|Year : 2019 | Volume
| Issue : 25 | Page : 1-9
A comprehensive review on eugenol's antimicrobial properties and industry applications: A transformation from ethnomedicine to industry
Kit-Kay Mak1, Masnah Banu Kamal2, Sunday Buru Ayuba3, Raghavendra Sakirolla4, Yew-Beng Kang5, Kavitha Mohandas6, Madhu Katyayani Balijepalli6, Sazali Hamzah Ahmad7, Mallikarjuna Rao Pichika8
1 Department of Pharmaceutical Chemistry, School of Pharmacy; School of Postgraduate Studies; Centre for Bioactive Molecules and Drug Delivery (BMDD), Institute for Research, Development and Innovation (IRDI), International Medical University, Bukit Jalil, 57000, Kuala Lumpur, Malaysia
2 Department of School of Postgraduate Studies, Institute for Research, Development and Innovation (IRDI), International Medical University, Bukit Jalil, 57000, Kuala Lumpur, Malaysia
3 Department of Medical Microbiology and Parasitology, Kaduna State University, Kaduna, Nigeria
4 Department of Chemistry, Central University of Karnataka, Gulbarga, Kanataka, India
5 Department of Pharmaceutical Chemistry, School of Pharmacy, Institute for Research, Development and Innovation (IRDI), International Medical University, Bukit Jalil, 57000, Kuala Lumpur, Malaysia
6 Faculty of Medicine, MAHSA University, Selangor, Malaysia
7 Institute of Science, University Teknologi MARA, Selangor, Malaysia
8 Department of Pharmaceutical Chemistry, School of Pharmacy; Centre for Bioactive Molecules and Drug Delivery (BMDD), Institute for Research, Development and Innovation (IRDI), International Medical University, Bukit Jalil, 57000, Kuala Lumpur, Malaysia
|Date of Web Publication||3-Apr-2019|
Dr. Mallikarjuna Rao Pichika
Department of Pharmaceutical Chemistry, School of Pharmacy, International Medical University, 126, Jalan Jalil Perkasa 19, Bukit Jalil, 57000 Kuala Lumpur
Source of Support: None, Conflict of Interest: None
| Abstract|| |
Eugenol and eugenol-containing plants are used in ethno and modern medicine for various biological activities including antimicrobial activity. This review article provides an insightful transformation of eugenol from being an ethnomedicine to being a food protectant in the food industry. Scientific publications on the antimicrobial activity of eugenol and its respective advancements were collected from scientific databases such as Scopus, PubMed, and Google Scholar published between 1995 and June 2018. The eugenol has shown significant broad-spectrum antimicrobial activities against Gram-positive, Gram-negative, fungi, and virus. The eugenol has also shown synergistic effects with conventional antimicrobials. Formulations, such as micro- and nanoemulsions, nanocapsules, and nanoparticles, are prepared to improve the aqueous solubility and efficacy of eugenol. Eugenol is used as a food protectant in storing plants, grains, fruits, and livestock. This review covers eugenol's antimicrobial activities, formulations to improve aqueous solubility, and applications in the food industry. Extensive scientific investigations validated the ethnomedicinal uses of eugenol as an antimicrobial agent. Its activity on multidrug-resistant pathogens should further be explored to identify the molecular mechanisms and synergistic/antagonistic effects with conventional antimicrobials. There were no studies on investigating eugenol's potential in in vivo infectious animal models. This is the first review on eugenol that details the antimicrobial potential of eugenol and its possible applications as a protectant in the food industry.
Keywords: Antimicrobial, antiviral, essential oil, eugenol, food protectant, food industry
|How to cite this article:|
Mak KK, Kamal MB, Ayuba SB, Sakirolla R, Kang YB, Mohandas K, Balijepalli MK, Ahmad SH, Pichika MR. A comprehensive review on eugenol's antimicrobial properties and industry applications: A transformation from ethnomedicine to industry. Phcog Rev 2019;13:1-9
|How to cite this URL:|
Mak KK, Kamal MB, Ayuba SB, Sakirolla R, Kang YB, Mohandas K, Balijepalli MK, Ahmad SH, Pichika MR. A comprehensive review on eugenol's antimicrobial properties and industry applications: A transformation from ethnomedicine to industry. Phcog Rev [serial online] 2019 [cited 2019 Sep 19];13:1-9. Available from: http://www.phcogrev.com/text.asp?2019/13/25/1/255393
| Introduction|| |
Despite the recognition of the ever-growing problem, global prevalence of microbial infections and associated health concerns continue to take a toll, resulting in increased cases of prolonged illness and death. This is worsened by increasing antimicrobial resistance that poses threats to the effective prevention and treatment of microbial infections. With this concern, various natural or synthetic compounds are actively explored for their efficacy in combating microbes. Eugenol, which is the major natural component found in clove oil, has been known for its versatility in pharmacological activities such as anti-inflammatory,, anticancer,,, analgesic,, and anesthetic activities.,, The chemical structure of eugenol is shown in [Figure 1].
|Figure 1: Chemical structure of eugenol (C10H12O2). Eugenol's IUPAC name is 2-methoxy-4-(2-propenyl) phenol|
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The eugenol is extracted from various plants such as cloves,,,, lemon grass,,, tulsi,, and cinnamon, via numerous methods of extraction including steam distillation, microwave-assisted extraction, supercritical carbon dioxide extraction, and ultrasound-based extraction. This prominent compound offers a number of therapeutic benefits via inhibition of generative reactive oxygen and nitrogen species, scavenging of free radicals, and disruption of biofilms of microbes., The efficacy of eugenol and its mechanism of action against bacteria, fungi, and viruses are of interest. Due to the increasing incidence of microbial resistance to conventional antibiotics, the effects of eugenol that could work synergistically with the current antibiotics to improve their antimicrobial efficacy against different microbial strains were compiled and explicated. The applications of eugenol and its formulations in the food industry and antimicrobial activity of eugenol containing essential oils/plant extracts were also compiled as shown in [Figure 2].
| Antibacterial Activity|| |
One of the predominant causes of bacterial infections arises from biomaterial implant failures or bacterial adherence and biofilm formation on medical implants. The prevalence of medical implants is increasing extensively in the past decades, and implant failure leads to relentless challenges in the medical field as its application. Accordingly, a hydrophilic copolymeric system using eugenol was tested and it showed success in inhibiting bacterial growth. Eugenol has been scientifically proven to be pharmacologically active against a number of bacteria, both Gram-negative and Gram-positive, as well as fastidious and facultative anaerobic oral bacteria. The current data that could substantiate these claims are concisely summarized in [Table 1].
|Table 1: Bacteria that are susceptible to eugenol in in vitro experimental models|
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Eugenol is capable of significantly increasing the permeability profile of the membrane and has disruptive action on cytoplasmic membrane. In addition, findings on the efficacy of eugenol suggest that inhibition of the production of virulence factors such as violacein, elastase, pyocyanin, and biofilm formation was successful. Eugenol has also displayed high efficacy as an antistaphylococcal and antilisterial biofilm agent.
