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PubMed1999

Clinical evaluation of glutaraldehyde with calcium hydroxide and glutaraldehyde with zinc oxide eugenol in pulpotomy of primary molars.

The objectives of this study were to clinically evaluate the effectiveness of 2% buffered glutaraldehyde in pulpotomies of human primary molars and to compare the success rate of glutaraldehyde with calcium hydroxide and glutaraldehyde with zinc oxide eugenol as dressing material on the radicular pulp. Pulpotomies were completed on 61 primary molars in 19 children. The teeth were divided into two groups by random allocation. One group had a dressing of zinc oxide-eugenol base (IRM) incorporated with one drop of 2% buffered glutaraldehyde while the other group had a dressing of calcium hydroxide base incorporated with one drop of 2% buffered glutaraldehyde after the initial placement of 2% buffered glutaraldehyde on cotton pellet for 3 min. All teeth had light-curing compomer (Dyract) placed over the dressing material followed by a stainless steel crown restoration within 1 or 2 weeks after the pulpotomy. Blind clinical and radiographic evaluations of 57 teeth available after 12 months showed a success rate of 92.9% and 73.6% respectively. The clinical and radiographic success rates for glutaraldehyde/zinc oxide eugenol pulpotomies were 96.5% and 75.8% respectively while those for glutaraldehyde-calcium hydroxide were 89.2% and 71.4%. There was no statistically significant difference between the two groups either clinically or radiographically. The overall clinical success rate suggested that 2% buffered glutaraldehyde was an effective agent in the pulpotomy of human primary molars.

Calcium Hydroxide↗
PubMed1982

In vitro antifungal activity of eugenol and vanillin against Candida albicans and Cryptococcus neoformans.

Eugenol and vanillin were examined for in vitro antifungal activity against the medically important yeasts, Candida albicans and Cryptococcus neoformans. Minimal inhibitory concentrations (MIC) and minimal fungicidal concentrations (MFC) were determined for each compound against 31 strains of C. albicans and 33 strains of C. neoformans. With eugenol, the mean MIC's for C. albicans and C. neoformans were 625 and 293 micrograms/mL, respectively, while the mean MFC's were 1209 and 521 micrograms/mL, respectively. With vanillin, the mean MIC's for C. albicans and C. neoformans were 1250 and 738 micrograms/mL, respectively, while the mean MFC's were 5000 and 1761 micrograms/mL, respectively. With C. albicans, inhibition and retardation of growth were similar for yeast and mycelial forms, but germ tube formation was inhibited at concentrations lower than those which inhibited growth. Short-term toxicity tests with mice using the intraperitoneal route gave maximum tolerated doses of 62.5 mg/kg for eugenol and 125 mg/kg for vanillin and excluded their use as therapeutic agents for systemic mycoses.

Candida albicans↗
PubMed1994

Suppressive effects of eugenol and ginger oil on arthritic rats.

This study examined the effect of eugenol and ginger oil on severe chronic adjuvant arthritis in rats. Severe arthritis was induced in the right knee and right paw of male Sprague-Dawley rats by injecting 0.05 ml of a fine suspension of dead Mycobacterium tuberculosis bacilli in liquid paraffin (5 mg/ml). Eugenol (33 mg/kg) and ginger oil (33 mg/kg), given orally for 26 days, caused a significant suppression of both paw and joint swelling. These findings suggest that eugenol and ginger oil have potent antiinflammatory and/or antirheumatic properties.

Animals↗
PubMed1979

Analysis and purification of eugenol.

The purity of several brands of eugenol was compared by using high performance liquid chromatography with a UV detector. Greater than 95% of the impurities seen in the USP eugenols were removed by preparative liquid chromatography. NMR spectroscopy suggests that there may be a difference in chemical reactivity between purified and stock eugenol.

Chromatography↗
PubMed2005

Antimicrobial activities of Eugenol and Cinnamaldehyde against the human gastric pathogen Helicobacter pylori.

