Chemical Composition and Pharmacological Activities of <i>Calamintha nepeta</i> Essential Oil

Authors

  • Somia Zaoui Department of Biology , Laboratory of Microbiology and Plant Biology, Faculty of Nature and Life Sciences, Abdelhamid Ibn Badis University, 27000 BP, Mostaganem, Algeria.
  • Fouad Bahri Department of Biology , Laboratory of Microbiology and Plant Biology, Faculty of Nature and Life Sciences, Abdelhamid Ibn Badis University, 27000 BP, Mostaganem, Algeria.
  • Hachemi Benhassaini Department of Agronomy Sciences, Laboratory of Conservation and Valorization, DjillaliLiabes University, Sidi Bel Abbes 22000, Algeria
  • Antoni Szumny Department of Food Chemistry and Biocatalysis,Faculty of Biotechnology and Food Science, Wrocaw University of Environmental and Life Sciences, 50-375 Wroclaw, Poland.
  • Karima Bentaiba Department of Biology , Laboratory of Sciences and Technics of Animal Production, Faculty of Nature and Life Sciences Abdelhamid Ibn Badis University, 27000 BP, Mostaganem, Algeria

DOI:

https://doi.org/10.26538/tjnpr/v8i5.8%20%20

Keywords:

pharmological activites, phytochemical, Anti-inflammatory activity, Antioxidant activity, Antimicrobial activity, GC-MS, Essential oil, Calamintha nepeta

Abstract

Calamintha nepeta (Lamiaceae), widely distributed throughout the Mediterranean area, is a small and fragrant perennial herb traditionally used for both culinary and medicinal purposes. It serves as an antiseptic, spasmolytic, diuretic, and cough suppressant. The objective of this research is to characterise the chemical constituents of Calamintha nepeta essential oil (EO) through GC-MS analysis and evaluate its antioxidant and antimicrobial properties against nine multidrug resistant bacterial strains and one yeast. The study also conducted an in vitro anti-inflammatory 5-lipoxygenase inhibition test and determined its lethal dose 50 (LD50) as well as the effects against carrageenan-induced paw edema in vivo. Analysis revealed that the primary components of C. nepeta included oxygenated monoterpenes, notably pulegone (58.36%), isoborneol (10.40%), menthone (8.91%), and piperitenone (3.86%). Antimicrobial tests demonstrated significant inhibition zones ranging from 10.2 to 37.12 mm. Essential oil exhibited minimum inhibitory concentrations and bactericidal/fungicidal concentrations ranging from 0.937 to 3.75 µL/mL and 0.937 to 15 µL/mL, respectively. Furthermore, it showed potent antioxidant activity against DPPH and a high total reducing power. Acute oral toxicity tests in Wistar rats indicated an LD50 of 2500 mg/kg. C. nepeta EO also exhibited strong anti-inflammatory properties against carrageenan-induced paw edema, with an IC50 value of 17.23 ± 0.32 μg/mL compared to diclofinac. Interestingly, this research highlights the importance of the phytochemical and antimicrobial properties of the essential oil of the Calamintha nepeta and accentuats its importance in pharmacological applications for treating inflammatory conditions.

References

Mahat MA, Patil BM. Evaluation of antiinflammatory activity of methanol extract of Phyllanthus amarus in experimental animal models. Indian J Pharm Sci. 2007;69(1):33-36. doi:10.4103/0250-474x.32104

Ingawale DK, Mandlik SK, Patel SS. An emphasis on molecular mechanisms of anti-inflammatory effects and glucocorticoid resistance. J Complement Integr Med. 2015;12(1):1-13. doi:10.1515/jcim-2014-0051

Sosa S, Balick MJ, Arvigo R, Esposito RG, Pizza C, Altinier G, Tubaro A. Screening of the topical anti-inflammatory activity of some Central American plants. J Ethnopharmacol. 2002;81(2):211-215. doi:10.1016/S0378-8741(02)00080-6

Roediger B, Weninger W. Resolving a chronic inflammation mystery. Nat Med. 2017;23(8):914-916. doi:10.1038/nm.4384

Ayoola GA, Akpanika GA, Awobajo FO, Sofidiya MO, Osunkalu VO, Odugbemi TO. Anti-Inflammatory Properties of the Fruits of. Bot Res Int. 2009;2(1):21-26.

W.H.O. Traditional Medicine Strategy (2002–2005). WHO/EDM/TRM/2002.1. Published online 2002.

