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Antioxidant and Anti-Inflammatory Activities of Eugenol and Its Derivatives from Clove (Eugenia caryophyllata Thunb.)
Abstract
Antioxidant and anti-inflammatory activities of eugenol and its derivatives from clove (Eugenia caryophyllata Thunb.) were evaluated using in vitro assay systems by measuring 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical, cyclooxygenase-2 (COX-2), and 15-lipoxygenase (15-LOX). Among eight different crude medicinal drugs tested, volatile extracts of clove extracted by steam distillation extraction (SDE) showed potent DPPH radical scavenging activity (=8.85 ) as well as strong inhibitory activity against COX-2 (58.15%) and 15-LOX (86.15%) at 10 and 25 , respectively. Major volatile components of clove were identified as eugenol, trans-caryophyllene, and acetyleugenol by GC-MS analysis. Out of three eugenol derivatives, eugenol, methyl eugenol, and acetyl eugenol, eugenol showed the strongest DPPH radical scavenging activity and COX-2 inhibitory activity, whereas methyl eugenol exhibited the strongest 15-LOX inhibitory activity. Finally, the contents of the three eugenol derivatives in clove were quantified by analytical HPLC. Contents of eugenol and acetyl eugenol in clove were 6.95% and 1.85% per dry weight, respectively. These results suggest that eugenol and its derivatives in steam distilled extract of clove may be useful as potential antioxidant and anti-inflammatory agents.
... Eugenol (EUG) is a naturally volatile phenolic compound isolated from the essential oil of traditional spices such as clove, nutmeg and cinnamon, nutmeg, and basil [8,9]. EUG possesses variable healthpromoting bioactivities including antiseptic, antibacterial, analgesic as well as antioxidant and anti-inflammatory activities [8]. ...
... Eugenol (EUG) is a naturally volatile phenolic compound isolated from the essential oil of traditional spices such as clove, nutmeg and cinnamon, nutmeg, and basil [8,9]. EUG possesses variable healthpromoting bioactivities including antiseptic, antibacterial, analgesic as well as antioxidant and anti-inflammatory activities [8]. The antioxidant capacity of EUG has been demonstrated against kidney injury induced by gentamycin [10], chromium [11], and cisplatin [12]. ...
... Treatment with a high dose of EUG significantly suppressed CCl 4 -induced elevation in serum levels of IL-6 and TNF-α as well as protein expressions of both caspase-3 and cytochrome c in rats' kidneys treated with CCl4. The reported antiinflammatory effect of EUG has been attributed to its ability to directly downregulate the expression of various inflammatory cytokines in macrophages including TNF-α [8,40] and such effect was shown to be dose-dependent [9]. ...
Chronic kidney disease is a crucial health problem associated with high morbidity and mortality. Eugenol is a natural phenolic plant compound with various pharmacological activities including antioxidant and anti-inflammatory properties. This study was designed to evaluate the possible protective effect of different eugenol doses in an experimental model of chronic CCl4-induced renal damage and investigate various mechanisms that underlie this postulated effect. Eugenol treatment (100 mg/kg) ameliorated kidney damage induced by CCl4 and rectified the distorted kidney function parameters and renal histological structure. Additionally, eugenol at a dose of 100 mg/kg suppressed the upregulated oxidative stress, inflammation and apoptosis in CCl4-treated rats as evident by down regulations of NADPH oxidase (NOX2 and NOX4), proinflammatory markers (IL-6 and TNF-α) and proapoptotic markers (cyt c and caspase-3), respectively. Importantly, eugenol co-administration in rats challenged with CCl4 downregulated the renal protein expressions of both TGF-β as well as pAkt compared with CCl4 group. In conclusion, eugenol showed a potent nephroprotective effect against CCl4-induced renal damage through its antioxidant, anti-inflammatory and anti-fibrotic activities.
... According to TMM main theory, the function of MMS-7 is to suppress "Rlung" and strengthen the body [14]. The modern chemical studies on this prescription`s components are reported such as, Amomum kravanh which contains volatile oil, 5-hydroxy-3, 7, 4'-trimethoxyflavone [14][15][16][17] and trace elements such as Ca, Mn, and K. ...
... According to TMM main theory, the function of MMS-7 is to suppress "Rlung" and strengthen the body [14]. The modern chemical studies on this prescription`s components are reported such as, Amomum kravanh which contains volatile oil, 5-hydroxy-3, 7, 4'-trimethoxyflavone [14][15][16][17] and trace elements such as Ca, Mn, and K. It has the effects of antigastric ulcer, enhances gastric motility, and protects gastric mucosa [18]. ...
Objectives: The aim of this study was to explore the mechanism of regulating the endocrine function of hyperplasia breast in rats with Mongolian Medicine Modified Sugmul-7 (MMMS-7) by Proteomics and provide an experimental basis for its development and clinical application. Methods: Ninety female SD rats were randomly divided into 6 groups: the intact group – the animal group that was injected with neither estradiol, nor progesterone, nor administered Mongolian Medicine Modified Sugmul-7; the negative control group – the group injected with estradiol and progesterone; the positive control group - injected with estradiol, progesterone and administered mastodynon 0.06 g/kg; and the treatment groups – injected with estradiol and progesterone, each in their respective dose groups. After the start of the experiment, each rat except the intact group was intra peritoneally injected with estradiol 25d and progesterone 6d at a standard dose of 0.3 mg / kg for a total of 31 days. Results: Four differential proteins were found through proteomic analysis, namely Ppp3cb, Cacybp, Gstz1, and Nmd3 and their 5 related pathways. Conclusions: The above pathways are all known to be related to the treatment of breast hyperplasia caused by endocrine disorders. Treatment with Mongolian Medicine Modified Sugmul-7 is completed through regulation of the gastrointestinal and endocrine systems.
... 10], antimicrobial [7,8], anthelmintic [9], anti-inflammatory [10], anticarcinogenic [11,12], anti-fumigant [13], anti-repellent [14] properties etc.From times Eugenol has been used as a traditional remedy to eliminate bad breath or ameliorate the pain of a bad tooth. Eugenol is a main component in cosmetics, perfumes, flavouring agents [15] etc.WHO (World Health Organization) and FAO (Food and Agriculture Organization) joint expert committee on food additives have allowed an acceptable daily intake of Eugenol of 2.5mg/Kg body weight for humans [16] Eugenol has found a wide range of uses in many areas of life due to its numerous properties. ...
... , antimicrobial [7,8], anthelmintic [9], anti-inflammatory [10], anticarcinogenic [11,12], anti-fumigant [13], anti-repellent [14] properties etc. ...
Physico-chemical properties plays an important role in determining toxicity of a material hence were calculated using acdlab/chemsketch and the data predicted is generated using ACD/Labs Percepta Platform - PhysChem Module. Gaussian 09, RevisionA.01, software package was used for the theoretical quantum chemical calculations of 2-methoxy-4-(prop-2-en-1-yl) phenol commonly called Eugenol. DFT/B3LYP/6-311G (d, p) basis was used to perform geometric optimization and vibrational frequency determination of the molecule. The statistical thermochemical calculations of the molecule were done at DFT/B3LYP/6-311G (d, p) basis set to calculate the standard thermodynamic functions: heat capacity (CV), entropy (S) and Enthalpy (E). DFT/B3LYP/6-311G (d, p) basis set was used to calculate the various NLO properties like dipole moment (µ), mean linear polarizability (α), anisotropic polarizability (Δα), first order hyperpolarizability (β), second order hyperpolarizability (γ) in terms of x, y, z components for Eugenol (2-methoxy-4-(prop-2-en-1-yl) phenol. Same basis set was used to carry out Mulliken population analysis. UV-Visible absorption spectra, ECD spectra, electronic transitions, vertical excitation energies and oscillator strengths of Eugenol (2-methoxy-4-(prop-2-en-1-yl) phenol) were computed by Time Dependent DFT (TD-DFT) method using the same basis set. FMO analysis, Molecular electrostatic potential study was also done using the same basis set.
... 9,16,17 Additionally, this compound has been reported to possess anti-inflammatory properties, by suppressing the expression of the cyclooxygenase II enzyme. 18 However, similarly to small peptides, the use of EOs in therapeutic approaches comes with limitations, including cytotoxicity at high concentrations, high volatility and sensitivity to external factors, such as temperature, light and oxygen. 9,13 Still, in recent years, research has been disclosed on the loading of EOs and therapeutic peptides onto polymeric fibers that increase these bioactive agent's physiological stability, while preserving their chemical features. ...
The incidence of bacterial infections associated with chronic wounds (CWs) has increased in recent years. Thus, a triaxial wet-spun fibrous system (containing three layers) was produced for CW healing. The triaxial fibers were loaded with cinnamon leaf oil (CLO), endowed with high antibacterial, antioxidant and anti-inflammatory features, and an antimicrobial peptide –alanine–alanine–proline–valine (AAPV) – capable of regulating the activity of human neutrophil elastase (HNE; highly expressed during inflammatory processes). To overcome the characteristic high volatility of essential oils (EOs), CLO was loaded at the system's core and blended with polycaprolactone (PCL) which has excellent elasticity and tensile strength. The intermediate layer was composed of sodium alginate (SA) which has high hydration capacity and AAPV. Finally, the shell was made of cellulose acetate (CA), ensuring the system's structural integrity and providing a porous network for the controlled release of AAPV and CLO. This research was divided into two parts, with the present addressing the biological characterization of the system, namely the controlled release of bioactive agents, their antibacterial, antioxidant and cytocompatibility profiles and the peptide-loaded fiber ability to inhibit HNE activity. AAPV-loaded wet-spun fibers attained a sustained release of up to 55% during 24 h of incubation in physiological-like media, also presenting effective HNE inhibition (≈65%). Additionally, CLO-loaded fibers demonstrated a controlled release of up to ≈52% during 24 h of incubation in PBS, reaching higher antibacterial and antioxidant profiles in comparison with the unloaded fibers. Data confirmed the biological potential, safety and suitability of the proposed system for future applications in CW care.
... of eugenol in in-vitro and in-vivo models (Leem et al., 2011;Grespan et al., 2012). ...
Background: Syzygium aromaticum Linn. (clove) is a dried flower bud from the Myrtaceae family, native to Indonesia's Maluku islands. Clove essential oil is recognized for its diverse biological activities, including antiseptic, analgesic, antibacterial, antiviral, antifungal, and anticancer properties. Its high concentration of bioactive compounds, particularly eugenol, caryophyllene, and eugenol acetate, contributes significantly to these effects, making clove a subject of increasing scientific interest. Methods: This review compiles and analyzes updated information on the ethnomedicinal uses, phytochemistry, and pharmacological activities of clove and its primary constituent, eugenol. A systematic literature review was conducted, focusing on peer-reviewed studies that detail the extraction methods, chemical composition, and bioactivity assays of clove essential oil. Results: Clove essential oil contains approximately 16-18% of essential oils, with eugenol constituting 59-88% of its composition. The oil exhibits notable antioxidant, antimicrobial, anti-inflammatory, analgesic, antipyretic, anticancer, antidiabetic, and antiviral properties. Clove has shown efficacy against various pathogens, including Pseudomonas aeruginosa, Staphylococcus aureus, and Helicobacter pylori. Furthermore, eugenol demonstrated significant cytotoxic effects against various cancer cell lines and showed promise in managing metabolic disorders and enhancing immune responses. Conclusion: Clove and eugenol possess extensive therapeutic potential, warranting further investigation to unlock their applications in modern medicine. Despite their benefits, attention to their toxicity and safety profiles is essential for ensuring appropriate usage in therapeutic contexts. This review highlights the need for continued research to validate traditional uses and explore novel applications of clove and its bioactive components.
... Eugenol (EU) reduced macrophage production of IL-1 and IL-6 (Rodrigues et al., 2009) and exert immunomodulatory/antiinflammatory effects by inhibiting lipopolysaccharide (LPS) action, possibly through NF-kB inhibition (Bachiega et al., 2012). EU also demonstrated anti-inflammatory and antioxidant effects in fish infected with Aeromonas (Leem et al., 2011;Yogalakshmi et al., 2010). Sub-inhibitory levels of EU significantly reduced red blood cell hemolysis in fish infected by Aeromonas and extended the lifespan of infected silver catfish. ...
