Comparative antimicrobial activity of Cymbopogon citratus essential oil and thiosemicarbazones derived from this oil

Amoussatou  Sakirigui; Kabirou Chabi  Sika; Allali Eugène  Koffi; Raymond Houssou  Fatondji; Louis  Fagbohoun; Franck  Yovo; Eléonore Yayi  Ladékan; Joachim Djimon  Gbénou

doi:10.30574/gscarr.2021.9.3.0300

Authors

Amoussatou Sakirigui Laboratory of Pharmacognosy and Essential Oils, Faculty of Sciences and Techniques/University of Abomey-Calavi (UAC) Cotonou, Republic of Benin.
Kabirou Chabi Sika Laboratory of Biology and Molecular Typing in Microbiology, Faculty of Sciences and Techniques, University of Abomey-Calavi, Cotonou, Republic of Benin.
Allali Eugène Koffi College of Agroforestry, Agrovalorisation Laboratory, Department of Biochemistry and Microbiology, Jean Lorougnon GUEDE University, Côte d'Ivoire.
Raymond Houssou Fatondji Kaba Research Laboratory in Chemistry and Applications (LaKReCA), University of Technical Sciences, Engineering and Mathematics (UNSTIM), Abomey, Republic of Benin.
Louis Fagbohoun Kaba Research Laboratory in Chemistry and Applications (LaKReCA), University of Technical Sciences, Engineering and Mathematics (UNSTIM), Abomey, Republic of Benin.
Franck Yovo Kaba Research Laboratory in Chemistry and Applications (LaKReCA), University of Technical Sciences, Engineering and Mathematics (UNSTIM), Abomey, Republic of Benin.
Eléonore Yayi Ladékan Laboratory of Pharmacognosy and Essential Oils, Faculty of Sciences and Techniques/University of Abomey-Calavi (UAC) Cotonou, Republic of Benin.
Joachim Djimon Gbénou Laboratory of Pharmacognosy and Essential Oils, Faculty of Sciences and Techniques/University of Abomey-Calavi (UAC) Cotonou, Republic of Benin.

DOI:

https://doi.org/10.30574/gscarr.2021.9.3.0300

Keywords:

Thiosemicarbazones, Hemi-synthesized, Cymbopogon citratus, Antimicrobial activities, Minimum inhibitory concentrations, Minimum bactericidal concentrations

Abstract

Introduction: The presence of microbes in our environment is always a permanent public health problem. In this context, research on natural treatment, less expensive and accessible to fight these microbial germs would be beneficial.

Methods: During this work, molecules of thiosemicarbazones due to their numerous biological activities were hemi-synthesized in situ in the essential oil of Cymbopogon citratus in order to evaluate their antimicrobial activities.

Results: Analysis of the essential oil extracted by hydrodistillation revealed the presence of 72.91% of citral. Citralthiosemicarbazone (CThio) and citral 4-phenyl-3-thiosemicarbazone (CPthio) were hemi-synthesized in this oil with interesting yields of 83% and 91%, respectively. After purification and confirmation of the structures of these molecules, the three substances were tested on eleven strains of microbes. Determination of the inhibition diameters showed that the activity of the essential oil is best in over 80% of strains. However, the largest diameter of inhibition (26 mm) was noted with CPthio against Salmonella typhi R 30951401. The determination of the minimum inhibitory concentrations showed that the oil remains more active with the smallest value of 0.3125 mg / ml against Micrococcus luteus. The lower value of minimum bactericidal concentrations was also obtained with the essential oil against Enterococcus foecalis ATCC 29212.

Conclusion: The essential oil of C. citratus remains more active in the majority cases. It could be a great alternative in the fight against bacteria, and the advantage is that it remains a natural substance.

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References

Mitscher LA, Pillai SP, Gentry EJ, Shankel DM. Multiple Drug Rresistance. Medicinal Research Reviews. 1999; 19: 477.

Harbart S, Albrich W, Goldman DA, and Huebner J. Control of multiply resistant cocci: do international comparisons help? The Lancet Infectious Diseases. 2001; 1: 251–261.

Berber I, Cokmus C; Atalan E. Characterization of Staphylococcus species by SDS-PAGE of whole cell and extracellular proteins. Microbiology. 2003; 72(1): 42-47.

Shim J, Jyothi NR, Farook Nam. Biological Applications of Thiosemicarbazones and Their Metal Complexes, Asian Journal of Chemistry. 2013; 25(10): 5838-5840.