Roy P, Amdekar S, Kumar A, Singh V. Preliminary study of the antioxidant properties of flowers and roots of Pyrostegia venusta (Ker Gawl) Miers. BMC Complement Altern Med. 2011;11(69):1-8. doi:10.1186/1472-6882-11-69

Bolouri P, Salami R, Kouhi S, Kordi M, Lajayer BA, Hadian J, Astatkie T. Applications of Essential Oils and Plant Extracts in Different Industries. Molecules. 2022;27(12):1-17.

Popović-Djordjević J, Cengiz M, Ozer MS, Sarikurkcu C. Calamintha incana: Essential oil composition and biological activity. Ind Crops Prod. 2019;128(10):162-166. doi:10.1016/j.indcrop.2018.11.003

Kampasakali E, Nakas A, Mertzanidis D, Kokkini S, Assimopoulou AN, Christofilos D. µ -Raman Determination of Essential Oils ’ Constituents from Distillates and Leaf Glands of Origanum Plants. Molecules. 2023;28(1):1-15.

Usai F, Sotto A Di. trans -Cinnamaldehyde as a Novel Candidate to Overcome Bacterial Resistance : An Overview of In Vitro Studies. antibiotics. 2023;12(1):1-19.

Abbad I, Bouchrab S, Abdelazizb A. Chemical composition, insecticidal and allelopathic properties of essential oils obtained from wild and cultivated Moroccan Satureja calamintha (L.) Abbad. J Nat Pestic Res. Published online 2023. doi:10.1016/j.napere.2023.100021

Medjdoub AR, Benmehdi H, Oukali Z. Chemical Composition And Antifungal Activity Of Essential Oil Of Satureja Calamintha Spp . Nepeta ( L .) Briq Against Some Toxinogenous Mold. Nat Volaitles Essent oils. 2022;9(1):1981-2000.

Bouzidi N, Mederbal K, Bouhadi D. Chemical composition of the essential oil of Satureja calamintha subsp. Nepeta of west Algerian. Moroccan J Chem. 2018;6(2):213-217.

Ceker S, Agar G, Alpsoy L, Nardemir G, Kizil HE. Protective role of essential oils of Calamintha nepeta L. on oxidative and genotoxic damage caused by aflatoxin B1in vitro. Fresenius Environ Bull. 2013;22(11):3258-3263.

Božovic M, Garzoli S, Sabatino M, Pepi F, Baldisserotto A, Andreotti E, Romagnoli C, Mai A, Manfredini S, Ragno R. Essential oil extraction, chemical analysis and anti-candida activity of calamintha nepeta (L.) Savi subsp. glandulosa (Req.) ball-new approaches. Molecules. 2017;22(2):1-12. doi:10.3390/molecules22020203

Negro C, Notarnicola S, De Bellis L, Miceli A. Intraspecific variability of the essential oil of Calamintha nepeta subsp. nepeta from Southern Italy (Apulia). Nat Prod Res. 2013;27(4-5):331-339. doi:10.1080/14786419.2012.691495

Demirci B, Temel HE, Portakal T, Kirmizibekmez H, Demirci F, Başer KHC. Inhibitory effect of calamintha nepeta subsp.glandulosa essential oil on lipoxygenase. Turkish J Biochem. 2011;36(4):290-295.

Marongiu B, Piras A, Porcedda S, Falconieri D, Maxia A, Goncalves MJ, Cavaleiro C, Salgueiro L. Chemical composition and biological assays of essential oils of Calamintha nepeta (L.) Savi subsp. nepeta (Lamiaceae). Nat Prod Res. 2010;24(9):1734-1742. doi:10.1080/14786410903108944

Božović M, Ragno R. Calamintha nepeta (L.) Savi and its main essential oil constituent pulegone: Biological activities and chemistry. Molecules. 2017;22(2). doi:10.3390/molecules22020290

Arantes SM, Piçarra A, Guerreiro M, Salvador C, Candeias F, Caldeira AT, Martins MR. Toxicological and pharmacological properties of essential oils of Calamintha nepeta, Origanum virens and Thymus mastichina of Alentejo (Portugal). Food Chem Toxicol. 2019;133(2). doi:10.1016/j.fct.2019.110747

Tu XF, Hu F, Thakur K, Li XL, Zhang YS, Wei ZJ. Comparison of antibacterial effects and fumigant toxicity of essential oils extracted from different plants. Ind Crops Prod. 2018;124(7):192-200. doi:10.1016/j.indcrop.2018.07.065

Queiroga MC, Pinto Coelho M, Arantes SM, Potes ME, Martins MR. Antimicrobial Activity of Essential Oils of Lamiaceae Aromatic Spices Towards Sheep mastitis-Causing Staphylococcus aureus and Staphylococcus epidermidis. J Essent Oil-Bearing Plants. 2018;21(5):1155-1165. doi:10.1080/0972060X.2018.1491330