In other industries – in broiler chicken for instance – eugenol-supplemented poultry feed reduces Salmonella More Details enterica serovar Enteritidis colonization in chickens. In the management of livestock waste on the other hand, eugenol has shown effectiveness in the inhibition of fermentation gas production, short-chain volatile fatty acids, and lactate and bacterial pollution in addition to its ability to stimulate lactate formation in cattle and swine waste.
Antibacterial effects of eugenol on multidrug-resistant bacteria also exhibited promising results. For instance, the Salmonella spp., Salmonella typhimurium SGI 1 (tet A), a Gram-negative bacterium that notably causes diseases of the intestines, is known to show resistance toward ampicillin, tetracycline, penicillin, bacitracin, erythromycin, and novobiocin (FIC <0.4) and nalidixic acid-resistant Salmonella enteritidis. In contrast, the effects of eugenol on the aerotolerant Gram-positive Streptococcus pyogenes ermB to erythromycin (FIC <0.5) showed synergistic effects with ampicillin, tetracycline, penicillin, erythromycin, and novobiocin.
To study the antibacterial studies of eugenol, a few discoveries regarding their mechanisms were made. The eradication of bloody diarrhea-causing agents such as Pseudomonas aeruginosa and enterohemorrhagic Escherichia More Details coli was also possible as eugenol was found to successfully reduce the production of pyocyanin and PQS as well as inhibit the EHEC biofilm formation, respectively. Eugenol was proven to possess the potential of a favorable target in the antibacterial area as it has the capabilities of downregulating YidC, a highly conserved bacterial protein which plays a vital role in membrane protein insertion. In addition, eugenol showed competence in the inhibition and eradication of biofilms produced by methicillin-resistant and sensitive Staphylococcus aureus. Another supporting study demonstrated membrane disruption in the bactericidal activity of E. coli, Listeria monocytogenes, and Lactobacillus sakei; this was achievable via the inhibition of their respective ATPase. It is also believed that eugenol decreases the virulence factors that are produced by E. coli such as VT1 and VT2. Another interesting finding involves the ability of eugenol to inhibit the FtsZ assembly that leads to the disruption of bacterial cell division. It was also found that the effects of eugenol in downregulating the transcription of genes associated with Acinetobacter baumannii biofilm production contributed to the source of biofilm inhibition as well as disrupting the biofilm architecture.
In addition to eugenol being used exclusively as a singular antibacterial agent, it has also successfully shown a synergistic effect with a few well-known antibacterial medications against various strains of bacteria as tabulated in [Table 2].
|Table 2: The synergistic effect of eugenol with current medications in combating bacteria|
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| Antifungal Activity|| |
Like antibacterial agents, new and potent antifungal agents are also invariably and actively discovered. Despite the discovery of many new antifungal agents which have greatly improved the treatment of invasive mycoses, these newer antifungal agents still face challenges as they present toxicity associated with long-term use; therefore, the discovery of new antifungal agents with better safety profiles is highly driven by the side effects of current conventional antifungal medication and fungal resistance.
Eugenol has exhibited significantly favorable antifungal activity on various preformed biofilms, adherent cells, subsequent biofilm formation, and cell morphogenesis of Candida albicans, without instigating hemolytic activity in human erythrocytes. The battle to deal with fungal infections in its numerous guises has been on-going for the past few decades. The assortment of strains of fungus that are currently proven to be susceptible to eugenol is summarized in [Table 3].
Remarkably, eugenol displayed tremendous fungicidal activity against isolates of pathogenic yeasts that have shown resistance toward azoles, and this was due to the inhibition of H+-ATPase activity. Antigonorrheal activity was also shown in a number of multi-resistant strains of Neisseria More Details gonorrhoeae. Interestingly, eugenol was found to be more active against fluconazole-resistant Candida dubliniensis than synthetic antiseptic chlorhexidine gluconate, cetylpyridinium chloride, and triclosan.
It is believed that cell wall alteration contributes to the attainment in antifungal activity of eugenol against Saccharomyces cerevisiae. The fungicidal causative effects of eugenol in C. albicans are mainly due to the disruption of membrane integrity as well as significantly weakening the defense system through free radical cascade-mediated LPO, which subsequently leads to membrane lesions. Interestingly, the interference with amino acid permeases contributes to the inhibitory effect of eugenol. A study has shown inhibitory effects of eugenol on two permeases (Tat1p and Gap1p) that are responsible for the transport of amino acids through the yeast cytoplasmic membrane. In addition, the synergistic antifungal effect of eugenol with cinnamaldehyde is a result of the interference of fungal cell wall synthesis as well as cell wall destruction in addition to a radical scavenging effect.
The synergistic effects of eugenol with currently available antifungal drugs and other compounds are listed in [Table 4].
|Table 4: The synergistic effect of eugenol with current medication in combating fungi|
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| Antiviral Activity|| |
As a potent natural product, eugenol is heavily investigated to understand its biological activity and therapeutic potential as an antimicrobial agent. There is also the synergistic effect between eugenol and acyclovir in the inhibition of herpes virus in vitro; on its own, topical application of eugenol was found to delay the growth of herpes virus-induced keratitis in mouse models. Eugenol displayed antiprotozoal activity against Leishmania, which is an assembly of diseases responsible for a wide spectrum of clinical manifestations, ovicidal activity against Haemonchus contortus, a parasite that resides in the gastrointestinal tract and virucidal activity against HSV-1 and HSV-2 viruses.,
| Essential Oils|| |
Eugenol essential oil can be extracted from plant sources, such as cloves, cinnamon, tulsi, and pepper,, as well as the leaves of Lippia multiflora, Mentha piperita, and Ocimum basilicum from Burkina Faso. Eugenol is commonly the main constituent in these plants, and this essential oil has prospects as a nutraceutical. Among many beneficial effects induced by eugenol such as anti-inflammation, anti-hyperglycemia and anticancer, it is also a highly potent antimicrobial agent.,
Eugenol essential oil showed potent anthelmintic activity in a Caenorhabditis elegans model. A few essential oils extracted from flowering plants showed antibacterial activity. For instance, eugenol essential oil is extracted from Syringa oblata flower buds against Ralstonia solanacearum and Syzygium aromaticum flower buds against Leishmania donovani.
The essential oil of eugenol and its interaction with ten antibiotics of hydrophobic and hydrophilic characteristics were studied against Gram-negative bacteria.
