Abstract
Phytochemical profiles of essential oil (EO), fatty acids, and n-hexane (CAH), diethyl ether (CAD), ethyl acetate (CAE) and methanol extracts (CAM) of Cota altissima L. J. Gay (syn. Anthemis altissima L.) were investigated as well as their antioxidant, anti-inflammatory, antidiabetic and antimicrobial activites. The essential oil was characterized by the content of acetophenone (35.8%) and β-caryophyllene (10.3%) by GC-MS/FID. Linoleic and oleic acid were found as main fatty acids. The major constituents of the extracts were found to be 5-caffeoylquinic acid, 3,5-dicaffeoylquinic acid, isorhamnetin glucoside, quercetin and quercetin glucoside by LC-MS/MS. Antioxidant activities of the extracts were determined by scavenging of DPPH and ABTS free radicals. Also, the inhibitory effects on lipoxygenase and α-glucosidase enzymes were determined. Antimicrobial activity was evaluated against Gram positive, Gram negative bacteria and yeast pathogens. CAM showed the highest antioxidant activity against DPPH and ABTS radicals with IC50 values of 126.60 and 144.40 μg/mL, respectively. In the anti-inflammatory activity, CAE demonstrated the highest antilipoxygenase activity with an IC50 value of 105.40 μg/mL, whereas, CAD showed the best inhibition of α-glucosidase with an IC50 value of 396.40 μg/mL in the antidiabetic activity. CAH was effective against Staphylococcus aureus at MIC = 312.5 µg/mL. This is the first report on antidiabetic, anti-inflammatory and antimicrobial activities of different extracts of C. altissima.
Funding source: TÜBITAK
Author contributions: GG designed the study and collected plant sample; MT identified the plant material; GG, MA, AŞ, FG, GÖ running the laboratory work, analysis of the data; GG drafted the paper; GÖ contributed to critical reading of the manuscript. All the authors have read the final manuscript and approved the submission.
Research funding: This work was partionally supported by the Tübitak SBAG 218S812.
Conflict of interest statement: The authors declare that there is no conflict of interest.
References
1. Özbek, MU. Cota J. Gay. Türkiye Bitkileri Listesi (Damarlı Bitkiler) [A Checklist of the Flora of Turkey (Vascular Plants)]. İstanbul: Nezahat Gökyiğit Botanical Garden and Floristic Research Society Publication; 2012.Search in Google Scholar
2. Oberprieler, C. Phylogenetic relationships in Anthemis L. (Compositae, Anthemideae) based on nrDNA ITS sequence variation. Taxon 2001;50:745–62.10.2307/1223705Search in Google Scholar
3. Presti, RML, Oppolzer, S, Oberprieler, C. A molecular phylogeny and a revised classification of the Mediterranean genus Anthemis sl (Compositae, Anthemideae) based on three molecular markers and micromorphological characters. Taxon 2010;59:1441–56.10.1002/tax.595010Search in Google Scholar
4. Tuzlacı, E. Türkiye bitkileri geleneksel ilaç rehberi. İstanbul: İstanbul Tıp Kitabevleri; 2016.Search in Google Scholar
5. Orhan, I, Deliorman-Orhan, D, Özçelik, B. Antiviral activity and cytotoxicity of the lipophilic extracts of various edible plants and their fatty acids. Food Chem 2009;115:701–5.10.1016/j.foodchem.2009.01.024Search in Google Scholar
6. Gönenç, TM, Erdogan, T F, Demirci, B, Baser, KHC, Kivcak, B. Chemical composition of the essential oils of Anthemis coelopoda var. bourgaei and A. aciphylla var. aciphylla. Chem Nat Compd 2012;48:332–4.10.1007/s10600-012-0241-1Search in Google Scholar
7. Özek, G, Özbek, MU, Arslan, M. Lipid and essential oil constituents of Cota hamzaoglui (Asteraceae). J Turkish Chem Soc, A: Chem 2018;5:1361–70.10.18596/jotcsa.476387Search in Google Scholar
8. Özek, G, Özbek, MU, Yur, S, Göger, F, Arslan, M, Özek, T. Assessment of endemic Cota fulvida (Asteraceae) for phytochemical composition and inhibitory activities against oxidation, α-amylase, lipoxygenase, xanthine oxidase and tyrosinase enzymes. Record Nat Prod 2019;13:333–45.10.25135/rnp.109.18.09.875Search in Google Scholar
