Variation of Eryngo (Eryngium caeruleum M.Bieb.) Essential Oil Content and Biological Activity in Wild and Cultivated Conditions

Document Type : Research Paper

Authors

1 Razi Herbal Medicines Research Center, Lorestan University of Medical Sciences, Khorramabad, Iran

2 Department of Pharmacognosy, Faculty of Pharmacy, Lorestan University of Medical Sciences, 6815144309, Khorramabad, Lorestan Province, Iran

3 Department of Organic Chemistry, Faculty of Chemistry, University of Mazandaran, Babolsar, 47416-95447, Iran

4 Department of Biology, Medicinal Plants and Drugs Research Institute, Shahid Beheshti University, G. C., Evin, Tehran, Iran

5 Student Research Committee, Faculty of Pharmacy, Lorestan University of Medical Sciences

Abstract

In this investigation essential oils of the wild and cultivated Eryngium caeruleum M.Bieb. were analysed by GC and GC/MS, and screened for their antimicrobial activities. At least seventy-three ingredients were identified in both specimens that limonene (16.4-32.3%), β-bisabolol (10.3-17.3%), δ-3-carene (6.6-9.4%), cis-limonene oxide (3.1-7.8%), (E)-β-farnesene (4.4-4.8%) and β-sesquiphellandrene (2.4-2.9%) were the major components. Also, the antibacterial and the antimycotic activities of these oils were reported against six bacterial and fungal strains. The antibacterial analysis displayed that both oils presented high activity versus all the tested Gram-negative strains in a range of MIC values from 4 to 8 mg/ml. The antifungal test results proved moderate activity against Candida krusei and Candida albicans (MIC values 1 to 4 mg/ml). Our results, have been proved that cultivation and domestication of this plant seems improved the microbial test results for the cultivated sample. These are aspects that turn this plant into useful crops for domestication and commercialization. Results of this investigation propose that it is noteworthy to grow this herb by the farmers in Babol, Mazandaran, Iran for pharmaceutical, therapeutic and food targets and natural bactericide agent.

