Anthemis tinctoria L. var. tinctoria L. Bitkisine Ait Fenolik Bileşiklerin LC-ESI-MS/MS ile Miktar Tayini ve Bitkinin Biyolojik Aktivitelerinin Belirlenmesi

Year 2020, Volume: 10 Issue: 4, 996 - 1006, 15.10.2020

Ahmet Emir Ceren Emir

https://doi.org/10.17714/gumusfenbil.687185

Cited By: 1

Abstract

Mevcut çalışmada, Tire/İzmir’den toplanan ve halk arasında, boyacı papatyası veya sarı papatya olarak adlandırılan Anthemis tinctoria var. tinctoria bitkisi fenolik profili ve biyolojik aktiviteleri bakımından incelenmiştir. Toplam fenolik ve flavonoit içeriği spektrofotometrik olarak belirlenmiş olup, 30 adet fenolik bileşiğin dedeksiyonu ve miktar tayini LC-ESI-MS/MS cihazı ile yapılmıştır. Bitkinin metanol ekstresine ait asetilkolinesteraz, bütirilkolinesteraz ve tirozinaz enzim inhibisyonları 96 kuyucuklu mikroplaka okuyucu ile saptanmıştır. Ayrıca bitkinin antioksidan kapasite tayini DPPH ve CUPRAC yöntemleriyle belirlenmiştir. Metanol ekstresinin toplam fenolik ve flavonoit miktarları sırasıyla 21.4±4.2 (mg GAE/g ekstre) ve 9.7±2.56 (mg QE/g ekstre) olarak bulunmuştur. Miktar tayininde, fenolik asit olarak 3-hidroksibenzoik asit (1167.3±0.72 µg/g ekstre) ve ferulik asit (845.8±1.98 µg/g ekstre), flavonoit olarak morin (1598.4±2.15 µg/g ekstre) ve kersetin (1416.0±1.83 µg/g ekstre) bileşikleri en yüksek konsantrasyonda bulunmuştur. Asetilkolinesteraz, bütirilkolinesteraz ve tirozinaz enzim inhibisyonlarının IC50 değerleri ise sırasıyla 254.7 ±4.86 μg/mL, 166.2±3.74 μg/mL ve 415.7±1.85 μg/mL olarak hesaplandı. Ayrıca bitkinin antioksidan kapasitesi sırasıyla 302.18±2.74 ve 514.62±3.82 mg TE/g ekstre olarak bulunmuştur.

Keywords

Anthemis tinctoria, Fenolikler, Kolinesterazlar, Tirozinaz

Quantification of Phenolic Compounds of Anthemis tinctoria L. var. tinctoria L. by LC-MS/MS and Determination of Biological Activities of the Plant

Abstract

In the present study, Anthemis tinctoria var tinctoria plant, collected from Tire / İzmir and named as the painter's daisy or yellow daisy among the people, was examined in terms of its phenolic profile and biological activities. Total phenolic and flavonoids content were determined spectrophotometrically. Detection and quantification of 30 phenolic compounds were performed by LC-ESI-MS/MS. Acetylcholinesterase, butyrylcholinesterase and tyrosinase enzyme inhibition of methanol extract of the plant were determined by 96-well microplate reader. In addition, antioxidant capacity of the plant was determined by DPPH and CUPRAC methods. Total phenolic and flavonoid contents of methanol extract were 21.4±4.2 (mg GAE/g extract) and 9.7±2.56 (mg QE/g extract), respectively. In the quantification assay, 3-hydroxybenzoic acid (1167.3±0.72 µg/g extract) and ferulic acid (845.8±1.98 µg / g extract) as phenolic acid, morin (1598.4±2.15 µg/g extract) and quercetin (1416.0±1.83 µg/g extract) as flavonoids were found at the highest concentration. IC50 values of acetylcholinesterase, butyrylcholinesterase and tyrosinase inhibition were 254.7±4.86 μg/mL, 166.2±3.74 μg/mL and 415.7±1.85 μg/mL, respectively. In addition, the antioxidant capacity of the plant was found as 302.18±2.74 and 514.62±3.82 mg TE/g extract, respectively.

