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PubMed1982

Comparison of calcium hydroxide and zinc oxide and eugenol pulpectomies in primary teeth of dogs.

The purpose of this investigation was to compare calcium hydroxide with zinc oxide and eugenol (ZOE) as root canal obturants in the pulpectomy procedure for irreversibly inflamed primary pulps of dogs. Clinical, radiographic, and histologic comparisons of calcium hydroxide and ZOE root canal filling materials were made in forty-two primary premolars of seven mongrel puppies. When the animals were 6 weeks of age, the pulps of all samples teeth were extirpated and the canals left open to the oral environment. The root canals were assigned to calcium hydroxide, ZOE, and control groups, instrumented, and filled 2 weeks later. The animals were killed 1 day, 1 week, 4 weeks, and 12 weeks after filling. Statistical analysis of all categories for comparison at 4 weeks indicated that calcium hydroxide gave significantly more favorable results than ZOE. Canals treated with calcium hydroxide exhibited less inflammation, less resorption, and more hard-tissue apposition than ZOE-treated and control groups.

Animals↗
PubMed1984

A histologic comparison of Hydron and zinc oxide-eugenol as endodontic filling materials in the primary teeth of dogs.

Currently available endodontic filling materials for primary teeth demonstrate several inadequacies. Therefore, this study histologically evaluates Hydron (2-hydroxyethylmethacrylate) and zinc oxide and eugenol (ZOE) as primary tooth endodontic filling materials in dogs to compare the materials' biocompatibility and to determine whether they undergo resorption in a physiologic manner. Primary molars of six mongrel dogs, 2 to 3 months old, received one-step endodontic therapy. By random selection, two thirds of the molars were filled with either Hydron or ZOE and the remainder were used as unoperated controls. Block sections taken during physiologic root resorption were used to obtain serial hematoxylin and eosin sections of periapical regions. Hydron was phagocytosed by mononuclear macrophages in a physiologic manner and at a rate comparable to that of root tissues. In contrast, ZOE demonstrated delayed resorption and transitory inflammation. Neither material showed cytotoxicity. Hydron may therefore be a suitable endodontic material for human primary teeth.

Animals↗
PubMed1992

Biotransformation of isoeugenol and eugenol by cultured cells of Eucalyptus perriniana.

Three new biotransformation products, eugenyl beta-rutinoside, and isoeugenyl beta-gentiobioside and beta-rutinoside, together with eugenyl beta-glucoside and beta-gentiobioside, and isoeugenyl beta-glucoside, were isolated from jar fermentor culture of Eucalyptus perriniana following administration of eugenol and isoeugenol, respectively. This is the first report of rhamnosylation in a biotransformation catalysed by cultured cells of E. perriniana.

Acetylation↗
PubMed1994

Effect of abietic acid and poly(methyl methacrylate) on the dissolution process of zinc oxide-eugenol cement.

The effects of abietic acid and poly(methyl methacrylate) (PMMA) on the dissolution process of zinc oxide-eugenol cement were studied in 0.01 M acetic acid buffer solution (pH 4). Abietic acid markedly reduced the elution of zinc from the cement, because of the matrix stabilization by the reaction between the acid and zinc oxide. The dissolution process of the cement without additives was controlled by surface reaction. With the cement containing abietic acid or PMMA, the diffusion of eluted species through the cement matrix participated in the dissolution process.

Abietanes↗
PubMed1990

Further evidence that eugenol does not bind to DNA in vivo.

The naturally-occurring alkenylbenzene, eugenol, was examined for its ability to form DNA adducts in the livers of mice that had been treated with up to 10 mg of the compound. No adducts were detected by 32P-postlabelling with a limit of detection of 1 adduct in 10(9) nucleotides. Under these conditions adducts were readily detected in liver DNA from the structurally-related hepatocarcinogen safrole.

Animals↗
PubMed2005

Effects of methyl-eugenol administration on behavioral models related to depression and anxiety, in rats.