9. Konstantinopoulou, M, Karioti, A, Skaltsas, S, Skaltsa, H. Sesquiterpene lactones from Anthemis altissima and their anti-Helicobacter pylori activity. J Nat Prod 2003;66:699–702.10.1021/np020472mSearch in Google Scholar PubMed
10. Akgul, C, Saglikoglu, G. Antibacterial activity of crude methanolic extract and its fractions of aerial parts of Anthemis tinctoria. Indian J Biochem Biophys 2005;42:395–7.Search in Google Scholar
11. Kıvcak, B, Mert, T, Saglam, H, Ozturk, T, Kurkcuoglu, M, Baser, KHC. Chemical composition and antimicrobial activity of the essential oil of Anthemis wiedemanniana from Turkey. Chem Nat Compd 2007;43:47–51.10.1007/s10600-007-0029-xSearch in Google Scholar
12. Kurtulmus, A, Fafal, T, Mert, T, Saglam, H, Kivcak, B, Ozturk, T, et al.. Chemical composition and antimicrobial activity of the essential oils of three Anthemis species from Turkey. Chem Nat Compd 2009;45:900–4.10.1007/s10600-010-9475-ySearch in Google Scholar
13. Abdolmaleki, M, Bahraminejad, S, Abbasi, S. Antifungal activity of some plant crude extracts on four phytopathogenic fungi. J Med Plants Res 2011;10:148–55.Search in Google Scholar
14. Samadi, N, Manayi, A, Vazirian, M, Samadi, M, Zeinalzadeh, Z, Saghari, Z, et al.. Chemical composition and antimicrobial activity of the essential oil of Anthemis altissima L. var. altissima. Nat Prod Res 2012;26:1931–4.10.1080/14786419.2011.617750Search in Google Scholar PubMed
15. Stojkovic, N, Stojkovic, M, Marinkovic, M, Chopra, G, Kostic, D, Zarubica, A. Polyphenol content and antioxidant activity of Anthemis cretica L. (Asteraceae). Oxid Commun 2014;37:237–46.Search in Google Scholar
16. Siasar-Karbasky, M, Tehranipour, M, Nejad-Shahrokhabadi, K. Neuroprotective effect of n-butanol, ethylacetate, aqueous and hydro-alcoholic fractions of Anthemis nobilis extracts through NGF gene expression after sciatic nerve injury in rats. J Gorgan Univ Med Sci 2017;18:49–55.Search in Google Scholar
17. Bardaweel, SK, Tawaha, KA, Hudaib, MM. Antioxidant, antimicrobial and antiproliferative activities of Anthemis palestina essential oil. BMC Compl Alternative Med 2014;14:297.10.1186/1472-6882-14-297Search in Google Scholar PubMed PubMed Central
18. Özkaynak, S, Kolatan, HE, Yilmaz, O, Kivcak, B. Anti-inflammatory activity of Anthemis aciphylla var. aciphylla Boiss. Turk J Biol 2011;35:757–62.10.3906/biy-1006-15Search in Google Scholar
19. Wei, A, Shibamoto, T. Antioxidant/lipoxygenase inhibitory activities and chemical compositions of selected essential oils. J Agric Food Chem 2010;58:7218–25.10.1021/jf101077sSearch in Google Scholar PubMed
20. Jassbi, AR, Firuzi, O, Miri, R, Salhei, S, Zare, S, Zare, M, et al.. Cytotoxic activity and chemical constituents of Anthemis mirheydari. Pharm Biol 2016;54:2044–9.10.3109/13880209.2016.1141220Search in Google Scholar PubMed
21. Afifi, FU, Kasabri. Pharmacological and phytochemical appraisal of selected medicinal plants from Jordan with claimed antidiabetic activities. Sci Pharm 2013;81:889–932.10.3797/scipharm.1212-20Search in Google Scholar PubMed PubMed Central
22. Gao, X, Ohlander, M, Jeppsson, N, Björk, L, Trajkovski, V. Changes in antioxidant effects and their relationship to phytonutrients in fruits of sea buckthorn (Hippophae rhamnoides L.) during maturation. J Agric Food Chem 2000;48:1485–90.10.1021/jf991072gSearch in Google Scholar PubMed
23. Yıldırım, A, Şen, A, Doğan, A, Bitis, L. Antioxidant and anti-inflammatory activity of capitula, leaf and stem extracts of Tanacetum cilicicum (Boiss.) Grierson. Int J Second Metab 2019;6:211–22.10.21448/ijsm.510316Search in Google Scholar