Aquaculture is a pivotal industry for global food production, facing challenges such as environmental conditions, and disease. Stress, a significant factor compromising fish health, suppresses immune functions and increases disease susceptibility. Anesthetic agents like eugenol (EU), derived from clove oil (Eugenia caryophyllata) , offer promising stress mitigation in aquaculture. EU, known for its anesthetic and analgesic properties in human medicine, shows potential as a safe anesthetic in aquaculture. This review examines EU's effects on cortisol levels, hematological, and biochemical parameters across various fish species, highlighting its role in stress reduction and improving production efficiency.
... The anti-inflammatory mechanism of Eugenol dimers involves the inhibition of cytokine expression in macrophages and modulation of the nuclear factor kappa B (NF-kB) gene expression, which regulates cell proliferation and survival. The chemo-preventive impact of clove oil primarily attributed to its eugenol components (Leem et al., 2011). ...
... Then, the temperature was held at 300 • C for 5 min. The temperature of the GC-MS interface was 290 • C, and the injection port was set to 280 • C. A scan mode of 45 to 500 m/z (mass-to-charge ratio) was used to capture a comprehensive spectrum of compounds in the fig extract sample, allowing the detection and identification of a wide variety of molecules with different masses [23,24]. The helium carrier gas flow rate was 1.0 mL/min. ...
Klebsiella pneumoniae (K. pneumoniae) is a multidrug-resistance Gram-negative organism responsible for carbapenem-resistant infections. These challenges have inspired studies on the use of natural products as alternatives to conventional drugs. The aim of this study was to analyze the antibacterial and antioxidant effects of Ficus carica L. (fig) branch extracts and to perform in vivo animal experiments to better understand the absorption mechanisms of the antibacterial components during the digestion process after oral administration. The antibacterial components of the fig branch extracts were analyzed via gas chromatography-mass spectrometry (GC-MS). An in vivo animal study and liquid chromatography-triple quadrupole-tandem mass spectrometry (LC-QQQ-MS/MS) analyses were performed to analyze the deacetylation reactions of the fig extracts after oral administration in mice. Ultimately, the antibacterial effects of the fig extracts increased with the fractional distillation time. The fig extracts showed excellent antibacterial effects against K. pneumoniae, as well as Escherichia coli (E. coli), Staphylococcus aureus (S. aureus), and Pseudomonas aeruginosa (P. aeruginosa). The three antibacterial and antioxidant components of the fig extracts were revealed to be eugenol, acetyleugenol, and psoralen. Interestingly, in this study, we identified acetyleugenol in the phenolic compounds of the fig extract for the first time. Through in vivo animal testing, we observed the deacetylation reaction of acetyleugenol to eugenol in the fig extract as digestion proceeded in the internal organs of the mice after oral administration. The results of this study suggest the use of natural fig extract as an effective therapeutic and prophylactic antibacterial agent for inflammation-related infections with a wide variety of biomedical applications.
... Due to the anti-inflammatory and antioxidant properties of Eugenol, it is reasonable to believe that this compound can promote the recovery of neural fibers post injury by inhibiting the inflammatory mediators that prevent the healing processes. Indeed, one of the plausible mechanisms is Eugenol's ability to promote cell repair by reducing inflammatory mediators (25,26). Although injured peripheral nerves may regenerate gradually by themselves; however, the longer the recovery process, the more likely is the potential for nerve atrophy (27). ...
... 6 Eugenol suppresses expression of cyclooxygenase II enzyme and cytokines, thus showing an anti-inflammatory effect. 7 It is also reported to exhibit antibacterial potential in both negative bacteria and gram-positive bacteria. 8 Antimicrobial activity of eugenol on some bacteria was due to induction of cell lysis via leakage of lipids and protein in cell membrane. ...
Objectives:
The present study focused on the formulation of mucoadhesive bilayer composite films for the treatment of periodontitis and evaluation of their physicochemical properties.
Materials and methods:
The solvent casting technique was used to prepare films. The primary layer (D) was prepared with flaxseed and hydroxypropyl methylcellulose composite to sustain the release of doxycycline hyclate. The second layer (S) comprised sodium alginate and polyvinyl alcohol composite for faster release of clove oil. Both layers were combined to generate the bilayer film (B). All formulations were characterized further to obtain an optimized formulation.
Results:
Attenuated total reflection-Fourier transform infrared radiation results showed intactness of drug and clove oil in the presence of excipients. The pH of the films was compatible with the periodontal cavity and the thickness was suitable for inserting into the cavity. The immediate release layer showed faster disintegration and swelling. The content of clove oil was above 80%. The rate of swelling of the primary layer was slow and drug content complied with the United States Pharmacopoeia. Scanning electron microscope analysis revealed intact, non-porous and smooth films. Films exhibited better mechanical strength and bioadhesiveness. Clove oil was released from the immediate release layer within 10 min, and doxycycline hyclate release was retarded to a minimum of up to 8 h in the primary layer as well as the bilayer. Formulation also had a significant effect on both Escherichia coli and Staphylococcus aureus.
Conclusion:
In the current study, bilayers were successfully prepared and characterized. The optimized formulation can be effectively used for the treatment of periodontitis.
... It is chemically 4-allyl-2-methoxyphenol and it imparts the spicy aroma to cloves [165,166]. Several studies have demonstrated different bioactivities of eugenol including anti-bacterial, anti-fungal, anti-viral, antioxidant, and antiinflammatory properties [167][168][169][170]. Moreover, it has exhibited intriguing potential to combat various types of cancers including gastric, colon, prostate, skin, breast cancer and other cancers [77,78,80,171] through various intricate mechanisms. ...
Simple Summary
Over the years, alternative and complementary medicine have garnered much attention all across the globe. To this end, phytochemicals have intriguing potential against myriads of disease conditions; nevertheless, as of yet, the molecular intricacies for their therapeutic potential is incompletely understood. It is widely acknowledged that proteomics technology has been ex-plored as a reliable approach to understand the molecular intricacies related to phytochemi-cal-based therapeutic interventions. Reckoning with this, the present review provides an overview of the proteomics studies performed to unravel the underlying molecular intricacies of various phytochemicals such as Curcumin, Genistein, and Tanshinone IIA.
Abstract
Phytochemicals possess various intriguing pharmacological properties against diverse pathological conditions. Extensive studies are on-going to understand the structural/functional properties of phytochemicals as well as the molecular mechanisms of their therapeutic function against various disease conditions. Phytochemicals such as curcumin (Cur), genistein (Gen), and tanshinone-IIA (Tan IIA) have multifaceted therapeutic potentials and various efforts are in progress to understand the molecular dynamics of their function with different tools and technologies. Cur is an active lipophilic polyphenol with pleiotropic function, and it has been shown to possess various intriguing properties including antioxidant, anti-inflammatory, anti-microbial, anticancer, and anti-genotoxic properties besides others beneficial properties. Similarly, Gen (an isoflavone) exhibits a wide range of vital functions including antioxidant, anti-inflammatory, pro-apoptotic, anti-proliferative, anti-angiogenic activities etc. In addition, Tan IIA, a lipophilic compound, possesses antioxidant, anti-angiogenic, anti-inflammatory, anticancer activities, and so on. Over the last few decades, the field of proteomics has garnered great momentum mainly attributed to the recent advancement in mass spectrometry (MS) techniques. It is envisaged that the proteomics technology has considerably contributed to the biomedical research endeavors lately. Interestingly, they have also been explored as a reliable approach to understand the molecular intricacies related to phytochemical-based therapeutic interventions. The present review provides an overview of the proteomics studies performed to unravel the underlying molecular intricacies of various phytochemicals such as Cur, Gen, and Tan IIA. This in-depth study will help the researchers in better understanding of the pharmacological potential of the phytochemicals at the proteomics level. Certainly, this review will be highly instrumental in catalyzing the translational shift from phytochemical-based biomedical research to clinical practice in the near future.
... It is the main extracted constituent (70-90%) of cloves [13]. Eugenol has potent anti-oxidant properties [14], inhibits lipid peroxidation [15], has anti-inflammatory properties, and can suppress the expression of the cyclooxygenase II (COX-2) enzyme and nuclear factor-kappa B (NF-B) [16]. Nanoemulsions about 20-200 nm nanodroplets, consist of nonpolar or polar bioactive compounds and emulsifiers [17]. ...
Pulmonary fibrosis (PF) is a chronic and progressive lung disease especially after severe acute coronavirus disease 2019 (COVID-19) infection, characterized by the formation of dense fibrous connective tissues. The present study is conducted to investigate the anti-fibrotic effects of eugenol oil (Eug) and eugenol nanoemulsion (Eug-NE) against pulmonary fibrosis induced by bleomycin (BLM) in rats. Lung fibrosis is induced by BLM in adult male rats. The animals were given Eug oil, Eug-NE, or dexamethasone (DXA) orally for 4 weeks, daily, starting one day after BLM. Lung injury, edema, and collagen deposition were determined. Some biochemical measurements, gene expression of apoptotic markers, immunohistochemistry, and histopathological examination of lung tissue are performed. The results revealed significant deterioration in lung tissues by BLM that is confirmed markedly by the pro-inflammatory, pro-oxidative, profibrotic, and pro-apoptotic conditions in lung tissues. However, treatment with Eug-NE potentially exhibited anti-fibrotic effects in lungs by downregulation of MMP-9, TGF-β and hence fibronectin expression. It also have the potential to cease the vicious cycle of epithelial injury caused by their anti-inflammatory and antiapoptotic effects. The effects of eugenol nanoemulsion were better than those of DXA. In conclusion the present study provides new insight into the use of natural oils in nano-emulsified formulations to treat pulmonary fibrosis which is one of the currently spread disorders as a result of severe COVID-19 infection.
... Umbelliferone is a phenol group that shows antioxidant, antiinflammatory, and anti-hyperglycemic potential (Mazimba, 2017). Acetyleugenol is a derivative of Eugenol which can be used as an antioxidant and anti-inflammatory agent (Leem et al., 2011), as shown in Table 1. ...
In several research areas, it is common to have a dataset with more explanatory variables than the number of observations, called high-dimensional data. This condition can lead to multicollinearity problem. The least absolute shrinkage and selection operator (LASSO) solves the problem by shrinking the estimated coefficient to zero so that it can simultaneously carry on the variable selection and the parameter estimation. But LASSO performs poorly when the data contains some outliers in the response or explanatory variables. Robust methods have addressed this problem based on the least-absolute-deviation approach, such as LAD-LASSO and WLAD-LASSO. This current research aims to evaluate the performance of the LAD-LASSO and WLAD-LASSO methods on high-dimensional and low-dimensional data containing outliers. To evaluate the performance of these methods, the simulation study was conducted. The simulation study used three scenarios (without outliers, outliers on the response variable (5%, 10%, 15%), outliers both on the response and explanatory variables (5%, 10%, 15%)). We also used the Minimum Regularized Covariance Determinant (MRCD) estimator in calculating the weights on the WLAD-LASSO. The best method from this simulation then will be applied to sembung leaf extract data to identify antioxidant marker compounds in sembung leaf extract. The simulation results show that LAD-LASSO tends to be very tight in selecting, while LASSO tends to be too loose. Meanwhile, WLAD-LASSO is in the middle of those two techniques and performs the best in identifying the important variables correctly. Even the existence of weights cause WLAD-LASSO more robust against the presence of outliers in the response and explanatory variables compared to LAD-LASSO. Furthermore, performance of these methods on high-dimensional data decrease compared to low-dimensional data. The performance of these methods also tends to decrease when the rate of outlier increases. The WLAD-LASSO was then implemented in actual data to find the compound of antioxidant markers in the sembung leaf extract. The compounds/formulas obtained are Umbelliferone, 12-Hydroxyjasmonic Acid, C22H14N8O2, and Acetyleugenol (with a prediction error is 0.133050). These compounds/formulas can be developed as natural antioxidants and have the potential to be developed as medicinal ingredients.
