Gas Chromatography-Mass Spectrometry Profiling, Antioxidant and Antibacterial Evaluations of Essential Oils Extracted from Mentha piperita and Mentha pulegium

Main Article Content

Mohamed Amine El maimouni
Soukaina El amrani
Sanae Lairini
Rabia Bouslamti
Mohammed Er-rajy
Somdutt Mujwar
Mohammed Chalkha
Khalid Chebbac
Fouad El Akhal
Abdelhakim El Ouali Lalami

Abstract

Synthetic food preservatives protect against oxidation and pathogens but can harm consumer health. Plant-based bioactive components like phenolic acids, flavonoids, and essential oils (EOs) are crucial for safe alternatives. The study investigated the chemical composition and biological activities of EOs extracted from Mentha piperita and Mentha pulegium. Essential oils from both plant species were extracted using hydro-distillation method. Gas chromatography-mass spectrometry (GC-MS) profiling was performed to determine the EOs' constituents. The EOs were assessed for antioxidant properties using three assays, while their antibacterial activity was evaluated against Escherichia coli and Staphylococcus aureus. Molecular docking and dynamic simulation studies were performed to elucidate the interaction between EO constituents and target enzymes. The results revealed that the main components in M. piperita and M. pulegium EOs were isomintlactone (35.55%) and pulegone (74.04%), respectively. The EOs of M. piperita and M. pulegium exhibited remarkable antioxidant activity, with inhibitory concentration (IC50) values of 3.24±0.22 and 3.51±0.22 mg/mL, respectively, in the 2,2-diphenyl-1-picrylhydrazyl radical scavenging (DPPH) assay. Strong antibacterial efficacy was observed with a minimum inhibitory concentration (MIC) of 4% for M. pulegium and moderate effects for M. piperita with MIC values of 0.5% against Staphylococcus aureus and its ATCC29213, and 1% against Escherichia coli and its ATCC25922. Molecular docking and dynamic molecular simulations showed that the identified chemical constituents in the test EOs have a good affinity to the target enzymes. These findings suggest that M. piperita and M. pulegium EOs are promising natural sources of antioxidant and antibacterial agents, potentially valuable in food preservation and health applications. 

Downloads

Download data is not yet available.

Article Details

How to Cite
El maimouni, M. A., El amrani, S., Lairini, S., Bouslamti, R., Er-rajy, M., Mujwar, S., Chalkha, M., Chebbac, K., El Akhal, F., & Lalami, A. E. O. (2024). Gas Chromatography-Mass Spectrometry Profiling, Antioxidant and Antibacterial Evaluations of Essential Oils Extracted from Mentha piperita and Mentha pulegium. Tropical Journal of Natural Product Research (TJNPR), 8(12), 9386-9398. https://doi.org/10.26538/tjnpr/v8i12.6
Section
Articles
Author Biographies

Mohammed Chalkha, Laboratory of Material Engineering for the Environment and Natural Resources, Faculty of Sciences and Techniques, University of Moulay Ismail of Meknès, Boutalamine, Errachidia, Morocco 

Engineering Laboratory of Organometallic, Molecular Materials and Environment, Faculty of Sciences Dhar EL Mahraz, Sidi Mohamed Ben Abdellah University, Atlas, Fez, Morocco  

Abdelhakim El Ouali Lalami, Materials, Processes, Catalysis, and Environment Laboratory, Higher School of Technology of Fez, Sidi Mohamed Ben Abdellah University, Imouzzer Road, Fez, Morocco 

Higher Institute of Nursing Professions and Health Techniques of Fez, Regional Directorate of Health, El Ghassani Hospital, Dhar El Mehraz, Fez, Morocco

How to Cite

El maimouni, M. A., El amrani, S., Lairini, S., Bouslamti, R., Er-rajy, M., Mujwar, S., Chalkha, M., Chebbac, K., El Akhal, F., & Lalami, A. E. O. (2024). Gas Chromatography-Mass Spectrometry Profiling, Antioxidant and Antibacterial Evaluations of Essential Oils Extracted from Mentha piperita and Mentha pulegium. Tropical Journal of Natural Product Research (TJNPR), 8(12), 9386-9398. https://doi.org/10.26538/tjnpr/v8i12.6

References

1. Poljsak B, Kovač V, Milisav I. Antioxidants, Food Processing and Health. Antioxidants 2021, 10 (3), 433.

2. Roy A, Khan A, Ahmad I, Alghamdi S, Rajab BS, Babalghith AO, Alshahrani MY, Islam S, Islam MdR. Flavonoids a Bioactive Compound from Medicinal Plants and Its Therapeutic Applications. BioMed Res. Int. 2022, 5445291.

