Eugenol

Phenylpropenes such as chavicol, t-anol, eugenol, and isoeugenol are produced by plants as defense compounds against animals and microorganisms and as floral attractants of pollinators. Moreover, humans have used phenylpropenes since antiquity for food preservation and flavoring and as medicinal agents. Previous research suggested that the phenylpropenes are synthesized in plants from substituted phenylpropenols, although the identity of the enzymes and the nature of the reaction mechanism involved in this transformation have remained obscure. We show here that glandular trichomes of sweet basil (Ocimum basilicum), which synthesize and accumulate phenylpropenes, possess an enzyme that can use coniferyl acetate and NADPH to form eugenol. 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. The basil and petunia phenylpropene-forming enzymes belong to a structural family of NADPH-dependent reductases that also includes pinoresinol-lariciresinol reductase, isoflavone reductase, and phenylcoumaran benzylic ether reductase.

Essential oils have been studied for their unique ability to act as antioxidants. Antioxidant activities of 423 essential oils of 48 different botanical families were evaluated for their antioxidant activities as free radical scavenging agents using the 1,1-diphenyl-2-picrylhydrazyl method. Seventy-three oils showed 50% or more inhibition at a concentration of 1.25 mg/mL. The 73 most active oil samples were further evaluated for their scavenging activities using series of dilutions to estimate their EC 50 . The EC 50 of the 73 most active oils ranged from 4 to 2000 μg/mL. Oils having an EC 50 of less than 300 μg/mL (20 selected samples) were subjected to β-carotene bleaching antioxidant activity test and more detailed analysis including thin layer chromatography, gas chromatography/mass spectrometry, high performance liquid chromatography and bioautography. Essential oils of the botanical families Lamiaceae and Myrtaceae were the most effective antioxidants. Thymol and carvacrol were the major constituents in most of the essential oils of the family Lamiaceae and eugenol was the major terpene in all of the essential oils of the family Myrtaceae.

The acaricidal activity of Eugenia caryophyllata essential oil was evaluated in vitro and in vivo on Psoroptes cuniculi, a mange mite. In vitro, diVerent concentrations of the oil were tested and the observed mites mortality was compared with that observed in untreated and treated (Acacerulen R ® ) controls. In vivo, six P. cuniculi infected rabbits were topically treated with the oil diluted at 2.5% and compared with untreated and treated control groups of six rabbits each. In vitro, up to the concentration of 0.10% the oil gave highly signiWcant (P < 0.01) percentages of mite mortality respect to the untreated controls, but only up to 0.16% it showed the same eYcacy of Acacerulen R ® . In vivo, the treatment with the essential oil cured all infested rabbits and no statistical diVerences were observed respect to the treated control group. The untreated rabbits remained infested.

The antioxidant, antifungal and antibacterial potentials of volatile oils and oleoresin of Cinnamomum zeylanicum Blume (leaf and bark) were investigated in the present study. The oleoresins have shown excellent activity for the inhibition of primary and secondary oxidation products in mustard oil added at the concentration of 0.02% which were evaluated using peroxide, thiobarbituric acid, p-anisidine and carbonyl values. Moreover, it was further supported by other complementary antioxidant assays such as ferric thiocyanate method in linoleic acid system, reducing power, chelating and scavenging effects on 1,1 0-diphenyl-2-picrylhydrazyl (DPPH) and hydroxyl radicals. In antimicrobial investigations, using inverted petriplate and food poison techniques, the leaf and bark volatile oils has been found to be highly effective against all the tested fungi except Aspergillus ochraceus. However, leaf oleoresin has shown inhibition only for Penicillium citrinum whereas bark oleoresin has caused complete mycelial zone inhibition for Aspergillus flavus and A. ochraceus along with Aspergillus niger, Aspergillus terreus, P. citrinum and Penicillium viridicatum at 6 lL. Using agar well diffusion method, leaf volatile oil and oleoresin have shown better results in comparison with bark volatile oil, oleoresin and commercial bactericide, i.e., ampicillin. Gas chromatographic-mass spectroscopy studies on leaf volatile oil and oleoresin resulted in the identification of 19 and 25 components, which accounts for the 99.4% and 97.1%, respectively of the total amount and the major component was eugenol with 87.3% and 87.2%, respectively. The analysis of cinnamon bark volatile oil showed the presence of 13 components accounting for 100% of the total amount. (E)-cinnamaldehyde was found as the major component along with d-cadinene (0.9%), whereas its bark oleoresin showed the presence of 17 components accounting for 92.3% of the total amount. The major components were (E)-cinnamaldehyde (49.9%), along with several other components.

Brazil j o u r n a l o f d e n t i s t r y 3 9 ( 2 0 1 1 ) 2 5 5 -2 6 2 Microtensile bond strength Dentine adhesive a b s t r a c t Objective: This study tested the hypothesis that bond strength of total-and self-etching adhesive systems to dentine is not affected by the presence of remnants from either eugenol-containing (EC) or eugenol-free (EF) temporary cements after standardized cleaning procedures.

Fusarium disease causes considerable losses in the cultivation of Piper nigrum, the black pepper used in the culinary world. Brazil was the largest producer of black pepper, but in recent years has lost this hegemony, with a significant reduction in its production, due to the ravages produced by the Fusarium solani f. sp. piperis, the fungus which causes this disease. Scientific research seeks new alternatives for the control and the existence of other Piper species in the Brazilian Amazon, resistant to disease, are being considered in this context. The main constituents of the oil of Piper divaricatum are methyleugenol (75.0%) and eugenol (10.0%). The oil and these two main constituents were tested individually at concentrations of 0.25 to 2.5 mg/mL against F. solani f. sp. piperis, exhibiting strong antifungal index, from 18.0% to 100.0%. The 3D structure of the β-glucosidase from Fusarium solani f. sp. piperis, obtained by homology modeling, was used for molecular docking and mol...

