Chemical Composition and Biological Activity of Ferula aucheri Essential Oil

Document Type : Original paper

Authors

1 Department of Pharmacognosy, Faculty of Pharmacy, Tehran University of Medical Sciences, Tehran, Iran.

2 Research Institute of Forest and Rangelands, Tehran, Iran.

Abstract

Background and objectives: Antibiotics resistance and unpleasant side effects of AChE inhibitors have led to an increased interest in herbs as potential sources. Ferula aucheri (Syn: Dorema aucheri) an indigenous species of Ferula (Apiaceae) grows in Iran and is used as food and medicinal plant. The present study was aimed to identify the oil composition and evaluate antimicrobial and AChE inhibitory activity of flowering tops, fruits and roots. Methods: The chemical composition of the oils was recognized by GC and GC‐MS. The antimicrobial effects were assessed on 12 microorganisms by disc diffusion and micro-well dilution methods and AChE inhibitory potentials by a modified version of Ellman's method. Results: Sixty five compounds were identified from different organs and the notable characteristics have been high amounts of sesquiterpenes. Germacrene B (14.96%) and β-caryophyllene (12.87%) were distinguished as major components of flowering tops. Cis-dihydroagarofuran (9.02%) and δ-cadinene (8.28%) were identified as the remarkable constituents of fruit. δ-cadinene (18.25%) and gurjunene (12.62%) were detected from the roots by high content. All volatile oils exhibited lower MICs on Bacillus subtilis, Klebsiella pneumonia, Shigella dysenteriae,and Salmonella paratyphi-A serotype compared with gentamicin. Root and fruit oils were more effective than gentamicin against Escherichia coli and flowering tops oils proved lower MICs versus Staphylococcus aureus. Fruits and root oils showed weak potency for inhibiting AChE with IC50 values 554.05±4.65 and 239.69±3.5 μg/mL, respectively and flowering tops exhibited moderate activity (179.06±4.3 μg/mL). Conclusion: The findings demonstrated that F. aucheri essential oils possessed antimicrobial activities with inhibition properties toward AchE.

Keywords

Main Subjects


[1] Bakkali F, Averbeck D, Idaomar MM. Biological effects of essential oils-a review. Food Chem Toxicol. 2008; 46(2): 446-475.

[2] Panahi M, Banasiak L, Piwczynski M, Puchalka R, Oskolski AA, Spalik K. Phylogenetic relationships among Dorema, Ferula and Leutea (Apiaceae: Scandiceae: Ferulinae) inferred from nrDNA ITS and cpDNA noncoding sequences. Taxon. 2015; 64(4): 770-783.

[3] Kurzyna-Młynik R, Oskolski AA, Downie SR, Kopacz R, Wojewódzka A, Spalik K. Phylogenetic position of the genus Ferula (Apiaceae) and its placement in tribe Scandiceae as inferred from nrDNA ITS sequence variation. Plant Syst Evol. 2008; 274(1-2): 47-66.

[4] Ajani Y, Ajani A, Cordes JM, Watson MF, Downie SR. Phylogenetic analysis of nrDNA ITS sequences reveals realationships within five groups  of Iranian Apiaceae subfamily Apioideae. Taxon. 2008; 57(2): 383-401.

[5] Panahi M, Banasiak Ł, Piwczyński M, Puchałka R, Kanani MR, Oskolski AA, Modnicki D, Miłobędzka A, Spalik K. Taxonomy of the traditional medicinal plant genus Ferula (Apiaceae) is confounded by incongruence between nuclear rDNA and plastid DNA. Bot J Linn Soc. 2018; 188(2): 173-189.

[6] Elibol Z, Menemen Y, Sağiroğlu M, Duman H. A molecular phylogenetic study on some Turkish Ferula (Apiaceae) species using nrDNA ITS sequences. Pak J Bot. 2012; 44(2): 589-594.

[7] Asili J, Sahebkar A, Fazly Bazzaz BS, Sharifi S, Iranshahi M. Identification of essential oil components of Ferula badrakema fruits by GC-MS and 13C NMR methods and evaluation of its antimicrobial activity. J Essent Oil Bear Pl. 2009; 12(1): 7-15.

[8] Nazari Z, Iranshahi M. Biologically active sesquiterpene coumarins from Ferula Species. Phytother Res. 2011; 25(3): 315-323.