3. Parham S, Kharazi AZ, Bakhsheshi-Rad HR, Nur H, Ismail AF, Sharif S, RamaKrishna S, Berto F. Antioxidant, Antimicrobial and Antiviral Properties of Herbal Materials. Antioxidants 2020, 9 (12), 1309.

4. Değirmenci H, Erkurt H. Relationship between Volatile Components, Antimicrobial and Antioxidant Properties of the Essential Oil, Hydrosol and Extracts of Citrus Aurantium L. Flowers. J. Infect. Public Health 2020, 13 (1), 58–67.

5. Bajpai VK, Baek K-H. Biological Efficacy and Application of Essential Oils in Foods-A Review. J. Essent. Oil-Bear. Plants 2016, 19 (1), 1–19.

6. Amorati R, Foti MC, Valgimigli L. Antioxidant Activity of Essential Oils. J. Agric. Food Chem. 2013, 61 (46), 10835–10847.

7. Bouyahya A, Et-Touys A, Bakri Y, Talbaui A, Fellah H, Abrini J, Dakka N. Chemical Composition of Mentha Pulegium and Rosmarinus Officinalis Essential Oils and Their Antileishmanial, Antibacterial and Antioxidant Activities. Microb. Pathog. 2017, 111, 41–49.

8. El amrani S, El Ouali Lalami A, Ez zoubi Y, Moukhafi K, Bouslamti R, Lairini, S. Evaluation of Antibacterial and Antioxidant Effects of Cinnamon and Clove Essential Oils from Madagascar. Mater. Today Proc. 2019, 13, 762–770.

9. Desam NR, Al-Rajab AJ, Sharma M, Mylabathula MM, Gowkanapalli RR, Albratty M. Chemical Constituents, in Vitro Antibacterial and Antifungal Activity of Mentha × Piperita L. (Peppermint) Essential Oils. J. King Saud Univ. - Sci. 2019, 31 (4), 528–533.

10. Adams RP. Identification of Essential Oil Components by Gas Chromatography/Quadrupole Mass Spectroscopy. Identif. Essent. Oil Compon. Gas Chromatogr. Mass Spectrosc. 2001.

11. Ijoma I, Ishmael V, Ajiwe V, Chukwudindu O. The Organic Extracts from the Leaves of Ficus Thonningii Blume, Jatropha Tanjorensis J.L Ellis and Saroja and Justicia Carnea Lindley as Potential Nutraceutical Antioxidants and Functional Foods. Azad University Journals Cloud, 2023, 7, 76–85.

12. De León-Zapata MA, Pastrana-Castro L, Rua-Rodríguez ML, Alvarez-Pérez OB, Rodríguez-Herrera R, Aguilar CN. Experimental Protocol for the Recovery and Evaluation of Bioactive Compounds of Tarbush against Postharvest Fruit Fungi. Food Chem. 2016, 198, 62–67.

13. Ouedrhiri W, Balouiri M, Bouhdid S, Moja S, Chahdi FO, Taleb M, Greche H. Mixture Design of Origanum Compactum, Origanum Majorana and Thymus Serpyllum Essential Oils: Optimization of Their Antibacterial Effect. Ind. Crops Prod. 2016, 89, 1–9.

14. Ez zoubi Y, Farah A, Saâd M, El Ouali Lalami A. In Vitro Antibacterial Efficacy of Essential Oils from Moroccan Plants Against Pathogenic Bacteria Isolated from Hospital Environment in Morocco. International Journal of Pharmaceutical and Clinical Research 2016; 8(6): 610-615

15. Ouedrhiri W, Bouhdid S, Balouiri M, Lalami A. E. O.; S; Moja, R.; Chahdi, F. O.; Greche, H. Chemical Composition of Citrus Aurantium L. Leaves and Zest Essential Oils, Their Antioxidant, Antibacterial Single and Combined Effects. J. Chem. Pharm. Res. 2015, 7 (1).

