Chemical composition and radical scavenging activity of essential oil and methanolic extract of Eremostachys azerbaijanica Rech.f. from Iran

Solmaz Asnaashari, Fariba Heshmati Afshar, Atefeh Ebrahimi, Sedigheh Bamdad Moghadam, Abbas Delazar

Abstract


In the present study the volatile organic compounds of E. azerbaijanica Rech.f. were identified. Phytochemical assessment of MeOH extract of aerial parts of this plant was also performed and its free radical scavenging properties was evaluated. The essential oil of the air-dried aerial parts was obtained by hydro-distillation using a Clevenger type apparatus. The oil was then analyzed by gas chromatography–mass spectrometry and gas chromatography with flame ionization detector. Soxhlet extraction was performed on the aerial parts using n-hexane, dichloromethane and MeOH. The MeOH extract was then subjected to solid-phase extraction using a C18 Sep-Pak cartridge. Isolation and structural elucidation of the pure components was done by high-performance liquid chromatography and spectroscopic methods (UV, 1H-NMR). The free radical scavenging properties were determined by 2, 2-diphenyl-1-picrylhydrazyl (DPPH) assay. A total of 59 components representing 95.9% of the oil constituents were identified which were primarily characterized by terpenoids or aliphatic skeletons. The major components of the oil were hexahydrofarnesyl acetone (27.1%), 2-methyl-6-propyl-dodecane (16.4%), and tricosane (9.3%). One flavonoid (luteolin-7-O-rutinoside) and one phenylethanoid (verbascoside) were isolated and identified from the MeOH extract. The results of DPPH showed that the essential oil of E. azerbaijanica possesses weak free radical scavenging properties. The MeOH extract and its pure constituents showed significant activity (expressed as RC50) on DPPH radicals.


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Azizian D, Cutler DF. Anatomical, cytological and phytochemical studies on Phlomis L and Eremostachys Bunge (Labiatae). Bot J Linn Soc. 1982;85:225-248.

Mozaffarian V. A dictionary of iranian plant names. Tehran: Farhang Moaser; 2007. p. 207-208.

Delazar A, Sarker SD, Nahar L, Barzegar-Jalali S, Modarresi M, Hamedeyazdan S, et al. Rhizomes of Eremostachys laciniata: isolation and structure elucidation of chemical constituents and a clinical trial on inflammatory diseases. Adv Pharm Bull. 2013;3:385–393.

Delazar A, Shoeb M, Kumarasamy Y, Byres M, Nahar L, Sarker SD. Two bioactive ferulic acid derivatives from Eremostachys glabra. Daru. 2004;12:49-53.

Delazar A, Habibi Asl B, Mohammadi O, Heshmati Afshar F, Nahar L, Modarresi M, et al. Evaluation of analgesic activity of Eremostachys laciniata in mice. J Nat Rem. 2009;9: 1-7.

Modaressi M, Delazar A, Nazemiyeh H, Fathi Azad F, Smith E, Rahman MM, et al. Antibacterial iridoid glucosides from Eremostavhys laciniata. Phytother Res. 2009;23:99-103.

Nisar M, Khan S, Dar A, Rehman W, Khan R, Jan I. Antidepressant screening and flavonoids isolation from Eremostachys laciniata (L) Bunge. Afr J Biotech. 2011;10:1696-1699.

Khan S, Nisar M, Simjee SU, Rehman W, Khan R, Jan I, et al. Evaluation of micronutrients level and antinociceptive property of Eremostachys laciniata (L) Bunge. Afr J Biotech. 2010;9:775-777.

Khan S, Nisar M, Rehman W, Khan R, Nasir F. Anti-inflammatory study on crude methanol extract and different fractions of Eremostachys laciniata. Pharm Biol. 2010;48:1115-1118.

Al Jaber HI, Al Qudah MA, Barhoumi LM, Abaza IF, Afifi FU. Variation in the essential oil composition of Eremostachys laciniata from Jordan at different flowering stages. J Essent Oil Res. 2012;24:289–297.

Najafpour Navaei M, Mirza M. Chemical composition of the oil of Eremostachys laciniata (L.) Bunge from Iran. Flav Frag J. 2006;21:645–646.

Esmaeili A. Biological activities of Eremostachys laevigata Bunge. grown in Iran. Pak J Pharm Sci. 2012;25:803-808.

Amiri H, Meshkat Al Sadat MH, Lari Yazdi H. Chemical composition of the essential oil of Eremostachys Laevigata bung. Daru. 2007;15:34-40.

Nori shargh D, Kiaei SM, Deyhimi F. The volatile constituents analysis of Eremostachys macrophylla Montbr.& Auch. From Iran. Nat Prod Res. 2007;21:733-735.

Rustaiyan A, Masudi S, Ezzatzadeh E, Akhlaghi H, Aboli J. Composition of the aerial part, flower, leaf and stem oils of Eremostachys macrophylla Montbr.& Auch. and Eremostachys labiosa Bunge. From Iran. J Essent Oil Bear Plan. 2011;14:84-88.

