Phytochemical Characterization of Achillea grandifolia Friv. Essential Oil and Its Potent Against Oxidative Damage, Acetylcholinesterase and a-Amylase

Yıl 2018, Cilt: 19 Sayı: 3, 671 - 684, 01.09.2018

Gulmira Ozek

Öz

The essential oil of Achillea grandifolia Friv. was obtained by hydrodistillation of aerial parts of the plant and analyzed with GC-FID and GC/MS techniques. The oil comprised mostly by the oxygenated monoterpenes (76.2 %) with a-terpinyl acetate (54.1 %) as main constituent. The monoterpene hydrocarbons were the second major compound group with p-cymene (17.7 %) as the main representative. The essential oil showed free radical scavenging activity against DPPH• radicals (Inh. 52 %) and ABTS+• cation radicals (TEAC 0.62 mM). The oil demonstrated hypoglycemic activity via inhibition of a-amylase (IC50 0.15 mg/mL). The effect of the oil on neurodegenerative disease was expressed via inhibition of AChE and found to be > 82 % of inhibition (an IC50 of 1.77 mg/mL).

Anahtar Kelimeler

Achillea grandifolia, Essential oil, GC/MS, GC-FID, Antioxidant, a-Amylase, Acetylcholinesterase

Kaynakça

• Reference [1]. Huber-Morath A. Achillea L. In: Davis PH, editor. Flora of Turkey and the Eastern Aegean Islands. 5. Edinburgh: University Press., 1975.
• Reference [2].Baltisberger M, Widmer A, Chromosome numbers and karyotypes within the genus Achillea (Asteraceae: Anthemideae). Willdenowia 2016, 46(1): 121-135.
• Reference [3].Almadiy AA, Nenaah GE, Al Assiuty BA, Moussa EA, Mira NM, Chemical composition and antibacterial activity of essential oils and major fractions of four Achillea species and their nanoemulsions against foodborne bacteria. LWT-Food Sci Technol 2016, 69: 529-537.
• Reference [4].Ertürk Ö, Screening of various solvents and extracts of Achillea latiloba Ledeb. ex Nordm for antibacterial and antifungal activities. Herba Polonica 2014, 60(2): 29-40.
• Reference [5].Choucry MA, Chemical composition and anticancer activity of Achillea fragrantissima (Forssk.) Sch. Bip.(Asteraceae) essential oil from Egypt. J Pharm Phytother 2017, 9(1): 1-5.
• Reference [6].Awad B, Ibrahim AK, Sand E, Wanas AS, Radwan MM, Elsohaly M, et al., editors. Anticancer metabolites from Achillea fragrantissima. Planta Med; 2015.
• Reference [7].Ashtiani M, Nabatchian F, Galavi HR, Saravani R, FarajianMashhadi F, Salimi S, Effect of Achillea wilhelmsii extract on expression of the human telomerase reverse transcriptase mRNA in the PC3 prostate cancer cell line. Biomed Rep 2017, 7(3): 251-256.
• Reference [8].Agar OT, Dikmen M, Ozturk N, Yilmaz MA, Temel H, Turkmenoglu FP, Comparative studies on phenolic composition, antioxidant, wound healing and cytotoxic activities of selected Achillea L. species growing in Turkey. Molecules 2015, 20(10): 17976-18000.
• Reference [9].Boutennoun H, Boussouf L, Kebieche M, Al-Qaoud K, Madani K, In vivo analgesic, anti-inflammatory and antioxidant potentials of Achillea odorata from north Algeria. South Afr J Bot 2017, 112: 307-313.
• Reference [10].Chávez-Silva F, Cerón-Romero L, Arias-Durán L, Navarrete-Vázquez G, Almanza-Pérez J, Román-Ramos R, et al., Antidiabetic effect of Achillea millefollium through multitarget interactions: α-glucosidases inhibition, insulin sensitization and insulin secretagogue activities. J Ethnopharm 2018, 212: 1-7.
• Reference [11].Abd-Alla HI, Shalaby NM, Hamed MA, El-Rigal NS, Al-Ghamdi SN, Bouajila J, Phytochemical composition, protective and therapeutic effect on gastric ulcer and α-amylase inhibitory activity of Achillea biebersteinii Afan. Arch Pharmacal Res 2016, 39(1): 10-20.
• Reference [12].Sevindik HG, Güvenalp Z, Yerdelen KÖ, Yuca H, Demirezer LÖ, The discovery of potential anticholinesterase compounds from Achillea millefolium L. Ind Crops Prod 2015, 76: 873-879.