BACKGROUND: Eradication of Helicobacter pylori is an important objective in overcoming gastric diseases. Many regimens are currently available but none of them could achieve 100% success in eradication. Eugenol and cinnamaldehyde that are commonly used in various food preparations are known to possess antimicrobial activity against a wide spectrum of bacteria. AIM: The present study was performed to assess the in vitro effects of eugenol and cinnamaldehyde against indigenous and standard H. pylori strains, their minimum inhibitory concentrations (MICs) and time course lethal effects at various pH. METHODS: A total of 31 strains (29 indigenous and one standard strain of H. pylori ATCC 26695, one strain of E. coli NCIM 2089) were screened. Agar dilution method was used for the determination of drug sensitivity patterns of isolates to the commonly used antibiotics and broth dilution method for the test compounds. RESULTS: Eugenol and cinnamaldehyde inhibited the growth of all the 30 H. pylori strains tested, at a concentration of 2 mug/ml, in the 9th and 12th hours of incubation respectively. At acidic pH, increased activity was observed for both the compounds. Furthermore, the organism did not develop any resistance towards these compounds even after 10 passages grown at sub-inhibitory concentrations. CONCLUSION: These results indicate that the two bioactive compounds we tested may prevent H. pylori growth in vitro, without acquiring any resistance.

Acrolein↗
PubMed2005

Trapping effect of eugenol on hydroxyl radicals induced by L-DOPA in vitro.

Many researchers have stated that eugenol might inhibit lipid peroxidation at the stage of initiation, propagation, or both, and many attempts have been made to elucidate the mechanism of its antioxidant activity. Nevertheless, details of its mechanism are still obscure. This study was carried out to investigate the trapping effect of eugenol on hydroxyl radical generated from L-3,4-dihydroxyphenylalanine (DOPA) in MiliQ water and the generation mechanism of the hydroxyl radical by this system which uses no metallic factor. This was studied by adding L-DOPA and 5,5-dimethyl-1-pyrroline N-oxide (DMPO) to phosphate buffered saline (PBS) or MiliQ water, and the generation of hydroxyl radical was detected on an ESR spectrum. By this method, the effect of antioxidants was detected as a modification of ESR spectra. We found that the eugenol trapped hydroxyl radicals directly, because it had no iron chelating action, did not trap L-DOPA semiquinone radical and inhibited hydroxyl radicals with or without iron ion.

Aniline Compounds↗
PubMed2005

Synthesis of ibuprofen eugenol ester and its microemulsion formulation for parenteral delivery.

The purpose of this study was to investigate the possibility of parenteral delivery of poorly water-soluble lipophilic drugs using a phospholipid-based microemulsion system. Ibuprofen eugenol ester (IEE), a highly lipophilic compound, was synthesized from ibuprofen and eugenol, and isolated as an amorphous whitish solid with a melting point at 40.2+/-0.1 degrees C, which structure was confirmed by IR, 1H-NMR and MS spectra. A pharmaceutically acceptable microemulsion system using Miglyol 812, soybean phosphatidylcholine (SbPC) and poly (ethylene glycol) (660)-12-hydroxystearate (Solutol HS-15), and PEG400 and ethanol as oil phase, surfactants and cosurfactants, respectively, was presented and characterized in terms of stability, droplet size distribution (DSD) and their solubilization capacity of IEE. The solubility of IEE in the optimized microemulsion formulation consisting of 6.4% ibuprofen eugenol, 9.6% Miglyol 812, 6% SbPC, 6% HS-15, 8.4% PEG400, 3.6% ethanol and 60% distilled water (w/w) was about 21,000 times higher than that in water. The ibuprofen blood concentration after intravenous administration of microemulsions was determined and compared with that of ibuprofen solution. It was concluded that the presented microemulsion system might be a promising intravenous dosage form of poorly water-soluble lipophilic drugs.

Animals↗
PubMed1985

Eugenol-mediated superoxide generation and cytotoxicity in guinea pig neutrophils.

Eugenol is the medicament used routinely as an anodyne and antiseptic in dentistry and a food flavour and fragrance agent. The drug stimulates the superoxide (O2-.) release of guinea pig neutrophils without a lag time. The production rate increases with the drug concentration and reaches a plateau at 5 mM. However, the induction accompanies the cytotoxicity. The stimulation system of O2-. production is sensitive to mild heating (45 degrees C, 15 min). The system proceeds without artifacts which may be mediated by a radical chain reaction with H2O2 and hydroxy radical, since neither catalase, mannitol nor azide changes the rate. Ca2+ and Ni2+ in the medium enhance the activity, but Mg2+ and Zn2+ have no effect. EDTA inhibits completely, suggesting that intracellular metal ions are involved in this system. Phenolic compounds used as dental medicaments other than eugenol act as potent stimulators of the O2-. production, with the following order of potency: thymol greater than eugenol greater than o-cresol. Resorcinol, guaiacol and hexachlorophene show little activity. This order of potency agrees with the order of hydrophobicity of these chemicals and that of the cytotoxicity to neutrophils. The data suggest that phenolic antiseptic drugs bind to the cell surface hydrophobically, trigger the oxygen burst and make the plasma membrane fragile at a high dose of drugs.