[9] Bostghrati Z, Iranshahi M. Ferula species: a rich source of antimicrobial compounds. J Herb Med. 2019; Article ID 100244.

[10] Sepahi E, Tarighi S, Ahmadi FS, Bagheri A. Inhibition of quorum sensing in Pseudomonas aeruginosa by two herbal essential oils from Apiaceae family. J Microbiol. 2015; 53(2): 176-180.

[11] Nahvinejad M, Pourrajab F, Hekmatimoghaddam S. Extract of Dorema aucheri induces PPAR-g for activating reactive oxygen species metabolism. J Herb Med. 2016; 6(4): 171-179.

[12] Akbarian A, Rahimmalek M, Sabzalian MR. Variation in essential oil yield and composition of Dorema aucheri Boiss, an endemic medicinal plant collected from wild populations in natural habitats. Chem Biodivers. 2016; 13(12): 1756-1766.

[13] Mosaddegh M, Naghibi F, Moazzeni H, Pirani A, Esmaeili S.  Ethnobotanical survey of herbal remedies traditionally used in Kohghiluyeh va Boyer Ahmad province of Iran. J Ethnopharmacol. 2012; 141(1): 80- 95.

[14] Rasouli Vani JTaghi Mohammadi MSarami Foroshani MRezazade E. Evaluation of the neuroprotective and antioxidant effects of Dorema aucheri extract on cerebral ischaemia-reperfusion injury in rats. Pharm Biol. 2019; 57(1): 255-262.

[15] Masoudi S, Esmaeili A, Khalilzadeh MA, Rustaiyan A, Moazami N, Akhgar MR, Varavipoor M. Volatile constituents of Dorema aucheri Boiss., Seseli libanotis (L.) W.D. Koch var. armeniacum Bordz. and Conium maculatum L. three Umbelliferae herbs growing wild in Iran. Flavour Fragr J. 2006; 21(5): 801-804.

[16] Khan A, Farooq U, Ullah F, Iqbal J, Khan AF, Sumera Z, Khan AR, Azarpira A. Determination of biological activities and total phenolic contents of flowers of Jasminum humile and roots of Dorema aucheri. J Chem Soc Pak. 2014; 36(2): 291-295.

[17] Van den Dool H, Kratz PD. A generalization of the retention index system including linear temperature programmed gas-liquid partition chromatography. J Chromatogr A. 1963; 11: 463-471.

[18] Massada Y. Analysis of essential oil by gas chromatography and spectrometry. New York: Wiley, 1976.

[19] Adams RP. Identification of essential oil components by gas chromatography, quadrupole mass spectroscopy. 3rd ed. Carol Stream: Allured Publishing Co, 2001.

[20] Murray PR, Baron EJ, Jorgensen JH, Pfaller MA, Yolken RH. Manual of clinical microbiology. Washington, DC: American Society for Microbiology Press, 2003.

[21] Tavakoli S, Yassa N, Delnavazi MR, Akhbari M, Hadjiakhoondi A, Hajimehdipoor H, Hajiaghaee R. Chemical composition and biological activities of the essential oils from different parts of Ferulago trifida Boiss. J Essent Oil Res. 2017; 29(5): 407-419.

[22] Snoussi M, Noumi E, Trabelsi N, Flamini G, Papetti A, De Feo V. Mentha spicata essential oil: chemical composition, antioxidant and antibacterial activities against planktonic and biofilm cultures of Vibrio spp. Strains. Molecules. 2015; 20(8): 14402-14424.

[23] Ellman GL, Courtney KD, Andres V, Featherstone RM. A new and rapid colorimetric determination of acetylcholinesterase activity. Biochem Pharmacol. 1961; 7(2): 88-95.

[24] Arjmand Z, Dastan D. Chemical characterization and biological activity of essential oils from the aerial part and root of Ferula haussknechtii. Flavour Fragr J. 2020; 35(1): 114-123.

[25] Sadeghei Takallo M, Sajjadifar S, Mansouji Avval M. Chemical composition of the essential oils from flowers, stems and roots of Dorema ammoniacum D. Don from Iran. Res J Pharm Biol Chem Sci. 2013; 4(4): 640-644.