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  1. Fayed E.M., Abd‐EIGawad A.M., Elshamy A.I., El‐Halawany E.S., EI‐Amier Y.A. Essential oil of Deverra tortuosa aerial parts: Detailed chemical profile, allelopathic, antimicrobial, and antioxidant activities. Chem. Biodivers. 2021; 18(4): 441-452.
  2. Kazemeini F., Asri Y., Mostafavi G., Kalvandi R., Mehregan I. Assessment of genetic diversity, population structure and morphological analyses in an Iranian endemic species Rhabdosciadium aucheri Boiss.(Apiaceae) using ISSR markers. Biologia. 2021; 76:441-51.
  3. Sonboli A., Mirzania F., Gholipour A. Essential oil composition of Dracocephalum kotschyi Boiss. from Iran. Nat. Prod. Res. 2019; 33(14):2095-8.
  4. Mozaffarian V. Umbelliferae. In: Flora of Iran. 2007. Research Institute of Forests and Rangelands, Tehran.
  5. Parveen I., Techen N., Khan I.A. Identification of species in the aromatic spice family Apiaceae using DNA mini-barcodes. Planta Med. 2019; 85(02):139-44.
  6. Mohammed M.S., Tawfik M.S., Ibrahim A.E. Influence of two extraction methods on essential oils of some Apiaceae family plants. Egypt. Pharm. J. 2019; 18(2):160.
  7. Zengin G., Mahomoodally M.F., Paksoy M.Y., Picot-Allain C, Glamocilja J, Sokovic M, Diuzheva A, Jekő J, Cziáky Z., Rodrigues M.J., Sinan K.I. Phytochemical characterization and bioactivities of five Apiaceae species: Natural sources for novel ingredients. Ind. Crops Prod. 2019; 135:107-21.
  8. Wang P., Su Z., Yuan W., Deng G., Li S. Phytochemical constituents and pharmacological activities of Eryngium L.(Apiaceae). Pharmaceutical Crops. 2012, 3: 99-120.
  9. Gaudeul M., Till-Bottraud I., Barjon F., Manel S. Genetic diversity and differentiation in Eryngium alpinum L.(Apiaceae): comparison of AFLP and microsatellite markers. Heredity. 2004; 92(6):508-18.
  10. Calvino C.I., Martínez S.G., Downie S.R. The evolutionary history of Eryngium (Apiaceae, Saniculoideae): Rapid radiations, long distance dispersals, and hybridizations. Mol. Phylogenet. Evol. 2008; 46(3):1129-50.
  11. Benmerache A., Magid A.A., Berrehal D., Kabouche A., Voutquenne-Nazabadioko L., Messaili S., Abedini A., Harakat D., Kabouche Z. Chemical composition, antibacterial, antioxidant and tyrosinase inhibitory activities of glycosides from aerial parts of Eryngium tricuspidatum L. Phytochem. Lett. 2016; 18:23-8.
  12. Ghahreman A. Flora of Iran. 1997, Recearch Institute of Forests and Rangelands, Tehran.
  13. Khoshbakht K., Hammer K., Pistrick K. Eryngium caucasicum Trautv. cultivated as a vegetable in the Elburz Mountains (Northern Iran). Genet. Resour. Crop Evol. 2007; 54:445-8.
  14. Riekandeh S.M., Mazandarani M., Ebrahimzadeh M.A., Zargari M. Antioxidant activities of Eryngium caucasicum inflorescence. Eur. Rev. Med. Pharmacol. Sci. 2016; 20(5):946-9.
  15. Ebrahimzadeh M.A., Chitsaz Z., Shokrzadeh M., Ataie A., Ataee R. Evaluation of anticonvulsant activities of eryngium caucasicum with maximal electroshock and kindling model of seizure in mice. IJPBS. 2017; 11(1): 1-5.
  16. Morteza-Semnani K. Essential oil composition of Eryngium bungei Boiss. J. Essent. Oil Res. 2005; 17(5):485-6.
  17. Adams, P.R. Identification of Essential Oils Components by Gas Chromatography/ Quadrupole Mass Spectroscopy, 2007, Allured Publishing, Carol Stream, United States.
  18. Jorgensen J.H., Turnidge J.D. Susceptibility test methods: Dilution and disk diffusion methods, DC: Manual of Clinical Microbiology, 2007, ASM Press, Washington.
  19. Ana V., Espinel-Ingroff, A.V. and Pfaller, M.A. Susceptibility Test Methods: Yeasts and Filamentous Fungi, Manual of Clinical Microbiology, 2007, ASM Press, Washington.
  20. Hashemabadi D., Kaviani B., Erfatpour M., Larijani K. Comparison of essential oils compositions of eryngo (Eryngium caucasicum Trautv.) at different growth phases by hydrodistillation method. Plant Omics. 2010; 3(4):135-9.
  21. Hashemabadi D., Kaviani B. Chemical constituents of essential oils extracted from the leaves and stems of Eryngium caucasicum Trautv. from Iran. J. Essent. Oil-Bear. Plants. 2011; 14(6):693-8.
  22. Tohidi B., Rahimmalek M., Arzani A. Essential oil composition, total phenolic, flavonoid contents, and antioxidant activity of Thymus species collected from different regions of Iran. Food chem. 2017; 220:153-61.