In view of the widespread emergence of resistant isolates, an attempt was made to isolate and characterise the component(s) of Ocimum sanctum with activity against Neisseria gonorrhoeae. Bioassay-guided purification of the hexane extract of leaves of O. sanctum was carried out, which yielded H12c as the active compound. H12c was characterised and was determined to be eugenol, with a minimum inhibitory concentration of 85–256 mg/L. The antigonorrhoeal efficacy of H12c was better against multiresistant strains. The 50% lethal dose (LD50) of H12c was found to be 2 g/kg body weight in rats. In view of its efficacy and lower toxicity, eugenol may be a potentially suitable molecule to be developed clinically in response to emerging resistant isolates of N. gonorrhoeae.

The natural forests and meadows of the Green Mountain of Libya are classified as the richest floristic region of the country. Among various species Cynara scolymus L. (Asteraceae), is the most used medicinal plant. C. scolymus L., has long been regarded as noncrop food and also as an effective medicinal plant. In the current study, total phenols as well as flavanoids were determined in methanolic and aqueous extracts the of C. scolymus L. rhizomes in order to assess their contribution to the antioxidant activity. Free radical scavenging activity of the extracts was investigated and compared with ascorbic acid. Methanolic extract exhibited a higher total phenols (45.11 mg GAE/g DW) and flavonoids (37.00 mg Rutin/g), that results in a high antioxidant activity with IC 50 (17.77 µg/ml). In contrast, aqueous extract showed a lower total phenolic and flavonoid contents (37.79 mg GAE/g DW and 15.51 mg Rutin/g DW, respectively) and IC 50 (66.3 µg/ml). Isolated flavonoids showed the highest free radical scavenging activities (IC 50 = 13.33 µg/ml). The in vitro antibacterial activity of C. scolymus L. rhizomes was investigated against various strains of bacteria by hole-plate diffusion method. The minimum inhibitory concentrations (MICs) of the crude methanol, flavonoids and alkaloids extracts found to be between 0.03 and 200 mg/ml for the susceptible organisms, with that of MRSA being the least.

This article describes an alternative technique for the fabrication of interim restorations. A thermoplastic, vacuumformed template and translucent vinyl polysiloxane material are combined in the waxed diagnostic cast to fabricate a matrix in which the interim material can be placed. With this matrix, a variety of materials, such as dual-polymerized or light-polymerized resins, can be used in a predictable way. The major advantage of this technique is that it allows for the fabrication of accurate restorations with excellent reproduction of surface anatomy and for alterations of the tooth shape with light-polymerized materials

β-Cyclodextrin (β-CD) inclusion complexes with carvacrol (1), thymol (2), and eugenol (3) (components of essential oils of vegetable origin) were prepared by the supercritical CO2 technique, and their structural characterization was achieved by means of 1H-NMR in aqueous solution and 13C-CPMAS NMR in the solid state. Evidence of the formation of the inclusion complexes for all the examined systems was obtained by 1H-NMR in solution, while 2D-ROESY-NMR experiments were used to investigate the geometry of inclusion. In addition, the dynamics of these inclusion complexes in the kHz timescale was investigated by analysis of the 1H and 13C spin-lattice relaxation times in the rotating frame.

Methyl eugenol (ME) and cue-lure (C-L) traps with solid lure dispensers were deployed in areas with low and high populations of oriental fruit ßy, Bactrocera dorsalis (Hendel), and melon ßy, Bactrocera cucurbitae (Coquillett), respectively. In low-density areas, standard Jackson traps or Hawaii Fruit Fly Areawide Pest Management (AWPM) traps with FT Mallet ME wafers impregnated with dimethyl dichloro-vinyl phosphate (DDVP) or AWPM traps with Scentry ME cones and vapor tape performed equally as well as standard Jackson traps with liquid ME/C-L and naled. Standard Jackson traps or AWPM traps with FT Mallet C-L wafers impregnated with DDVP or AWPM traps with Scentry C-L plugs with vapor tape performed equally as well as standard Jackson traps with a lure-naled solution. In high density areas, captures with traps containing FT Mallet wafers (ME and C-L) outperformed AWPM traps with Scentry cones and plugs (ME and C-L) with DDVP insecticidal strips over a 6-mo period. Captures of B. dorsalis and B. cucurbitae with wafers containing both ME and raspberry ketone (FT Mallet MC) were equivalent to those containing separate lures. From a worker safety and convenience standpoint, FT Mallet ME and C-L wafers with DDVP or Scentry plugs, with or without DDVP vapor tape, are more convenient and safer to handle than standard liquid insecticide formulations used for monitoring and male annihilation programs in Hawaii, and for detections traps used on the U.S. mainland. Furthermore, the FT Mallet MC wafer might be used in a single trap in place of two separate traps for detection of both ME and C-L responding fruit ßies.

Eugenol (2-methoxy-4-allyl-phenol) was used as a reducing agent for one-pot synthesis of gold nanoparticles in a mild alkaline aqueous/organic solution at room temperature. In this reaction, eugenol acts also as a stabilizing agent, since it undergoes polymerization upon oxidation. As a result, stable colloids of polyeugenol (PE)-capped gold nanoparticles are formed during the reaction with the average particle size of 44 nm. Moreover, conducting supports, such as ITO glass, are covered by Au/PE composite film when immersed in the reaction medium. The modified ITO shows redox activity assignable to residual quinone moieties of PE with redox couples at a potential range of −0.2 to 0.4 V (vs. Ag/AgCl at pH 7.4). Redox properties of Au/PE nanoparticulate films can be exploited for the electrocatalytic oxidation of NADH with over 0.5 V reduction of the reaction overpotential vs. unmodified ITO. Nanoparticulate composite films were characterized by UV-vis spectroscopy, XPS and FT-IR spectroscopy. The characterization revealed structural similarity of the formed PE to lignin.