[26] Alipour Z, Taheri P, Samadi N. Chemical composition and antibacterial activity of the essential oils from flower, leaves and stem of Ferula cupularis growing wild in Iran. Pharm Biol. 2015; 53(4): 483-487. 

[27] Yousefzadi M, Heidari M, Akbarpour M, Mirjalili MH, Zeinali A, Parsa M. In vitro cytotoxic activity of the essential oil of Dorema ammoniacum D. Don. Middle East J Sci Res. 2011; 7(4): 511-514.

[28] Ghasemi Y, Faridi P, Mehregan I, Mohagheghzadeh A. Ferula gummosa fruits: an aromatic antimicrobial agent. Chem Nat Compd. 2005; 41(3): 311-314.

[29] Delnavazi MR, Tavakoli S, Rustaie A, Batooli H, Yassa N. Antioxidant and antibacterial activities of the essential oils and extracts of Dorema ammoniacum roots and aerial parts. Res J Pharmacogn. 2014; 1(4): 11-18.

[30] Delnavazi MR, Hadjiakhoondi A, Delazar A, Ajani Y, Yassa N. Azerosides A and B: Two new phloroacetophenone glycosides from the roots of Dorema glabrum Fisch. & C.A. Mey. Med Chem Res. 2014; 24(2): 787-796.

[31] Asnaashari S, Dadizadeh E, Talebpour AH, Eskandani M, Nazemiyeh H. Free radical scavenging potential and essential oil composition of the Dorema glabrum Fisch. CA Mey roots from Iran. BioImpacts. 2011; 1(4): 241-244.

[32] Delnavazi MR, Hadjiakhoondi A, Delazar A, Ajani Y, Tavakoli S, Yassa N. Phytochemical and antioxidant investigation of the aerial parts of Dorema glabrum Fisch. & C.A. Mey. Iran J Pharm Res. 2015; 14(3): 925-931.

[33] Khanahmadi M, Miraghaee SS, Karimi I. Evaluation of the antioxidant and antimicrobial properties of Dorema aucheri plant. Iran Red Cres Med J. 2012; 14(10): 684-685.

[34] Kamyab Moghadas B, Safekordi AA, Honarvar B, Fathi kaljahi J, Vaziri Yazdi SA. Experimental study of Dorema aucheri extraction with supercritical carbon dioxide. Asian J Chem. 2012; 24(8): 3691-3694.

[35] Tabatabaei Yazdi F, Alizadeh Behbahani B, Vasiee A, Mortazavi SA, Tabatabaei Yazdi F. An investigation on the effect of alcoholic and aqueous extracts of Dorema aucheri (Bilhar) on some pathogenic bacteria in vitro. J Paramed Sci.2015; 6(1): 58-64.

[36] Mahizan NK, Yang SK, Moo CL, Song AAL, Chong CM, Chong CW, Abushelaibi A, Lim SE, Lai KS. Terpene derivatives as a potential agent against antimicrobial resistance (AMR) pathogens. Molecules. 2019; 24(14): 2631-2652.

[37] Tariq S, Wani S, Rasool W, Shafi K, Bhata MA, Prabhakar A, Shalla AH, Rathera MA. A comprehensive review of the antibacterial, antifungal and antiviral potential of essential oils and their chemical constituents against drug resistant microbial pathogens. Microb Pathog. 2019; 134: 103580-103600.

[38] Santos TC, Gomes TM, Pinto BAS, Camara AL, Paes AMA. Naturally occurring acetylcholinesterase inhibitors and their potential use for Alzheimer's disease therapy. Front Pharmacol. 2018; 9: 1192-1206.

[39] Owokotomo IA, Ekundayo O, Abayomi TG, Chukwuka AV. In-vitro anti-cholinesterase activity of essential oil from four tropical medicinal plants. Toxicol Rep. 2015; 2: 850-857.

[40] Patel MB, Amin D. Sphaeranthus indicus flower derived constituents exhibits synergistic effect against acetylcholinesterase and possess potential antiamnestic activity. J Complement Integr. 2012; 9(1): 1-14.

[41] Yu ZW, Wang BC, Yang FM, Sun QY, Yang ZN, Zhu LC. Chemical composition and anti-acetylcholinesterase activity of flower essential oils of Artemisia annua at different flowering stage. Iran J Pharm Res. 2011; 10(2): 265-271.