16. Basri DF, Luoi CK, Azmi AM, Latip J. Evaluation of the Combined Effects of Stilbenoid from Shorea Gibbosa and Vancomycin against Methicillin-Resistant Staphylococcus Aureus (MRSA). Pharm. Basel Switz. 2012, 5 (9), 1032–1043.

17. Allinger NL. Conformational Analysis. 130. MM2. A Hydrocarbon Force Field Utilizing V1 and V2 Torsional Terms. J. Am. Chem. Soc. 1977, 99 (25), 8127–8134.

18. Umi Baroroh SS, Muscifa ZS, Destiarani W, Rohmatullah FG, Yusuf M. Molecular Interaction Analysis and Visualization of Protein-Ligand Docking Using Biovia Discovery Studio Visualizer. Indones. J. Comput. Biol. 2023, 2 (1), 22–30.

19. Herrera-Calderon O, Chacaltana-Ramos LJ, Huayanca-Gutiérrez IC, Algarni MA.; Alqarni M, Batiha GE-S. Chemical Constituents, In Vitro Antioxidant Activity and In Silico Study on NADPH Oxidase of Allium Sativum L. (Garlic) Essential Oil. Antioxid. Basel Switz. 2021, 10 (11), 1844.

20. Priyanka N, Singh V, Ekta N, Katiyar D. Synthesis, Antimicrobial, Cytotoxic and E. Coli DNA Gyrase Inhibitory Activities of Coumarinyl Amino Alcohols. Bioorganic Chem. 2017, 71, 120–127.

21. Kumar V, Parate S, Danishuddin N, Zeb A, Singh P, Lee G, Jung TS, Lee KW, Ha MW. 3D-QSAR-Based Pharmacophore Modeling, Virtual Screening, and Molecular Dynamics Simulations for the Identification of Spleen Tyrosine Kinase Inhibitors. Front. Cell. Infect. Microbiol. 2022, 12, 909111.

22. Shah K, Mujwar S. Delineation of a Novel Non-Steroidal Anti-Inflammatory Drugs Derivative Using Molecular Docking and Pharmacological Assessment. Indian J. Pharm. Sci. 2022, 84 (3), 642–653.

23. Shinu P, Sharma M, Gupta GL, Mujwar S, Kandeel M, Kumar M, Nair AB, Goyal M, Singh P, Attimarad M, Venugopala KN, Nagaraja S, Telsang M, Aldhubiab BE, Morsy MA. Computational Design, Synthesis, and Pharmacological Evaluation of Naproxen-Guaiacol Chimera for Gastro-Sparing Anti-Inflammatory Response by Selective COX2 Inhibition. Mol. Basel Switz. 2022, 27 (20), 6905.

24. Er-rajy M, El fadili M, Mrabti NN, Zarougui S, Elhallaoui M. QSAR, Molecular Docking, ADMET Properties in Silico Studies for a Series of 7-Propanamide Benzoxaboroles as Potent Anti-Cancer Agents. Chin. J. Anal. Chem. 2022, 50 (12), 100163.

25. Hai NTT, Huong DTQ, Hoang NV, Bui TQ, Quy PT, Phu NV, Chau ND, Huy TQ, Hue DT, Nhung NTA. Antibacterial Potentials of Blumea Balsamifera L. Essential Oil Against Streptococcus Pyogenes and Streptococcus Pneumoniae: In Vitro and In Silico Screening. Trop. J. Nat. Prod. Res. TJNPR 2024, 8 (7), 7658–7671.

26. Pires DEV, Blundell TL, Ascher DB. pkCSM: Predicting Small-Molecule Pharmacokinetic and Toxicity Properties Using Graph-Based Signatures. J. Med. Chem. 2015, 58 (9), 4066–4072.