Among the factors which could explain avoidance behavior toward dental care, the typical clinging odor of the dental office, due to eugenol, is investigated in this study. The hypothesis is supported by the well-known effects of odorants which may influence cognition, emotion, and behavior. The aisociation between the odor of eugenol and dental fear and anxiety could be explained by the fact that eugenates (eugenol-containing cements) are often used in potentially painful restorative dentistry on vital teeth. The emotional impact of the odors of eugenol and two other dental products (menthol and methyl methacrylate) was evaluated on volunteer subjects through autonomic nervous system (ANS) analysis by recording the variations of six ANS parameters (two electrodermal, two thermovascular, and two cardiorespiratory) induced by the inhalation of the odorants. After the experiment, subjects were asked to fill out an 11-point hedonic scale to rate the pleasantness vs. unpleasantness for each odorant. Results were compared between two groups of subjects divided according to their own dental experience (fearful and non-fearful dental-care subjects). These showed that, in both groups, menthol was rated as pleasant and methyl methacrylate as very unpleasant, whereas eugenol was judged pleasant by nonfearful subjects but unpleasant by fearful subjects. Concerning autonomic analysis, only eugenol induced significantly different patterns of ANS responses between the two groups, with stronger variations for dentally fearful subjects, mainly observed through the electrodermal channel. These results suggest that eugenol can be responsible for different emotional states, depending on the unpleasantness of the subjects' dental experience. This seems to confirm the role of odors as elicitors of emotional memories and to support the possible influence of eugenol odor on the avoidance behavior of some subjects toward dental care.

Ocimum basilicum cv. Genovese Gigante is the basil cultivar used the most in the production of a typical Italian sauce called pesto. The aromatic composition of plants at different growth stages was determined. Plants from different areas of northwestern Italy were analyzed at 4 and 6 weeks after sowing and showed methyleugenol and eugenol as the main components. The content of these compounds was correlated with plant height rather than plant age. Particularly, methyleugenol was predominant in plants up to 10 cm in height, whereas eugenol was prevalent in taller plants. These results are important in the evaluation of risk to human health posed by dietary ingestion of methyleugenol contained in pesto.

Oil-in-water nanoemulsion was formulated using sesame oil, non-ionic surfactant (Tween20/Tween80) and water by ultrasound cavitation method. Development of nanoemulsion was optimized for process parameters such as surfactant type, surfactant concentration and emulsification time to obtain lower droplet diameter with greater stability. Increase in surfactant concentration and emulsification time resulted in nanoemulsion with minimized droplet diameter. Tween80 was more effective in reducing droplet size when compared to that of Tween20. Selected formulation with optimized process parameter (with oil-surfactant mixing ratio of 1:3 v/v and Tween80 as surfactant) was used for delivery of eugenol. Eugenol-loaded nanoemulsion was formulated with droplet diameter of 13 nm and was stable for more than 1 month. Sesame oil blended eugenol-loaded nanoemulsion demonstrated lower droplet size and higher stability than only-eugenol (without sesame oil) nanoemulsion. Eugenol-loaded nanoemulsion S3E3 exhibited antibacterial activity against Staphylococcus aureus. Inactivation kinetics of S. aureus showed time and concentration killing of bacteria upon treatment with S3E3 nanoemulsion. Fluorescence microscopy results demonstrated that S3E3 nanoemulsion treatment resulted in alteration of membrane permeability. In situ assessment of S3E3 in orange juice exhibited a significant reduction in the native bacteria population.

The purpose of this study was to investigate EEG changes in subjects directly after inhalation of essential oils, and subsequently, to observe any effect on subjective evaluations. EEG and sensory evaluation were assessed in 13 healthy female subjects in four odor conditions. Four odor conditions (including lavender, chamomile, sandalwood and eugenol) were applied respectively for each subject in the experiment. The results were as follows. 1) Four basic factors were extracted from 22 adjective pairs by factor analysis of the sensory evaluation. The first factor was &quot;comfortable feeling&quot;, the second &quot;cheerful feeling&quot;, the third &quot;natural feeling&quot; and the fourth &quot;feminine feeling&quot;. In the score of the first factor (comfortable feeling), the odors in order of high contribution are lavender, eugenol, chamomile and sandalwood. 2) Alpha 1 (8-10 Hz) of EEG at parietal and posterior temporal regions significantly decreased soon after the onset of inh...

An HPTLC densitometric method for the simultaneous determination of cinnamaldehyde and eugenol as well as trace amounts of piperine in pepper-contaminated cinnamon was developed. The applicability of the method was tested with cinnamon bark powder adulterated with pepper powder, cinnamon oil, clove powder, clove oil and a commercial preparation containing cinnamaldehyde and eugenol. The method was validated for specificity, precision, accuracy and robustness. The method was found to be precise for different concentrations of cinnamaldehyde, eugenol and piperine. The accuracy of the method was checked by conducting a recovery study at three different levels. The linearity was found to be in the ranges 52.54-735.56, 533.2-8531.2 and 50-300 ng/spot, respectively, with correlation coefficients of 0.9985 +/- 0.04, 0.9982 +/- 0.06 and 0.9937 +/- 0.11 for cinnamaldehyde, eugenol and piperine.