As previously discussed, eugenol essential oil conferred antifungal activity against Fusarium oxysporum f. sp. Lycopersici 1322, which suggests that eugenol can be used in preventive and therapeutic applications. Eugenol extracted from the essential oil of Piper divaricatum showed activity against cladosporioides and Cladosporium sphaerospermum while essential oil from Nephrolepis exaltata and Nephrolepis cordifolia showed antibacterial and antifungal activities. The eugenol-containing essential oil extracted from Cinnamomum verum, S. aromaticum, Cymbopogon citratus and Cymbopogon martini were found to transform the hyphal ultrasound and virulence factors of Aspergillus fumigatus and Trichophyton rubrum. Eugenol from Ocimum sanctum showed activity against Aspergillus flavus NKDHV8 that causes biodeterioration of food stuff. It was also reported that volatile oil of Cinnamomum zeylanicum Blume' s leaves and barks showed fungal inhibitory activity against A. flavus, Aspergillus ochraceus, Aspergillus niger, Aspergillus terreus, Penicillium citrinum, and Penicillium viridicatum. The antifungal activity of eugenol-containing essential oils is summarized in [Table 5].
|Table 5: Source of eugenol essential oil extracts and their respective susceptible strains |
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| Formulations|| |
Beyond its role as a simple antimicrobial agent, eugenol was investigated in numerous formulations. Eugenol/cyclodextrin inclusion complexes encapsulated in electrospun polyvinyl alcohol nanofibers were shown to have enhanced thermal stability and subsequently result in the slow release of eugenol. Eugenol-containing microemulsion can be prepared by simply solubilizing the eugenol (0.75–1.5 wt.%) essential oil in surfactant micelles (Surfynol 465; 5–10 wt. %). In addition, findings from another study reported that eugenol-incorporated micelles had higher efficacy than that of pure application of eugenol.
A variety of formulated products that incorporated eugenol were found to be potent. The consecutive application of eugenol and lauric arginate was shown to inhibit the growth of Staphylococcus carnosus, Listeria innocua, L. monocytogenes, E. coli (K12 and O157:H7), Pseudomonas fluorescens, and S. enteritidis., Synergistic antimicrobial activity was exhibited in the multi-agent formulation comprising eugenol/beta-pinene/salicylic acid and eugenol/beta-pinene/2-phenoxyethanol/potassium sorbate where the mechanism is facilitated via cellular permeabilization in addition to inhibition of efflux pump activity. Another formulation that yielded higher antimicrobial activity than that of eugenol itself is the inclusion complex between water-soluble β-cyclodextrin-grafted chitosan derivatives (βCD-g-CS) and eugenol to produce a mucoadhesive drug carrier. This formulation has potent antimicrobial activity against C. albicans, S. oralis, and S. mutans and antifungal activity against Peronophythora litchi.
Eugenol is sometimes encapsulated as it can improve the water solubility profile; such preparation showed growth inhibition of E. coli O157:H7 (H1730, F4546, 932, and E0019) and L. monocytogenes (Scott A, 101, 108, and 310). Another way of improving the water solubility profile is by formulating eugenol as nanoparticles in water-based microemulsion systems.
Microemulsions of eugenol inhibited the growth of foodborne pathogens such as L. monocytogenes, E. coli (O157:H7 and C 600), and L. innocua completely., Formulated carbopol hydrogels incorporated with eugenol-loaded solid lipid nanoparticles (EG-SLN) were beneficial for the epidermal treatment in the attempt to treat fungal infection in the skin. Various nanoemulsions with incorporated eugenol were prepared and tested against different pathogens. For example, sesame oil-blended eugenol-loaded nanoemulsion displayed antibacterial activity against S. aureus, eugenol-chitosan particles exhibited significant antibacterial activity against E. coli and S. aureus, and eugenol-beta-cyclodextrin nanoparticles showed antivirulence activity against E. coli and S. aureus. Dispersion of eugenol in nanocapsules formulated with conjugates of whey protein isolate and maltodextrin also showed potency against E. coli O157:H7 strains ATCC 43889 and 43894 and L. monocytogenes strains Scott A and 101. Encapsulation of eugenol in poly (DL-lactide-co-glycolide) (PGLA) nanoparticles enhanced its antimicrobial delivery against the growth of Salmonella spp and Listeria spp. Solid lipid nanoparticles (SLN) loaded with eugenol showed in vivo antifungal activity in immunosuppressed rats of oral candidiasis. A gum Arabic and lecithin-eugenol incorporated nanoemulsion prepared as a food-grade natural emulsifier successfully displayed antimicrobial activity against L. monocytogenes and S. enteritidis.
The significant leishmanicidal activity of eugenol against promastigotes and intracellular amastigotes of L. donovani carried out in vitro and in vivo was shown when it was formulated in an oil-in-water emulsion. In addition, eugenol emulsions showed antibacterial activity against Xanthomonas campestris pv. Phaseoli var. fuscans. The eugenol-incorporated formulations reported in the literature and their respective antimicrobial activities are summarized in [Table 6].
|Table 6: Summary of current eugenol-incorporated formulations in the enhancement of antimicrobial activity |
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| Applications in the Food Industry|| |
Productive applications in science stem from the ability to connect unanticipated observations to develop new areas of explorations – the usage of eugenol in the food industry for instance. From the identification of eugenol as a potent antimicrobial agent, it has been gradually introduced to the food industry [Table 7]. Some of the most prevalent foodborne pathogenic bacteria affected by the antibacterial activity of eugenol include S. aureus, E. coli, S. enterica serovar Typhimurium, and L. monocytogenes,, and fungi comprising Cladosporium spp. (MIC: 100 mug/mL), Aspergillus spp. (MIC: 100 mug/mL), Cladosporium spp. (MIC: 350 mug/mL), and Aspergillus spp. and Cladosporium spp. as shown in [Table 2].
|Table 7: List of pathogens that are susceptible to the antimicrobial activity of eugenol |
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Plants and grains
The potency of eugenol as a prospective biocontrol agent in grains was suggested as it contributes to the inhibition of ochratoxin A production caused by A. ochraceus – a frequent contaminant found in the storage of grains. Another possibility is to diminish the population of Salmonella in soil to reduce probable contamination of fresh organic produce.
The broad spectrum of eugenol's protective effects can be observed in various foodborne pathogens. Eugenol worked against the common nalidixic acid-resistant S. enteritidis found in contaminated eggs,, and it was found to inhibit the growth and colonization in the chicken reproductive tract. In a more general application, eugenol was capable of enhancing food safety and stability without instigating any bacterial adaptation of S. enterica serovar Typhimurium. Treatment and prevention of bacterial diseases in fish is also possible as eugenol is active against a fish pathogen called A. hydrophila without posing toxicity effects to the fish.