27. Daina A, Michielin O, Zoete V. SwissADME: A Free Web Tool to Evaluate Pharmacokinetics, Drug-Likeness and Medicinal Chemistry Friendliness of Small Molecules. Sci. Rep. 2017, 7, 42717.

28. Lipinski CA. Lead- and Drug-like Compounds: The Rule-of-Five Revolution. Drug Discov. Today Technol. 2004, 1 (4), 337–341.

29. de Sousa Guedes JP, da Costa Medeiros JA, de Souza E, Silva RS, de Sousa JMB, da Conceição ML, de Souza EL. The Efficacy of Mentha Arvensis L. and M. Piperita L. Essential Oils in Reducing Pathogenic Bacteria and Maintaining Quality Characteristics in Cashew, Guava, Mango, and Pineapple Juices. Int. J. Food Microbiol. 2016, 238, 183–192.

30. de Sousa Barros A, de Morais SM, Ferreira PAT, Vieira ÍGP, Craveiro AA, dos Santos Fontenelle RO, de Menezes JESA, da Silva FWF, de Sousa HA. Chemical Composition and Functional Properties of Essential Oils from Mentha Species. Ind. Crops Prod. 2015, 76, 557–564.

31. Benabdallah A, Boumendjel M, Aissi O, Rahmoune C, Boussaid M, Messaoud C. Chemical Composition, Antioxidant Activity and Acetylcholinesterase Inhibitory of Wild Mentha Species from Northeastern Algeria. South Afr. J. Bot. 2018, 116, 131–139.

32. Ahmad A, Khan A, Samber N, Manzoor N. Antimicrobial Activity of Mentha Piperita Essential Oil in Combination with Silver Ions. Synergy 2014, 1 (2), 92–98.

33. Park YJ, Baskar TB, Yeo SK, Arasu MV, Al-Dhabi NA, Lim SS, Park SU. Composition of Volatile Compounds and in Vitro Antimicrobial Activity of Nine Mentha Spp. SpringerPlus 2016, 5 (1), 1628.

34. Mahboubi M, Kazempour N. Chemical Composition and Antimicrobial Activity of Peppermint (Mentha Piperita L.) Essential Oil. Songklanakarin J. Sci. Technol. 2014, 36, 83–87.

35. Chraibi M, Farah A, Lebrazi S, El Amine O, Iraqui Houssaini M, Fikri-Benbrahim K. Antimycobacterial Natural Products from Moroccan Medicinal Plants: Chemical Composition, Bacteriostatic and Bactericidal Profile of Thymus Satureioides and Mentha Pulegium Essential Oils. Asian Pac. J. Trop. Biomed. 2016, 6 (10), 836–840.

36. El Asbahani A, Jilale A, Voisin SN, Aït Addi EH; Casabianca H, El Mousadik A, Hartmann DJ, Renaud FNR. Chemical Composition and Antimicrobial Activity of Nine Essential Oils Obtained by Steam Distillation of Plants from the Souss-Massa Region (Morocco). J. Essent. Oil Res. 2015, 27 (1), 34–44.

37. Ait-Ouazzou A, Lorán S, Arakrak A, Laglaoui A, Rota C, Herrera A, Pagán R, Conchello P. Evaluation of the Chemical Composition and Antimicrobial Activity of Mentha Pulegium, Juniperus Phoenicea, and Cyperus Longus Essential Oils from Morocco. Food Res. Int. 2012, 45 (1), 313–319.

38. Mahboubi M, Haghi G. Antimicrobial Activity and Chemical Composition of Mentha Pulegium L. Essential Oil. J. Ethnopharmacol. 2008, 119 (2), 325–327.

39. Satmi FRS, Hossain MA. In Vitro Antimicrobial Potential of Crude Extracts and Chemical Compositions of Essential Oils of Leaves of Mentha Piperita L Native to the Sultanate of Oman. Pac. Sci. Rev. Nat. Sci. Eng. 2016, 18 (2), 103–106.

40. Bouyahya A, Dakka N, Talbaoui A, Et-Touys A, El-Boury H, Abrini J, Bakri Y. Correlation between Phenological Changes, Chemical Composition and Biological Activities of the Essential Oil from Moroccan Endemic Oregano (Origanum Compactum Benth). Ind. Crops Prod. 2017, 108, 729–737.