... Eugenol dan asetil eugenol dari minyak cengkih dapat bertindak sebagai agen antioksidan dan antiinflamasi [2]. Selain itu, hasil percobaan yang dilakukan oleh [3] menemukan bahwa senyawa o-asetil-eugenol mampu bertindak memberikan aktivitas antileishmanial yang lebih baik daripada senyawa eugenol itu sendiri. ...
Eugenol is the active molecule naturally found in clove oil. The calculations have been done for the eugenol and its derivatives computationally. This computational calculation aims to obtain a stable structure and electronic properties of eugenol, methyl eugenol, and acetyl eugenol. The computational calculation used DFT for geometry optimization in the gas phase using B3LYP functional and 6-31G(d) as the basis set. The optimized structure of eugenol and its derivatives is not planar. The presence of methoxy replacing hydroxy increases the bond length and decreases the bond angle and the dihedral. The electronic properties such as atomic charge and density of HOMO-LUMO show the difference between the three molecules.
... As a part of the investigation of the mechanism of the anti-inammatory activity, the ability of the synthesized compounds and standard diclofenac to inhibit protein denaturation was studied. [30][31][32][33] At various concentrations, it proved efficient in preventing heat-induced albumin denaturation, as shown in (Table 6). The novel synthesized compounds signicantly (p < 0.05) inhibited the albumin denaturation was shown in (Fig. 9) and maximum inhibition of 48.08 AE 1.143 at 200 mM was observed for 1C when compared with standard diclofenac 48.28 AE 3.139 at 150 mM. ...
Eugenol is a natural product abundantly found in clove buds known for its pharmacological activities such as anti-inflammatory, antidiabetic, antioxidant, and anticancer activities. It is well known from the literature that peroxisome proliferator-activated receptors (PPARγ) have been reported to regulate inflammatory responses. In this backdrop, we rationally designed semi-synthetic derivatives of eugenol with the aid of computational studies, and synthesized, purified, and analyzed four eugenol derivatives as PPARγ agonists. Compounds were screened for PPARγ protein binding by time-resolved fluorescence (TR-FRET) assay. The biochemical assay results were favorable for 1C which exhibited significant binding affinity with an IC50 value of 10.65 μM as compared to the standard pioglitazone with an IC50 value of 1.052 μM. In addition to the protein binding studies, as a functional assay, the synthesized eugenol derivatives were screened for in vitro anti-inflammatory activity at concentrations ranging from 6.25 μM to 400 μM. Among the four compounds tested 1C shows reasonably good anti-inflammatory activity with an IC50 value of 133.8 μM compared to a standard diclofenac sodium IC50 value of 54.32 μM. Structure-activity relationships are derived based on computational studies. Additionally, molecular dynamics simulations were performed to examine the stability of the protein-ligand complex, the dynamic behavior, and the binding affinity of newly synthesized molecules. Altogether, we identified novel eugenol derivatives as potential anti-inflammatory agents via PPARγ agonism.
... Nikoui et al. [84] have also reported that clove oil administration has anti-inflammatory and antipyretic properties in dogs after surgery. Leem et al. [85] have reported that, among the volatile distillate extracts of 8 herbal medicines, the distillate extract of cloves exhibited the strongest antioxidant activity (IC 50 = 8.85 μg/mL) and COX-2 inhibitory activity (inhibition rate was 58.15% at 10 μg/mL concentration), whereas 15-LOX inhibitory activity (inhibition rate was 86.15% at 25 μg/mL concentration) was the second highest after Angelica. They also measured an antioxidant and anti-inflammatory activities of eugenol and its derivatives (methyl eugenol and acetyl eugenol), eugenol (IC 50 = 5.99 μg/mL), which exhibited the highest antioxidant activity, whereas methyl eugenol and acetyl eugenol exhibited a little activity. ...
All over the world, Plants have found to be a valuable source of herbs and spices for a long period of time to maintain the human health. Varieties of herbs and spices have been used to impart an aroma and taste to food for last few centuries. Several applications of plants species have been reported as antioxidative, anti-inflammatory, antidiabetic, antihypertensive and antimicrobial activities. Currently efforts are focused on their scientific merits, to provide science-based evidence for their traditional uses and to develop either functional foods or nutraceutical behavior. India is well recognized all over the world for their variety of herbs, spices and medicinal biodiversity. The WHO has listed more than 21000 plants, which are used for their medicinal purposes either in the form of essential oil or in the form of flavor. Among these, more than 2500 species and herbs are found in India, however; among them more than 150 species are used commercially on large scale. In India, the use of spices and herbs in the form of essential oil or in the form of flavor are traditionally used in routine treatment. For example, Curcumin which is found in turmeric are frequently used in medical facilities to wound healing, rheumatic disorders, and gastrointestinal symptoms etc.
... 암, 동맥경화증 및 염증을 예방해주는 생리활성물질로서 각광 을 받고 있다 [5]. 그 중 합성항산화제는 대량생산이 가능하고 가 격이 저렴하지만 발암성 및 독성 등 안전성 문제가 제기되면서 인체에 무해하고 항산화 효능이 우수한 천연항산화제의 개발이 요구되고 있는 실정이다 [6]. ...
... The scavenging activity of the DPPH radical (DPPH • ) by pure MEug was examined comparatively to that of pure Eug in methanol to test experimentally the theoretical findings. The determination of IC 50 values showed that MEug had some activity but low (IC 50 [25,35,36]. The magnitude of the reported difference varies (Eug vs. MEug: 1.23-fold up to >21-fold more efficient). ...
The present study examined the radical scavenging potential of the two benzene derivatives found in the bay laurel essential oil (EO), namely methyl eugenol (MEug) and eugenol (Eug), theoretically and experimentally to make suggestions on their contribution to the EO preservative activity through such a mechanism. Calculation of appropriate molecular indices widely used to characterize chain-breaking antioxidants was carried out in the gas and liquid phases (n-hexane, n-octanol, methanol, water). Experimental evidence was based on the DPPH• scavenging assay applied to pure compounds and a set of bay laurel EOs chemically characterized with GC-MS/FID. Theoretical calculations suggested that the preservative properties of both compounds could be exerted through a radical scavenging mechanism via hydrogen atom donation. Eug was predicted to be of superior efficiency in line with experimental findings. Pearson correlation and partial least square regression analyses of the EO antioxidant activity values vs. % composition of individual volatiles indicated the positive contribution of both compounds to the radical scavenging activity of bay laurel EOs. Eug, despite its low content in bay laurel EOs, was found to influence the most the radical scavenging activity of the latter.
... There is a growing interest in using natural products, especially essential oils, which are generally recognized as safe (GRAS) against bacteria of clinical origin, fungi, and viruses [11]. Many previously reported studies have shown that eugenol and its derivatives exhibited a wide spectrum of functional properties in pharmaceuticals, such as antiseptic [12], anticancer [13,14], anti-bacterial [15], and antiinflammatory [16]. For example, Carassco et al. [13] claimed that eugenol derivatives, which were 5-allyl-3nitrobenzene-1,2-diol and 2-methoxy-5-nitrophenyl acetate had shown potential human tumor cell growth inhibitory effects. ...
Eugenol is the major compound of clove and has demonstrated various pharmacological activities. In this study, nine eugenol derivatives (1-9) were synthesized, characterized, and further evaluated for their anti-amoebic properties against Acanthamoeba castellanii (A. castellanii) trophozoites. The derivatives were obtained through etherification or esterification reaction at the hydroxyl group (-OH) of eugenol. The chemical structures of the synthesized derivatives were characterized on the basis of 1 H and 13 C Nuclear Magnetic Resonance (NMR) spectroscopy and Fourier Transform Infrared (FTIR) spectroscopy. For anti-amoebic activity, the cytotoxicity of the derivatives was tested on A. castellanii trophozoites. The samples were prepared at varying concentrations (in the range of 0.47 to 60 μg/mL). The IC50 values were examined based on MTT assay while light and fluorescence microscopy were used to visualize the morphology changes of amoeba in detail. The results obtained were compared with the standard drug, which was chlorhexidine. Several of the tested derivatives possessed cytotoxic effects against throphozoite cells with IC50 in the range of 0.58 to 27.83 μg/mL with significant decrease (p < 0.05) in cell viability as the concentration was increased up to 30 μg/mL. Among them, derivative 4 provided the strongest cytotoxic effect against A. castellanii, suggesting a promising new anti-amoebic agent. Altogether, this finding may potentially serve as the milestone for developing an alternative treatment for Acanthamoeba keratitis.
... There is a growing interest in using natural products, especially essential oils, which are generally recognized as safe (GRAS) against bacteria of clinical origin, fungi, and viruses [11]. Many previously reported studies have shown that eugenol and its derivatives exhibited a wide spectrum of functional properties in pharmaceuticals, such as antiseptic [12], anticancer [13,14], anti-bacterial [15], and antiinflammatory [16]. For example, Carassco et al. [13] claimed that eugenol derivatives, which were 5-allyl-3nitrobenzene-1,2-diol and 2-methoxy-5-nitrophenyl acetate had shown potential human tumor cell growth inhibitory effects. ...
Eugenol is the major compound of clove and has demonstrated various pharmacological activities. In this study, nine eugenol derivatives (1-9) were synthesized, characterized, and further evaluated for their anti-amoebic properties against Acanthamoeba castellanii (A. castellanii) trophozoites. The derivatives were obtained through etherification or esterification reaction at the hydroxyl group (-OH) of eugenol. The chemical structures of the synthesized derivatives were characterized on the basis of 1 H and 13 C Nuclear Magnetic Resonance (NMR) spectroscopy and Fourier Transform Infrared (FTIR) spectroscopy. For anti-amoebic activity, the cytotoxicity of the derivatives was tested on A. castellanii trophozoites. The samples were prepared at varying concentrations (in the range of 0.47 to 60 μg/mL). The IC50 values were examined based on MTT assay while light and fluorescence microscopy were used to visualize the morphology changes of amoeba in detail. The results obtained were compared with the standard drug, which was chlorhexidine. Several of the tested derivatives possessed cytotoxic effects against throphozoite cells with IC50 in the range of 0.58 to 27.83 μg/mL with significant decrease (p < 0.05) in cell viability as the concentration was increased up to 30 μg/mL. Among them, derivative 4 provided the strongest cytotoxic effect against A. castellanii, suggesting a promising new anti-amoebic agent. Altogether, this finding may potentially serve as the milestone for developing an alternative treatment for Acanthamoeba keratitis.
... (30). These enzymes are involved in the inflammation and carcinogenesis processes, therefore it is recognized that potential COX-2 inhibitors can be considered anti-inflammatory or cancer chemo preventive agents (27).We thought the anti-inflammatory effect that produced from clove buds extract may be due to present of high amount of eugenol and acetyleugenol which have great effect on COX-2 .And that corresponding with Leem, H ,et al 2011 (31) who conducted The clove buds oil exhibited strong inhibitory activity against COX-2 (58.15%) and 15-LOX (86.15%) enzymes at 10 μg/mL and 25 μg/mL, respectively. Other researchers Daniel., et al 2009(3), were studied The antiinflammatory activity of eugenol by using carrageenan-induced paw edema tests in rats at 200 and 400 mg/kg of clove buds oil, and founded reduce in volume of pleural exudates without changing the total blood leukocyte count indicating the antiinflammatory potential of eugenol. ...
The study was carried out to evaluate the analgesic and anti-inflammatory properties of an hydro alcoholic syzygium aromaticum extract (SAE) .The analgesic activity was measured by using the hot plate test with Twenty four (24) mice divided randomly into four groups , T1, T2 received 100 , 200 mg /kg.bw of (SAE) while T3 dosed 50 mg /kg.bw of diclofanic acid and T4 used as control negative and dosed distilled water (D.W.) . The anti-inflammatory activity was measured by using formalin test with Twenty four (24) mice divided randomly into four groups , T1and T2 dosed with 100 and 200 mg /kg.bw respectively of (SAE) while T3 group dosed 0.3 mg/kg.bw of meloxicam and T4 dosed with (D.W.) , (all groups dosed orally before half hour of test) and then calculate the time of analgesia and anti-inflammatory effects . The result showed there is significant increase(p˂0.05) in time of analgesia and significant decreases (p˂0.05) in number of licking in animal exposed to (SAE) comparing with that of control , also there is significant increase(p˂0.05) in time of analgesia and decrease in licking in animals received diclofanic acid and meloxicam respectively comparing with those received (SAE) and D.W the increase was dose dependent manner. In conclusion the hydro-alcoholic extract of clove E.C showed analgesic and anti-inflammatory effect .