Pham VH, Phan TPD, Phan DC, Vu BD. Synthesis and Bioactivity of Thiosemicarbazones Containing Adamantane Skeletons Molecules. 2020; 25(324): 1-14.

Zakir HM, Jesmin M, Ali SMM. Antibacterial Activities of Benzoin Thiosemicarbazone and Its Complexes with Co (II) and Ni (II). Asian J. Med. Pharm. Res. 2016; 6(4): 32-40.

Siddiqui EJ, Azad I, Khan AR, Khan T. Thiosemicarbazone Complexes as Versatile Medicinal Chemistry Agents: A Review, Journal of Drug Delivery & Therapeutics. 2019; 9(3):689-703.

Asifa M, Alghamdib S. Chemical and Biological potentials of semicarbazide and thiosemicarbazide derivatives and their metals complexes, Advanced Journal of Chemistry, Section B. 2021; 3(3), 243-270.

Parul N, Subhangkar N, Mahato A. Antimicrobial Activity of Different Thiosemicarbazone Compounds against Microbial Pathogens. International Research Journal of Pharmacy. 2012; 3: 350-363.

Siwek A, Stefanska J, Dzitko K, Ruszezak A. Antifungal effect of 4-arylthiosemicarbazides against Candida species. Search for molecular basis of antifungal activity of thiosemicarbazide derivatives. J. Mol. Model. 2012; 18: 4159-4170.

Debjani B, Yogeeswari P, Pritesh B, Anisha T, Madala S, Dharmarajan S. Novel isatinyl thiosemicarbazones derivatives as potential molecule to combat HIV-TB co-infection. European Journal of Medicinal Chemistry. 2011; 46(1): 106-121

Teytz Y, Ronen D, Vansover A, Stematsky T Riggs JL. Inhibition of Human Immunodeficiency Virus by N-methylisatin-beta 4':4'-Diethylthiosemicarbazoneand N-Allylisatin-beta4':4'-diallythiosemicarbazone. Antiviral Research. 1994; 24: 305-314.

Tahmeena K, Rumana A, Seema J, Khan, AR. Anticancer Potential of Metal Thiosemicarbazone Complexes. A Review. Der Chemica Sinica. 2015; 6: 1-11.

Yu P, Deng J, Cai J, Zhang Z, Zhang J. Anticancer and biological properties of a Zn-2,6- diacetylpyridine bis(thiosemicarbazone) complex Metallomics. 2019; 11: 1372-1386.

Jacob ÍTT, Gomes FOS, de Miranda MDS. Anti-inflammatory activity of novel thiosemicarbazone compounds indole-based as COX inhibitors. Pharmacol. Rep. 2021 73: 907–925.

Dantas LLSFR, Fonseca AG, Pereira JR, Gomes PATM, Fernandes-Pedrosa MF, Leite ACL, Rêgo MJBM, Pitta MGR Lemos, TMAM. Anti-inflammatory and antinociceptive effects of the isatin derivative (Z)-2-(5-chloro-2-oxoindolin-3-ylidene)-N-phenyl-hydrazinecarbothioamide in mice Brazilian Journal of Medical and Biological Research. 2020; 53(10). e10204.

Pavan FR, da S Maia PI, Leite SR, Deflon VM, Batista AA, Sato DN, Franzblau SG, Leite CQ. Thiosemicarbazones, semicarbazones, dithiocarbazates and hydrazide/hydrazones: anti-Mycobacterium tuberculosis activity and cytotoxicity. Eur J Med Chem. 2010; 45(5): 1898-905.

Hussein MB, Mohammed MM, Gobara A, Wady AF, Holy ASI. Synthesis, characterization, and antimicrobial activity of 4-imidazolecarboxaldehyde thiosemicarbazone and its Pt (II) and Pd (II) complexes. European Journal of Chemistry. 2021; 12(1): 56-59.

Khan SA, Kumar P, Joshi R, Iqbal PF, Saleem K. Synthesis and in vitro antibacterial activity of new steroidal thiosemicarbazone derivatives, European Journal of Medicinal Chemistry. 2008; 43(9): 2029-2034.

Bisceglie F, Bacci C, Vismarra A, Barilli E, Pioli M, Orsoni N, Pelosi G. Antibacterial activity of metal complexes based on cinnamaldehyde thiosemicarbazone analogues, Journal of Inorganic Biochemistry. 2020; 203: 110888.