Animals↗
PubMed1990

Induction of liver microsomal UDP-glucuronyltransferase in the rat administered with a plant phenol, eugenol.

UDP-glucuronyltransferase activity toward xenobiotics in rat liver microsomes was increased about 2.6-fold by administration of a eugenol (4-allyl-2-methoxyphenol). Km value of the induced enzyme toward UDP-glucuronic acid, however, did not change. Immunoblotting analysis revealed that the amount of UDP-glucuronyltransferase protein was increased in the microsomes of eugenol-treated rat liver. In vitro translation assay showed that the level of translatable mRNA encoding this enzyme increased in the liver. These results indicate that mRNA specific for production of UDP-glucuronyltransferase has accumulated, presumably by de novo synthesis in response to a plant phenol, eugenol.

Animals↗
PubMed2006

Impact of the arylhydrocarbon receptor on eugenol- and isoeugenol-induced cell cycle arrest in human immortalized keratinocytes (HaCaT).

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. Previously, we found a cell cycle arrest and an arylhydrocarbon receptor (AhR)-mediated activation of cytochromes in immortalized keratinocytes (HaCaT) induced by both compounds. In the present study we investigated whether the cell cycle arrest of eugenol and isoeugenol is mediated by the AhR in HaCaT cells. Analysis of the cell cycle status by fluorescence-activated cell sorting (FACS) revealed an arrest of cells (32-34%) in the G0/G1 phase induced by both compounds. This was found in synchronized HaCaT cells, natural HaCaT, and siRNA AhR transfected HaCaT. The induced G0/G1 arrests were reduced in the presence of the highly selective AhR antagonist 3'-methoxy-4'-nitroflavone (MNF). In summary, these results, together with our previous findings that both compounds induce translocation of the AhR into the nucleus, provide good evidence that the effects of eugenol and isoeugenol in skin and keratinocytes are mediated by the AhR. Furthermore, these data suggest that the known growth suppressive effects of these compounds in some skin cells may be mediated by AhR interactions.

Benzo(a)pyrene↗
PubMed2006

Effect of eugenol-based endodontic cement on the adhesion of intraradicular posts.

The present study evaluated, in vitro, the influence of an eugenol-based endodontic sealer (EndoFill) on the adhesion of intra-radicular posts cemented with a resin-based cement (Enforce) ou a zinc phosphate cement. Twenty-four single-rooted maxillary canines were divided into 2 groups (n=12) and obturated with either gutta-percha points plus EndoFill or gutta-percha points alone (no cement). In each group, half of intracanal posts (n=6) were cemented with Enforce resin-based cement and half with zinc phosphate cement. Specimens were submitted to pull-out test in an Instron machine and tensile force was applied at a crosshead speed of 0.5 mm/min until post dislodgement. The maximum forces required for post removal was recorded (N) and means were submitted to statistical analysis by Kruskal-Wallis test (p<0.01). Posts cemented with zinc phosphate cement were significantly more retentive (353.4 N) than those cemented with Enforce (134.9 N) (p<0.01). Regarding the influence of the eugenol-based cement (EndoFill) on post retention, there was statistically significant difference (p<0.01) only between the groups cemented with Enforce, i.e., in the canals filled with EndoFill + guta-percha there was lower bond strength than in the canals filled with gutta-percha points alone (101.5 and 168.2 N, respectively). In conclusion, the zinc-phosphate-based cement showed greater post retention than the resin-based cement. The findings of this study suggest that the eugenol-containing sealer interfered with the adhesive properties of the resin-based cement.

Dental Cements↗
PubMedDate not supplied

Radical modulating activity and cytotoxic activity of synthesized eugenol-related compounds.