In the fruit sector, eugenol has been commonly used as fungicides. Eugenol was found to inhibit the growth of fungi that causes decay of strawberries. Eugenol oil inhibited the growth in both in vitro and in vivo tests of numerous apple fungus, namely P. vagabunda, P. expansum, B. cinerea, and Monilinia fructigena. A few fungi such as Sclerotinia sclerotiorum (Lib.), R. stolonifera (Ehrenb. ex Fr.) Vuill, and Mucor spp. (Fisher) cause deterioration and decay in peaches especially during marketing, shipping, and storage; eugenol works synergistically with linalool as a potent fungicide.
In a study looking at the type of microflora that are responsible in fruit juice spoilage, eugenol was also biologically active against foodborne bacteria such as L. plantarum, L. brevis, and B. coagulans and foodborne yeasts such as Saccharomyces bayanus, Pichia membranifaciens, and Rhodotorula bacarum.
Eugenol is incorporated into polyhydroxybutyrate-based antimicrobial films as an approach to enhance the shelf life of food. As a preservative, positive results were also observed against S. cerevisiae and Zygosaccharomyces bailii.
Certain results suggest a mechanism that involves the inhibition of tumor necrosis factor-inducing and hemolytic activities of S. aureus supernatants by reducing the production of staphylococcus enterotoxin A and B and toxic shock syndrome toxin 1 as well as the expression of alpha-hemolysin.
The authors would like to thank the International Medical University for the facilities and the Ministry of Higher Education for their financial support.
Financial support and sponsorship
The study was funded by the ERGS grant from the Ministry of Higher Education of Malaysia (ERGS/1/2012/STG01/IMU/02/1).
Conflicts of interest
There are no conflicts of interest.
| References|| |
Huang X, Liu Y, Lu Y, Ma C. Anti-inflammatory effects of eugenol on lipopolysaccharide-induced inflammatory reaction in acute lung injury via regulating inflammation and redox status. Int Immunopharmacol 2015;26:265-71.
Koh T, Murakami Y, Tanaka S, Machino M, Sakagami H. Re-evaluation of anti-inflammatory potential of eugenol in IL-1β-stimulated gingival fibroblast and pulp cells. In vivo
Hussain A, Brahmbhatt K, Priyani A, Ahmed M, Rizvi TA, Sharma C. Eugenol enhances the chemotherapeutic potential of gemcitabine and induces anticarcinogenic and anti-inflammatory activity in human cervical cancer cells. Cancer Biother Radiopharm 2011;26:519-27.
Jaganathan SK, Supriyanto E. Antiproliferative and molecular mechanism of eugenol-induced apoptosis in cancer cells. Molecules 2012;17:6290-304.
Al-Sharif I, Remmal A, Aboussekhra A. Eugenol triggers apoptosis in breast cancer cells through E2F1/survivin down-regulation. BMC Cancer 2013;13:600.
Park SH, Sim YB, Lee JK, Kim SM, Kang YJ, Jung JS, et al.
The analgesic effects and mechanisms of orally administered eugenol. Arch Pharm Res 2011;34:501-7.
Lee MH, Yeon KY, Park CK, Li HY, Fang Z, Kim MS, et al.
Eugenol inhibits calcium currents in dental afferent neurons. J Dent Res 2005;84:848-51.
Pramod K, Ansari SH, Ali J. Eugenol: A natural compound with versatile pharmacological actions. Nat Prod Commun 2010;5:1999-2006.
Park CK, Kim K, Jung SJ, Kim MJ, Ahn DK, Hong SD, et al.
Molecular mechanism for local anesthetic action of eugenol in the rat trigeminal system. Pain 2009;144:84-94.
Chung G, Oh SB. Eugenol as local anesthetic. In: Natural Products. Berlin, Heidelberg: Springer Berlin Heidelberg; 2013. p. 4001-15.
Cortés-Rojas DF, de Souza CR, Oliveira WP. Clove (Syzygium aromaticum
): A precious spice. Asian Pac J Trop Biomed 2014;4:90-6.
Sanae F, Kamiyama O, Ikeda-Obatake K, Higashi Y, Asano N, Adachi I, et al.
Effects of eugenol-reduced clove extract on glycogen phosphorylase b and the development of diabetes in db/db mice. Food Funct 2014;5:214-9.
Yun SM, Lee MH, Lee KJ, Ku HO, Son SW, Joo YS. Quantitative analysis of eugenol in clove extract by a validated HPLC method. J AOAC Int 2010;93:1806-10.
Chanthai S, Prachakoll S, Ruangviriyachai C, Luthria DL. Influence of extraction methodologies on the analysis of five major volatile aromatic compounds of citronella grass (Cymbopogon nardus
) and lemongrass (Cymbopogon citratus
) grown in Thailand. J AOAC Int 2012;95:763-72.
Grice ID, Rogers KL, Griffiths LR. Isolation of bioactive compounds that relate to the anti-platelet activity of Cymbopogon ambiguus
. Evid Based Complement Alternat Med 2011;2011:467134.
Niu C, Gilbert ES. Colorimetric method for identifying plant essential oil components that affect biofilm formation and structure. Appl Environ Microbiol 2004;70:6951-6.
Chatterjee D, Ghosh PK, Ghosh S, Bhattacharjee P. Supercritical carbon dioxide extraction of eugenol from tulsi leaves: Process optimization and packed bed characterization. Chem Eng Res Des 2017;118:94-102.
Cohen MM. Tulsi – Ocimum sanctum
: A herb for all reasons. J Ayurveda Integr Med 2014;5:251-9.
] [Full text]
Jayawardena B, Smith RM. Superheated water extraction of essential oils from Cinnamomum zeylanicum
(L.). Phytochem Anal 2010;21:470-2.
Gopu CL, Aher S, Mehta H, Paradkar AR, Mahadik KR. Simultaneous determination of cinnamaldehyde, eugenol and piperine by HPTLC densitometric method. Phytochem Anal 2008;19:116-21.
Khalil AA, Rahman UU, Khan MR, Sahar A, Mehmood T, Khan M. Essential oil eugenol: Sources, extraction techniques and nutraceutical perspectives. RSC Adv 2017;7:32669-81.
Fujisawa S, Atsumi T, Ishihara M, Kadoma Y. Cytotoxicity, ROS-generation activity and radical-scavenging activity of curcumin and related compounds. Anticancer Res 2004;24:563-9.
Veerachamy S, Yarlagadda T, Manivasagam G, Yarlagadda PK. Bacterial adherence and biofilm formation on medical implants: A review. Proc Inst Mech Eng H 2014;228:1083-99.
Ribeiro M, Monteiro FJ, Ferraz MP. Infection of orthopedic implants with emphasis on bacterial adhesion process and techniques used in studying bacterial-material interactions. Biomatter 2012;2:176-94.
Rojo L, Barcenilla JM, Vázquez B, González R, San Román J. Intrinsically antibacterial materials based on polymeric derivatives of eugenol for biomedical applications. Biomacromolecules 2008;9:2530-5.