Worldwide, an important aspect of invasive insect pest management is more effective, safer detection and control systems. Phenyl propanoids are attractive to numerous species of Dacinae fruit flies. Methyl eugenol (ME) (4-allyl-1, 2-dimethoxybenzene-carboxylate), cue-lure (C-L) (4-(p-acetoxyphenyl)-2-butanone), and raspberry ketone (RK) (4-(p-hydroxyphenyl)-2-butanone) are powerful male-specific lures. Most evidence suggests a role of ME and C-L/RK in pheromone synthesis and mate attraction. ME and C-L/RK are used in current fruit fly programs for detection, monitoring, and control. During the Hawaii Area-Wide Pest Management Program in the interest of worker safety and convenience, liquid C-L/ME and insecticide (i.e., naled and malathion) mixtures were replaced with solid lures and insecticides. Similarly, Male Annihilation Technique (MAT) with a sprayable Specialized Pheromone and Lure Application Technology (SPLAT), in combination with ME (against Bactrocera dorsalis, oriental fruit fly) or C-L/RK (against B. cucurbitae, melon fly), and the reduced-risk insecticide, spinosad, was developed for area-wide suppression of fruit flies. The nontarget effects of ME and C-L/RK to native invertebrates were examined. Although weak attractiveness was recorded to flower-visiting insects, including bees and syrphid flies, by ME, effects to native Drosophila and other Hawaiian endemics were found to be minimal. These results suggested that the majority of previously published records, including those of endemic Drosophilidae, were actually for attraction to dead flies inside fruit fly traps. Endemic insect attraction was not an issue with C-L/RK, because B. cucurbitae were rarely found in endemic environments.

This review discusses the occurrence and distribution (within a plant) of methyl eugenol in different plant species (> 450) from 80 families spanning many plant orders, as well as various roles this chemical plays in nature, especially in the interactions between tephritid fruit flies and plants.

This publication is the seventh in a series of safety evaluations performed by the Expert Panel of the Flavor and Extract Manufacturers' Association (FEMA). In 1993, the Panel initiated a comprehensive program to re-evaluate the safety of more than 1700 GRAS flavouring substances under conditions of intended use. In this review, scientific data relevant to the safety evaluation of the allylalkoxybenzene derivatives methyl eugenol and estragole is critically evaluated by the FEMA Expert Panel. The hazard determination uses a mechanism-based approach in which production of the hepatotoxic sulfate conjugate of the 1 0 -hydroxy metabolite is used to interpret the pathological changes observed in different species of laboratory rodents in chronic and subchronic studies. In the risk evaluation, the effect of dose and metabolic activation on the production of the 1 0 -hydroxy metabolite in humans and laboratory animals is compared to assess the risk to humans from use of methyl eugenol and estragole as naturally occurring components of a traditional diet and as added flavouring substances. Both the qualitative and quantitative aspects of the molecular disposition of methyl eugenol and estragole and their associated toxicological sequelae have been relatively well defined from mammalian studies. Several studies have clearly established that the profiles of metabolism, metabolic activation, and covalent binding are dose dependent and that the relative importance diminishes markedly at low levels of exposure (i.e. these events are not linear with respect to dose). In particular, rodent studies show that these events are minimal probably in the dose range of 1À10 mg/ kg body weight, which is approximately 100-1000 times the anticipated human exposure to these substances. For these reasons it is concluded that present exposure to methyl eugenol and estragole resulting from consumption of food, mainly spices and added as such, 0278-6915/02/$ -see front matter # 2002 Elsevier Science Ltd. All rights reserved. P I I : S 0 2 7 8 -6 9 1 5 ( 0 2 ) 0 0 0 1 2 -1 does not pose a significant cancer risk. Nevertheless, further studies are needed to define both the nature and implications of the doseresponse curve in rats at low levels of exposure to methyl eugenol and estragole. #

Aroma extract from dried clove buds [Syzygium aromaticum (L.) Merr. et Perry] was obtained by using steam-distillation under mild conditions (55 C and 95 mm Hg). The antioxidant property of the aroma extract was evaluated in two different assays. The aroma extract isolated from clove buds inhibited the oxidation of hexanal for 30 days at a level of 50 mg/ml. Clove bud extract inhibited malonaldehyde formation from cod liver oil by 93% at the 160 mg/ml level. Twenty-two compounds were identified in the extracts of clove buds by gas chromatography and gas chromatography/mass spectrometry. The major aroma constituents of clove buds were eugenol (24.371 mg/g) and eugenyl acetate (2.354 mg/g). Eugenol, eugenyl acetate, and benzyl alcohol inhibited the oxidation of hexanal by 99, 99, and 82%, respectively, for a period of 30 days at 500 mg/ml. Eugenol, eugenyl acetate, and benzyl alcohol inhibited malonaldehyde formation from cod liver oil by 88, 79, and 63%, respectively, at 160 mg/ml. The antioxidant activity of clove bud extract and its major aroma components, eugenol and eugenyl acetate, were comparable to that of the natural antioxidant, a-tocopherol (vitamin E). #

Extending the residence time of a dosage form at a particular site and controlling the release of drug from the dosage form are useful especially for achieving controlled plasma level of the drug as well as improving bioavailability. The objective of this study was to extend the GI residence time of the dosage form and control the release of Tramadol HCl using mucoadhesive tablet to achieve controlled plasma level of the drug which is especially useful for 12 hrs. Matrix tablets of Tramadol HCl were formulated using different mucoadhesive polymers namely guar gum, xanthan gum and Methocel (HPMC K15M and HPMC K100M). Formulations were evaluated for preformulation parameters, in vitro drug release profile and release kinetics. The formulations were found to have good preformulation characteristics. FTIR spectroscopy indicated the absence of any significant chemical interaction within dug and excipients. The release mechanism of Tramadol HCl from matrix tablets indicated anomalous (non...