The ability of nine synthetic eugenol-related compounds to scavenge O2- (generated by the hypoxanthine-xanthine oxidase reaction) was compared with their radical generation and cytotoxic activity. ESR spectroscopy showed that eugenol (4-allyl-2-methoxyphenol), 2-allyl-4-methoxyphenol, 2-allyl-4-t-butylphenol and 2,4-dimethoxyphenol efficiently scavenged O2- and produced radicals under alkaline conditions. 2-allyl-4-t-butylphenol showed the highest cytotoxic activity and DNA-synthesis inhibitory activity, possibly due to the hydrophobic radical reactivity. 2-allyl-4-methoxyphenol and 2,4-dimethoxyphenol showed higher antioxidant activity than 3-t-butyl-4-hydroxyanisol (BHA), but all these compounds showed comparable cytotoxic activity with each other. These findings suggest a possible link between the cytotoxic activity and radical generation/scavenging activity in eugenol-related compounds.

Antineoplastic Agents↗
PubMedDate not supplied

Methyleugenol and eugenol variation in Ocimum basilicum cv. Genovese gigante grown in greenhouse and in vitro.

The variation of the two main aromatic compounds in Ocimum basilicum cv Genovese Gigante grown in greenhouse and "in vitro" was analyzed. The content of methyleugenol and eugenol was correlated to the plants' height rather than to the plants' age and the growth site. Particularly, methyleugenol was prevalent in plants up to 6.5 cm, as plants grew it was replaced by eugenol that was dominant in taller plants. Analysis of basil 20 cm in height showed that methyleugenol is prevalently localized in the low part while eugenol is prevalent in the upper part of the plant. Moreover, a chronic and acute toxicity of methyleugenol was evidentiated in an assay using chicken embryos.

Eugenol↗
PubMed1995

[Eugenol in root canal cement:possible cause for urticarial reactions].

A case is reported of a patient with chronic urticaria. The correlation between the symptoms and dental treatment gave rise to the supposition that a root canal cement was causing the trouble. This hypothesis has been tested with epicutaneous patch tests and intradermal tests in cooperation with the Utrecht University Hospital (the Netherlands), Institute of Dermatology, Clinical Allergy Section. A causal relationship with eugenol, a cement constituent, could only be established through provocative oral ingestion. Nevertheless, caution is needed when dealing with chronic urticaria in view of the risk of anaphylactic reaction. Consequently, the article highlights the allergenic aspects of eugenol, as a substance associated with balsam of Peru. Attention is focused on the fact that eugenol, used in dental materials, is able to elicit and maintain urticaria protractedly.

Adult↗
PubMed1992

Effect of eugenol-containing endodontic sealer on retention of prefabricated posts luted with adhesive composite resin cement.

Reported studies have implicated eugenol in the reduction in retention of restorations luted with chemically cured composite resin cement. This study investigated the effect of residual eugenol in the root canal on the retention of ParaPost dowels cemented with Panavia EX composite resin. An attempt was also made to identify and to determine the most effective cleansing procedure. Findings of this study demonstrated a substantial decrease in retention of posts luted with Panavia composite resin cement in the presence of eugenol. Irrigation with ethyl alcohol (ethanol) or etching with 37% phosphoric acid gel was found to be effective in restoring the resistance to dislodgment of the posts, but alcohol produced the most consistent and reliable results.

Acetone↗
PubMedDate not supplied

Induction of cytotoxicity and apoptosis and inhibition of cyclooxygenase-2 gene expression by eugenol-related compounds.

Induction of cytotoxicity and internucleosomal DNA fragmentation by 4-allyl-2-methoxyphenol (eugenol, EUG), 2-methoxy-4-methylphenol (MMP), 3,3'-dimethoxy-5,5'-di-2-propenyl-1,1'-biphenyl-2,2'-diol (bis-EUG) and 3,3'-di-methoxy-5,5'-dimethyl-1,1'-biphenyl-2,2'-diol (bis-MMP) were investigated in HL-60 leukemia cells. The 50% cytotoxic concentrations (CC50) for EUG, MMP, bis-EUG and bis-MMP were 0.38 mM, 0.38 mM, 0.18 mM and 0.20 mM, respectively. DNA fragmentation was induced most strongly by bis-EUG, followed by EUG, MMP and bis-MMP. The expression of MnSOD and, less strongly, Cu/ZnSOD activity, as assessed by acrylamide gel electrophoresis, was inhibited by EUG, suggesting mitochondrial dysfunction. The expression of the mRNAs for MnSOD and Cu/ZnSOD in HL-60 cells, as assessed by RT-PCR, was significantly inhibited by treatment with 1 mM EUG for 1 hour. Furthermore, inhibition of SOD mRNAs expression by EUG was strongly potentiated by the addition of 5 mM N-acetyl cysteine (NAC) or glutathione (GSH), whereas NAC or GSH alone did not affect the expression of SOD mRNAs. The cytotoxicity of EUG was significantly enhanced by high concentrations of NAC or GSH, which may be attributed to the inhibition of SOD mRNAs expression by the synergistic action of EUG and GSH or NAC. The regulatory effects of eugenol-related compounds on lipopolysaccharide (LPS)-induced cyclooxygenase-2 (COX-2) gene expression in RAW 264.7 cells were investigated by Northern blot analysis. Bis-EUG, MMP and bis-MMP inhibited COX-2 gene expression at concentrations of 300 microM, 500 microM and 500 microM, respectively. In contrast, no inhibitory effect of EUG was found over the wide concentration range of 10-500 microM, possibly as a result of the extensive mitochondrial dysfunction induced by this compound, which possesses potent pro-oxidative activity. Eugenol-related compounds, particularly bis-EUG, may act as nonsteroidal anti-inflammatory drug (NSAID)-like compounds.