... It can also be used effectively to reduce intra-operative endodontic pain. However, it's dose should be tittered to avoid cytotoxicity of the adjacent mammalian tissues [48]. ...
Endodontic therapy can land up in failures leading to intra-operative and post-operative pain due to multiple factors. Managing
such pain becomes a crucial factor for success of endodontic treatment and patient satisfaction in dental practice. Various treatment modalities are utilized to manage such conditions such as de-occluding from antagonist, re-instrumentation, cortical trephination,
incision followed by drainage, administrating systemic antibiotics and analgesics. Transformations in the regimen of therapy to has
evolved from radical to conservative mode which nowadays utilize prolonged contact of the analgesic, antibiotic or anesthetic agents
to alleviate intra and/or post-operative endodontic pain through controlled drug release system minimizing the risk of systemic as
well as local tissue toxicity, and at the same time providing maximum benefits to the patients. Thus, aim of this paper is to review and
highlight various controlled drug delivery techniques to manage intra and post-operative endodontic pain.
... The anti-inflammatory effects of eugenol were attributed to its effect to prevent neutrophil/macrophage chemotaxis and prostaglandin synthesis as well as cyclooxygenase II enzyme expressions [35]. Moreover, eugenol dimers exhibited a chemopreventive effect by inhibiting the cytokines expression in macrophages [110]. Eugenol has been suggested to possess recovery effects on arthritis and thus can be used in the treatment of arthritis [111]. ...
Herbal medicinal products have been documented as a significant source for discovering new pharmaceutical molecules that have been used to treat serious diseases. Many plant species have been reported to have pharmacological activities attributable to their phytoconstituents such are glycosides, saponins, flavonoids, steroids, tannins, alkaloids, terpenes, etc. Syzygium aromaticum (clove) is a traditional spice that has been used for food preservation and possesses various pharmacological activities. S. aromaticum is rich in many phytochemicals as follows: sesquiterpenes, monoterpenes, hydrocarbon, and phenolic compounds. Eugenyl acetate, eugenol, and β-caryophyllene are the most significant phytochemicals in clove oil. Pharmacologically, S. aromaticum has been examined toward various pathogenic parasites and microorganisms, including pathogenic bacteria, Plasmodium, Babesia, Theileria parasites, Herpes simplex, and hepatitis C viruses. Several reports documented the analgesic, antioxidant, anticancer, antiseptic, anti-depressant, antispasmodic, anti-inflammatory, antiviral, antifungal, and antibacterial activity of eugenol against several pathogenic bacteria including methicillin-resistant Staphylococcus epidermidis and S. aureus. Moreover, eugenol was found to protect against CCl4−induced hepatotoxicity and showed a potential lethal efficacy against the multiplication of various parasites including Giardia lamblia, Fasciola gigantica, Haemonchus contortus, and Schistosoma mansoni. This review examines the phytochemical composition and biological activities of clove extracts along with clove essential oil and the main active compound, eugenol, and implicates new findings from gas chromatography-mass spectroscopy (GC-MS) analysis.
... 4 ders. 5 The pharmacological activities of eugenol include anti-oxidant, 5 antibacterial, 6,7 anti -inflammatory, 8 and antipyretic effects. 9 Eugenol has been reported to improve motor coordination and decrease plasma corticosterone level in immobilized stress-induced Wistar rats. 10 Moreover, it was reported that in vitro eugenol decreases the migration of leukocytes and aids in inflammatory process. ...
... (30). These enzymes are involved in the inflammation and carcinogenesis processes, therefore it is recognized that potential COX-2 inhibitors can be considered anti-inflammatory or cancer chemo preventive agents (27).We thought the anti-inflammatory effect that produced from clove buds extract may be due to present of high amount of eugenol and acetyleugenol which have great effect on COX-2 .And that corresponding with Leem, H ,et al 2011 (31) who conducted The clove buds oil exhibited strong inhibitory activity against COX-2 (58.15%) and 15-LOX (86.15%) enzymes at 10 μg/mL and 25 μg/mL, respectively. Other researchers Daniel., et al 2009(3), were studied The antiinflammatory activity of eugenol by using carrageenan-induced paw edema tests in rats at 200 and 400 mg/kg of clove buds oil, and founded reduce in volume of pleural exudates without changing the total blood leukocyte count indicating the antiinflammatory potential of eugenol. ...
The study was carried out to evaluate the analgesic and anti-inflammatory properties of an hydro alcoholic syzygium aromaticum extract (SAE) .The analgesic activity was measured by using the hot plate test with Twenty four (24) mice divided randomly into four groups , T1, T2 received 100 , 200 mg /kg.bw of (SAE) while T3 dosed 50 mg /kg.bw of diclofanic acid and T4 used as control negative and dosed distilled water (D.W.) . The anti-inflammatory activity was measured by using formalin test with Twenty four (24) mice divided randomly into four groups , T1and T2 dosed with 100 and 200 mg /kg.bw respectively of (SAE) while T3 group dosed 0.3 mg/kg.bw of meloxicam and T4 dosed with (D.W.) , (all groups dosed orally before half hour of test) and then calculate the time of analgesia and anti-inflammatory effects . The result showed there is significant increase(p˂0.05) in time of analgesia and significant decreases (p˂0.05) in number of licking in animal exposed to (SAE) comparing with that of control , also there is significant increase(p˂0.05) in time of analgesia and decrease in licking in animals received diclofanic acid and meloxicam respectively comparing with those received (SAE) and D.W the increase was dose dependent manner. In conclusion the hydro-alcoholic extract of clove E.C showed analgesic and anti-inflammatory effect .
... The use of plants and their products as substrates of molecules with biological activity is a leading strategy in research due to its lower toxicity and greater bioavailability. 5 Eugenol is a phenolic monoterpene with anaesthetic, bactericidal, fungicidal and antioxidant properties, among others [6][7][8][9] ; it is extracted as the main component of clove essential oil (Syzygium aromaticum), honey, bay leaves and cinnamon. 5,10 Its antifungal activity against dermatophyte fungi was reported by Pinto et al 11 mechanisms have also been reported in fungi exposed to eugenol: de Oliveira 2013 reported the mechanism of action of eugenol on T. rubrum, a species of highly prevalent dermatophyte related to chronic cases and resistant to local therapies. ...
Background
Microsporum spp. are keratinophilic dermatophytes that mainly invade the stratum corneum of the skin and hair causing clinical symptoms associated with tinea. Its treatment has several limitations, and the search for new active molecules is necessary.
Objective
To evaluate the antifungal and cytotoxic potential of Eugenia caryophyllus essential oil (EO), eugenol, isoeugenol and methylisoeugenol against Microsporum canis, M. gypseum and Vero cells.
Methods
The EO was extracted by conventional heating‐assisted hydrodistillation, the eugenol obtained commercially and the derivatives through Williamson synthesis. Minimal inhibitory concentration (MICs), minimum fungicidal concentration, inhibition of radial mycelial growth and germination inhibition were used to evaluate the antifungal activity. In addition, a colorimetric test was conducted to evaluate cytotoxic activity.
Results
MIC and MFC values for all compounds were 62.5‐500 μg/mL for both of the species of Microsporum evaluated. Also, concentrations of 300 μg/mL of the compounds inhibited 100% of M. canis mycelium. The inhibition of germination was observed after 6 hours of treatment (11.86 ± 3.46‐85.31 ± 0%). No cytotoxicity was observed in Vero cells (CC50 > 105 μg/mL), whereas terbinafine showed CC50 31.00 ± 0.61 μg/mL.
Conclusions
Our study indicates an interesting bioactivity of isoeugenol and methylisoeugenol against M. canis, M. gypseum and mammalian cells.
... Because of these suggested activities, eugenol has been indicated to have chemo preventive effect. 21 Macroscopic studies, clinical evidences of collagen-induced arthritis and treatment with eugenol in a murine model, showed that eugenol may have inhibitory effects on mononuclear cell infiltration into the knee joints of arthritic mice. Eugenol lowered the levels of cytokines such as TNF-α, interferon gamma and TNF-β in the ankle joints. ...
Eugenol is a volatile phenolic constituent of clove essential oil obtained from Eugenia caryophyllata buds and leaves. It is a functional ingredient of numerous products which have been used in the pharmaceutical, food and cosmetic industry in restricted concentrations. Its derivatives have been used in medicine as a local antiseptic and anesthetic. The wide range of eugenol activities includes antimicrobial, anti-inflammatory, analgesic and antioxidant. Although eugenol is considered safe as a product, due to the vast range of different applications and extensive use, there has been a great concern about its toxicity in recent years. However, studies about cytotoxicity and genotoxicity of eugenol are very limited and controversial. The pharmacological and toxicological properties of eugenol will be discussed in this review.
... The inhibition activity may be attributed to the presence of eugenol, which is known as the LOX inhibitor. Leem et al. (2011) showed that the essential Kovats index from literature (Adams, 2001). Bold value refer to the major components. ...
Context: The ethnopharmacological study of Beilschmiedia indicates that several species are
used for the treatment of various ailments.
Objective: This is the first study of the chemical composition of Beilschmiedia pulverulenta
Kosterm (Lauraceae) essential oil and its antioxidant, antimicrobial, antityrosinase, antiinflammatory,
and anticholinesterase activities.
Materials and methods: The antioxidant activities were evaluated by b-carotene, 1,1-diphenyl-2-
picrylhydrazyl (DPPH) radical scavenging, ferric-reducing antioxidant power (FRAP), and
phenolic content at different concentrations. The antimicrobial activities against Gram-positive
and Gram-negative bacteria and fungi were revealed by disk diffusion and microdilution. The
antityrosinase and anti-inflammatory activities were assayed against mushroom tyrosinase and
lipoxygenase enzymes. The anticholinesterase activity was analyzed using acetylcholinesterase
(AChE) and butyrylcholinesterase (BChE) enzymes.
Results: Forty-two components were detected in B. pulverulenta oil with eugenol (45.3%) being
the major component. The oil phenolic content and the FRAP were 660.1mg gallic acid/g and
604.0mg ascorbic acid/g, respectively. The oil gave an IC50 value of 94.5 mg/mL and an
inhibition of 93.9% in DPPH and b-carotene, respectively. The antimicrobial activity showed that
the oil had strong activity against all Gram-positive bacteria with an minimum inhibitory
concentration (MIC) value each of 62.5 mg/mL and moderate against all fungi with MIC and
minimum bactericidal concentration (MBC) values each of 125 mg/mL. The oil showed
significant antityrosinase and anti-inflammatory activities with 67.6 and 62.5% inhibition,
respectively. In addition, the oil had moderate AChE (56.5%) and BChE (48.2%) activities.
Discussion and conclusion: The results show that the oil could potentially be used for
nutraceutical industries, food manufactures, and therapeutic agents against various diseases
such as inflammation and rheumatism.
... 한편, 50 μg/mL의 농 도에서는 천궁이 가장 큰 NO 생성 저해효과를 나타내었으 며, 다음으로 당귀, 애엽, 박하 및 노간주 순으로 나타났다. 이전의 in vitro 결과에서는 당귀가 COX-2 및 15-LO(15-lipoxygenase) 저해활성이 상당히 큰 것으로 보고한 바 있다(29). 따라서 5가지 생약 중 항염증 활성이 클 것으로 사료되 는 천궁 및 당귀 향기추출물을 농도별로 처리한 결과, 모두 농도의존적으로 NO의 생성을 억제하였다(Fig. ...