Croton zehntneri (Cz) is a popular plant in Brazilian folk medicine. Recently, the use of its essential oil showed depressive activity response in the central nervous system (CNS). Chemical studies show that the main compound of this oil is the methyl-eugenol (ME). This work seeks to evaluate the ME activity in behavioral models of depression and anxiety, in the rat. Male rats (60 days old) were divided into four groups (n = 10) and treated with doses of 1.0, 3.0 and 10.0 ml/100 g body wt., v.o., of ME (experimental) and saline (control). One hour after treatment, they were observed in the forced swimming test and 15 min later in the open-field test. A decrease was observed in the immobility time during the forced swimming test for all experimental groups, in comparison with control group (C = 168.8 +/- 27.3; 1.0 microl = 139.1 +/- 23.5; 3.0 microl = 137.2 +/- 18.7 and 10.0 microl = 139.8 +/- 23.6). The open-field results showed no differences in comparison to the control group. The same was observed for social interaction, plus-maze and holeboard tests, suggesting no alterations in anxiety behavior. These data suggest that ME administration induced antidepressive CNS alterations, expressed by the smallest immobility in the swimming model, and not of a level able to alter motor and exploratory activity in the open-field. The absence of effects observed in the open-field can be a result of the experimental contingency, taking low anxiety levels. These data are in contradiction to observations with Cz essential oil in these models.

Animals↗
PubMed2006

Biotransformation of thymol, carvacrol, and eugenol by cultured cells of Eucalyptus perriniana.

The biotransformations of aroma compounds of spices, such as thymol (1), carvacrol (2), and eugenol (3), were investigated using cultured plant cells of Eucalyptus perriniana. Besides a beta-glucoside product (4, 3%), a biotransformation product, i.e., 5-methyl-2-(1-methylethyl)phenyl 6-O-(beta-d-glucopyranosyl)-beta-d-glucopyranoside (5, beta-gentiobioside, 87%), was isolated from the suspension cells after the five-day incubation of 1. On administration of 2, a beta-glucoside (6, 5%) and a beta-gentiobioside, i.e., 2-methyl-5-(1-methylethyl)phenyl 6-O-(beta-d-glucopyranosyl)-beta-d-glucopyranoside (7, 56%), were produced. Furthermore, E. perriniana cells also converted 3 into the corresponding beta-glucoside (8, 7%) and beta-gentiobioside (9, 58%). The cultured cells of E. perriniana are able to convert these aroma compounds of spices into glycosides which are accumulated in the cells.

Biotransformation↗
PubMed1992

Comparison of apical leakage in teeth obturated with a polyamide varnish or zinc oxide and eugenol cement using lateral condensation.

The sealing ability of copal varnish has been investigated when used as an adjunct in restorative procedures, retrofilling procedures, and dontic obturation procedures. Barrier, a polyamide-type polymer cavity varnish, has been compared with copal varnishes in restorative dentistry. This investigation compared the apical sealing properties of a zinc oxide and eugenol sealer (Roth) with a polyamide varnish (Barrier). Twenty-four teeth were instrumented and divided into two groups, one obturated with gutta-percha and Roth sealer and one with gutta-percha and Barrier, using submersion in methylene blue dye to demonstrate apical leakage. Roth sealer exhibited less dye penetration than Barrier when used as an endodontic sealant (p < 0.02).

Dental Cavity Lining↗
PubMed1990

Root canal sealer cytotoxicity on human gingival fibroblasts. 1. Zinc oxide-eugenol-based sealers.