Mirniyam G, Rahimmalek M, Arzani A, Matkowski A, Gharibi S, Szumny A. Changes in Essential Oil Composition, Polyphenolic Compounds and Antioxidant Capacity of Ajowan (Trachyspermum ammi L.) Populations in Response to Water Deficit. Foods. 2022;11(9). doi:10.3390/foods11193084

Łyczko J, Kiełtyka-Dadasiewicz A, Skrzyński M, Klisiewicz K, Szumny A. Chemistry behind quality – The usability of herbs and spices essential oils analysis in light of sensory studies. Food Chem. 2023;411(6). doi:10.1016/j.foodchem.2023.135537

Kwaśnica A, Pachura N, Carbonell-Barrachina ÁA, Issa-Issa H, Szumny D, Figiel A, Masztalerz K, Klemens M, Szumny A. Effect of Drying Methods on Chemical and Sensory Properties of Cannabis sativa Leaves. Molecules. 2023;28(12). doi:10.3390/molecules28248089

CLSI. Performance Standards for Antimicrobial Disk Susceptibility Tests: Approved Standard - Eleventh Edition. Vol 32.; 2012. doi:M02-A11

Sharma K, Guleria S, Razdan VK, Babu V. Synergistic antioxidant and antimicrobial activities of essential oils of some selected medicinal plants in combination and with synthetic compounds. Ind Crops Prod. 2020;154(5). doi:10.1016/j.indcrop.2020.112569

Hamed D, Keddari S, Boufadi MY, Bessad L. Lycopene Purification with DMSO anti-solvent: Optimization using Box-Behnken’s experimental design and evaluation of the synergic effect between

lycopene and Ammi visnaga.L essential oil. Chem Pap. 2022;76(6):6335-6347. doi:10.1007/s11696-022-02302-0

Ouguirti N, Bahri F, Bouyahyaoui A, Wanner J. Chemical characterization and bioactivities assessment of artemisia herba-alba asso essential oil from South-Western Algeria. Nat Volatiles Essent Oils. 2021;8(2):27-36. doi:10.37929/nveo.844309

Boussena A, Bahri F, Bouyahyaoui A, Kouidri M, Meziane M. Screening of Phytochemical, Evaluation of Phenolic Content, Antibacterial and Antioxydant Activities of Ephedra Alata From the Algerian Sahara. J Appl Biol Sci E. 2022;16(2):220-229. doi:10.5281/zenodo.6590258

Duraisamy N, Sangeetha D, Shaik MR, Shaik AH, Shaik J ilan. P, Shaik B. Evaluation of Antioxidant, Cytotoxic, Mutagenic and Other Inhibitory Potentials of Green Synthesized Chitosan Nanoparticles. crystals. 2022;12(10):1-16. doi:10.1201/b13120

Bentaiba K, Belhocine M, Chougrani F, Bououdina M, Mostari A, Fernini M, Bouzouina M. Effectiveness of Withania frutescens root extract on testicular damage induced by lead acetate in adult albino rats. Reprod Toxicol. 2023;115(12):102-110. doi:10.1016/j.reprotox.2022.12.006

OECD. The Organization of Economic Co-operation and Development Guidelines Test No. 423: Acute Oral toxicity - Acute Toxic Class Method, OECD Guidelines for the Testing of Chemicals, Section 4. Oecd. 2001;(2):1-14.

Winter CA, Risley EA, Nuss GW. Carrageenin-induced edema in hind paw. Exp Biol Med. 1962;3(9):544-547.

Andrade C, Ferreres F, Gomes NGM, Duangsrisai S, Srisombat N, Vajrodaya S, Pereira DM, Gil-Izquierdo A, Andrade PB, Valentão P. Phenolic profiling and biological potential of ficus curtipes corner leaves and stem bark: 5-Lipoxygenase inhibition and interference with NO Levels in LPS-stimulated RAW264.7 Macrophages. Biomolecules. 2019;9(9):1-17. doi:10.3390/biom909040037.

Boutoub O, El-Guendouz S, Manhita A, Dias CB, Estevinho LM, Paula VB, Carlier J, Costa MC, Rodrigues B, Raposo S, Aazza S, El Ghadraoui L, Miguel MG.Comparative study of the antioxidant and enzyme inhibitory activities of two types of moroccan euphorbia entire honey and their phenolic extracts. Foods. 2021;10(8). doi:10.3390/foods10081909

Kerbouche L, Hazzit M, Baaliouamer A. Essential Oil of Satureja calamintha subsp. nepeta (L.) Briq. from Algeria: Analysis, Antimicrobial and Antioxidant Activities. TBAP 3. 2013;3(4):266-272. doi:10.1080/22311866.2013.833466

Labiod R, Aouadi S, Bouhaddouda N. Chemical composition and antifungal activity of essential oil from satureja calamintha nepeta against phytopathogens fungi. Int J Pharm Pharm Sci. 2015;7(7):208-211.