The effects of volatile flavor extracts of eight different herbal medicines, Juniperus rigida(JR), Saussurea lappaSL), Cnidium officinale(CO), Angelica gigas(AG), Eugenia caryophyllata(EC), Angelica tenuissima(AT), Mentha arvense(MA), and Artemisiae argyi(AA), were investigated on LPS-stimulated inflammation using Raw 264.7 cells. The volatile flavor extracts of CO and AG considerably inhibited LPS-stimulated NO, PGE2, IL-6, and TNF-α (except AG) production, as well as iNOS expression. Major volatile components of CO were identified as ligustilide and of β-eudesmol as AG by GC-MS analysis. Thus, these results suggest that the volatile extracts of CO and AG may be useful as potential therapeutic agents for inflammation-associated disorders.
Gingerbread is a concentrate of exotic spices – cinnamon, star anise, clove, cardamom and nutmeg –, which were rare and expensive for many centuries. Now affordable for most people, many health effects are attributed to them. However, few clinical studies are available to support these claims and some of these spices contain compounds that can have harmful health effects if consumed in amounts higher than recommended.
Introduction
Throughout history, medicinal plants have been used as essential for humans treatment. The antibacterial applications of Tarragon (Artemisia dracunculus) in phytotherapy will be covered in this review study. Despite the advancements in pharmaceuticals, herbal remedies continue to be vital, especially in areas where access to modern therapy is limited. In addition, the antibacterial qualities of Tarragon plant extracts and their innovative extraction techniques are described in this review article.
Methods
A thorough examination of the literature looked at the chemical composition, historical uses, and modern extraction techniques of Tarragon (Artemisia dracunculus). The extraction techniques, such as the IS-R-DLLME, UAE, DES, and PLE, and the methosds of review analysis the antibacterial properties of Tarragon (Artemisia dracunculus) extracts against dangerous microbes.
Results
Both Gram-positive and Gram-negative bacteria can be effectively resistant by Tarragon (Artemisia dracunculus) essential oils and extracts. Also the primary bioactive components were limonene, methyl eugenol, and estragole. The yield and purity of bioactive components were enhanced by novel extraction techniques such as IS-R-DLLME and UAE. At minimum inhibitory concentrations (MIC). Therefore, the essential oils demonstrated strong antibacterial action against Escherichia coli and Staphylococcus aureus.
Discussion/Conclusions
The Tarragon (Artemisia dracunculus) plant may be regarded as a potent natural antibacterial agent, especially for antibiotic-resistant illnesses. By combining traditional botanical knowledge with contemporary extraction methods, new medicinal compounds can be created. This study highlighted the need to explore the synergistic effects of tarragon's bioactive components and improve extraction methods in order to optimize therapeutic advantages. Ultimately, Tarragon (Artemisia dracunculus) may help antibiotic resistance and microbial illnesses.
One lucrative method for overcoming challenges in drug discovery or for enhancing undesirable properties of already-approved medications is prodrug design. The goal of this review is to present researchers with a profile of naturally occurring Phytophenols as carriers that would be used for prodrug synthesis as well as their advantages. Phytophenols offer several advantages when used as promoieties as they also possess antioxidant and analgesic properties, they are obtained naturally and their safety profile is well established. Several phytophenols like menthol, thymol, eugenol, guaiacol, sesamol, vanillin, and umbelliferone are some of the phytophenols that have several beneficial properties and are extensively employed in the field of food processing and medicine. In the current review, we have listed all types of promoieties that are used for prodrug synthesis and phytophenols are reviewed in detail, which may help researchers to select phytophenols based on their need and suitability for drug candidates.
Cloves (Syzygium aromaticum) are the aromatic flower buds, commonly used as a spice, belonging to the family Myrtaceae. Cloves are available as different cultivars throughout the year due to different environmental conditions in different countries. Cloves are commonly used in spices, but they also have importance in different commercial formulations. Cloves possess a wide range of bioactive compounds, but the most important are phenolics. Besides other phenolics, eugenol and its derivatives are present in considerable quantity as the most active functional metabolites. These compounds in cloves are strong radical scavengers/antioxidants and make cloves a choice for commercial sources of phenolics. Clove oil eugenol is also used as an anesthetic in aquaculture for many species of fish worldwide. Its use with gilthead seabream has been considered safe with no compromise on immune depression in anesthetized fish. Considering emulsion formulations of essential oils as bio-safe, biocompatible with good pharmacological potential, clove oil emulsion has also been formulated to substitute chemical (i.e., synthetic gels and antibiotic-based ointments) topical products used in the treatment of inflammation and healing wounds. Eugenol has essential applications in treating teeth, especially the products of eugenol-based root canal sealers are considered safer and more effective. In this chapter, eugenol-based commercially important products are discussed to highlight their importance and comparison with other products focusing on cost and functional effectiveness, and safety.
Eugenol (1-hydroxy-2-methoxy-4-allylbenzene) is a phenolic compound; the natural sources are clove, basil, and cinnamon. To extract eugenol from a natural source, many methods are practiced globally. Researchers reported many therapeutic benefits of eugenol such as antimicrobial, antiviral, and antioxidant effects. The primary mechanisms involved in its therapeutic effects are free radical scavenging activity, blocking the generation of reactive oxygen species, inhibiting the production of reactive nitrogen species, enhancing cytoantioxidant potential, and disordering DNA and proteins. Nutraceuticals impart many benefits in treating chronic diseases such as diabetes, obesity, cardiovascular conditions, and cancer. Nutraceuticals are available as food supplements, functional food, and medicinal food. The product’s efficacy relies upon bioavailability, making this product effective by using a suitable carrier. The motive of using a carrier is to protect the encapsulated molecule from external conditions, preserve functionality, and deliver effectively to the target site. It is free from unwanted effects and is cheaper because it is obtained from a natural source.
Bulk metallic glasses (BMGs) have gained a lot of attention in recent years due to their outstanding properties such as high hardness and excellent wear and corrosion resistance. However, they are restricted in industrial applications due to their extreme brittleness. Iron based amorphous coatings from BMGs are the best solution to use them by overcoming the problem of extreme brittleness. The coatings can be sprayed by various thermal techniques such as flame spraying (FS), high velocity air fuel (HVAF), High velocity oxy fuel (HVOF) spraying process and plasma spray (PS) process. In this study, we have developed iron-based amorphous coating via HVOF and found interesting effect of structural relaxation at low temperature. Iron-based amorphous alloy powder with Fe48Mo14Cr15Y2C15B6 composition was used as the feedstock powder. The coatings sprayed by HVOF the techniques showed compact coatings as observed by the Scanning electron microscopy (SEM) results and amorphous phase was confirmed by the X-ray diffraction analysis at various temperature. Further investigations on the mechanical properties and chemical properties show that low temperature sintering improve the property of coatings.
Gastric ulcer disease induced by the consumption of NSAIDs is a major public health problem. The therapy used for its treatment causes adverse effects in the patient. Propolis is a natural product that has been used for the treatments of different diseases around the world. Nevertheless, there is little information about the activity of propolis in gastric ulcers caused by treatment with NSAIDs. Therefore, this review evaluates and compares the gastroprotective potential of propolis and its function against NSAID-induced gastric ulcers, for which a systematic search was carried out in the PubMed and ScienceDirect databases. The main criteria were articles that report the gastroprotective activity of propolis against the damage produced by NSAIDs in the gastric mucosa. Gastroprotection was related to the antioxidant, antisecretory, and cytoprotective effects, as well as the phenolic compounds present in the chemical composition of propolis. However, most of the studies used different doses of NSAIDs and propolis and evaluated different parameters. Propolis has proven to be a good alternative for the treatment of gastric ulcer disease. However, future studies should be carried out to identify the compounds responsible for these effects and to determine their potential use in people.
Bajakah is a woody-liana known for traditional medicine by the Dayak and Banjar tribes in Central Kalimantan. Three bajakah, which were identified as Salacia sp., Uncaria acida , and Uncaria gambir , were collected from their natural habitats in peatland hydrological unit of Sebangau–Kahayan rivers. GC-MS pyrolysis was used to analyze the identity of phytochemical compounds in the wood and bark of bajakah. The results showed that phytochemical compounds were varied both in the woods and barks which ranges from 30 to 40 types, with the largest component is phenol. Seven phytochemical compounds were not identified. Phenolic compounds varied among 3-8 types. The next step was determining total flavonoid and phenol content using Folin-Ciocalteu method. Results showed that bark of Uncaria acida has the highest total phenol and flavonoid content, which were 0.013% and 0.028%, respectively. Wood of Salacia sp. has the lowest total phenolic and flavonoid content, which were 0.013% and 0.028%, respectively. The commercial bajakah that are usually sold in the market, which was unidentified, has medium total phenolic and flavonoid content, which are 0.010% and 0.025%, respectively. In summary, the composition and content of phytochemical compounds in bajakah were determined by the species.
Nine medicinal plants and their stick-type medicinal concentrated beverages (SMCB-I and SMCB-II) with different combination ratio were evaluated on antioxidant, nitric oxide (NO) inhibitory, and antibacterial effects against pathogenic bacteria involved in respiratory system illnesses. Antioxidant activity was high in Syzygium aromaticum, Pueraria lobata, Plantago asiatica, and Kalopanax pictus which have higher contents of total phenolics and total flavonoids. The NO inhibitory activity was high in Syzygium aromaticum, Plantago asiatica, and Glycyrrhiza uralensis. Syzygium aromaticum, Plantago asiatica, Kalopanax pictus and Glycyrrhiza uralensis showed higher antibacterial activity than the other five medicinal plants against Staphylococcus aureus, Corynebacterium diphtheriae, and Mycobacterium sp. SMCB-II exhibited higher antioxidant, NO inhibitory, and antibacterial effects than SMCB-I, since Syzygium aromaticum, Pueraria lobata, and Kalopanax pictus were only used for the production of SMCB-II. The SMCBs would be expected to contribute to an easy-to-carry, easy-to-consume, and high value-added health beverage for the modern people.
Barley (Hardeum vulgare L.) sprout has received much attention in recent years as a functional food in many countries, especially in Korea and Japan. It has been reported that barley sprouts are comprised of 52.6% polysaccharides, 34.1% proteins, and 4.97% fats, along with a variety of vitamins, minerals, and polyphenols. The purpose of this study was to assess the anti-oxidant and anti-inflammatory activities of the ethanol extracts of barley sprouts. We examined the inhibitory effect of barley sprout extracts (BSE) on inducible nitric oxide synthase (iNOS) and cyclooxygenase-2 (COX-2) expression, and nitric oxide (NO), prostaglandin E2 (PGE2) and cytokine production in lipopolysaccharide (LPS)-stimulated RAW 264.7 mouse macrophage cells. BSE contains high amounts of phenolics and flavonoids and exhibits potent anti-oxidative activity, as depicted by the DPPH radical-scavenging experiment. The concentration of total phenols was 17.55 ?g/ml, and flavonoids, 13.98 ?g/ml. We also investigated the anti-inflammatory activities of BSE in LPS-stimulated RAW 264.7 cells. Tumor necrosis factor-alpha and PGE2 production, which had increased as a result of treatment with LPS, were significantly inhibited by BSE in a dose-dependent manner. BSE also significantly suppressed LPS-induced production of NO, and this was accompanied by a decrease in the expression of the iNOS and COX-2 proteins. These results indicate that barley sprouts may be a highly valuable natural product owing to its high-quality functional components as well as its anti-oxidant and anti-inflammatory activities.
Seven kinds (acacia, cochineal, catechu, grape peel, persimmon, gallnut and clove) of color powders obtained from natural resources and their mixtures were evaluated for their biological activities, such as antioxidant (ABTS and DPPH radicals scavenging), cholesterol absorption, and COX-2 inhibitory activities. Catechu, gallnut and clove were selected for the further studies due to its the best activities. The cholesterol absorption, COX-2 inhibitory, α-amylase inhibitory and α-glucosidase inhibitory activities were measured using the mixtures of catechu, gallnut and clove. The ABTS radical scavenging activity of the seven types of natural color powders were higher than the DPPH radical scavenging activity. The cholesterol absorption activity was significantly higher in cloves. The COX-2 inhibitory activity was significantly lower in acacia. The α-amylase inhibitory activity was higher in catechu and gallnut, indicating that there were no significant difference between two mixtures. The α-glucosidase inhibitory activity was the highest in catechu, which was higher than that of the catechu-containing mixtures. From all these results, a synergistic effect could be obtained when utilizing a mixture of powders rather than using only individual type. Since the activity of each powder was different, further studies will be required for clarifying the interactions between mixtures.