Shapiro S, Meier A, Guggenheim B. The antimicrobial activity of essential oils and essential oil components towards oral bacteria. Oral Microbiol Immunol 1994;9:202-8.
Ben Arfa A, Combes S, Preziosi-Belloy L, Gontard N, Chalier P. Antimicrobial activity of carvacrol related to its chemical structure. Lett Appl Microbiol 2006;43:149-54.
Sharma G, Raturi K, Dang S, Gupta S, Gabrani R. Combinatorial antimicrobial effect of curcumin with selected phytochemicals on Staphylococcus epidermidis
. J Asian Nat Prod Res 2014;16:535-41.
Yadav MK, Park SW, Chae SW, Song JJ, Kim HC. Antimicrobial activities of Eugenia caryophyllata
extract and its major chemical constituent eugenol against Streptococcus pneumoniae
. APMIS 2013;121:1198-206.
Sharma UK, Sharma AK, Pandey AK. Medicinal attributes of major phenylpropanoids present in cinnamon. BMC Complement Altern Med 2016;16:156.
Devi KP, Nisha SA, Sakthivel R, Pandian SK. Eugenol (an essential oil of clove) acts as an antibacterial agent against Salmonella typhi
by disrupting the cellular membrane. J Ethnopharmacol 2010;130:107-15.
Olasupo NA, Fitzgerald DJ, Gasson MJ, Narbad A. Activity of natural antimicrobial compounds against Escherichia coli
and Salmonella enterica
. Lett Appl Microbiol 2003;37:448-51.
Kim YG, Lee JH, Kim SI, Baek KH, Lee J. Cinnamon bark oil and its components inhibit biofilm formation and toxin production. Int J Food Microbiol 2015;195:30-9.
Walsh SE, Maillard JY, Russell AD, Catrenich CE, Charbonneau DL, Bartolo RG. Activity and mechanisms of action of selected biocidal agents on Gram-positive and -negative bacteria. J Appl Microbiol 2003;94:240-7.
Fraňková A, Marounek M, Mozrová V, Weber J, Klouček P, Lukešová D. Antibacterial activities of plant-derived compounds and essential oils toward Cronobacter sakazakii
and Cronobacter malonaticus
. Foodborne Pathog Dis 2014;11:795-7.
Devi KP, Sakthivel R, Nisha SA, Suganthy N, Pandian SK. Eugenol alters the integrity of cell membrane and acts against the nosocomial pathogen Proteus mirabilis
. Arch Pharm Res 2013;36:282-92.
Ali SM, Khan AA, Ahmed I, Musaddiq M, Ahmed KS, Polasa H, et al.
Antimicrobial activities of eugenol and cinnamaldehyde against the human gastric pathogen Helicobacter pylori
. Ann Clin Microbiol Antimicrob 2005;4:20.
Zhou L, Zheng H, Tang Y, Yu W, Gong Q. Eugenol inhibits quorum sensing at sub-inhibitory concentrations. Biotechnol Lett 2013;35:631-7.
Apolónio J, Faleiro ML, Miguel MG, Neto L. No induction of antimicrobial resistance in Staphylococcus aureus
and Listeria monocytogenes
during continuous exposure to eugenol and citral. FEMS Microbiol Lett 2014;354:92-101.
Kollanoor-Johny A, Mattson T, Baskaran SA, Amalaradjou MA, Babapoor S, March B, et al.
Reduction of Salmonella enterica
serovar enteritidis colonization in 20-day-old broiler chickens by the plant-derived compounds trans-cinnamaldehyde and eugenol. Appl Environ Microbiol 2012;78:2981-7.
Varel VH, Miller DN, Lindsay AD. Plant oils thymol and eugenol affect cattle and swine waste emissions differently. Water Sci Technol 2004;50:207-13.
Upadhyaya I, Upadhyay A, Kollanoor-Johny A, Baskaran SA, Mooyottu S, Darre MJ, et al.
Rapid inactivation of Salmonella enteritidis
on shell eggs by plant-derived antimicrobials. Poult Sci 2013;92:3228-35.
Palaniappan K, Holley RA. Use of natural antimicrobials to increase antibiotic susceptibility of drug resistant bacteria. Int J Food Microbiol 2010;140:164-8.
Patil SD, Sharma R, Srivastava S, Navani NK, Pathania R. Downregulation of yidC in Escherichia coli
by antisense RNA expression results in sensitization to antibacterial essential oils eugenol and carvacrol. PLoS One 2013;8:e57370.
Yadav MK, Chae SW, Im GJ, Chung JW, Song JJ. Eugenol: A phyto-compound effective against methicillin-resistant and methicillin-sensitive Staphylococcus aureus
clinical strain biofilms. PLoS One 2015;10:e0119564.
Gill AO, Holley RA. Disruption of Escherichia coli, Listeria monocytogenes
and Lactobacillus sakei
cellular membranes by plant oil aromatics. Int J Food Microbiol 2006;108:1-9.
Takemasa N, Ohnishi S, Tsuji M, Shikata T, Yokoigawa K. Screening and analysis of spices with ability to suppress verocytotoxin production by Escherichia coli
O157. J Food Sci 2009;74:M461-6.
Rastogi N, Domadia P, Shetty S, Dasgupta D. Screening of natural phenolic compounds for potential to inhibit bacterial cell division protein FtsZ. Indian J Exp Biol 2008;46:783-7.
Karumathil DP, Surendran-Nair M, Venkitanarayanan K. Efficacy of trans-cinnamaldehyde and eugenol in reducing Acinetobacter baumannii
adhesion to and invasion of human keratinocytes and controlling wound infection in vitro
. Phytother Res 2016;30:2053-9.
Lee SY, Jin HH. Inhibitory activity of natural antimicrobial compounds alone or in combination with nisin against Enterobacter sakazakii
. Lett Appl Microbiol 2008;47:315-21.
Olasupo NA, Fitzgerald DJ, Narbad A, Gasson MJ. Inhibition of Bacillus subtilis
and Listeria innocua
by nisin in combination with some naturally occurring organic compounds. J Food Prot 2004;67:596-600.
Pei RS, Zhou F, Ji BP, Xu J. Evaluation of combined antibacterial effects of eugenol, cinnamaldehyde, thymol, and carvacrol against E. coli
with an improved method. J Food Sci 2009;74:M379-83.
Miladi H, Zmantar T, Kouidhi B, Chaabouni Y, Mahdouani K, Bakhrouf A, et al.
Use of carvacrol, thymol, and eugenol for biofilm eradication and resistance modifying susceptibility of Salmonella enterica
strains to nalidixic acid. Microb Pathog 2017;104:56-63.
Santiesteban-López A, Palou E, López-Malo A. Susceptibility of food-borne bacteria to binary combinations of antimicrobials at selected a(w) and pH. J Appl Microbiol 2007;102:486-97.