The cytotoxicity of six different zinc oxide-eugenol root canal sealers was tested by determining the incorporation of [L-14C]leucine in human gingival fibroblasts that had been in contact with root canal sealers after setting for 24 and 48 h. The biopsies were obtained from healthy patients. In some cases there was a significant difference shown in the fibroblasts' protein synthesis ([L-14C]leucine incorporation) between the group that was coveted with fibroblasts 24 h and the group that was covered 48 h after mixing (p less than 0.05). The fibroblasts were cultured with the different sealers for 21 days. In the 24-h group, Pulp Canal Sealer showed initially moderate cytotoxic potential but, after 13 days, fibroblast recovery was noticeable. Tubli-Seal, Endoseal, Hermetic, Proco-Sol, and Wach's Formula showed slight recovery at the end phase of the test. Hermetic and Endoseal showed also in the 48-h group a similar development as in the 24-h group. A relative low cytotoxicity was observed with Tubli-Seal, Proco-Sol, Pulp Canal Sealer, and Wach's Formula at the beginning of the test period. Pulp Canal Sealer showed at the middle phase of the trial a toxic increase, but after the 15th day recovery of the fibroblasts was noticed. In this group constant toxic potential increase was observed with Wach's Formula and Tubli-Seal.

Adult↗
PubMed2003

Induction of cyclooxygenase-2 mRNA and protein expression by epoxy resin and zinc oxide-eugenol based root canal sealers in human osteoblastic cells.

An ideal root canal sealer should be nonirritating to the surrounding tissues. Unfortunately, all histological investigation demonstrated that all types of root canal sealer can induce mild to severe inflammatory alternations. However, there is little information on the precise mechanisms about root canal sealers-induced inflammatory reaction. Cyclooxygenase-2 (COX-2) is an inducible enzyme believed to be responsible for prostaglandin synthesis at site of inflammation. The aim of the present study was to investigate the effects of epoxy resin (AH26) and zinc oxide-eugenol based (Endomethansone and N2) root canal sealers on the expression of COX-2 mRNA gene and protein in cultured human osteoblastic cells. Investigations of the time dependence of COX-2 mRNA expression in root canal sealer-treated human osteoblastic cells revealed a rapid accumulation of the transcript, a significant signal first detectable within 2h and diminished to control level after 24h. In addition, all root canal sealers also induced COX-2 protein expression in human osteoblastic cells. Furthermore, to elucidate whether induction of COX-2 is associated with cytotoxicity, NS-398 (a selective COX-2 inhibitor), was added to test its protective effects. NS-398 at non-cytotoxic dose is not able to prevent root canal sealers-induced cytotoxicity. Taken together, the activation of COX-2 expression may be one of the pathogenesis of root canal sealers-induced periapical inflammation. In addition, root canal sealers-induced cytotoxicity is not directly via the induction of COX-2 expression.

Cells, Cultured↗
PubMed2001

Allomonal and hepatotoxic effects following methyl eugenol consumption in Bactrocera papayae male against Gekko monarchus.

Methyl eugenol (ME), is converted into two major phenylpropanoids, 2-allyl-4,5-dimethoxyphenol and trans-coniferyl alcohol, following consumption by the male fruit fly Bactrocera papayae. Chemical analysis of wild male B. papayae rectal glands, where the compounds are sequestered, revealed the presence of ME metabolites in varying quantities. These phenylpropanoids are shown to be involved in the fruit fly defense both in no-choice and choice feeding tests against the Malayan spiny gecko, Gekko monarchus. After being acclimatized to feeding on fruit flies, geckos consumed significantly fewer ME-fed male flies than controls that consumed all the ME-deprived male flies offered throughout a two-week period. Diagnosis of dissected livers from geckos that consumed ME-fed male flies revealed various abnormalities. These included discoloration and hardening of liver tissue, whitening of the gallbladder, or presence of tumor-like growths in all geckos that consumed ME-fed male flies. Control geckos fed on ME-deprived male flies had healthy livers. When given an alternative prey, geckos preferred to eat untreated house flies, Musca domestica to avoid preying on ME-fed fruit flies.

Animals↗
PubMed2004

Male sex pheromonal components derived from methyl eugenol in the hemolymph of the fruit fly Bactrocera papayae.