24. Zhang, R, Zeng, Q, Deng, Y, Zhang, M, Wei, Z, Zhang, Y, et al.. Phenolic profiles and antioxidant activity of litchi pulp of different cultivars cultivated in Southern China. Food Chem 2013;136:1169–76.10.1016/j.foodchem.2012.09.085Search in Google Scholar PubMed
25. Zou, Y, Chang, SK, Gu, Y, Qian, SY. Antioxidant activity and phenolic compositions of lentil (Lens culinaris var. morton) extract and its fractions. J Agric Food Chem 2011;59:2268–76.10.1021/jf104640kSearch in Google Scholar PubMed PubMed Central
26. Phosrithong, N, Nuchtavorn, N. Antioxidant and anti-inflammatory activites of Clerodendrum leaf extracts collected in Thailand. Eur J Integr Med 2016;8:281–5.10.1016/j.eujim.2015.10.002Search in Google Scholar
27. Ramakrishna, R, Sarkar, D, Schwarz, P, Shetty, K. Phenolic linked anti-hyperglycemic bioactives of barley (Hordeum vulgare L.) cultivars as nutraceuticals targeting type 2 diabetes. Ind Crop Prod 2017;107:509–17.10.1016/j.indcrop.2017.03.033Search in Google Scholar
28. Şen, A, Kurkcuoglu, M, Senkardeş, I, Bitis, L, Baser, KHC. Chemical composition, antidiabetic, anti-inflammatory and antioxidant activity of Inula ensifolia L. essential oil. J Essent Oil-Bear Plants 2019;22:1048–57.10.1080/0972060X.2019.1662333Search in Google Scholar
29. Göger, G, Demirci, B, Ilgın, S, Demirci, F. Antimicrobial and toxicity profiles evaluation of the chamomile (Matricaria recutita L.) essential oil combination with standard antimicrobial agents. Ind Crop Prod 2018;120:279–85.10.1016/j.indcrop.2018.04.024Search in Google Scholar
30. Clinical and Laboratory Standards Institute (CLSI). Reference method for broth dilution antifungal susceptibility testing of yeast approved standard, M27-A2. Wayne, Pennsylvania, USA: Clinical and Laboratory Standards Institute. 940 West Valley Road; 2002.Search in Google Scholar
31. Clinical and Laboratory Standards Institute (CLSI). Methods for dilution antimicrobial susceptibility tests for bacteria that grow aerobically. Wayne, Pennsylvania, USA: CLSI M7-A7 Clinical and Laboratory Standards Institute. 940 West Valley Road; 2006.Search in Google Scholar
32. Yusufoglu, HS, Tabanca, N, Bernier, UR, Li, AY, Salkini, MA, Alqasoumi, SI, et al.. Mosquito and tick repellency of two Anthemis essential oils from Saudi Arabia. Saudi Pharmaceut J 2018;26:860–4.10.1016/j.jsps.2018.03.012Search in Google Scholar PubMed PubMed Central
33. Vuckovic, I, Vujisic, L, Vajs, V, Tesevic, V, Janackovic, P, Milosavljevic, S. Phytochemical investigation of Anthemis cotula. J Serb Chem Soc 2006;71:127–33.10.2298/JSC0602127VSearch in Google Scholar
34. Venditti, A, Frezza, C, Rossi, G, Di Cecco, M, Ciaschetti, G, Serafini, M, et al.. Secondary metabolites with ecologic and medicinal implications in Anthemis cretica subsp. petraea from Majella National Park. AIMS Mol Sci 2016;3:648–60.10.3934/molsci.2016.4.648Search in Google Scholar
35. Saroglou, V, Dorizas, N, Kypriotakis, Z, Skaltsa, HD. Analysis of the essential oil composition of eight Anthemis species from Greece. J Chromatogr A 2006;1104:313–22.10.1016/j.chroma.2005.11.087Search in Google Scholar PubMed
36. Kilic, O, Kocak, A, Bagci, E. Composition of the volatile oils of two Anthemis L. taxa from Turkey. Z Naturforsch C Biosci 2011;66:535–40.10.1515/znc-2011-11-1201Search in Google Scholar PubMed
37. Grace, MH. Chemical composition and biological activity of the volatiles of Anthemis melampodina and Pluchea dioscoridis. Phytother Res: An Int J Devoted Pharmacol Toxicol Eval Nat Prod Deriv 2002;16:183–5.10.1002/ptr.872Search in Google Scholar PubMed
38. Javidnia, K, Miri, R, Kamalinejad, M, Sarkarzadeh, H, Jamalian, A. Chemical composition of the essential oils of Anthemis altissima L. grown in Iran. Flavour Fragrance J 2004;19:213–16.10.1002/ffj.1277Search in Google Scholar