Lewis RE. Current concepts in antifungal pharmacology. Mayo Clin Proc 2011;86:805-17.
Srinivasan A, Lopez-Ribot JL, Ramasubramanian AK. Overcoming antifungal resistance. Drug Discov Today Technol 2014;11:65-71.
He M, Du M, Fan M, Bian Z.In vitro
activity of eugenol against Candida albicans
biofilms. Mycopathologia 2007;163:137-43.
Khan MS, Ahmad I. Antibiofilm activity of certain phytocompounds and their synergy with fluconazole against Candida albicans
biofilms. J Antimicrob Chemother 2012;67:618-21.
Chami F, Chami N, Bennis S, Trouillas J, Remmal A. Evaluation of carvacrol and eugenol as prophylaxis and treatment of vaginal candidiasis in an immunosuppressed rat model. J Antimicrob Chemother 2004;54:909-14.
Chami N, Bennis S, Chami F, Aboussekhra A, Remmal A. Study of anticandidal activity of carvacrol and eugenol in vitro
and in vivo
. Oral Microbiol Immunol 2005;20:106-11.
Campaniello D, Corbo MR, Sinigaglia M. Antifungal activity of eugenol against Penicillium, Aspergillus
, and Fusarium
species. J Food Prot 2010;73:1124-8.
Menniti AM, Gregori R, Neri F. Activity of natural compounds on Fusarium verticillioides
and fumonisin production in stored maize kernels. Int J Food Microbiol 2010;136:304-9.
Ahmad A, Khan A, Khan LA, Manzoor N.In vitro
synergy of eugenol and methyleugenol with fluconazole against clinical Candida
isolates. J Med Microbiol 2010;59:1178-84.
Bennis S, Chami F, Chami N, Bouchikhi T, Remmal A. Surface alteration of Saccharomyces cerevisiae
induced by thymol and eugenol. Lett Appl Microbiol 2004;38:454-8.
Park MJ, Gwak KS, Yang I, Kim KW, Jeung EB, Chang JW, et al.
Effect of citral, eugenol, nerolidol and alpha-terpineol on the ultrastructural changes of Trichophyton mentagrophytes
. Fitoterapia 2009;80:290-6.
Cheng SS, Liu JY, Chang EH, Chang ST. Antifungal activity of cinnamaldehyde and eugenol congeners against wood-rot fungi. Bioresour Technol 2008;99:5145-9.
de Oliveira Pereira F, Mendes JM, de Oliveira Lima E. Investigation on mechanism of antifungal activity of eugenol against Trichophyton rubrum
. Med Mycol 2013;51:507-13.
Gayoso CW, Lima EO, Oliveira VT, Pereira FO, Souza EL, Lima IO, et al.
Sensitivity of fungi isolated from onychomycosis to Eugenia
cariophyllata essential oil and eugenol. Fitoterapia 2005;76:247-9.
Fontenelle RO, Morais SM, Brito EH, Brilhante RS, Cordeiro RA, Lima YC, et al.
Alkylphenol activity against Candida
spp. and Microsporum canis
: A focus on the antifungal activity of thymol, eugenol and O-methyl derivatives. Molecules 2011;16:6422-31.
Mensi M, Salgarello S, Pinsi G, Piccioni M. Mycetoma of the maxillary sinus: Endodontic and microbiological correlations. Oral Surg Oral Med Oral Pathol Oral Radiol Endod 2004;98:119-23.
Vázquez BI, Fente C, Franco CM, Vázquez MJ, Cepeda A. Inhibitory effects of eugenol and thymol on Penicillium citrinum
strains in culture media and cheese. Int J Food Microbiol 2001;67:157-63.
Odell E, Pertl C. Zinc as a growth factor for Aspergillus
sp. and the antifungal effects of root canal sealants. Oral Surg Oral Med Oral Pathol Oral Radiol Endod 1995;79:82-7.
Jahanshiri Z, Shams-Ghahfarokhi M, Allameh A, Razzaghi-Abyaneh M. Inhibitory effect of eugenol on aflatoxin B1 production in Aspergillus parasiticus
by downregulating the expression of major genes in the toxin biosynthetic pathway. World J Microbiol Biotechnol 2015;31:1071-8.
Braga PC, Sasso MD, Culici M, Alfieri M. Eugenol and thymol, alone or in combination, induce morphological alterations in the envelope of Candida albicans
. Fitoterapia 2007;78:396-400.
Ahmad A, Khan A, Yousuf S, Khan LA, Manzoor N. Proton translocating ATPase mediated fungicidal activity of eugenol and thymol. Fitoterapia 2010;81:1157-62.
Shokeen P, Bala M, Singh M, Tandon V.In vitro
activity of eugenol, an active component from Ocimum sanctum
, against multiresistant and susceptible strains of Neisseria gonorrhoeae
. Int J Antimicrob Agents 2008;32:174-9.
Reginato CF, Bandeira LA, Zanette RA, Santurio JM, Alves SH, Danesi CC. Antifungal activity of synthetic antiseptics and natural compounds against Candida dubliniensis
before and after in vitro
fluconazole exposure. Rev Soc Bras Med Trop 2017;50:75-9.
Khan A, Ahmad A, Akhtar F, Yousuf S, Xess I, Khan LA, et al.
Induction of oxidative stress as a possible mechanism of the antifungal action of three phenylpropanoids. FEMS Yeast Res 2011;11:114-22.
Darvishi E, Omidi M, Bushehri AA, Golshani A, Smith ML. The antifungal eugenol perturbs dual aromatic and branched-chain amino acid permeases in the cytoplasmic membrane of yeast. PLoS One 2013;8:e76028.
Yen TB, Chang ST. Synergistic effects of cinnamaldehyde in combination with eugenol against wood decay fungi. Bioresour Technol 2008;99:232-6.
Nozaki A, Takahashi E, Okamoto K, Ito H, Hatano T. Antifungal activity of essential oils and their constituents against Candida
spp. and their effects on activity of amphotericin B. Yakugaku Zasshi 2010;130:895-902.
Zore GB, Thakre AD, Jadhav S, Karuppayil SM. Terpenoids inhibit Candida albicans
growth by affecting membrane integrity and arrest of cell cycle. Phytomedicine 2011;18:1181-90.
Ueda-Nakamura T, Mendonça-Filho RR, Morgado-Díaz JA, Korehisa Maza P, Prado Dias Filho B, Aparício Garcia Cortez D, et al.
Antileishmanial activity of eugenol-rich essential oil from Ocimum gratissimum
. Parasitol Int 2006;55:99-105.
Pessoa LM, Morais SM, Bevilaqua CM, Luciano JH. Anthelmintic activity of essential oil of Ocimum gratissimum
linn. and eugenol against Haemonchus contortus
. Vet Parasitol 2002;109:59-63.