Pharmacophagy of methyl eugenol (ME)--a highly potent male attractant, by Bactrocera papayae results in the hydroxylation of ME to sex pheromonal components, 2-ally-4,5-dimethoxyphenol (DMP) and (E)-coniferyl alcohol (CF). These compounds, which are also male attractants, are then sequestered and stored in the rectal gland prior to their release during courtship at dusk. Chemical analyses of the digestive tract (excluding the crop and rectal gland) showed the absence of the sex pheromonal components and their precursor, ME. However, B. papayae males were attracted to and fed on the ME-fed male hemolymph extracts but not on hemolymph extracts of ME-deprived males. After thin layer chromatography in a hexane:ethyl acetate solvent system, flies were attracted to and fed on the original point on the TLC plate where the hemolymph extract had been spotted, suggesting that the pheromone components were bound in polar complexes. Chemical analyses of the ME-fed male hemolymph and crop extracts revealed the presence of the sex pheromonal components. The presence of the ME-derived pheromonal components and the absence of ME in the hemolymph suggest that the hemolymph is involved in the transportation of sex pheromonal components from the crop to the rectal gland.

Animals↗
PubMed2005

Enhanced hypotensive effects of the essential oil of Ocimum gratissimum leaves and its main constituent, eugenol, in DOCA-salt hypertensive conscious rats.

The cardiovascular effects of intravenous (i.v.) treatment with the essential oil of Ocimum gratissimum (EOOG) and its main constituent, eugenol (Eug) were investigated in the experimental model of deoxycorticosterone acetate (DOCA-salt)-hypertensive rats. In both conscious DOCA-salt hypertensive rats and their uninephrectomized controls, i.v. bolus injections of EOOG (1 - 20 mg/kg) or Eug (1 - 10 mg/kg) induced dose-dependent hypotension and bradycardia. Treatment with DOCA-salt significantly enhanced the maximal decreases in mean aortic pressure (MAP) elicited by hexamethonium (30 mg/kg, i.v.) as well as the hypotensive responses to both EOOG and Eug without affecting the bradycardia. However, the enhancement of EOOG-induced hypotension in hypertensive rats remained unaffected by i.v. pretreatment with either hexamethonium (30 mg/kg) or methylatropine (1 mg/kg). These results show that i.v. treatment with EOOG or Eug dose-dependently decreased blood pressure in conscious DOCA-salt hypertensive rats, and this action is enhanced when compared with uninephrectomized controls. This enhancement appears related mainly to an increase in EOOG-induced vascular smooth relaxation rather than to enhanced sympathetic nervous system activity in this hypertensive model.

Animals↗
PubMed2000

Influence of albumin and collagen on the cell mortality evoked by zinc oxide-eugenol in vitro.

Zinc oxide-eugenol (ZOE) is cytotoxic in vitro but does not cause pulp damage. Various dentin proteins may play a protective role in vivo. We investigated the influence of bovine serum albumin (BSA) and collagen on ZOE cytotoxicity in the Millipore filter test and a dentin barrier test. Agar or agarose with 1% or 5% BSA or calf collagen (1% and 2%) were introduced between L-929 fibroblasts and test specimens. ZOE was severely toxic in the absence of BSA. However BSA (1% and 3%) reduced cell damage to 50% and 35%. In contrast, collagen did not provide protection from ZOE cytotoxicity. When dentin was loaded with 3% BSA and the "pulpal" side of a dentin barrier test chamber was perfused with cell culture medium containing 3% BSA, cytotoxicity of ZOE was completely inhibited. Therefore we conclude that albumin may be one factor responsible for the absence of ZOE toxicity in pulp studies.

Agar↗
PubMed1999

Eugenodilol: a third-generation beta-adrenoceptor blocker, derived from eugenol, with alpha-adrenoceptor blocking and beta2-adrenoceptor agonist-associated vasorelaxant activities.