The aim of this study was to evaluate the antioxidant activities and anti-inflammatory effects of water and ethanolic extracts from Allium hookeri roots and leaves. Antioxidant activities of Allium hookeri extracts were determined based on various radical scavenging activities using an ESR spectrophotometer, ferric reducing antioxidant power, 2,2'-azinobis-(3-ethybenzothiazoline-6-sulfonic acid) radical scavenging activity, and oxygen radical absorbance capacity assays. In addition, we investigated anti-inflammatory effects of Allium hookeri extract on lipopolysaccharide (LPS)-induced inflammation in RAW264.7 cells. We also explored the effects of extract from Allium hookeri root on suppression of pro-inflammatory mediators such as nitric oxide (NO) and pro-inflammatory cytokines such as IL-6 and TNF-α against LPS-induced activation of RAW264.7 cells. Our results demonstrated superior antioxidant activity for leaf extract of Allium hookeri compared to extract from root of Allium hookeri. On the other hand, root extract of Allium hookeri showed better anti-inflammatory activity compared to leaf extract. Our study suggests that Allium hookeri extract exhibits strong antioxidant activity and anti-inflammatory effects and can be developed as a potential therapeutic candidate for diseases involving oxidative stress and inflammation.
Methyleugenol (1), one of the main bioactive constituents of the seeds of Myristica fragrans Houtt. (family: Myristicaceae), was incubated with rat hepatic microsomes from rats pretreated with sodium phenobarbital. Eight biotransformation products named (R)1′ methoxymethyleugenol (2), 3(3,4dimethoxyphenyl) lmethoxyprop2ene (3), cis3,4dimethoxycinnamyl acetate (4), trans3,4dimethoxycinnamyl acetate (5), (R)1′ hydroxymethyleugenol (6), trans3,4dimethoxycinnamyl alcohol (7), cis3,4dimethoxycinnamyl alcohol (8), and (R)3(3,4dimethoxyphenyl) propane1,2diol (9) were obtained and their structures were elucidated by NMR and MS data analysis and by comparison with the previously reported data. The biotransformation of 1 may provide valuable information for the use of methyleugenol. The NMR data of compounds 4 and 6 were reported for the first time. © 2014 Journal of Chinese Pharmaceutical Sciences, School of Pharmaceutical Sciences, Peking University.
Laminaria japonica roots have not been used practically in Korea. In this study, in order to promote the use of these by-products, the anti-inflammatory activity of an ethanol extract of Laminaria japonica root (LJREE) was investigated using a lipopolysaccharide (LPS) to induce an inflammatory response in RAW 264.7 cells. To examine the potential anti-inflammatory effects of LJREE, levels of nitric oxide (NO) and pro-inflammatory cytokines, such as interleukin-6 (IL-6), tumor necrosis factor-α (TNF-α), and interleukin-1β (IL-1β), and cell proliferation were measured. We found that NO levels decreased in a dose-dependent manner, the production of IL-6, TNF-α, and IL-1β was suppressed, and the production of IL-1β was inhibited over 30% after treatment with 100 μg/mL LJREE. In conclusion, the proliferation of RAW 264.7 cells, measured by MTT assay, confirmed that LJREE may have significant effects on inflammatory factors without any cytotoxicity, making it a potential anti-inflammatory agent.
The antifungal properties of eugenol were tested against ten plant pathogenic fungal species and detailed studies were conducted regarding in vitro activity of eugenol on Botrytis cinerea. The EC50 value of eugenol on mycelial radial growth of B. cinerea was 38.6 μg/mL; however, eugenol had no bioactivity against conidia germination. B. cinerea hyphae treated with eugenol showed strong propidium iodide fluorescence in the cytosol. Eugenol increased the concentration of potassium ion and cellular materials in the medium. Furthermore, light and scanning electron microscopy observations on hyphae exposed to eugenol revealed considerable morphological alterations in hyphae, such as cytoplasmic coagulation, vacuolation, and hyphal shriveling. Eugenol induced the generation of H2O2 and increased free Ca2+ in the cytoplasm. These results strongly support the idea that the antifungal activity of eugenol is due to membrane binding and permeability alteration, leading to destabilization and disruption of the plasma membrane.
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 μg/ml. Clove bud extract inhibited malonaldehyde formation from cod liver oil by 93% at the 160 μg/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 μg/ml. Eugenol, eugenyl acetate, and benzyl alcohol inhibited malonaldehyde formation from cod liver oil by 88, 79, and 63%, respectively, at 160 μg/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, α-tocopherol (vitamin E).
This article reviews the anti-inflammatory relative and anti-infectious effects of Evodia rutaecarpa and its major bioactive components and the involvement of the nitric oxide synthases, cyclooxygenase, NADPH oxidase, nuclear factor kappa B, hypoxia-inducible factor 1 alpha, reactive oxygen species, prostaglandins, tumor necrosis factor, LIGHT, amyloid protein and orexigenic neuropeptides. Their potential applications for the treatment of endotoxaemia, obesity, diabetes, Alzheimer's disease and their uses as cardiovascular and gastrointestinal protective agents, analgesics, anti-oxidant, anti-atherosclerosis agents, dermatological agents and anti-infectious agents are highlighted. Stimulation of calcitonin gene-related peptide release may partially explain the analgesic, cardiovascular and gastrointestinal protective, anti-obese activities of Evodia rutaecarpa and its major bioactive components.
Whether pattern similarity causes misdiagnosis and undiagnosis in Chinese medicine is unknown. This study aims to test the effect of pattern similarity and examination methods on diagnostic outcomes of pattern differentiation algorithm (PDA).
A dataset with 73 Zangfu single patterns was used with manifestations according to the Four Examinations, namely inspection (Ip), auscultation and olfaction (AO), inquiry (Iq) and palpation (P). PDA was applied to 100 true positive and 100 true negative manifestation profiles per pattern in simulation. Four runs of simulations were used according to the Four Examinations: Ip, Ip+AO, Ip+AO+Iq and Ip+AO+Iq+P. Three pattern differentiation outcomes were separated, namely correct diagnosis, misdiagnosis and undiagnosis. Outcomes frequencies, dual pattern similarity and pattern-dataset similarity were calculated.
Dual pattern similarity was associated with Four Examinations (gamma = -0.646, P < 0.01). Combination of Four Examinations was associated (gamma = -0.618, P < 0.01) with decreasing frequencies of pattern differentiation errors, being less influenced by pattern-dataset similarity (Ip: gamma = 0.684; Ip+AO: gamma = 0.660; Ip+AO+Iq: gamma = 0.398; Ip+AO+Iq+P: gamma = 0.286, P < 0.01 for all combinations).
Applied in an incremental manner, Four Examinations progressively reduce the association between pattern similarity and pattern differentiation outcome and are recommended to avoid misdiagnosis and undiagnosis due to similarity.
Cyclooxygenase and lipoxygenase, two important enzymes involved in arachidonic acid metabolism, are major targets of non-steroidal anti-inflammatory drugs (NSAIDs). Recent investigations suggest that arachidonic cascades and their metabolites may be involved in maintaining inner ear functions. The excessive use of aspirin may cause tinnitus in humans and impairment of the outer hair cell functions in experimental animals. On the other hand, NSAIDs reportedly exhibit protective effects against various kinds of inner ear disorder. The present review summarizes the effects of NSAIDs on cochlear pathophysiology. NSAIDs are a useful ameliorative adjunct in the management of inner ear disorders.
Pain associated with inflammation involves prostaglandins synthesized from arachidonic acid (AA) through cyclooxygenase-2 (COX-2) pathways while thromboxane A(2) formed by platelets from AA via cyclooxygenase-1 (COX-1) mediates thrombosis. COX-1 and COX-2 are both targets of nonselective nonsteroidal antiinflammatory drugs (nsNSAIDs) including aspirin whereas COX-2 activity is preferentially blocked by COX-2 inhibitors called coxibs. COXs are homodimers composed of identical subunits, but we have shown that only one subunit is active at a time during catalysis; moreover, many nsNSAIDS bind to a single subunit of a COX dimer to inhibit the COX activity of the entire dimer. Here, we report the surprising observation that celecoxib and other coxibs bind tightly to a subunit of COX-1. Although celecoxib binding to one monomer of COX-1 does not affect the normal catalytic processing of AA by the second, partner subunit, celecoxib does interfere with the inhibition of COX-1 by aspirin in vitro. X-ray crystallographic results obtained with a celecoxib/COX-1 complex show how celecoxib can bind to one of the two available COX sites of the COX-1 dimer. Finally, we find that administration of celecoxib to dogs interferes with the ability of a low dose of aspirin to inhibit AA-induced ex vivo platelet aggregation. COX-2 inhibitors such as celecoxib are widely used for pain relief. Because coxibs exhibit cardiovascular side effects, they are often prescribed in combination with low-dose aspirin to prevent thrombosis. Our studies predict that the cardioprotective effect of low-dose aspirin on COX-1 may be blunted when taken with coxibs.
Aim: The aim of this study is gas chromatographic analysis of Eugenia caryaphyllata (clove) essential oil and investigation of its anti-inflammatory effects. Methods: The study involved eight groups; Serum physiologic, ethyl alcohol, indomethacin (3 mg/kg), etodolac (50 mg/kg), cardamom (0.05 mL/kg), EC-I (0.025 mL/kg), EC-II (0.050 mL/kg), EC-III (0.100 mL/kg) and EC-IV (0.200mL/kg). After measuring the volumes of right hind-paws of rats using a plethysmometer, drugs were injected intraperitoneally and lambda-carrageenan were injected subcutaneously into the plantar region. Three hours after the injections the volume measurements of the right hind-paws were repeated and the difference between the volumes were compared. Results: The composition of the essential oil was as follows: β-caryophyllen % 44.7, eugenol % 44.2, α-humulen % 3.5, eugenyl acetate % 1.3 and α-copaen % 1.0. It was found that indomethazin reduced the inflammation by 95.70%, etodolac by 43.42 %, EC-I by 46.55 %, EC-II by 90.15 %, EC-III by 66.94 % and EC-IV by 82.78 %. The essential oil of Eugenia caryophyllata had an anti-inflammatory effect matching to that of etodolac at 0.025 and 0.1 mL/kg and to that of indomethacin at 0.05 and 0.2 mL/kg doses. Conclusion: As a result Eugenia caryophyllata essential oil extract was shown to have an anti-inflammatory effect.
Since the inhibitory effect of eugenol (a), which was isolated as an antioxidative component from plant, Caryopylli flos, on lipid peroxidation was less than that of alpha-tocopherol, we synthesized the eugenol-related compounds dieugenol (b), tetrahydrodieugenol (c), and dihydroeugenol (d), to find new strong antioxidants and assessed them for their inhibitory effect on lipid peroxidation and scavenging ability for superoxide and hydroxyl radicals. The antioxidative activities were in the order: (b)>(c)>(d)>(a) for the thiobarbituric acid reactive substance (TBARS) formation. These results suggest that the dimerized compounds have higher antioxidant activities than that of the monomers. Electron spin resonance (ESR) spin trapping experiments revealed that eugenol and its dimer, having allyl groups in the structure, scavenged superoxide, and that only eugenol trapped hydroxyl radicals under the conditions used. These finding suggest that eugenol and dieugenol have a different mechanism of antioxidation, i.e. eugenol may inhibit lipid peroxidation at the level of initiation, however, the related dimeric compounds may inhibit lipid peroxidation at the level of propagation of free radical chain reaction like alpha-tocopherol.