Vyshali P, Suchetha M, Thara Saraswathi KJ. Evaluation of antioxidant and antimicrobial properties in Cymbopogon citratus (DC.) Stapf. Mahidol University Journal of Pharmaceutical Sciences. 2012; 39(2): 28-36.

Adukwu EC, Bowles M, Edwards-Jones V, Bone H. Antimicrobial activity, cytotoxicity and chemical analysis of lemongrass essential oil (Cymbopogon flexuosus) and pure citral Appl Microbiol Biotechnol. 2016; 100: 9619–9627.

Sakirigui A, Nonviho G, Hounkpatin ASY, Chabi Sika K. Comparative chemical analysis and antimicrobial activity of the volatile and no-volatile extracts of Cymbopogon citratus leave. Int. J. Green Herb. Chem. 2020; (9)4: 492-501.

Sakirigui A, Kossouoh C, Gbaguidi F, Kpoviessi S, Fatondji RH, Poupaert J, Accrombessi GC. Hémi-synthèse et activités antiparasitaires sur Trypanosoma brucei brucei de thiosemicarbazones du citral dans l’huile essentielle de Cymbopogon citratus du Bénin. J. Soc. Ouest-Afr. Chim. 2011; 031: 11-20.

Sakirigui A, Kpoviessi SDS, Gbaguidi F, Kossouoh C, Bero J, Quetin-Leclercq J, Moudachirou M, J Poupaert, Accrombessi G C. Selective trypanocide activity of some substituted thiosemicarbazones of citral from Benin Cymbopogon citratus essential oil and their toxicity against Artemia salina leach. International Journal of Research and Reviews in Applied Sciences. 2012; 12(3): 454-462.

Sakirigui A, Fatondji HR, Gbaguidi AF, Kpoviessi DSS, Poupaert J, Leclercque J, Accrombessi CG. Hemi-Synthesized of Trypanocidal Thiosemicarbazones in Three Essential Oils Rich in Carbonyl Compounds. International Journal of Chemical and Physical Sciences. 2016; 5(5): 77-88.

Clevenger JF. Apparatus for the Determination of Volatile Oil. Journal of the American Pharmaceutical Association. 1928; 17(4): 346-349.

Adams RP, Identification of essential components by gas chromatography/mass spectrometry, 4th Ed. Allured Publishing, Carol Stream, IL, USA. 2007.

Mohd IN, Bashir AF, Ebenezar J, Javid AB, Antibacterial activity of lemongrass (Cymbopogon citratus) oil against some selected pathogenic bacterias Asian Pac. J. Trop. Med. 2010; 29: 535-538.

Bauer AW, Kirby WM, Sherris JC, Turck M. Antibiotic susceptibility testing by a standardized single disk method. AJCP. 1996; 45: 493-496.

Adesokan AA, Akanji MA, Yakubu MT, Adesokan AA, Akanji MA, Yakubu MT. Antibacterial potentials of aqueous extract of Enantia chlorantha stem bark. Afr J Biotechnol. 2007; 6(22):2502-2505.

Delarras C. Microbiology 90 hours of practical work. Gaétan Morien Publisher. 1998; 169-178.

Farshori NN, Al-Sheddi ES, Al-Oqail MM, Musarrat J, Al-Khedhairy AA, Siddiqui MA. Anticancer activity of Petroselinum sativum seed extracts on MCF-7 Human Breast Cancer Cells. Asian Pacific J Cancer Prev. 2013; 14(10): 5719-5723.

Marques AM, Lima CHP, Alviano DS, Alviano CS, Esteves RL, Kaplan MAC, Traditional use, chemical composition and antimicrobial activity of Pectis brevipedunculata essential oil: a correlated lemongrass species in Brazil. J. Food Agric; 2013; 25: 798-808.

Tajidin NE, Ahmad SH, Rosenani AB, Azimah H, Munirah M, Chemical composition and citral content in lemongrass (Cymbopogon citratus) essential oil at three maturity stages. Afr. J. Biotechnol. 2012; 11: 2685-2693.

Mbah JA, Ayimele GA, Eyonganyoh EN, Nfor EN. Synthesis, Molecular Structure and Antibacterial Activity of Benzylmethyl-4-Methyl-3-Thiosemicarbazone International Journal of Organic Chemistry. 2017; 7: 83-90.