Javidnia K, Miri R, Soltani M, Khosravi AR. Essential oil composition of two species of Eremostachys from Iran (E. adenantha Jaub. et Spach and E. macrophylla Montbr. et Auch.). J Essen Oil Res. 2008;20:226-228.

Delazar A, Byres M, Gibbons S, Kumarasamy Y, Modarresi M, Nahar L, et al. Iridoid glycosides from Eremostachys glabra. J Nat Prod. 2004;67:1584-1587.

Delazar A, Modarresi M, Shoeb M, Nahar L, Reid RG, Kumarasamy Y, et al. Eremostachiin: a new furanolabdane diterpene glycoside from Eremostachys glabra. Nat Prod Res. 2006;20: 167-172.

Delazar A, Gibbons S, Kumarasamy Y, Nahar L, Shoeb M, Sarker SD. Antioxidant phenylethanoid glycosides from the rhizomes of Eremostachys glabra (Lamiaceae). Biochem Sys Ecol. 2005;33: 87-90.

Mughal UR, Fatima I, Malik A, Tareen RB. Loasifolin, a new flavonoid from Eremostachys loasifolia. J Asian Nat Prod Res. 2010;12:328-330.

Mughal UR, Fareed G, Zubair A, Malik A, Versiani MA, Afza N, et al. Loasins A and B, new flavonoids from Eremostachys loasifolia. Nat Prod Res. 2013;27:1906-1910.

Ali B, Mehmood R, Mughal UR, Malik A, Safder M, Hussain R, et al. Eremosides A–C., New Iridoid Glucosides from Eremostachys loasifolia. Helv Chim Acta. 2012;95:586-593.

Calis I, Guvenc A, Armagan M, Koyuncu M, Gotfredsen CH, Jensen SR. Iridoid Glucosides from Eremostachys moluccelloides Bunge. Helv Chim Acta. 2007;90:1461-1466.

Imran M, Mehmood R, Mughal UR, Ali B, Malik A. Vicarin, a new isoflavone from Eremostachys vicaryi. J Asian Nat Prod Res. 2012;14:293-296.

Adams RP. Identification of essential oil of components by gas chromatography/quadrupole mass spectroscopy. 3rd ed. Carol Stream: Allured Publishing Corporation; 2001. p. 66-426.

Chima NK, Nahar L, Majinda RRT, Celik S, Sarker SD. Assessment of free-radical scavenging activity of Gypsophila pilulifera: assay-guided isolation of verbascoside as the main active component. Rev Bras Farmacogn. 2014;24:38-43.

Nazemiyeh H, Rahman MM, Gibbons S, Nahar L, Delazar A, Ghahramani MA, et al. Assessment of the antibacterial activity of phenylethanoid glycosides from Phlomis lanceolata against multiple-drug resistant strains of Staphylococcus aureus. J Nat Med. 2008;62,91-95.

Cakir A, Mavi A, Kazaz C, Yildirim A, Kufrevioglu OI. Antioxidant activities of the extracts and components of Teucrium orientale L. var. orientale. Turk J Chem. 2006;30:483-494.

Abeer T. Flavonoid content of Vangueria infausta extract grown in Egypt: investigation of its antioxidant activity. Int Res J Pharm. 2011;2;157-161.

Manafi H, Shafaghat Ali. Chemical composition of essential oil of Eremostachys azerbaijanica Rech.f. from Iran. J Essent Oil Bear Pl. 2010;13:412-415.

Abad MJ, Bedoya LM, Apaza L, Bermejo P. The Artemisia L. genus: A review of bioactive essential oils. Molecules. 2012;17:2542-2566.

Mojarrab M, Delazar A, Esnaashari S, Heshmati Afshar F. Chemical composition and general toxicity of essential oils extracted from the aerial parts of Artemisia armeniaca Lam. and A. incana (L.) Druce growing in Iran. Res Pharm Sci. 2013;8:65-69.

Fouladnia M, Modarresi M. Phenylethanoid glycosides from Eremostachys azerbaijanica Rech. F. Res Pharm Sci. 2012;7:S760.

Mabry TJ, Markham KR, Thomas MB. The systematic identification of flavonids. 1st ed. New York: Spring-Verlag; 1970. p. 274-345.

Modarresi M, Fouladnia M, Rafiee Z, jafari A, Zarzasangan K. Iridoid glycosides from Eremostachys azerbaijanica Rech.F. root. J Med Plant. 2013;12:66-77.

Nazemiyeh H, Bahadori F, Delazar A, Ay M, Topcu G, Kolak U, et al. Antioxidant phenolic compounds from the leaves of Erica arborea (Ericaceae). Nat Prod Res. 2008;22:1385-1392.

Nazemiyeh H, Delazar A, Movahedin N, Jodari M, Imani Y, Ghahramani MA, et al. Free radical scavengers from the aerial parts of Grammosciadium platycarpum Boiss. & Hausskn. (Apiaceae) and GC-MS analysis of the essential oils from its fruits. Rev Bras Farmacogn. 2009;19:914-918.

Majewska M, Skrzycki M, Podsiad M, Czeczot H. Evaluation of antioxidant potential of flavonoids: an In vitro study. Acta Pol Pharm. 2011;68:611-615.


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