A Comparison of efficiency of (AMP) and its derivative (AMPAA) against some pathogenic bacteria

Suzan S. Hussain


Eugenol (4-allyl-2-methoxyphenol, AMP), is a well known a biologically active phenolic compo-nent and essential oil from Eugenia caryophyllata, which widely used of Eugenol as an antiseptic and analgesic in dental care, so it is active against oral bacteria associated with dental caries and periodontal disease as well as previous studies have shown the effect of Eugenol antifungal; anti-carcinogenic; anti-allergic; anti-mutagenic activity; antioxidant and insecticidal properties, there-fore it can be used in preparation of various food as a flavouring agent and cosmetic. This study aimed to synthesize derivative new medical material 2-(4-allyl-2-methoxyphenoxy) acetic acid (AMPAA) from eugenol (4-allyl-2-methoxyphenol) (AMP) and investigate the anti-microbial activities of both AMP and derivative component (AMPAA), The minimum inhibitory concentration (MIC); minimum bactericidal concentration (MBC) and sensitivity against six pathogenic bacterial isolates: Streptococcus. pyogens; Enterococcus. faecalis; Escherichia. coli ; Klebsiella pneumoniae; Bacillus. subtilis and Proteus. mirabilis with study compare the efficien-cy for both AMP and AMPAA on the same bacterial isolate obtained from Iraqi hospitals. In this present study synthesize new medical material (AMPAA) from AMP by reacting sodium eugenate with sodium chloroacetic acid and prepare soluble water from eugenol and its derivative AMPAAto scanning the antimicrobial efficacy against some pathogenic bacteria isolatesby two common methods; well diffusion and broth dilution methods. Results of the present study show all bacterial isolates were sensitive to both AMP and AMPAA in low concentration except K. pneumoniae, also 10.0 and 5.0 μg/mL of AMP and AMPAA as MBC for bacterial isolates except K. pneumoniae and P. mirabilis that’s meaning the new deriva-tive compound AMPAA has more efficacy on six bacterial isolate than eugenol (AMP). By using Well diffusion method all bacterial isolates were sensitive to both (AMP and AMPAA) in low concentration, but K. pneumoniae was killed in same concentration, so all isolates have been killed at concentrations between (10 - 50 μg/mL) of new derivative compound (AMPAA), at the same concentration of AMP were killed for K. pneumoniae and P. mirabilis) ,as well as all isolates have varying degrees of sensitivity towards both (AMP and AMPAA), whereas all iso-lates where more sensitive to AMPAA than AMP. In conclusion, all bacterial isolate were sensitive to both AMP and AMPAA in low concentration except K. pneumoniae, also 10.0 and 5.0 μg/mL of AMP and AMPAA respectively conceder as MBC for bacterial isolate except K. pneumoniae and P. mirabilis, that killed in these concentra-tion,so at the same concentration of AMP and AMPAA bacterial isolates were sensitivity by well diffusion method, whilst its killed by broth method, that’s consulate broth method was best than diffusion method


AMP, Eugenol, 4-allyl-2-methoxyphenol, AMPAA, 2-(4-allyl-2-methoxyphenoxy) acetic acid.

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Gayoso, C. W. ; Lima, E. O. ; Oliveira, V. T. ; Pereira, F. O. ; Souza, E. L. and Lima. I. O., (2005), "Sensitivity of fungi isolated

from onychomy-cosisto Eugenia cariophyllata essential oil and eugenol. ", Fitoterapia, 76:247-9.

Pisano, M. ; Pagnan, G. ; Loi, M. ; Mura, M. E. ; Tilocca, M. G. ; Palmieri, G. ; Fabbri, D. ; Dettori, M. A. ; Delogu, G. ; Ponzoni, M., (2007). "Antiproliferative and pro-apopto. ", Appl. Environ. Microbiol., 68 (4): 1561-68.

Abad, M. J. ; Ansuategui, M. and Bermejo, P. (2007). "Active antifungal substances from natural sources. ",Archivoc, (207):116–145.

Cosentino, S. ; Tuberoso, C. I. ; Pisano, B. ; Satta, M. ; Mascia, V. ;Arzedi, E. and Palmas, F., (1999), "In-vitroantimicrobial activity and chemical composition of Sardinian. Thymus essential oils. ",Lett. Appl. Microbiol., 29(2): 130-135.