The essential oil (EC-oil) obtained from the buds of Eugenia caryophyllata (Myrtaceae) was examined for its free radical-scavenging activity, cytotoxicity, and in vivo toxicity. To find the xenobiotic properties of EC-oil, serum thiobarbituric acid reactive substances (TBARS) level and hepatic drug-metabolizing enzyme activities were measured. It was found that EC-oil displayed xenobiotic properties like bromobenzene. The cytotoxicities of eugenol and of the EC-oil were greatly attenuated by the sulfhydryl-containing TV-acetyl-L-cysteine (NAC), suggesting that eugenol was susceptible to nucleophilic sulfhydryl. In addition, eugenol also showed potent free radical-scavenging activity in the 1,1-diphenyl-2-picrylhydrazyl (DPPH) assay. Moreover, methyleugenol considerably exhibited less cytotoxicity and less potent free radical-scavenging activity than eugenol, and the cell viability of the methyleugenol was more increased with NAC treatment than the eugenol. These results indicate that the phenolic OH in eugenol may play a crucial role in both cytotoxicity and free radical-scavenging activity. The fashion on oxidative stress and hepatic drug-metabolizing enzyme activities of eugenol resembled those of bromobenznene.
A description is given of a modification of the Likens and Nickerson apparatus for isolating volatiles from foods, beverages, and other agricultural products by simultaneous steam distillation and extraction (SDE) with an organic solvent. The new apparatus was evaluated by experiments with dilute aqueous solutions of a model mixture of 12 volatile compounds, representative of those found in fruit essences. Analysis of the recovered material was done by quantitative gas chromatography. Most of the components showed nearly quantitative recovery after 1 h (some, better than 90% in 10 min), but ethyl 3-hydroxyhexanoate required 4 h to reach 90% recovery. Hexane was shown to be an excellent extracting solvent for most of the components except low molecular weight, water-soluble compounds (ethanol and ethyl acetate, which form azeotropes with hexane). For these compounds, diethyl ether gave considerably better results. Although most of the components appeared to be chemically stable when the initial solution in the still pot was acidic, down to pH 3.4, linalool and citronellal showed instability in the lower part of this pH range. This was corrected by raising the pH to 6.5. SDE at reduced pressure (100 mm of Hg), and thus at a lower temperature, also favored stability, but recovery of the hydroxy ester was decreased drastically.
The present study investigated the preventive effect of eugenol, a naturally occurring food flavouring agent on thioacetamide (TA)-induced hepatic injury in rats. Adult male Wistar rats of body weight 150–180 g were used for the study. Eugenol (10.7 mg/kg b.w./day) was administered to rats by oral intubation for 15 days. TA was administered (300 mg/kg b.w., i.p.) for the last 2 days at 24 h interval and the rats were sacrificed on the 16th day. Markers of liver injury (aspartate transaminase, alanine transaminase, alkaline phosphatase, γ-glutamyl transferase and bilirubin), inflammation (myeloperoxidase, tumor necrosis factor-α and interleukin-6), oxidative stress (lipid peroxidation indices, protein carbonyl and antioxidant status) and cytochrome P4502E1 activity were assessed. Expression of cyclooxygenase-2 (COX-2) and the extent of DNA damage were analyzed using immunoblotting and comet assay, respectively. Liver injury and collagen accumulation were assessed using histological studies by hematoxylin and eosin and Masson trichrome staining. Rats exposed to TA alone showed increased activities of hepatocellular enzymes in plasma, lipid peroxidation indices, inflammatory markers and pro-inflammatory cytokines and decreased antioxidant status in circulation and liver. Hepatic injury and necrosis were also evidenced by histology. Eugenol pretreatment prevented liver injury by decreasing CYP2E1 activity, lipid peroxidation indices, protein oxidation and inflammatory markers and by improving the antioxidant status. Single-cell gel electrophoresis revealed that eugenol pretreatment prevented DNA strand break induced by TA. Increased expression of COX-2 gene induced by TA was also abolished by eugenol. These findings suggest that eugenol curtails the toxic effects of TA in liver.
The antiradical activities of various antioxidants were determined using the free radical, 2,2-Diphenyl-1-picrylhydrazyl (DPPH*). In its radical form. DPPH* has an absorption band at 515 nm which dissappears upon reduction by an antiradical compound. Twenty compounds were reacted with the DPPH* and shown to follow one of three possible reaction kinetic types. Ascorbic acid, isoascorbic acid and isoeugenol reacted quickly with the DPPH* reaching a steady state immediately. Rosmarinic acid and δ-tocopherol reacted a little slower and reached a steady state within 30 min. The remaining compounds reacted more progressively with the DPPH* reaching a steady state from 1 to 6 h. Caffeic acid, gentisic acid and gallic acid showed the highest antiradical activities with a stoichiometry of 4 to 6 reduced DPPH* molecules per molecule of antioxidant. Vanillin, phenol, γ-resorcylic acid and vanillic acid were found to be poor antiradical compounds. The stoichiometry for the other 13 phenolic compounds varied from one to three reduced DPPH* molecules per molecule of antioxidant. Possible mechanisms are proposed to explain the experimental results.
The present study was undertaken to evaluate the anti-stress effect of the hydro-alcoholic extract of clove.
The anti-stress effect was evaluated on cold restraint induced gastric ulcers, sound stress induced biochemical changes and anoxic stress induced convulsions. Clove extract was administered orally at two different doses of 100 and 200 mg/kg. Zeetress, a known anti-stress formulation (14 mg/kg p.o) was used as the standard drug.
Both the doses of clove extract showed good anti-stress effect in all the tested models. The clove extract reduced the development of cold restraint induced gastric ulcers and prevented the biochemical changes induced by sound stress such as increase in plasma levels of aspartate aminotransferase, alanine aminotransferase, alkaline phosphatase, glucose, cholesterol and corticosterone. Clove extract was also effective in increasing the latency of anoxic stress induced convulsions in mice.
The hydro-alcoholic extract of clove at doses of 100 and 200 mg/kg orally possesses good anti-stress activity.
Eugenol, a methoxyphenol component of clove oil, suppresses cyclooxygenase-2 expression, while eugenol dimers prevent nuclear factor-kappaB (NF-kappaB) activation and inflammatory cytokine expression in lipopolysaccharide-stimulated macrophages. Our aim was to examine the in vivo anti-inflammatory effects of eugenol. BALB/c mice were divided into four groups. Mice received saline [0.05 ml intratracheally (it), control (Ctrl) and eugenol (Eug) groups] or Escherichia coli LPS (10 microg it, LPS and LPSEug groups). After 6 h, mice received saline (0.2 ml ip, Ctrl and LPS groups) or eugenol (160 mg/kg ip, Eug and LPSEug groups). Twenty-four hours after LPS injection, pulmonary resistive (DeltaP1) and viscoelastic (DeltaP2) pressures, static elastance (E(st)), and viscoelastic component of elastance (DeltaE) were measured. Lungs were prepared for histology. In parallel mice, bronchoalveolar lavage fluid was collected 24 h after LPS injection. TNF-alpha was determined by ELISA. Lung tissue expression of NF-kappaB was determined by EMSA. DeltaP1, DeltaP2, E(st), and DeltaE were significantly higher in the LPS group than in the other groups. LPS mice also showed significantly more alveolar collapse, collagen fibers, and neutrophil influx and higher TNF-alpha levels and NF-kappaB expression than the other groups. Eugenol treatment reduced LPS-induced lung inflammation, improving lung function. Our results suggest that eugenol exhibits in vivo anti-inflammatory action in LPS-induced lung injury.
The present study was designed to investigate the protective efficacy of eugenol against skin cancer and probe into the mechanistic aspects. Skin tumors were initiated by applying 160 nmol DMBA and promoted by twice weekly applications of 8.5 nmol TPA for 28 wk. All mice developed tumors by 13 wk of promotion. However, in mice pretreated with 30 microL eugenol, no tumors were detected until 8 wk (following anti-initiation protocol) and until 14 wk (following antipromotion protocol) of tumor promotion. PCNA and TUNEL immunohistochemistry of tumors revealed eugenol to ameliorate cell proliferation and elevate apoptosis respectively. The effect of eugenol was assessed on specific stages of carcinogenesis. Initiation with DMBA led to a significant upregulation of p53 expression with a concomitant increase in p21(WAF1) levels in epidermal cells indicating induction of damage to the DNA. However, pretreatment with eugenol led to overexpression of these genes, which probably helped stimulate apoptosis of the initiated cells. To ascertain the molecular mechanisms implicated in the antitumor promoting activity of eugenol, its effect was investigated on markers of tumor promotion and inflammation: ODC activity and iNOS and COX-2 expression, and on levels of proinflammatory cytokines (IL-6, TNF-alpha, and PGE(2)). Eugenol markedly inhibited all. Eugenol also inhibited the upstream signaling molecule: NF-kappaB, which regulates the expression of these genes. TPA-induced depletion of cutaneous GSH and antioxidant enzymes armory was also precluded by eugenol. From these results, it could be concluded that eugenol markedly protects against chemically induced skin cancer and acts possibly by virtue of its antiproliferative, anti-inflammatory, and antioxidant activities.
To determine the effect of combinations of cyclooxygenase (COX) inhibitors and inhibitors of leukotriene (LT) syntheses on collagen induced arthritis (CIA) in mice.
The CIA model was evaluated for the presence of eicosanoids in the paw tissue. Several selective cyclooxygenase 2 (COX-2) inhibitors or non-selective non-steroidal anti inflammatory drugs (NSAIDs) were evaluated alone or in combination with leukotriene (LT) synthesis inhibitors in the CIA model.
Arthritic paw tissue showed increased levels of prostaglandins and leukotrienes in comparison to normal paws. Analysis of mRNA levels indicated the inducible form of the COX-2 enzyme to be the source of prostaglandins. NSAIDs, COX-2 or leukotriene synthesis inhibitors administered alone in CIA decreased severity but had little effect on disease incidence. However, the combination of selective COX-2 inhibitors with leukotriene synthesis inhibitors produced significant decreases in both incidence and severity, suggesting an additive or synergistic effect. This effect was reversible with removal of drug. Little decrease in incidence was observed with the NSAID/5-LO inhibitor combinations.
These results suggest that the induction of the disease in CIA is mediated by products of the COX-2 enzyme and LTB4 production, and that blockade of both pathways is required to prevent CIA.
Butylated hydroxyanisole and butylated hydroxytoluene are used extensively as food antioxidants. It is estimated that man
consumes ca. 0.1 mg/kg body wt daily of these antioxidants. At levels 500 times this level (50 mg/kg/day), both butylated
hydroxyanisole and butylated hydroxytoluene appear to be free of any obviously injurious effects. However, at larger doses
(500 mg/kg/day), both butylated hydroxyanisole and butylated hydroxytoluene result in certain pathological, enzyme, and lipid
alterations in both rodents and monkeys, and butylated hydroxytoluene, in some cases, has been reported to have certain teratogenic
and carcinogenic effects upon rodents. These alterations appear to differ markedly between rodents and monkeys, apparently
as a result of differences which exist in the metabolism and excretion of butylated hydroxyanisole and butylated hydroxytoluene
by these two species. However, in both animal species, the alterations appear to be physiological responses which are reversible
upon removal of butylated hydroxyanisole and butylated hydroxytoluene from the diet. Long term chronic ingestion of butylated
hydroxyanisole and butylated hydroxytoluene may be beneficial in sparing vitamin E and in modifying the acute toxicity of
a number of mutagenic and carcinogenic chemicals.
Carcinogenicity tests showed that addition of the antioxidant BHA to the diet of F344 rats induced high incidences of papilloma and squamous cell carcinoma of the forestomach of both sexes. Male hamsters given BHA for 24 weeks also developed papilloma showing downward growth into the submucosa of the forestomach. These results indicate that BHA should be classified in the category of "sufficient evidence of carcinogenicity" as judged by IARC criteria. The 3-tert isomer of BHA seemed to be responsible for the carcinogenicity of crude BHA in the forestomach of rats. BHT was not found to be carcinogenic in rats or mice. In two-stage carcinogenesis in rats after appropriate initiation, BHA enhanced carcinogenesis in the forestomach and urinary bladder of rats, but inhibited carcinogenesis in the liver. BHT enhanced the induction of urinary bladder tumors and inhibited that of liver tumors, but had no effect on carcinogenesis in the forestomach. BHT could be a promoter of thyroid carcinogenesis. Sodium L-ascorbate enhanced forestomach and urinary bladder carcinogenesis. Ethoxyquin enhanced kidney and urinary bladder carcinogenesis, but inhibited liver carcinogenesis. Thus, these antioxidants modify two-stage chemical carcinogenesis in the forestomach, liver, kidney, urinary bladder, and thyroid, but show organ-specific differences in effects.