Objective. This study evaluated the pulp response to a tri-cure resin-modified glass ionomer cement and compared this response to those elicited by a zinc oxide-eugenol cement and a silicate cement. Materials were placed in nonexposed class V cavity preparations on human teeth. Study Design. Sixty premolars were selected in orthodontic patients in a voluntary group of teenagers. All cavities were prepared according to International Dental Federation specifications. Resin-modified glass ionomer and silicate applications were carried out according to the manufacturers' instructions. Result. All teeth were asymptomatic. Pulp responses to the resin-modified glass ionomer cement were slightly greater than to the zinc-oxide-eugenol cement. Bacterial staining attempts were inconclusive with regard to time intervals and pulp responses. No necrotic pulps were seen in any teeth. Conclusion. The tri-cure resin-modified glass ionomer cement elicited a slightly greater adverse pulp response than did the zincoxide-eugenol cement with respect to the healing process of the pulp.

Cachaç a, the most popular alcoholic beverage in Brazil, is a sugar cane spirit similar to rum. Its production is around 2 billion liters per year, of which <1% is exported. Although rum is similar to cachaç a its flavor difference is easily recognizable. Using gas chromatography-olfactometry (GCO) to separate and characterize the odorants present in cachaç a and rum, these two sugar cane products were compared and standards identified to use in a descriptive sensory analysis (DSA). In the DSA cachaç a was more intense in the grassy, spicy, sulfury, and vinegar descriptors, whereas apple and caramel were the same in both rum and cachaç a. The GCO data for the apple-smelling compounds -damascenone along with ethyl butyrate, isobutyrate, and 2-methylbutyrate were at the same potency in both cachaç a and rum, whereas the spicy-smelling eugenol, 4-ethylguaiacol, and 2,4-nonadienal were much more potent in cachaç a.

Eugenol (4-allyl-2-methoxyphenol) is a volatile phenolic bioactive compound derived from a natural resource. This compound has been identified in several aromatic plants, among which Syzygium aromaticum (L.) Merr. and L.M. Perry contains between 45 and 90% of eugenol in its essential oil compared to other natural sources. Eugenol has been studied over the years and has shown to display a wide range of biological activities as antifungal, antimicrobial, anti-inflammatory, antioxidant, analgesic, anticancer, and antiparasitic. It has been extensively used in cosmetics, in food processing industry, and also as a starting material for total synthesis of several natural products. The 4-allyl-2-methoxyphenol has a simple structure, which presents three active sites: hydroxyl, allylic, and aromatic groups. Thus, the chemistry of this natural component emphasizes its potential impact in the synthesis of novel drugs, compounds that can be useful for human resources. Therefore, the present article reviews the latest developments in the methodologies of synthesis, pharmacological properties, and further applications of eugenol derivatives.

The natural forests and meadows of the Green Mountain of Libya are classified as the richest floristic region of the country. Among various species Cynara scolymus L. (Asteraceae), is the most used medicinal plant. C. scolymus L., has long been regarded as noncrop food and also as an effective medicinal plant. In the current study, total phenols as well as flavanoids were determined in methanolic and aqueous extracts the of C. scolymus L. rhizomes in order to assess their contribution to the antioxidant activity. Free radical scavenging activity of the extracts was investigated and compared with ascorbic acid. Methanolic extract exhibited a higher total phenols (45.11 mg GAE/g DW) and flavonoids (37.00 mg Rutin/g), that results in a high antioxidant activity with IC 50 (17.77 µg/ml). In contrast, aqueous extract showed a lower total phenolic and flavonoid contents (37.79 mg GAE/g DW and 15.51 mg Rutin/g DW, respectively) and IC 50 (66.3 µg/ml). Isolated flavonoids showed the highest free radical scavenging activities (IC 50 = 13.33 µg/ml). The in vitro antibacterial activity of C. scolymus L. rhizomes was investigated against various strains of bacteria by hole-plate diffusion method. The minimum inhibitory concentrations (MICs) of the crude methanol, flavonoids and alkaloids extracts found to be between 0.03 and 200 mg/ml for the susceptible organisms, with that of MRSA being the least.

In traditional medicine, myrtle (Myrtus communis L.) is frequently consumed as an infusion and decoction. In this study, we investigate the phenolic and volatile compositions and antioxidant and antibacterial activities of leaf infusions prepared during 3 different times. The total phenolics contents (146.74 to 179.55 mg GAE/g DM) varied significantly between infusions. Eleven phenolic compounds were identified by reversed-phase high-performance liquid chromatography. Phenolic acids (7.64 to 14.28 μmol/g DM) and flavonol glycosides (7.05 to 12.11 μmol/g DM) were the major phenolic fractions of infusions. Significant quantitative variation in 6 phenolic components was observed between infusions. Sixteen volatile components were identified by gas chromatography (GC) and GC mass spectrometry analyses. The main constituents were 1,8-cineole (42.58% to 51.39%), α-terpineol (9.45% to 9.72%), methyl eugenol (6.69% to 7.11%), and linalool (5.91% to 6.06%). Quantitative variations of the volatile components of the analyzed oils in relation to the infusion time were observed. The antioxidant properties of infusions, assayed through DPPH (2,2-diphenyl-1-picrylhydrazyl) method, β-carotene bleaching test, chelating effect on ferrous ions, and ferric reducing power method, were considerable and varied according to the infusion time. Myrtle infusions exhibited a substantial antimicrobial activity against 6 tested bacteria.