41. Číž M, Čížová H, Denev P, Kratchanova M, Slavov A, Lojek A. Different Methods for Control and Comparison of the Antioxidant Properties of Vegetables. Food Control 2010, 21 (4), 518–523.

42. Baali F, Boumerfeg S, Napoli E, Boudjelal A, Righi N, Deghima A, Baghiani A, Ruberto G. Chemical Composition and Biological Activities of Essential Oils from Two Wild Algerian Medicinal Plants: Mentha Pulegium L. and Lavandula Stoechas L. J. Essent. Oil Bear. Plants 2019, 22 (3), 821–837.

43. Raeisi M, Hashemi M, Aminzare M, Afshari A, Zeinali T, Jannat B. An Investigation of the Effect of Zataria Multiflora Boiss and Mentha Piperita Essential Oils to Improve the Chemical Stability of Minced Meat. Vet. World, 2018, 11 (12), 1656–1662.

44. Benabdallah A, Rahmoune C, Boumendjel M, Aissi O, Messaoud C. Total Phenolic Content and Antioxidant Activity of Six Wild Mentha Species (Lamiaceae) from Northeast of Algeria. Asian Pac. J. Trop. Biomed. 2016, 6 (9), 760–766.

45. Singh R, Shushni MAM, Belkheir A. Antibacterial and Antioxidant Activities of Mentha Piperita L. Arab. J. Chem. 2015, 8 (3), 322–328.

46. Kamkar A, Javan AJ, Asadi F, Kamalinejad M. The Antioxidative Effect of Iranian Mentha Pulegium Extracts and Essential Oil in Sunflower Oil. Food Chem. Toxicol. 2010, 48 (7), 1796–1800.

47. Teixeira B, Marques A, Ramos C, Batista I, Serrano C, Matos O, Neng NR, Nogueira JMF, Saraiva JA, Nunes ML. European Pennyroyal (Mentha Pulegium) from Portugal: Chemical Composition of Essential Oil and Antioxidant and Antimicrobial Properties of Extracts and Essential Oil. Ind. Crops Prod. 2012, 36 (1), 81–87.

48. Đurović S, Micić D, Pezo L, Radić D, Bazarnova JG, Smyatskaya YA, Blagojević S. Influence of the Mowing and Drying on the Quality of the Peppermint (Mentha x Piperita L.) Essential Oil: Chemical Profile, Thermal Properties, and Biological Activity. Ind. Crops Prod. 2022, 177, 114492.

49. Sebai E, Abidi A, Serairi R, Marzouki M, Saratsi K, Darghouth MA, Sotiraki S, Akkari H. Essential Oil of Mentha Pulegium Induces Anthelmintic Effects and Reduces Parasite-Associated Oxidative Stress in Rodent Model. Exp. Parasitol. 2021, 225, 108105.

50. Benabed K, Gourine N, Ouinten M, Bombarda I, Yousfi M. Chemical Composition, Antioxidant and Antimicrobial Activities of the Essential Oils of Three Algerian Lamiaceae Species. Curr. Nutr. Food Sci. 2017, 13 (2), 97–109.

51. Benahmed A, Harfi B, Belkhiri A. Biological Activity of Essential Oils of Mentha Pulegium from Field-Grown and Acclimated in Vitro Plants. Curr. Sci. 2019, 116 (11), 1897–1904.

52. Boukhebti H, Chaker A, Belhadj H, Sahli F, Messaoud R, Laouer H, Harzallah D. Chemical Composition and Antibacterial Activity of Mentha Pulegium L.and Mentha Spicata L. Essential Oils; Der Pharmacia Lettre, 2011, 3(4):267-275.

53. Cherrat L, Espina L, Bakkali M, Pagán R, Laglaoui A. Chemical Composition, Antioxidant and Antimicrobial Properties of Mentha Pulegium, Lavandula Stoechas and Satureja Calamintha Scheele Essential Oils and an Evaluation of Their Bactericidal Effect in Combined Processes. Innov. Food Sci. Emerg. Technol. 2014, 22, 221–229.