Xiaojun, K. ; Xiwang, L. ; Jianyong, L. I. and Yajun, Y. (2014). Advances in Pharmacological Research of Eugenol. CurrOpin Complement Alternat. Med. ; (1):8-11.

Saravana K., J. and Eko, S. (2012). Antiproliferative and Molecular Mechanism of Eugenol-Induced Apoptosis in Cancer Cells,Molecules, 17.

Wie, M. B. ; Won, M. H. ;Lee, K. H. ;Shin, J. H. ;Lee, J. C. ; Suh; H. W. ; Song ,D. K and Kim, Y. H. (1997). Eugenol protects neuronal cells from excitotoxic and oxidative injury in primary cortical cultures. NeurosciLett. 1997 Apr 4;225(2):93-6.

Burt, S. A. and Reinders, R. D., 2003. Antibacterial activity of selected plant essential oils against Escherichia coli O157:H7. Letters in Applied Microbiology 36 (3), 162– 167.

Burt, S. (2004). "Essential oils: Their antibacterial properties and potential applications in foods a review. ", Int. J. Food Microbiol. ; 94(3): 223-53.

Chen ,H; Jin ,X ; Li ,Y and Tian,J. (2016). Investigation into the physical stability of a eugenol nanoemulsion in the presence of a high content of triglyceride;RSC Adv. ,93,(6):91060-91067.

Hussain A Comparison of efficiency of (AMP) and its derivative (AMPAA) against some pathogenic bacteria 2017

Hamri ,S ; Rhazri,K. ; Hafid,A. ; Ouchetto,H. ; Hajbi,Y. and Khouili,M. (2013). Clove (Eugenia Caryophyllata) Extraction and Synthesis of new Pyrazole Derivatives from Eugenol, Global Journal of Science Frontier Research Chemistry, 13 (7): 1-7.

Sayyah, M. ; Valizadeh, J. and Kamalinejad, M., (2002), "Anticonvulsant activity of the leaf essential oil of Laurusnobilis against pentylenetetrazole- and maximal electroshock-induced seizures. ", Phytomedicine 9, 212.

Won, M. H. ; Lee, J. C. ; Kim, Y. H. ; Song, D. K. ; Suh, H. W. ; Oh, Y. S. ; Kim, J. H. ; Shin, T. K. ; Lee, Y. J. and Wie, M. B. (1998). Postischemic hypothermia induced by eugenol protects hippocampal neurons from global ischemia in gerbils, Neurosci. Lett., 254, 101.

Lambert, R. J. ; Skandamis, P. N. ;Coote, P. J. and Nychas, G. J., (2001), "A study of the minimum inhibitory concentration and mode of action of oregano essential oil, thymol and carvacrol. ", Appl. Microbiol., 91(3):453-462.

Ultee, A. ;Bennik, M. H and Moezelaar, R., (2002). "The phenolic hydroxyl group of carvacrol is essential for action against the food-born pathogen Bacillus cereus. ", Appl. Environ. Microbiol., 68 (4): 1561-68.

Thosar, N. ; Basak, S. ; Bahadure, R. N. and Monali, R. (2013). Antimicrobial efficacy of five essential oils against oral pathogens: An in vitro study., Eur J. Dent.; 7(Suppl 1): S71–S77.

Walsh, S. E. ; Maillard ,J. Y. ; Russel, A. D. ;Catrenich, C. E. ; Charbonneau, D. L. and Bartolo, R. G. (2003). Activity and mechanisms of action of selected biocidal agents on Gram-positive and –negative bacteria, J. Appl. Microbiol., 94: 240-247.

Bennis, S. ; Chami, F. ; Chami, N. ; Rhayour, K. ; Tantaoui-Elaraki, A. and Remmal, A., (2001), "Eugenol induces damage of bacterial and fungal envelope. ", Moroccan J. Biol.1, 33-39.

Oyedemi, S. O. ; Okoh, A. I. ; Mabinya, L.; Piro9 Chenva, V. G., and Afolayan, A. J., (2009). "The proposed mechanism of bactericidal action of eugenol, α-terpineol and -terpinene against Listeria

monocytogenes, Streptococcus pyogenes, Proteus vulgaris and Escherichia coli. ", African Journal of Biotechnology, 8 (7):1280-1286.

DOI: http://dx.doi.org/10.23851/mjs.v28i2.496


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