  23. Sefidkon F., Dabiri M., Alamshahi A. Chemical composition of the essential oil of Eryngium billardieri F. Delaroche from Iran. J. Essent. Oil Res. 2004; 16(1):42-3.
  24. Palá-Paúl J., Perez-Alonso M.J., Velasco-Negueruela A., Vadaré J., Villa A.M., Sanz J., Brophy J.J. Essential oil composition of the different parts of Eryngium bourgatii Gouan from Spain. Journal of Chromatography A. 2005; 1074(1-2):235-9.
  25. Palá-Paúl J., Brophy J.J., Pérez-Alonso M.J., Usano J., Soria S.C. Essential oil composition of the different parts of Eryngium corniculatum Lam.(Apiaceae) from Spain. J. Chromatogr. A. 2007; 1175(2):289-93.
  26. Mirzania F., Sarrafi Y., Farimani M.M. Comparison of chemical composition, antifungal antibacterial activities of two populations of Salvia macilenta Boiss. Essential oil. Rec. Nat. Prod. 2018; 12: 385-90.
  27. Mirzania F., Sarrafi Y., Moridi Farimani M. Comparative evaluation of chemical compositions and biological activities of wild and cultivated Froriepia subpinnata L. essential oils. JAST. 2019; 21(2):331-40.
  28. Tock M.L., Kamatou G.P., Combrinck S., Sandasi M., Viljoen A.M. A chemometric assessment of essential oil variation of three Salvia species indigenous to South Africa. Phytochem. 2020; 172:112249.
  29. Mirzania F., Moridi Farimani M., Sarrafi Y., Nejad Ebrahimi S., Troppmair J., Kwiatkowski M., Stuppner H., Alilou M. New Sesterterpenoids from Salvia mirzayanii Rech. f. and Esfand. Stereochemical Characterization by Computational Electronic Circular Dichroism. Front. Chem. 2022, 20; 9:1166.
  30. Pirbalouti A.G., Hashemi M., Ghahfarokhi F.T. Essential oil and chemical compositions of wild and cultivated Thymus daenensis Celak and Thymus vulgaris L. Ind. Crops Prod. 2013; 48: 43-8.
  31. Mirzania F., Farimani M.M. Biochemical evaluation of antioxidant activity, phenol and flavonoid contents of dracocephalum kotschyi boiss extracts obtained with different solvents. HBB. 2018; 1:32-44.
  32. Merghache D., Boucherit-Otmani Z., Merghache S., Chikhi I., Selles C., Boucherit K. Chemical composition, antibacterial, antifungal and antioxidant activities of Algerian Eryngium tricuspidatum L. essential oil. Nat. Prod. Res. 2014; 28(11):795-807.
  33. Çelik A., Aydınlık N., Arslan I. Phytochemical constituents and inhibitory activity towards methicillin‐resistant Staphylococcus aureus strains of Eryngium species (Apiaceae). Chem. Biodivers. 2011; 8(3):454-9.
  34. Erdem S.A., Nabavi S.F., Orhan I.E., Daglia M., Izadi M., Nabavi S.M. Blessings in disguise: a review of phytochemical composition and antimicrobial activity of plants belonging to the genus Eryngium. DARU J. Pharm. Sci. 2015; 23:1-22.
  35. Cavaleiro C., Gonçalves M.J., Serra D., Santoro G., Tomi F., Bighelli A., Salgueiro L., Casanova J. Composition of a volatile extract of Eryngium duriaei subsp. juresianum (M. Laínz) M. Laínz, signalised by the antifungal activity. JPBA. 2011; 54(3):619-22.
  36. Merghache D., Boucherit-Otmani Z., Merghache S., Chikhi I., Selles C., Boucherit K. Chemical composition, antibacterial, antifungal and antioxidant activities of Algerian Eryngium tricuspidatum L. essential oil. Nat. Prod. Res. 2014; 28(11):795-807.
  37. Çelik A., Aydınlık N., Arslan I. Phytochemical constituents and inhibitory activity towards methicillin‐resistant Staphylococcus aureus strains of Eryngium species (Apiaceae). Chem. Biodivers. 2011; 8(3):454-9.
  38. Guo R., Duan Z.K., Li Q., Yao G.D., Song S.J., Huang X.X. Guide isolation of guaiane-type sesquiterpenoids from Daphne tangutica maxim. And their anti-inflammatory activities. Phytochem. 2023; 206:113523.
  39. Sefidkon F., Adbollahi M., Salehi Shanjani P., Tavakoli M. Variability in Essential Oil Content and Composition of Achillea tenuifolia Lam. Populations in Field Conditions. JAST. 2021; 23(3):673-83.
  40. Canan S., Ceyhan V. Exploring the farm level opportunity cost for protecting environment: evidence from Turkey. JAST. 2021; 23(2):253-63.
  41. Riahi Rad K., Babaei A., Mozaffarian V., Potter D. Phylogenetic affinities of wild and cultivated Ornithogaloideae based on ITS and trnL–F DNA sequences by extended sampling from Iran. JAST. 2019; 21(4):1005-21.