Ambrico A, Trupo M, Martino M, Sharma N. Essential oil of Calamintha nepeta (L.) Savi subsp. nepeta is a potential control agent for some postharvest fruit diseases. Org Agric. Published online 2019:35-48. doi:10.1007/s13165-019-00251-9

Arantes S, Piçarra A, Candeias F, Caldeira AT, Martins MR, Teixeira D. Antioxidant activity and cholinesterase inhibition studies of four flavouring herbs from Alentejo. Nat Prod Res. 2017;31(1):2183-2187. doi:10.1080/14786419.2017.1278598

Gormez A, Bozari S, Yanmis D, Gulluce M, Sahin F, Agar G. Chemical composition and antibacterial activity of essential oils of two species of Lamiaceae against phytopathogenic bacteria. Polish J Microbiol. 2015;64(2):121-127. doi:10.33073/pjm-2015-018

Sbayou H, Ababou B, Boukachabine K, Zerouali AMK, Souad A. Chemical composition and antibacterial activity of Mentha pulegium L. and Mentha spicata L. essential oils. J Life Sci. 2014;8(1):35-41.

Garzoli S, Pirolli A, Vavala E, Di Sotto A, Sartorelli G, Božović M, Angiolella L, Mazzanti G, Pepi F, Ragno R. Multidisciplinary approach to determine the optimal time and period for extracting the essential oil from mentha suaveolens ehrh. Molecules. 2015;20:9640-9655. doi:10.3390/molecules20069640

Khodja NK, Boulekbache L, Chegdani F, Dahmani K, Bennis F, Madani K. Chemical composition and antioxidant activity of phenolic compounds and essential oils from Calamintha nepeta L. J Complement Integr Med. 2018;15(4):1-12. doi:10.1515/jcim-2017-0080

Alsaraf S, Hadi Z, Al-Lawati WM, Al Lawati AA, Khan SA. Chemical composition, in vitro antibacterial and antioxidant potential of Omani Thyme essential oil along with in silico studies of its major constituent. J King Saud Univ - Sci. 2020;32(1):1021-1028. doi:10.1016/j.jksus.2019.09.006

Monforte MT, Tzakou O, Nostro A, Zimbalatti V, Galati EM. Chemical Composition and Biological Activities of Calamintha officinalis Moench Essential Oil. J Med Food. 2011;14(3):297-303.

Khan S, Khan T, Shah AJ. Total Phenolic and Flavonoid Contents and Antihypertensive Effect of the Crude Extract and Fractions of Calamintha vulgaris. Phytomedicine. Published online 2018. doi:10.1016/j.phymed.2018.04.046

Jean YH, Chen WF, Duh CY, Huang SY, Hsu CH, Lin CS, Sung CS, Chen IM, Wen ZH. Inducible nitric oxide synthase and cyclooxygenase-2 participate in anti-inflammatory and analgesic effects of the natural marine compound lemnalol from Formosan soft coral Lemnalia cervicorni. Eur J Pharmacol. 2008;578(2-3):323-331. doi:10.1016/j.ejphar.2007.08.048

Huang SY, Chen NF, Chen WF, Hung HC, Lee HP, Lin YY, Wang HM, Sung PJ, Sheu JH, Wen ZH. Sinularin from indigenous soft coral attenuates nociceptive responses and spinal neuroinflammation in carrageenan-induced inflammatory rat model. Mar Drugs. 2012;10(9):1899-1919. doi:10.3390/md10091899

Coruzzi G, Adami M, Guaita E, de Esch IJP, Leurs R. Antiinflammatory and antinociceptive effects of the selective histamine H4-receptor antagonists JNJ7777120 and VUF6002 in a rat model of carrageenan-induced acute inflammation. Eur J Pharmacol. 2007;563(1-3):240-244. doi:10.1016/j.ejphar.2007.02.026

Solanki HK, Shah DA, Maheriya PM, Patel CA. Evaluation of anti-inflammatory activity of probiotic on carrageenan-induced paw edema in Wistar rats. Int J Biol Macromol. 2015;72:1277-1282. doi:10.1016/j.ijbiomac.2014.09.059

Karim N, Khan I, Khan W, Khan I, Khan A, Halim SA, Khan H, Hussain J, Al-Harrasi A. Anti-nociceptive and anti-inflammatory activities of asparacosin a involve selective cyclooxygenase 2 and inflammatory cytokines inhibition: An in-vitro, in-vivo, and in-silico approach. Front Immunol. 2019;10(3):1-11. doi:10.3389/fimmu.2019.00581

Amraoui A, Bahri F, Wanner J. Chemical composition, anti-inflammatory and antimicrobial activity of algerian Ammi visnaga essential oil. Plant Arch J. 2022;22(1):249-254.