• Reference [13].Barut EN, Barut B, Engin S, Yıldırım S, Yaşar A, Türkiş S, et al., Antioxidant capacity, anti-acetylcholinesterase activity and inhibitory effect on lipid peroxidation in mice brain homogenate of Achillea millefolium. Turk J Biochem 2017, 42(4): 493-502.
• Reference [14].Boutennoun H, Boussouf L, Rawashdeh A, Al-Qaoud K, Abdelhafez S, Kebieche M, et al., In vitro cytotoxic and antioxidant activities of phenolic components of Algerian Achillea odorata leaves. Arab J Chem 2017, 10(3): 403-409.
• Reference [15].Yaeesh S, Jamal Q, Khan Au, Gilani AH, Studies on hepatoprotective, antispasmodic and calcium antagonist activities of the aqueous‐methanol extract of Achillea millefolium. Phytother Res 2006, 20(7): 546-551.
• Reference [16].Konyalioglu S, Karamenderes C, The protective effects of Achillea L. species native in Turkey against H 2 O 2-induced oxidative damage in human erythrocytes and leucocytes. J Ethnopharm 2005, 102(2): 221-227.
• Reference [17].Mohammadhosseini M, Sarker SD, Akbarzadeh A, Chemical composition of the essential oils and extracts of Achillea species and their biological activities: A review. J Ethnopharmacol 2017, 199: 257-315.
• Reference [18].Skaf J, Hamarsheh O, Berninger M, Balasubramanian S, Oelschlaeger TA, Holzgrabe U, Improving anti-trypanosomal activity of alkamides isolated from Achillea fragrantissima. Fitoterapia 2017.
• Reference [19].Sezik E, Yeşilada E, Honda G, Takaishi Y, Takeda Y, Tanaka T, Traditional medicine in Turkey X. Folk medicine in central Anatolia. J Ethnopharm 2001, 75: 95-115.
• Reference [20].Unal EL, Mavi A, Kara AA, Cakir A, Şengül M, Yildirim A, Antimicrobial and antioxidant activities of some plants used as remedies in Turkish traditional medicine. Pharm Biol 2008, 46(3): 207-224.
• Reference [21].Sezik E, Yesilada E. Turkish folk medicine containing volatile oils. In: Kirimer N, Mat A, editors. Essential Oils, In honour of Prof Dr K Hüsnü Can Başer on his 50th birthday. Eskişehir: Anadolu University, 1999.
• Reference [22].Baytop T. Türkiye’de Bitkiler ile Tedavi. Phytoterapy in Turkey. 2nd ed. Istanbul: Nobel Tıp Kitabevleri Ltd., Şti., 1999.
• Reference [23].Karamenderes C, Apaydin S, Antispasmodic effect of Achillea nobilis L. subsp. sipylea (O. Schwarz) Bässler on the rat isolated duodenum. J Ethnopharm 2003, 84(2-3): 175-179.
• Reference [24].Akalin E, Alpinar K, Tekirdağ'in tibbi ve yenen bitkileri hakkinda bir araştirma. Ege Üniv Ecz Fak Derg 1994, 2: 1-11.
• Reference [25].Güner A, Aslan S, Ekim T, Vural M, Babaç MT. Türkiye Bitkileri Listesi (Damarlı Bitkiler). List of the Plants of Turkey (Vascular Plants). İstanbul: Nezahat Gökyiğit Botanik Bahçesi ve Flora Araştırmaları Derneği Yayını, 2012.
• Reference [26].Konyalioglu S, Karamenderes C, Screening of total flavonoid, phenol contents and antioxidant capacities of some Achillea L. species growing in Turkey. ACTA Pharm Sci 2004, 46(3): 163-170.
• Reference [27].Stankovic N, Mihajilov-Krstev T, Zlatkovic B, Matejic J, Jovanovic VS, Kocic B, et al., Comparative study of composition, antioxidant, and antimicrobial activities of essential oils of selected aromatic plants from Balkan peninsula. Planta Med 2016, 82(7): 650-661.
• Reference [28].Pavlovic M, Petrovic S, Milenkovic M, Kukic J, Couladis M, Tzakou O, et al., Composition and antiradical capacity of Achillea grandifolia essential oil from Serbia. Planta Med 2008, 74(9): 1191-1191.
• Reference [29].Hanlidou E, Kokkalou E, Kokkini S, Volatile constituents of Achillea grandifolia. Planta Med 1992, 58(1): 105-107.