Animals↗
PubMed1991

Hepatotoxicity of eugenol and related compounds in mice depleted of glutathione: structural requirements for toxic potency.

Eugenol produces hepatic injury in mice depleted of glutathione (GSH) by pretreatment with buthionine sulfoximine (BSO). Several eugenol analogs were examined for their ability to cause hepatic injury after administration to mice in combination with BSO. Hepatotoxicity was assessed by measuring relative liver weight, liver blood volume, and serum GPT activity in mice. Comparison of the tested compounds showed that the structural requirements for toxic potency was a phenolic ring having an allyl substituent at the 4-position. These structural requirements can be explained by assuming that a vinylogous quinone methide formed by metabolic oxidation of eugenol plays a role in inducing hepatotoxicity in GSH-depleted mice.

Alanine Transaminase↗
PubMed1989

[Clinico-pathological studies on the effects of calcium hydroxide eugenol preparations to the human vital pulp tissues].

The present paper reports results of a study to evaluate clinico-pathologically the effects of calcium hydroxide eugenol preparations on exposed pulp tissues in permanent human teeth. The experiments were performed on 80 vital human teeth from patients ranging in age from 12 to 54 years. The experimental teeth were arbitrarily divided into the following 4 groups. Group CRCS: 20 cases treated with CRCS (Hygienic, Akron, Ohio, USA). Group KEZ: 20 cases treated with Dentalis KEZ (Neo Dental Chemical Products, Tokyo, Japan). Group CE: 20 cases treated with calcium hydroxide eugenol (positive control) Group E: 20 cases treated with pure eugenol (negative control). After local anesthesia, the experimental teeth were isolated with rubber dums or cotton rolls. Following preparation of Black's simple class 1 cavities with a diamond instrument mounted high-speed air turbine, the pulp was intentionally exposed by means of a steel bur mounted electric engine. The cavity and exposed pulp surface were cleaned with saline and dried on absorbent material. Then the experimental materials (agents) were applied to exposed pulp surface. The cavity was lined with gutta-percha temporally stopping, and the remainder was filled with silver amalgam. The teeth were clinically observed at various intervals from immediately to 530 days after treatment and then extracted under local anesthesia and prepared for histopathological study. Decalcified sections were stained with hematoxylin and eosin. 1) CLINICAL OBSERVATIONS: During the observation period, symptoms occurred in the following: Group CRCS: 4 (20%) out of 20 cases. Group KEZ: 4 (20%) out of 20 cases. Group CE: 6 (30%) out of 20 cases. Group E: None of 20 cases No spontaneous pain was observed in these groups. 2) Clinical evaluations Group: CRCS: 16 cases (80%) were good, 3 cases (15%) were satisfactory, and 1 cases (5%) were failure. Group KEZ: 16 cases (80%) were good, 1 cases (5%) were satisfactory, and 3 cases (15%) were failure. Group CE: 14 cases (70%) were good, 4 cases (20%) were satisfactory, and 2 cases (10%) were failure. Group E: 20 cases (100%) were good. 3) Histopathological observations. Various kinds and degree of pulp changes were occurred in each group. Hyperemia and round-cell infiltration resulting from damage caused by treatment and medicaments were frequent in each group. No suppurative inflammation occurred in group CE. Pulp cicatrization and apposition of dentin on pulp chamber walls were observed frequently in each groups. Hard tissue formation was observed in numerous cases of group CE and in some cases in group CRCS and KEZ.(ABSTRACT TRUNCATED AT 400 WORDS)

Adolescent↗