breaks and exchanges per Chinese hamster ovary (CHO) cell. A potentiating (enhancing) action was also evident when 2 clastogens were used at doses which would not lead to a detectable increase in the frequency of chromosome aberrations when applied individually. It may be useful to distinguish between a "genotoxic range", which would be applicable to individually assayed compounds, and a "cogenotoxic range", which may include concentrations at which a chemical exerts a potentiating effect when combined with other genotoxic or non-genotoxic compounds.

Animals↗
PubMed1994

Genotoxic evaluation of eugenol using the bone marrow micronucleus assay.

Eugenol, a widely used chemical in clinical dentistry, was evaluated for genotoxicity using the bone marrow micronucleus (Mn) assay in mice. Three doses (100, 400 or 600 mg/kg) were administered intraperitoneally (i.p.). The animals were killed 30 h post-treatment and the frequency of Mn in 1000 polychromatic erythrocytes (PCE) was determined. Corn oil and methyl methanesulfonate (MMS) were used as negative and positive controls, respectively. Only 400 and 600 mg/kg doses showed significant induction of Mn. We also studied the effect of eugenol at different recovery times (24, 30 or 48 h) with a dose of 400 mg/kg. A positive Mn response was seen at all three post-treatment times, but the differences between them were not significant. For treatment and control groups, the cytotoxicity was in the normal range, measured as the ratio of PCE/NCE (normochromatic erythrocytes).

Animals↗
PubMed1996

Effect of curcumin and eugenol on iron-induced hepatic toxicity in rats.

Male Wistar rats injected i.p. with 30 mg Fe2+/kg body weight show hepatic damage as measured by an increase in lipid peroxides which correlated with elevated serum enzymes, alanine aminotransferase (ALAT), aspartate aminotransferase (ASAT) and lactate dehydrogenase (LDH). Oral administration of spice principles, curcumin from turmeric (30 mg/kg body weight) or eugenol from cloves (100 mg/kg body weight), for 10 days lowered the liver and serum lipid peroxide levels, serum ALAT, ASAT and LDH, enhanced by i.p. injection of iron. This study indicates that curcumin or eugenol reduces the iron-induced hepatic damage by lowering lipid peroxidation.

Alanine Transaminase↗
PubMed1996

Gas chromatographic determination of eugenol in ethanol extract of cloves.

An ethanolic extract of cloves was analyzed by gas chromatography directly to identify eugenol and other major phenolic compounds without previous separation of other components. Separation was performed on a fused-silica capillary column of 30 m x 0.53 mm I.D., 0.53 microns film thickness. The detector was a flame ionization detector. Helium gas at a flow-rate of 3 ml/min was used as a carrier gas. The analysis were performed with linear temperature programming. Nine components were detected and special attention was given to the major phenolic compound, eugenol.

Chromatography, Gas↗