Essential oils from leaves of Lippia multiflora, Mentha x piperita and Ocimum basilicum from Burkina Faso were analysed by GC-FID and GC-MS. Major components were p-cymene, thymol, β-caryophyllene, carvacrol and carvone for L. multiflora, menthol and iso-menthone for M. x piperita and, linalool and eugenol for O. basilicum. The essential oils and their major monoterpene alcohols were tested against nine bacterial strains using the disc diffusion and broth microdilution methods. The essential oils with high phenolic contents were the most effective antimicrobials. The checkerboard method was used to quantify the efficacy of paired combinations of essential oils and their major components. The best synergetic effects among essential oils and major components were obtained with combinations involving O. basilicum essential oil and eugenol, respectively. As phenolic components are characterized by a strong spicy aroma, this study suggests that the selection of certain combinations of EOs could help to reduce the amount of essential oils and consequently reduce any adverse sensory impact in food.

Simple and selective extractive spectrophotometric methods for the determination of quetiapine hemifumarate (QF) were developed and validated. The methods were based on the formation of yellow ion-pair complexes between QF and acidic dyes namely bromcresol purple (BCP) and bromcresol green (BCG) at room temperature in phosphate buffer (pH 3.0). The formed complexes were extracted with chloroform and the absorbances were measured at 406.5 nm for BCP and at 416 nm for BCG complexes. The compositions of the ion-pairs were found as 1:1 by mole-ratio method. The reaction conditions such as concentration, pH, color formation time, temperature and chromogen stability were optimized. Good linear relationship was obtained between the absorbance and the concentration of QF in the range of 0.5 -20 Hg/mL for both BCP and BCG (r > 0.9974). LOD values were found as 0.12 and 0.16 \ig/mLfor BCP and BCG complexes, respectively. Intra-day precisions were found less than 1 % in the methods. The developed methods were applied successfully to the determination of QF in tablets marketed in Turkey.

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×0.53 mm I.D,, 0.53 /zm 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.

Aim of the study: To evaluate the antibacterial activity of eugenol and its mechanism of bactericidal action against Salmonella typhi. Materials and methods: The antibacterial activity was checked by disc-diffusion method, MIC, MBC, time course assay and pH sensitivity assay. The chemo-attractant property of eugenol was verified by chemotaxis assay. The mode of action of eugenol was determined by crystal violet assay, measurement of release of 260 nm absorbing material, SDS-PAGE, FT-IR spectroscopy, AFM and SEM. Results: Treatment with eugenol at their MIC (0.0125%) and MBC (0.025%) reduced the viability and resulted in complete inhibition of the organism. Eugenol inactivated Salmonella typhi within 60 min exposure. The chemo-attractant property of eugenol combined with the observed high antibacterial activity at alkaline pH favors the fact that the compound can work more efficiently when given in vivo. Eugenol increased the permeability of the membrane, as evidenced by crystal violet assay. The measurement of release of 260 nm absorbing intracellular materials, SDS-PAGE, SEM and AFM analysis confirmed the disruptive action of eugenol on cytoplasmic membrane. The deformation of macromolecules in the membrane, upon treatment with eugenol was verified by FT-IR spectroscopy. Conclusion: The results suggest that the antibacterial activity of eugenol against Salmonella typhi is due to the interaction of eugenol on bacterial cell membrane.

The composition and antifungal activity of clove essential oil (EO), obtained from Syzygium aromaticum, were studied. Clove oil was obtained commercially and analysed by GC and GC-MS. The EO analysed showed a high content of eugenol (85.3 %). MICs, determined according to Clinical and Laboratory Standards Institute protocols, and minimum fungicidal concentration were used to evaluate the antifungal activity of the clove oil and its main component, eugenol, against Candida, Aspergillus and dermatophyte clinical and American Type Culture Collection strains. The EO and eugenol showed inhibitory activity against all the tested strains. To clarify its mechanism of action on yeasts and filamentous fungi, flow cytometric and inhibition of ergosterol synthesis studies were performed. Propidium iodide rapidly penetrated the majority of the yeast cells when the cells were treated with concentrations just over the MICs, meaning that the fungicidal effect resulted from an extensive lesion of the cell membrane. Clove oil and eugenol also caused a considerable reduction in the quantity of ergosterol, a specific fungal cell membrane component. Germ tube formation by Candida albicans was completely or almost completely inhibited by oil and eugenol concentrations below the MIC values. The present study indicates that clove oil and eugenol have considerable antifungal activity against clinically relevant fungi, including fluconazole-resistant strains, deserving further investigation for clinical application in the treatment of fungal infections.

The hydrodistillation of the aerial parts of Stachys palaestina L. collected in Lebanon in the Kadisha Valley, yielded 0.1% (w/w) of essential oil. GC and GC-MS analyses enabled the identification of 87 compounds representing 90.8% of the total oil. Hexadecanoic acid (10%), hexahydrofarnesyl acetone (6.9%), eugenol (4.3%) and (E)-caryophyllene (4.3%) were the main components. On the whole, the oil was constituted mainly of sesquiterpenes (37.7%), among which sesquiterpene hydrocarbons (20.7%) slightly prevailed over oxygenated sesquiterpenes (17.0%). This is the first report on the chemical composition of S. palaestina essential oil.