Benencia F, Courrèges MC.In vitro
and in vivo
activity of eugenol on human herpesvirus. Phytother Res 2000;14:495-500.
Tragoolpua Y, Jatisatienr A. Anti-herpes simplex virus activities of Eugenia caryophyllus
(Spreng.) bullock and Harrison SG and essential oil, eugenol. Phytother Res 2007;21:1153-8.
Ali S, Prasad R, Mahmood A, Routray I, Shinkafi TS, Sahin K, et al.
Eugenol-rich fraction of Syzygium aromaticum
(Clove) reverses biochemical and histopathological changes in liver cirrhosis and inhibits hepatic cell proliferation. J Cancer Prev 2014;19:288-300.
Prakash P, Gupta N. Therapeutic uses of Ocimum sanctum
linn (Tulsi) with a note on eugenol and its pharmacological actions: A short review. Indian J Physiol Pharmacol 2005;49:125-31.
Usta J, Kreydiyyeh S, Barnabe P, Bou-Moughlabay Y, Nakkash-Chmaisse H. Comparative study on the effect of cinnamon and clove extracts and their main components on different types of ATPases. Hum Exp Toxicol 2003;22:355-62.
Bassolé IH, Lamien-Meda A, Bayala B, Tirogo S, Franz C, Novak J, et al.
Composition and antimicrobial activities of Lippia multiflora
L. and Ocimum basilicum
L. essential oils and their major monoterpene alcohols alone and in combination. Molecules 2010;15:7825-39.
Hamed SF, Sadek Z, Edris A. Antioxidant and antimicrobial activities of clove bud essential oil and eugenol nanoparticles in alcohol-free microemulsion. J Oleo Sci 2012;61:641-8.
Asha MK, Prashanth D, Murali B, Padmaja R, Amit A. Anthelmintic activity of essential oil of Ocimum sanctum
and eugenol. Fitoterapia 2001;72:669-70.
Bai W, Kong F, Lin Y, Zhang C. Extract of Syringa oblata
: A new biocontrol agent against tobacco bacterial wilt caused by Ralstonia solanacearum
. Pestic Biochem Physiol 2016;134:79-83.
Islamuddin M, Sahal D, Afrin F. Apoptosis-like death in Leishmania donovani
promastigotes induced by eugenol-rich oil of Syzygium aromaticum
. J Med Microbiol 2014;63:74-85.
Hemaiswarya S, Doble M. Synergistic interaction of eugenol with antibiotics against Gram negative bacteria. Phytomedicine 2009;16:997-1005.
Sharma A, Rajendran S, Srivastava A, Sharma S, Kundu B. Antifungal activities of selected essential oils against Fusarium oxysporum
f. sp. lycopersici 1322, with emphasis on Syzygium aromaticum
essential oil. J Biosci Bioeng 2017;123:308-13.
da Silva JK, Andrade EH, Guimarães EF, Maia JG. Essential oil composition, antioxidant capacity and antifungal activity of Piper divaricatum
. Nat Prod Commun 2010;5:477-80.
El-Tantawy ME, Shams MM, Afifi MS. Chemical composition and biological evaluation of the volatile constituents from the aerial parts of Nephrolepis exaltata
(L.) and Nephrolepis cordifolia
(L.) C. presl grown in Egypt. Nat Prod Res 2016;30:1197-201.
Khan MS, Ahmad I.In vitro
antifungal, anti-elastase and anti-keratinase activity of essential oils of Cinnamomum
- and Cymbopogon
-species against Aspergillus fumigatus
and Trichophyton rubrum
. Phytomedicine 2011;19:48-55.
Kumar A, Shukla R, Singh P, Dubey NK. Chemical composition, antifungal and antiaflatoxigenic activities of Ocimum sanctum
L. essential oil and its safety assessment as plant based antimicrobial. Food Chem Toxicol 2010;48:539-43.
Singh G, Maurya S, DeLampasona MP, Catalan CA. A comparison of chemical, antioxidant and antimicrobial studies of cinnamon leaf and bark volatile oils, oleoresins and their constituents. Food Chem Toxicol 2007;45:1650-61.
Kayaci F, Ertas Y, Uyar T. Enhanced thermal stability of eugenol by cyclodextrin inclusion complex encapsulated in electrospun polymeric nanofibers. J Agric Food Chem 2013;61:8156-65.
Kriegel C, Kit KM, McClements DJ, Weiss J. Nanofibers as carrier systems for antimicrobial microemulsions. Part I: Fabrication and characterization. Langmuir 2009;25:1154-61.
Gaysinsky S, Davidson PM, Bruce BD, Weiss J. Growth inhibition of Escherichia coli
O157:H7 and Listeria monocytogenes
by carvacrol and eugenol encapsulated in surfactant micelles. J Food Prot 2005;68:2559-66.
Manrique Y, Gibis M, Schmidt H, Weiss J. Influence of application sequence and timing of eugenol and Lauric arginate
(LAE) on survival of spoilage organisms. Food Microbiol 2017;64:210-8.
Ma Q, Davidson PM, Zhong Q. Antimicrobial properties of lauric arginate alone or in combination with essential oils in tryptic soy broth and 2% reduced fat milk. Int J Food Microbiol 2013;166:77-84.
Saviuc C, Ciubucă B, Dincă G, Bleotu C, Drumea V, Chifiriuc MC, et al.
Development and sequential analysis of a new multi-agent, anti-acne formulation based on plant-derived antimicrobial and anti-inflammatory compounds. Int J Mol Sci 2017;18. pii: E175.
Sajomsang W, Nuchuchua O, Gonil P, Saesoo S, Sramala I, Soottitantawat A, et al.
Water-soluble β-cyclodextrin grafted with chitosan and its inclusion complex as a mucoadhesive eugenol carrier. Carbohydr Polym 2012;89:623-31.
Gong L, Li T, Chen F, Duan X, Yuan Y, Zhang D, et al.
An inclusion complex of eugenol into β-cyclodextrin: Preparation, and physicochemical and antifungal characterization. Food Chem 2016;196:324-30.
Gaysinsky S, Davidson PM, Bruce BD, Weiss J. Stability and antimicrobial efficiency of eugenol encapsulated in surfactant micelles as affected by temperature and pH. J Food Prot 2005;68:1359-66.
Pérez-Conesa D, McLandsborough L, Weiss J. Inhibition and inactivation of Listeria monocytogenes
and Escherichia coli
O157:H7 colony biofilms by micellar-encapsulated eugenol and carvacrol. J Food Prot 2006;69:2947-54.
Gaysinsky S, Taylor TM, Davidson PM, Bruce BD, Weiss J. Antimicrobial efficacy of eugenol microemulsions in milk against Listeria monocytogenes
and Escherichia coli
O157:H7. J Food Prot 2007;70:2631-7.