54. Amalich S, Zerkani H, Cherrat A, Soro NK, Bourakhouadar M, Mahjoubi M, Hilali FE, Zair T. Study on Mentha Pulegium L. from M’rirt (Morocco): Antibacterial and Antifungal Activities of a Pulegone-Rich Essential Oil. J. Chem. Pharm. Res. 2016, 8 (5).

55. Chraibi M, Benbrahim KF, Ou-yahyia D, Balouiri M, Farah A. Radical scavenging and disinfectant effect of essential oil from moroccan mentha pulegium. Int. J. Pharm. Pharm. Sci. 2016, 116–119.

56. Mimica-Dukić N, Bozin B, Soković M, Mihajlović B, Matavulj M. Antimicrobial and Antioxidant Activities of Three Mentha Species Essential Oils. Planta Med. 2003, 69 (5), 413–419.

57. Gallucci MN, Oliva M, Casero C, Dambolena J, Luna A, Zygadlo J, Demo M. Antimicrobial Combined Action of Terpenes against the Food-Borne Microorganisms Escherichia Coli, Staphylococcus Aureus and Bacillus Cereus. Flavour Fragr. J. 2009, 24 (6), 348–354.

58. Al Zuhairi JJMJ, Jookar Kashi F, Rahimi-Moghaddam A, Yazdani M. Antioxidant, Cytotoxic and Antibacterial Activity of Rosmarinus Officinalis L. Essential Oil against Bacteria Isolated from Urinary Tract Infection. Eur. J. Integr. Med. 2020, 38, 101192.

59. Faleiro ML. The mode of antibacterial action of essential oils. In: Méndez-Vilas A., editor. Science Against Microbial Pathogens: Communicating Current Research and Technological Advances. Boca Raton, Fla, USA: Brown Walker Press; 2011. Vol. 2, pp. 1143–1156.

60. Chraibi M, Fadil M, Farah A, Lebrazi S, Fikri-Benbrahim K. Antimicrobial Combined Action of Mentha Pulegium, Ormenis Mixta and Mentha Piperita Essential Oils against S. Aureus, E. Coli and C. Tropicalis: Application of Mixture Design Methodology. LWT 2021, 145, 111352.

61. Bouyahya A, Bakri Y, Khay E, Edaoudi F, Talbaoui A, Et-Touys A, Abrini J, Dakka N. Antibacterial, Antioxidant and Antitumor Properties of Moroccan Medicinal Plants: A Review. Asian Pac. J. Trop. Dis. 2017, 7, 57–64. https://doi.org/10.12980/apjtd.7.2017D6-294.

62. Djabou N, Lorenzi V, Guinoiseau E, Andreani S, Giuliani M-C, Desjobert J-M, Bolla J-M, Costa J, Berti L, Luciani A, Muselli A. Phytochemical Composition of Corsican Teucrium Essential Oils and Antibacterial Activity against Foodborne or Toxi-Infectious Pathogens. Food Control 2013, 30 (1), 354–363.

63. Burt S. Essential Oils: Their Antibacterial Properties and Potential Applications in Foods—a Review. Int. J. Food Microbiol. 2004, 94 (3), 223–253.

64. Greenblatt DJ, Abernethy DR, Divoll M. Is Volume of Distribution at Steady State a Meaningful Kinetic Variable? J. Clin. Pharmacol. 1983, 23 (8–9), 391–400.

65. Ghose AK, Herbertz T, Hudkins RL, Dorsey BD, Mallamo JP. Knowledge-Based, Central Nervous System (CNS) Lead Selection and Lead Optimization for CNS Drug Discovery. ACS Chem. Neurosci. 2012, 3 (1), 50–68.

66. Zanger UM, Schwab M. Cytochrome P450 Enzymes in Drug Metabolism: Regulation of Gene Expression, Enzyme Activities, and Impact of Genetic Variation. Pharmacol. Ther. 2013, 138 (1), 103–141.

67. Varma MVS, Feng B, Obach RS, Troutman MD, Chupka J, Miller HR, El-Kattan A. Physicochemical Determinants of Human Renal Clearance. J. Med. Chem. 2009, 52 (15), 4844–4852.