The natural forests and meadows of the Green Mountain of Libya are classified as the richest floristic region of the country. Among various species Cynara scolymus L. (Asteraceae), is the most used medicinal plant. C. scolymus L., has long been regarded as noncrop food and also as an effective medicinal plant. In the current study, total phenols as well as flavanoids were determined in methanolic and aqueous extracts the of C. scolymus L. rhizomes in order to assess their contribution to the antioxidant activity. Free radical scavenging activity of the extracts was investigated and compared with ascorbic acid. Methanolic extract exhibited a higher total phenols (45.11 mg GAE/g DW) and flavonoids (37.00 mg Rutin/g), that results in a high antioxidant activity with IC 50 (17.77 µg/ml). In contrast, aqueous extract showed a lower total phenolic and flavonoid contents (37.79 mg GAE/g DW and 15.51 mg Rutin/g DW, respectively) and IC 50 (66.3 µg/ml). Isolated flavonoids showed the highest free radical scavenging activities (IC 50 = 13.33 µg/ml). The in vitro antibacterial activity of C. scolymus L. rhizomes was investigated against various strains of bacteria by hole-plate diffusion method. The minimum inhibitory concentrations (MICs) of the crude methanol, flavonoids and alkaloids extracts found to be between 0.03 and 200 mg/ml for the susceptible organisms, with that of MRSA being the least.

Context: The blowfly Chrysomya putoria is widely distributed throughout the Neotropical region and, besides transmitting pathogens; they could cause secondary myiasis. Botanical insecticides provide an alternative to synthetic pesticides because the excessive use of synthetic insecticides resulted in a progressive resistance of the pests to these chemicals, diminishing their effectiveness and generating consequences with negative environmental impact. The essential oil extracted from Ocimum sanctum (basil) has showed insecticidal activity against some insects but has no reported studies on the activity of this plant against flies.

Aims: To evaluate the insecticidal effects of Ocimum sanctum var. cubensis Gomes essential oil on the post embryonic development of Chrysomya putoria.

Methods: The colonies of Chrysomya putoria were established and maintained at the Laboratório de Entomologia Médica e Forense (FIOCRUZ), Rio de Janeiro, Brazil. The basil essential oil was tested in six concentrations (4.13, 8.25, 20.63, 41.25, 61.87 and 80,25 mg/mL). Mortality and changes in life cycle were recorded daily.

Results: β-caryophyllene, β-selinene and eugenol, were the main constituents of the basil essential oil. The experiments demonstrated that in all concentrations tested, this essential oil shortening the duration of all post embryonic stages having a direct impact in the viability of this fly estimating the LC50 in 7.47 mg/mL of concentration. In addition, the essential oil caused morphological alterations in abdomen, wings and ptilinum at lower concentrations.

Conclusions: This essential oil emerge as a good option for the control of the disease vector blowfly Chrysomya putoria.

The essential oil composition of Feronia elephantum Correa (family: Rutaceae) was examined by capillary gas chromatography (GC) and gas chromatography–mass spectroscopy (GC–MS). The analysis revealed the presence of 24 constituents, of which 18 constituents were identified. Trans-anethole (57.73%) and methyl chavicol (37.48%) were the major compounds, while cis-anethole, p-anisaldehyde, (E)-jasmone, methyl eugenol, β-caryophyllene, linalool and (E)-methyl isoeugenol were also present as the minor constituents.

A new, simple and versatile method is presented for the determination of different concentration levels of alkenylbenzenes (eugenol, isoeugenol, eugenol methyl ether, myristicin, anethole and estragole) and the related flavour compounds (coumarin and pulegone) in food samples. The method involves the use of a stationary phase (capillary column) for the enrichment with appropriate elution. After the sample had completely passed through the capillary column the eluent was changed and the separation/detection was achieved. Excellent linearity was obtained under the proposed conditions for a direct determination method and a method including on-line preconcentration. The limits of detection were in the ranges 97-148 and 9.5-14.2 ng/mL, respectively. Evidence for a matrix effect was not found and recoveries between 92 and 110% were obtained. The precision of the method, expressed as relative standard deviation values, was below 5% in all cases. The applicability of this methodology was tested by analyzing synthetic and real food samples.

Major active compounds from essential oils are well-known to possess antimicrobial activity against both pathogen and spoilage microorganisms. The aim of this work was to determine the alteration of the membrane fatty acid profile as an adaptive mechanism of the cells in the presence of a sublethal concentration of antimicrobial compound in response to a stress condition. Methanolic solutions of thymol, carvacrol, limonene, cinnamaldehyde, and eugenol were added into growth media of Escherichia coli O157:H7, Salmonella enterica serovar typhimurium, Pseudomonas fluorescens, Brochothrix thermosphacta, and Staphylococcus aureus strains. Fatty acid extraction and gas chromatographic analysis were performed to assess changes in membrane fatty acid composition. Substantial changes were observed on the long chain unsaturated fatty acids when the E. coli and Salmonella strains grew in the presence of limonene and cinnamaldehyde and carvacrol and eugenol, respectively. All compounds influenced the fatty acid profile of B. thermosphacta, while Pseudomonas and S. aureus strains did not show substantial changes in their fatty acid compositions.

In the absence of effective and safe treatment of Kala-azar (VL) -a most devastating parasitic disease caused by Leishmania donovani a need for the search of antileishmanial from natural resources, in common use, is imperative. Recently, a comparative in vitro antileishmanial activity of methanolic extract of two landraces of Piper betle-Bangla Mahoba (PB-BMM) and Kapoori Vellaikodi (PB-KVM) has been reported. Herein, the putative pathway responsible for death induced by the effective extract of PB-BMM in promastigotes as well as intracellular amastigotes form of L. donovani was assessed using various biochemical approaches. It was observed that PB-BM is capable of selectively inhibiting both the stages of Leishmania parasites by accelerating apoptotic events by generation of ROS targeting mitochondrion without any cytotoxicity to macrophages. Study was extended to reason out the presence/absence of activity in PB-BMM and PB-KVM on the basis of differences in essential oil composition present in methanolic extract assessed by gas chromatography and mass spectra. The essential oil from PB-BM was found to be rich in eugenol as compared to PB-KV. The antileishmanial efficacy of PB-BMM mediated through apoptosis is probably due to the higher content of eugenol in active landrace. This observation emphasizes the need of extending the studies related to traditional medicines from bioactive plants below species to gender/landrace level for better efficacy and reproducibility.