Terjung N, Löffler M, Gibis M, Hinrichs J, Weiss J. Influence of droplet size on the efficacy of oil-in-water emulsions loaded with phenolic antimicrobials. Food Funct 2012;3:290-301.
Garg A, Singh S. Targeting of eugenol-loaded solid lipid nanoparticles to the epidermal layer of human skin. Nanomedicine (Lond) 2014;9:1223-38.
Ghosh V, Mukherjee A, Chandrasekaran N. Eugenol-loaded antimicrobial nanoemulsion preserves fruit juice against, microbial spoilage. Colloids Surf B Biointerfaces 2014;114:392-7.
Chen F, Shi Z, Neoh KG, Kang ET. Antioxidant and antibacterial activities of eugenol and carvacrol-grafted chitosan nanoparticles. Biotechnol Bioeng 2009;104:30-9.
Piletti R, Bugiereck AM, Pereira AT, Gussati E, Dal Magro J, Mello JM, et al.
Microencapsulation of eugenol molecules by β-cyclodextrine as a thermal protection method of antibacterial action. Mater Sci Eng C Mater Biol Appl 2017;75:259-71.
Shah B, Davidson PM, Zhong Q. Nanodispersed eugenol has improved antimicrobial activity against Escherichia coli
O157:H7 and Listeria monocytogenes
in bovine milk. Int J Food Microbiol 2013;161:53-9.
Gomes C, Moreira RG, Castell-Perez E. Poly (DL-lactide-co-glycolide) (PLGA) nanoparticles with entrapped trans-cinnamaldehyde and eugenol for antimicrobial delivery applications. J Food Sci 2011;76:N16-24.
Garg A, Singh S. Enhancement in antifungal activity of eugenol in immunosuppressed rats through lipid nanocarriers. Colloids Surf B Biointerfaces 2011;87:280-8.
Hu Q, Gerhard H, Upadhyaya I, Venkitanarayanan K, Luo Y. Antimicrobial eugenol nanoemulsion prepared by gum arabic and lecithin and evaluation of drying technologies. Int J Biol Macromol 2016;87:130-40.
Islamuddin M, Chouhan G, Want MY, Ozbak HA, Hemeg HA, Afrin F, et al.
Immunotherapeutic potential of eugenol emulsion in experimental visceral leishmaniasis. PLoS Negl Trop Dis 2016;10:e0005011.
Lo Cantore P, Shanmugaiah V, Iacobellis NS. Antibacterial activity of essential oil components and their potential use in seed disinfection. J Agric Food Chem 2009;57:9454-61.
Peng S, Zou L, Liu W, Gan L, Liu W, Liang R, et al.
Storage stability and antibacterial activity of eugenol nanoliposomes prepared by an ethanol injection-dynamic high-pressure microfluidization method. J Food Prot 2015;78:22-30.
Liu Q, Niu H, Zhang W, Mu H, Sun C, Duan J. Synergy among thymol, eugenol, berberine, cinnamaldehyde and streptomycin against planktonic and biofilm-associated food-borne pathogens. Lett Appl Microbiol 2015;60:421-30.
Abbaszadeh S, Sharifzadeh A, Shokri H, Khosravi AR, Abbaszadeh A. Antifungal efficacy of thymol, carvacrol, eugenol and menthol as alternative agents to control the growth of food-relevant fungi. J Mycol Med 2014;24:e51-6.
Hua H, Xing F, Selvaraj JN, Wang Y, Zhao Y, Zhou L, et al.
Inhibitory effect of essential oils on Aspergillus ochraceus
growth and ochratoxin A production. PLoS One 2014;9:e108285.
Yossa N, Patel J, Millner P, Lo M. Inactivation of Salmonella
in organic soil by cinnamaldehyde, eugenol, ecotrol, and sporan. Foodborne Pathog Dis 2011;8:311-7.
Upadhyaya I, Yin HB, Surendran Nair M, Chen CH, Lang R, Darre MJ, et al.
Inactivation of Salmonella enteritidis
on shell eggs by coating with phytochemicals. Poult Sci 2016;95:2106-11.
Upadhyaya I, Yin HB, Nair MS, Chen CH, Upadhyay A, Darre MJ, et al.
Efficacy of fumigation with trans-cinnamaldehyde and eugenol in reducing Salmonella enterica
serovar enteritidis on embryonated egg shells. Poult Sci 2015;94:1685-90.
Upadhyaya I, Upadhyay A, Kollanoor-Johny A, Darre MJ, Venkitanarayanan K. Effect of plant derived antimicrobials on Salmonella enteritidis
adhesion to and invasion of primary chicken oviduct epithelial cells in vitro
and virulence gene expression. Int J Mol Sci 2013;14:10608-25.
Sutili FJ, Kreutz LC, Noro M, Gressler LT, Heinzmann BM, de Vargas AC, et al.
The use of eugenol against Aeromonas hydrophila
and its effect on hematological and immunological parameters in silver catfish (Rhamdia quelen
). Vet Immunol Immunopathol 2014;157:142-8.
Wang CY, Wang SY, Yin JJ, Parry J, Yu LL. Enhancing antioxidant, antiproliferation, and free radical scavenging activities in strawberries with essential oils. J Agric Food Chem 2007;55:6527-32.
Amiri A, Dugas R, Pichot AL, Bompeix G.In vitro
and in vivo
[corrected] activity of eugenol oil (Eugenia caryophylata
) against four important postharvest apple pathogens. Int J Food Microbiol 2008;126:13-9.
Edris AE, Farrag ES. Antifungal activity of peppermint and sweet basil essential oils and their major aroma constituents on some plant pathogenic fungi from the vapor phase. Nahrung 2003;47:117-21.
Bevilacqua A, Corbo MR, Sinigaglia M.In vitro
evaluation of the antimicrobial activity of eugenol, limonene, and citrus extract against bacteria and yeasts, representative of the spoiling microflora of fruit juices. J Food Prot 2010;73:888-94.
Narayanan A, Neera N, Mallesha L, Ramana KV. Synergized antimicrobial activity of eugenol incorporated polyhydroxybutyrate films against food spoilage microorganisms in conjunction with pediocin. Appl Biochem Biotechnol 2013;170:1379-88.
Dai Y, McLandsborough LA, Weiss J, Peleg M. Concentration and application order effects of sodium benzoate and eugenol mixtures on the growth inhibition of Saccharomyces cerevisiae
and Zygosaccharomyces bailii
. J Food Sci 2010;75:M482-8.
Qiu J, Feng H, Lu J, Xiang H, Wang D, Dong J, et al.
Eugenol reduces the expression of virulence-related exoproteins in Staphylococcus aureus.
Appl Environ Microbiol 2010;76:5846-51.
[Figure 1], [Figure 2]
[Table 1], [Table 2], [Table 3], [Table 4], [Table 5], [Table 6], [Table 7]