Mammeri B, Bahri F, Kouidri M, Boudani B, Arioui F. Evaluation of chemical composition , anti- inflammatory , antibacterial activity and synergistic effect between antibiotics and the essential oil of Artemisia campestris L . J Appl Biol Sci. 2022;16(2):230-247. doi:10.5281/zenodo.6590285

Mekkaoui M, Bouidida EH, Naceiri Mrabti H, Ouaamr A, Lee LH, Bouyahya A, Cherrah Y, Alaoui K. Investigation of Chemical Compounds and Evaluation of Toxicity, Antibacterial, and Anti-Inflammatory Activities of Three Selected Essential Oils and Their Mixtures with Moroccan Thyme Honey. Foods. 2022;11:1-20. doi:10.3390/foods11193141

Bidian C, Filip GA, David L, Moldovan B, Baldea I, Olteanu D, Filip M, Bolfa P, Potara M, Toader AM, Clichici S. Viburnum opulus fruit extract-capped gold nanoparticles attenuated oxidative stress and acute inflammation in carrageenan-induced paw edema model. Green Chem Lett Rev. 2022;15(2):319-335. doi:10.1080/17518253.2022.2061872

Smain A, Martin D, Guillemo S, josé-Luis Ríos. Anti-inflammatory, anti-oxidant, and apoptotic activities of four plant species used in folk medicine in the Mediterranean basin. Pak J Pharm Sci. 2012;25(1):65-72.

Kameda, J. MK, Miyazawa M. Cyclooxygenase-2 inhibitory effects of monoterpenoids with a p-menthane skeleton. Int J Essent Oil. 2008;4(2):145-148. doi:10.1177/1934578x1701200734

Hilfiger L, Triaux Z, Marcic C, Héberlé E, Emhemmed F, Darbon P, Marchioni E, Petitjean H, Charlet A. Anti-Hyperalgesic Properties of Menthol and Pulegone. Front Pharmacol. 2021;12(9):1-13. doi:10.3389/fphar.2021.753873

Ali-Rachedi F, Meraghni S, Touaiba N, Sabrina M. Quantitative analysis of phenolic compounds of an Algerian endemic Scabiosa Atropurpurea sub.Maritima L. Manuscript. Bull la Société R des Sci Liège. 2018;87(2):13-21.

Lin YY, Jean YH, Lee HP, Chen WF, Sun YM, Su JH, Lu Y, Huang SY, Hung HC, Sung PJ, Sheu JH, Wen ZH. A Soft Coral-Derived Compound, 11-epi-Sinulariolide Acetate Suppresses Inflammatory Response and Bone Destruction in Adjuvant-Induced Arthritis. PLoS One. 2013;8(5):1-11. doi:10.1371/journal.pone.0062926

Serhan CN, Savill J. Resolution of inflammation: The beginning programs the end. Nat Immunol. 2005;6(12):1191-1197. doi:10.1038/ni1276

Wang H, Li Y, Li Z, Ma R, Bai X, Zhan X, Luo K, Su R, Li X, Xia X, Shi C. Inhibition of Cronobacter sakazakii by Litsea cubeba Essential Oil and the Antibacterial Mechanism. Foods. 2022;11(12):1-17. doi:10.3390/foods11233900

Cervello M, Montalto G. Cyclooxygenases in hepatocellular carcinoma. World J Gastroenterol. 2006;12(6):5113-5121. doi:10.3748/wjg.v12.i32.5113

Njenga EW, Viljoen AM. In vitro 5-lipoxygenase inhibition and anti-oxidant activity of Eriocephalus L. (Asteraceae) species. South African J Bot. 2006;72(4):637-641. doi:10.1016/j.sajb.2006.03.007

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Published

2024-05-30

How to Cite

Zaoui, S., Bahri, F., Benhassaini, H., Szumny, A., & Bentaiba, K. (2024). Chemical Composition and Pharmacological Activities of <i>Calamintha nepeta</i> Essential Oil. Tropical Journal of Natural Product Research (TJNPR), 8(5), 7097–7105. https://doi.org/10.26538/tjnpr/v8i5.8