• Reference [30].Küçükbay F, Çetin H, Determination of some essential elements and composition of the essential oils of Achillea grandifolia Friv.(Asteraceae) from different localities. Analyt Chem Lett 2012, 2(6): 337-350.
• Reference [31].EDQM. Determination of Essential Oils in Herbal Drugs 9th ed. Europe Co, editor. Strasbourg: European Directorate for the Quality of Medicines and Healthcare, 2017. 285-286 p.
• Reference [32].Özek G, Ishmuratova M, Tabanca N, Radwan MM, Göger F, Özek T, One‐step multiple component isolation from the oil of Crinitaria tatarica (Less.) Sojak by preparative capillary gas chromatography with characterization by spectroscopic and spectrometric techniques and evaluation of biological activity. J Sep Sci 2012, 35(5-6): 650-660.
• Reference [33].Joulain D, König WA, Hochmuth DH. Library of MassFinder-4. In: Hochmuth DH, editor. Terpenoids and Related Constituents of Essential oils. Hamburgh, Germany: Hochmuth Scientific Consulting, 2001.
• Reference [34].Adams RP. Identification of Essential Oil Components by Gas Chromatography / Mass Spectrometry. 4th ed. Adams RP, editor: Allured Pub Corp., 2007. 804 p.
• Reference [35].Brand-Williams W, Cuvelier ME, Berset CLWT, Use of a free radical method to evaluate antioxidant activity. LWT-Food Sci Technol 1995, 28(1): 25-30.
• Reference [36].Re R, Pellegrini N, Proteggente A, Pannala A, Yang M, Rice-Evans C, Antioxidant activity applying an improved ABTS radical cation decolorization assay. Free Rad Biol Med 1999, 26(9): 1231-1237.
• Reference 37].Yang XW, Huang MZ, Jin Y, Sun LN, Song Y, Chen HS, Phenolics from Bidens bipinnata and their amylase inhibitory properties. Fitoterapia 2012, 83(7): 1169-1175.
• Reference [38].Ellman GL, Courtney KD, V. AJ, Featherstone RM, A new and rapid colorimetric determination of acetylcholinesterase activity. Biochem Pharmacol 1961, 7(2): 88-95.
• Reference [39].Ahmadi K, Wassim A, Ream N, Evaluation of hypoglycemic effect of Achillea biebersteinii Afan., growing in Syria, in induced diabetic rats. Int Journal Pharm Phytochem Res 2017, 9(2): 215-222.
• Reference [40].Kumar BD, Mitra A, Manjunatha M, In vitro and in vivo studies of antidiabetic Indian medicinal plants: A review. J Herbal Med Tox 2009, 3(2): 9-14.
• Reference [41].Andrade PB, Valentão P, Pereira DM. Natural Products Targeting Clinically Relevant Enzymes. Weinheim, Germany: John Wiley & Sons, 2017.
• Reference [42].Das A, Shanker G, Nath C, Pal R, Singh S, Singh HK, A comparative study in rodents of standardized extracts of Bacopa monniera and Ginkgo biloba: anticholinesterase and cognitive enhancing activities. Pharmacol Biochem Behav 2002, 73(4): 893-900.
• Reference [43].Mukherjee PK, Kumar V, Mal M, Houghton PJ, In vitro acetylcholinesterase inhibitory activity of the essential oil from Acorus calamus and its main constituents. Planta Med 2007, 73(03): 283-285.
• Reference [44].Parveen S, Khalid A, Farooq A, Choudhary MI, Acetyl and butyrylcholinesterase-inhibiting triterpenoid alkaloids from Buxus papillosa. Phytochem 2001, 58(6): 963-968.
• Reference [45].Sevindik HG, Güvenalp Z, Yerdelen KÖ, Yuca H, Demirezer LÖ, Research on drug candidate anticholinesterase molecules from Achillea biebersteinii Afan. using by molecular docking and in vitro methods. Med Chem Res 2015, 24(11): 3794-3802.
• Reference [46].Radulović NS, Mladenović MZ, Randjelovic PJ, Stojanović NM, Dekić MS, Blagojević PD, Toxic essential oils. Part IV: The essential oil of Achillea falcata L. as a source of biologically/pharmacologically active trans-sabinyl esters. Food Chem Tox 2015, 80: 114-129.
• Reference [47].Elmann A, Ofir R, Kashman Y, Anti-neuroinflammatory and protective compounds in Achillea fragrantissima. Israel 2017, Patent US15039429.