Eugenodilol, derived from natural eugenol, was first investigated with in vivo and in vitro models. In our in vivo study, eugenodilol (0.5, 1.0, and 1.5 mg/kg, i.v.) produced dose-dependent hypotensive and bradycardic responses in pentobarbital-anesthetized Wistar rats. Eugenodilol also inhibited the tachycardia and arterial pressor effects induced by (-)isoproterenol and phenylephrine, respectively. In our in vitro study, eugenodilol competitively antagonized (-)isoproterenol-induced positive inotropic and chronotropic effects and tracheal-relaxation responses on isolated guinea pig tissues in a concentration-dependent manner. The apparent pA2 values were 7.88+/-0.12 for right atria, 7.52+/-0.05 for left atria, and 7.33+/-0.15 for trachea, indicating that eugenodilol was a nonselective beta-adrenoceptor blocker. In thoracic aorta experiments, the apparent pA2 values of alpha-adrenoceptor blockade were 7.05+/-0.25 and 6.87+/-0.08 for eugenodilol and labetalol, respectively. In addition, eugenodilol produced cumulative relaxation responses on isolated guinea pig tracheal strips. The effects were competitively antagonized by ICI 118,551 (10(-8)-10(-6) M), a relatively selective beta2-adrenoceptor antagonist. In the radioligand-binding assay, the Ki values of [3H]CGP-12177 binding to rat ventricle and lung membranes were 9.72 and 48.29 nM, respectively, and the value of [3H]prazosin binding to rat brain membrane was 38.72 nM. These results further confirmed the alpha/beta-adrenoceptors-blocking activities of eugenodilol reported in the functional studies. We conclude that eugenodilol is a novel third-generation beta-adrenoceptor blocker with ancillary blocking activity at alpha-adrenoceptors and weak sympathomimetic activity at beta2-adrenoceptors.

Adrenergic beta-Agonists↗
PubMed2004

Cardiovascular effects of eugenol, a phenolic compound present in many plant essential oils, in normotensive rats.

Cardiovascular effects of intravenous (i.v.) treatment with eugenol (Eug), a natural pungent present in many plant essential oils, were investigated in normotensive rats. In either anesthetized or conscious rats, i.v. bolus injections of Eug (1 to 10 mg/kg) elicited immediate and dose-dependent hypotension and bradycardia. Magnitude of Eug-induced hypotension was similar in both groups. Pretreatment of anesthetized rats with bilateral vagotomy almost abolished the bradycardic responses to Eug without affecting the hypotension. Likewise, i.v. pretreatment of conscious rats with methylatropine (1 mg/kg) or hexamethonium (30 mg/kg) significantly reduced the Eug-induced bradycardia without affecting the hypotension. However, i.v. pretreatment with the nitric oxide synthase inhibitor, NG-nitro-L-arginine methyl (L-NAME, 20 mg/kg), affected neither the hypotension nor the bradycardia elicited by Eug. In rat mesenteric bed preparations precontracted with potassium (60 mM), Eug (0.1-2 mM) induced a reversible and concentration-dependent vasodilator effect, which remained unaffected by atropine (1 microM). These results show that i.v. treatment of rats with Eug induces dose-dependent hypotension and bradycardia, which occurred independently. The bradycardia appears dependent upon the presence of an intact and functional parasympathetic nerve drive to the heart while the hypotension is due to an active vascular relaxation rather than withdrawal of sympathetic tone. Released nitric oxide from vascular endothelial cells seems to be not involved in the mediation of Eug-induced hypotension.

Animals↗
PubMed2004

Effects of eugenol, an essential oil, on the mechanical and electrical activities of cardiac muscle.

Eugenol (EUG) acts as a calcium antagonist but effects on the contractile proteins could also occur. We investigated inotropic effects of EUG in rat left ventricular papillary muscles, measuring isometric force, time variables, and post rest potentiation and EUG actions on the effects of Ca2+ (0.62 to 2.5 mM) and isoproterenol (5 ng/ml), on myosin ATPase activity and on the calcium currents in single ventricular myocytes. EUG reduced tension and time variables without altering the sarcoplasmic reticulum activity increasing post-pause relative potentiation. Isoproterenol and Ca2+ counteract these negative inotropic effects. Tetanic tension diminished, but not the myosin ATPase activity suggesting an isolated sarcolemmal effect. EUG 0.1 mM decreased the Ca2+ current amplitude in the entire potential range tested and 0.5 mM almost completely blocked this inward current. Results suggested that EUG depresses force without affecting the contractile machinery and its action is the only dependent blockade of the calcium inward current.

Animals↗