Essential oils from leaves of Lippia multiflora, Mentha x piperita and Ocimum basilicum from Burkina Faso were analysed by GC-FID and GC-MS. Major components were p-cymene, thymol, β-caryophyllene, carvacrol and carvone for L. multiflora, menthol and iso-menthone for M. x piperita and, linalool and eugenol for O. basilicum. The essential oils and their major monoterpene alcohols were tested against nine bacterial strains using the disc diffusion and broth microdilution methods. The essential oils with high phenolic contents were the most effective antimicrobials. The checkerboard method was used to quantify the efficacy of paired combinations of essential oils and their major components. The best synergetic effects among essential oils and major components were obtained with combinations involving O. basilicum essential oil and eugenol, respectively. As phenolic components are characterized by a strong spicy aroma, this study suggests that the selection of certain combinations of EOs could help to reduce the amount of essential oils and consequently reduce any adverse sensory impact in food.

Objective. The purpose was to show the capacity of zinc oxide and eugenol to affect the growth of Aspergillus fumigatus. Study design. An in vitro microbiological analysis was conducted on samples from infected maxillary sinuses and on 3 different endodontic sealers.

O manejo de peixes em cativeiro proporciona situações de estresse que influenciam diretamente na sanidade dos animais. Nessa situação, o estresse acarreta em uma maior movimentação dos peixes, resultando em perda de muco, escamas e quebra das nadadeiras. Outras reações negativas causadas por atividades de manejo ocorrem a níveis fisiológicos e bioquímicos, causando muitas vezes mortalidade. Neste contexto, o presente trabalho avaliou a influência de concentrações de eugenol na anestesia e tempo de recuperação do rosacéu Hyphessobrycon sp. O trabalho foi realizado no laboratório de aquicultura tropical, UFRA, Belém, PA. Um total de 42 peixes com peso médio de 0,36 ± 0,10 g e comprimento total médio de 2,28 ± 2,12 cm foram submetidos a sete concentrações de eugenol, 10, 20, 30, 40, 50, 60 e 70 mg L⁻¹, sendo monitorados até alcançarem o estágio de anestesia cirúrgica. Após essa etapa, os peixes foram transferidos para aquários com água sem a presença de eugenol para avaliação da recuperação. A temperatura média tanto na fase de indução a anestesia quanto na fase de recuperação foi de 30 ± 0,27 °C. Os peixes alcançaram o estágio de anestesia cirúrgica em todas as concentrações avaliadas. Em geral, as maiores concentrações proporcionaram os menores tempo de indução a anestesia, sendo que não ocorreram diferenças estatísticas entre os tempos de indução das concentrações de 30 a 70 mg L -1 . As concentrações entre 20 a 40 mg L -1 apresentaram tempos de indução a anestesia similares entre si. A concentração de 10 mg L -1 apresentou o maior tempo de indução a anestesia quando comparado com as demais concentrações, e esse foi de 226 ± 28 segundos. O tempo de recuperação do estágio de anestesia cirúrgica dos peixes submetidos a concentração de 10, 20, 30 e 40 mg L -1 de eugenol foi similar estatisticamente e variou de 41 ± 8 a 66 ± 16 segundos, respectivamente. As maiores concentrações (50, 60, 70 mg L -1 ) apresentaram um aumento no tempo de recuperação dos peixes, sendo que esses foram estatisticamente semelhantes entre as concentrações de 60 e 70 mg L -1 de eugenol. Não ocorreram diferenças significativas entre o tempo de recuperação dos peixes submetidos às concentrações de 10, 20, 30 e 40 mg L -1 , os quais foram menores e variaram de 41 ± 8 a 66 ± 16 segundos, respectivamente. Com os resultados encontrados nesse trabalho, recomenda-se que peixes ornamentais de pequeno porte, como o rosacéu, sejam anestesiados com segurança na concentração de 10 mg L -1 , pois apresentou um tempo de anestesia cirúrgica e recuperação dentro da faixa recomendada para peixes.

Alcoholic extract of Piper betle (Piper betle L.) leaves was recently found to induce apoptosis of CML cells expressing wild type and mutated Bcr-Abl with imatinib resistance phenotype. Hydroxychavicol (HCH), a constituent of the alcoholic extract of Piper betle leaves, was evaluated for anti-CML activity. Here, we report that HCH and its analogues induce killing of primary cells in CML patients and leukemic cell lines expressing wild type and mutated Bcr-Abl, including the T315I mutation, with minimal toxicity to normal human peripheral blood mononuclear cells. HCH causes early but transient increase of mitochondria-derived reactive oxygen species. Reactive oxygen species-dependent persistent activation of JNK leads to an increase in endothelial nitric oxide synthasemediated nitric oxide generation. This causes loss of mitochondrial membrane potential, release of cytochrome c from mitochondria, cleavage of caspase 9, 3 and poly-adenosine diphosphate-ribose polymerase leading to apoptosis. One HCH analogue was also effective in vivo in SCID mice against grafts expressing the T315I mutation, although to a lesser extent than grafts expressing wild type Bcr-Abl, without showing significant bodyweight loss. Our data describe the role of JNK-dependent endothelial nitric oxide synthase-mediated nitric oxide for anti-CML activity of HCH and this molecule merits further testing in pre-clinical and clinical settings. (Cancer Sci, I matinib (also known as STI571 or Gleevec), a small-molecule inhibitor of the Bcr-Abl kinase, has been used successfully to treat chronic myeloid leukemia, (1) but resistance has emerged against this drug. The T315I mutation is the most predominant among the mutations found in imatinib-resistant patients.