To clarify the possible link between radicals and the cytotoxicity of eugenol-related compounds, 2-allyl-4-X-phenols (2-allyl-4-chlorophenol (1), 2-allyl-4-phenylphenol (2), 2-allyl-4-methoxyphenol (3), 2-allyl-4-acetylphenol (4), 2-allyl-4-nitrophenol (5), 2-allyl-4-t-butylphenol (6), 2-allyl-4-methyphenol (7), 2-allyl-4-bromophenol (8), 2,4-dimethoxyphenol (9)), and dimeric compounds from eugenol (4-allyl-2-methoxyphenol), BHA (2-t-butyl-4-methoxyphenol) or MMP (2-methoxy-4-methylphenol); bis-EUG (3,3'-dimethoxy-5,5'-di-2-propenyl-1, 1'-biphenyl-2,2'-diol) (10), bis-MMP (3,3'-dimethoxy-5,5'-dimethyl-1,1'-biphenyl-2,2'-diol) (11) bis-BHA (3,3'-di-t-butyl-5,5'-dimethoxy-1,1'-biphenyl-2,2'-diol) (12) were synthesized. The radical production, radical-scavenging activity and the cytotoxicity of these synthetic compounds and conventional antioxidants (i.e. butylhydroxytoluine, BHT; butylhydroxyanisole, BHA; alpha-tocopherol (alpha-Toc); eugenol, phenol) were studied. Erectron spin resonance (ESR) spectroscopy suggested that compounds of 3, 6, 9, eugenol and BHA, but not compounds of 10, 11, and 12 produced radicals in alkaline solutions (pH>9.5) and compounds, 3, eugenol and 9 most efficiently scavenged reactive oxygen species (ROS, O(2)(-)). The cytotoxic activity of 6 toward human submandibular gland carcinoma (HSG) cells was the highest and was 1000-fold greater than that of eugenol and 100-fold greater than that of BHA, possibly due to the high hydrophobicity and stable phenoxy radicals of this compound. The kinetic polymerization method in the presence of methyl methacrylate (MMA), an antioxidant, and 2,2'-azobisisobutyronitrile (AIBN) was developed for the measurements of the number of moles of peroxy radicals trapped by moles of the relative phenols (stoichiometric factors, n), the inhibition rate of polymerization (R(inh)), and the inhibition rate constants (k(inh), the rate constants for scavenging of radicals by an antioxidant). The n values of conventional phenolic antioxidants decreased in the order: alpha-Toc>BHT>eugenol>phenol. Those for eugenol and phenol, less hindered phenols, were much less than two, whereas those for alpha-Toc and BHT, hindered phenols, were approximately two. The R(inh) of alpha-Toc significantly increased tcompared with that of BHT, eugenol and phenol. The k(inh) of the polymer radicals of the MMA reaction with conventional phenolic antioxidants was a low value of 1-2x10(2) M(-1) s(-1), suggesting that the antioxidants trapped radicals quickly. The comparative cytotoxicity of methoxyphenols against HSG cells was investigated. The cytotoxic activity of dimers of 10 and 12 was markedly lower than that of their corresponding monomers, whereas that of the dimer of MMP, 11 was not reduced even after the dimerization. In particular, visible-light (VL) exposure enhanced the cytotoxicity of 11 similar to the monomers of eugenol, BHA and MMP. Changes in BDE (ph(O-H)) (homolytic bond dissociation energy) for phenols is well known to be associated with the n and k(inh) values, and consequently the cytotoxic activity. Thus, the BDE was calculated using a PM3 semiempirical method. The n and k(inh) values for monophenols, but not for dimers were correlated to the BDE, possibly due to the steric hindrance of orthosubstituents of dimers. The quantitative structure-activity relationship (QSAR) of eugenol-related compounds was investigated, indicating that logP (octanol-water partition coefficients), the redox potential measured in culture medium, was effective as a term for QSAR. A parabolic relation between the cytotoxic activity and the logP or the redox potential, but not the BDE was observed with an optimum value. In conclusion, the cytotocity of eugenol-related compounds was significantly associated with the activity of the production of phenoxyl radicals, their stability of the subsequent quinonemethide (QM) and the hydrophobicity.
Drugs can have adverse effects on any part of the gastrointestinal (GI) tract from mouth to colon. It is essential that a detailed and accurate drug history is taken in patients presenting with GI complaints. Many drug-induced effects will regress or heal on cessation of treatment. NSAIDs are usually associated with gastric and duodenal ulcers but are also recognised to cause lichen planus in the mouth, oesophageal inflammation and strictures, and small bowel and colonic ulcers and strictures. A newer class of anti-inflammatory drugs, the cyclooxygenase-2 (COX-2)-selective inhibitors, have been developed and have a more favourable GI safety profile than standard NSAIDs. Acute diarrhoea, relapse of inflammatory bowel disease (IBD), microscopic colitis and acute pancreatitis are also induced by ingestion of standard NSAIDs. The calcium antagonists, phenytoin and cyclosporin, induce gum hyperplasia, particularly in patients with poor oral hygiene. Alendronate, a bisphosphonate, has been associated with development of oesophageal ulcers, and specific recommendations are now given to reduce this complication. Of the many different forms of colitis associated with drug ingestion, the most frequent is pseudomembranous colitis. This is a complication of antibiotics and is caused by the toxin produced by Clostridium difficile. Many drugs have been associated with the development of acute pancreatitis, although a definite cause and effect relationship has been shown for only a few drugs. These include didanosine, furosomide, corticosteroids, azathioprine and sodium valproate.
Eugenol exhibits antioxidant and anti-inflammatory activities, but at higher concentrations acts as an oxidant and potent allergen. It was earlier shown that bis-eugenol synthesized by the oxidation of eugenol was less cytotoxic and more highly antioxidative than eugenol. But its anti-inflammatory mechanism remains yet unclear. Since nuclear factor-kappa B (NF-kappa B) is a key transcriptional factor in the expression of inflammatory cytokines, we examined whether eugenol and bis-eugenol are inhibitors of NF-kappa B activation. We observed that bis-eugenol, but not eugenol, clearly inhibited the degradation of inhibitory kappa B-alpha in RAW264.7 murine macrophages stimulated with lipopolysaccharide and, consequently, the transcriptional activity of the stimulated NF-kappa B in the cells. In addition, bis-eugenol actually inhibited LPS-stimulated expression of inflammatory cytokines at both gene and protein levels. These findings suggest that bis-eugenol acts as a potent inhibitor of NF-kappa B.
o-Methoxyphenols such as eugenol and isoeugenol exhibit anti-oxidant and anti-inflammatory activities, but at higher concentrations act as oxidants and potent allergens. We recently demonstrated the eugenol dimer bis-eugenol to be an efficient inhibitor of lipopolysaccharide (LPS)-induced inflammatory cytokine expression in macrophages without cytotoxicity. This result suggested that dimer compound of o-methoxyphenols may possess anti-inflammatory activity. Thus, we further synthesized dehydrodiisoeugenol and alpha-diisoeugenol from isoeugenols, and investigated whether these dimers could inhibit LPS-stimulated nuclear factor kappa B (NF-kappaB) activation and cyclooxygenase (COX)-2 gene expression, both of which are closely involved in inflammation and mutagenesis. The expression of the COX-2 gene was strongly inhibited by dehydrodiisoeugenol in RAW264.7 murine macrophages stimulated with LPS. In contrast, isoeugenol and alpha-diisoeugenol did not inhibit it. Dehydrodiisoeugenol also significantly inhibited LPS-stimulated phosphorylation-dependent proteolysis of inhibitor kappaB-alpha and transcriptional activity of NF-kappaB in the cells. These findings suggest that dehydrodiisoeugenol acts as a potent anti-inflammatory agent.
Antioxidant action of eugenol compounds was analyzed in relation to the role of transition metal. Iron-mediated lipid peroxidation and autooxidation of Fe2+ ion were inhibited markedly by isoeugenol, and less effectively by eugenol. Copper-dependent oxidation of low density lipoprotein (LDL) was potently inhibited by eugenol and isoeugenol to the same extent: eugenol compounds showed protective effects by prolonging lag phase and by suppressing propagation rate in the absence and presence of alpha-tocopherol. Inhibition of LDL oxidation by eugenol compounds was closely related to activities reducing copper and scavenging a stable radical, 1,1'-diphenyl-2-picrylhydrazyl (DPPH). Antioxidant properties of eugenol compounds can be explained by forming complexes with reduced metals. Potent inhibitory effect of isoeugenol on lipid peroxidation may be related to the decreased formation of perferryl ion or the iron-oxygen chelate complex as the initiating factor of lipid peroxidation by keeping iron at a reduced state. Inhibition of LDL oxidation by eugenol compounds is due to the suppression of free radical cascade of lipid peroxidation in LDL by reducing copper ion.
Since the discovery of COX-2, a second subtype of cyclooxygenase, selective inhibitors or "coxibs" were developed with the idea that this isoform was inducible at the site of inflammation whereas COX-1 was expressed constitutively in several tissues including gastric epithelium. This new class of non steroidal anti-inflammatory agents was though to be safer for ulcerations of the gastroinstestinal mucosa observed with non selective COX-2 inhibitors. Nevertheless, at the end of September 2004, Merck & Co announced the voluntary withdrawal of rofecoxib (Vioxx) worldwide because of an increased risk of cardiovascular events. This decision raised serious concerns about safety of selective COX-2 inhibitors which are actively marketed today, and the ones currently under development. The mechanism of this cardiovascular toxicity could lie in the inhibition of COX-2 itself, and thus be a class effect. On the other hand, these cardiovascular side effects could be limited on rofecoxib and be dependent on its chemical and/or pharmacological own properties. This hypothesis is undermined by the unexpected findings of one colon cancer study which has shown that celecoxib might also increase the chance of heart attack and stroke in some patients. In this review, we compared the different coxibs marketed to date on the basis of their clinical, pharmacological and chemical properties with the aim of providing some clues in the understanding of their potential or revealed "cardiovascular effects".
Recent study has demonstrated that Sasa quelpaertensis (Korean name, Jeju-Joritdae) extracts inhibit cellular melanogenesis implicating potential use in the control of skin pigmentation.
The purpose of the present study was to elucidate the active constituents of this plant inhibiting melanogenesis and the associated mechanism.
The effect of the plant-derived materials on melanin production and/or tyrosinase expression was examined in murine melanoma B16/F10 cells and neonatal human melanocytes.
When tested in melanoma B16/F10 cells treated with the alpha-melanocyte stimulating hormone (alpha-MSH), the aqueous ethanol extract of S. quelpaertensis culm inhibited the cellular melanogenesis more effectively than its leaf extract. A major active compound was isolated from the culm extract by solvent fractionation and column chromatography, and identified to be p-coumaric acid by spectroscopic and chromatographic analyses. The compound (p-coumaric acid) inhibited alpha-MSH-stimulated cellular melanogenesis more effectively than arbutin or other structurally similar compounds including 3-(4-hydroxyphenyl) propionic acid, cinnamic acid and caffeic acid. It also attenuated alpha-MSH-dependent increase of tyrosinase protein. The antimelanogenic effect of p-coumaric acid was also verified in neonatal human melanocytes.
The present study identified p-coumaric acid as a main constituent of S. quelpaertensis inhibiting cellular melanogenesis. Because of its structural similarity, p-coumaric acid may interfere with l-tyrosine action in the control of tyrosinase expression in response to alpha-MSH.
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(2011년 6월 16일 접수; 2011년 8월 31일 채택)
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