39. Gönenç, TM, Akkol, EK, Süntar, I, Erdoğan, TF, Kıvçak, B. Fatty acid composition and preclinical researches on Anthemis wiedemanniana Fisch & Mey Discovery of a new anti-inflammatory agent. Phcog Mag 2014;10:53–60.10.4103/0973-1296.126660Search in Google Scholar PubMed PubMed Central
40. Taştan, P, Gönenç, T, Tüzün, BS, Özçınar, Ö, Kıvçak, B, Fafal, T. Fatty acid profile of four Anthemis species growing in İzmir, Turkey. Ecol Life Sci (NWSAELS) 2017;12:39–44.10.12739/NWSA.2017.12.3.5A0086Search in Google Scholar
41. Abu-Reidah, IM, Contreras, MM, Arráez-Román, D, Segura-Carretero, A, Fernández-Gutiérrez, A. Reversed-phase ultra-high-performance liquid chromatography coupled to electrospray ionization-quadrupole-time-of-flight mass spectrometry as a powerful tool for metabolic profiling of vegetables: Lactuca sativa as an example of its application. J Chromatogr A 2013;1313:212–27.10.1016/j.chroma.2013.07.020Search in Google Scholar
42. Sarikurkcu, C. Anthemis chia: biological capacity and phytochemistry. Ind Crop Prod 2020;153:112578.10.1016/j.indcrop.2020.112578Search in Google Scholar
43. Gouveia, S, Goncalves, J, Castilho, PC. Characterization of phenolic compounds and antioxidant activity of ethanolic extracts from flowers of Andryala glandulosa ssp. varia (Lowe ex DC.) R. Fern., an endemic species of Macaronesia region. Ind Crop Prod 2013;42:573–82.10.1016/j.indcrop.2012.06.040Search in Google Scholar
44. Clifford, MN, Wu, W, Kirkpatrick, J, Kuhnert, N. Profiling the chlorogenic acids and other caffeic acid derivatives of herbal chrysanthemum by LC− MSn. J Agric Food Chem 2007;55:929–36.10.1021/jf062314xSearch in Google Scholar
45. Clifford, MN, Johnston, KL, Knight, S, Kuhnert, N. Hierarchical scheme for LC-MS n identification of chlorogenic acids. J Agric Food Chem 2003;51:2900–11.10.1021/jf026187qSearch in Google Scholar
46. Clifford, MN, Knight, S, Kuhnert, N. Discriminating between the six isomers of dicaffeoylquinic acid by LC-MS. J Agric Food Chem 2005;53:3821–32.10.1021/jf050046hSearch in Google Scholar
47. Harborne, J, Heywood, V, Saleh, N. Chemosystematics of the composiate: flavonoid patterns in the Chrysanthemum complex of the tribe Anthemideae. Phytochemistry 1970;9:2011–17.10.1016/S0031-9422(00)85354-6Search in Google Scholar
48. Williams, CA, Greenham, J, Harborne, JB. The role of lipophilic and polar flavonoids in the classification of temperate members of the Anthemideae. Biochem Systemat Ecol 2001;29:929–45.10.1016/S0305-1978(01)00039-4Search in Google Scholar
49. Karatoprak, GŞ, Yücel, Ç, Göger, F, Sobarzo-Sanchez, E, Akkol, EK. Potential antioxidant and enzyme inhibitory effects of nanoliposomal formulation prepared from Salvia aramiensis Rech. f. extract. Antioxidants 2020;9:293.10.3390/antiox9040293Search in Google Scholar PubMed PubMed Central
50. Orlando, G, Zengin, G, Ferrante, C, Ronci, M, Recinella, L, Senkardes, I, et al.. Comprehensive chemical profiling and multidirectional biological investigation of two wild anthemis species (Anthemis tinctoria var. pallida and A. cretica subsp. tenuiloba): focus on neuroprotective effects. Molecules 2019;24:2582.10.3390/molecules24142582Search in Google Scholar PubMed PubMed Central
51. Uzel, A, Guvensen, A, Cetin, E. Chemical composition and antimicrobial activity of the essential oils of Anthemis xylopoda O. Schwarz from Turkey. J Ethnopharmacol 2004;95:151–4.10.1016/j.jep.2004.06.034Search in Google Scholar PubMed
52. Güven, K, Karabacak, E, Çelik, S, Uysal, I. Antimicrobial activity of Centaura derderiifolia, Stachys aleurites and Anthemis aciphylla. J Appl Biol Sci 2009;3:154–9.Search in Google Scholar
53. Jalal, MS, Veli, SS, Farrux, BK. The study of the composition of the extract and antimycotic properties Anthemis altissima L. Химия растительного сырья Chem Plant Raw Mater 2019;4:129–34.10.14258/jcprm.2019045267Search in Google Scholar
© 2021 Walter de Gruyter GmbH, Berlin/Boston