Keywords

Anthemis tinctoria, Phenolics, Cholinesterases, Tyrosinase

References

• Afanasev, I.B., Dcrozhko, A.I., Brodskii, A.V., Kostyuk, V.A. ve Potapovitch, A.I., 1989. Chelating and Free Radical Scavenging Mechanisms of Inhibitory Action of Rutin and Quercetin in Lipid Peroxidation. Biochemical Pharmacology. 38, 1763–1769.
• Afifi, F.U. ve Kasabri, V., 2013. Pharmacological and phytochemical appraisal of selected medicinal plants from Jordan with claimed antidiabetic activities. Scientia Pharmaceutica. 81(4), 889-932.
• Albayrak, S. ve Aksoy, A., 2013. Evaluation of Antioxidant and Antimicrobial Activities of Two Endemic Anthemis Species in Turkey. Journal of Food Biochemistry. 37(6), 639–645.
• Al-Snafi, A.E., 2016. Medical importance of Anthemis nobilis (Chamaemelum nobile)-A review. Asian Journal of Pharmaceutical Science and Technology. 6(2), 89–95.
• Apak, R., Güçlü, K., Özyürek, M. ve Çelik, S.E., 2008. Mechanism of Antioxidant Capacity Assays and the CUPRAC (Cupric Ion Reducing Antioxidant Capacity) Assay. Microchimica Acta. 160(4), 413–419.
• Asanuma, M., Miyazaki, I. ve Ogawa, N., 2003. Dopamine- or L-DOPA-Induced Neurotoxicity: The Role of Dopamine Quinone Formation and Tyrosinase in a Model Of Parkinson’s Disease. Neurotoxicity Research. 5(3), 165-76.
• Baytop, T., 1999. Türkiye’de Bitkilerle Tedavi, Geçmişte ve Bugün. Nobel Tıp Kitabevi, İstanbul, 313s.
• Blois, M.,S., 1958. Antioxidant Determinations by the Use of a Stable Free Radical. Nature. 181, 1199-1200.
• Bremer, K. ve Humpries, C.J., 1993. Generic monograph of the Asteraceae-Anthemideae. Bulletin of the Natural History Museum. 23(2), 71-177.
• Bursal, E., Aras, A., Kılıç, A. ve Buldurun, K., 2020. Chemical constituent and radical scavenging antioxidant activity of Anthemis kotschyana Boiss. Natural Product Research, doi: 10.1080/14786419.2020.1723089.
• Cakilcioglu, U., Khatun, S., Turkoglu, I. ve Hayta, S., 2011. Ethnopharmacological survey of medicinal plants in Maden (Elazig-Turkey). Journal of Ethnopharmacology. 137, 469-486.
• Chemsa, A.E., Zellagui, A., Öztürk, M., Erol, E., Ceylan, O., Duru, M. E. ve Lahouel, M., 2018. Chemical Composition, Antioxidant, Anticholinesterase, Antimicrobial and Antibiofilm Activities of Essential Oil and Methanolic Extract of Anthemis stiparum subsp. sabulicola (Pomel) Oberpr. Microbial Pathogenesis. 119(March), 233–240.
• Conforti, F., Menichini, F., Formisano, C., Rigano, D., Senatore, F., Bruno, M., Rosselli, S. ve Çelik, S., 2012. Anthemis wiedemanniana essential oil prevents LPS-induced production of NO in RAW 264.7 macrophages and exerts antiproliferative and antibacterial activities in vitro. Natural Product Research. 26(17), 1594-1601.
• De Mieri, M., Monteleone, G., Ismajili, I., Kaiser, M. ve Hamburger, M., 2017. Antiprotozoal activity-based profiling of a dichloromethane extract from Anthemis nobilis flowers. Journal of Natural Products. 80(2), 459-470.
• Dziri, S., Hassen, I., Fatnassi, S., Mrabet, Y., Casabianca, H., Hanchi, B. ve Hosni, K., 2012. Phenolic Constituents, Antioxidant and Antimicrobial Activities of Rosy Garlic (Allium roseum var. odoratissimum). Journal of Functional Foods. 4(2), 423–432.
• Ellman, L., Courtney, K.D., Andres, Jr V. ve Featherstone, R.M., 1961. New and Rapid Colorimetric Determination of Acetylcholinesterase Activity. Biochemical Pharmacology. 7, 88–95.
• Emir, A., Emir, C. ve Yıldırım, H., 2020a. Characterization of Phenolic Profile by LC-ESI-MS / MS and Enzyme Inhibitory Activities of Two Wild Edible Garlic: Allium nigrum L. and Allium subhirsutum L. The Journal of Food Biochemistry. 44(4), e13165.
• Emir, A., Emir, C. ve Yıldırım, H., 2020b. Chemical and biological comparison of different parts of two Allium species: Allium paniculatum L. subsp. villosulum (Hal.) Stearn and Allium paniculatum L. subsp. paniculatum L. Chemical Papers, doi: 10.1007/s11696-020-01311-1.
• Eser, F., Yaglioglu, A.S., Dolarslan, M., Aktas, E. ve Onal, A., 2017. Dyeing, Fastness, and Cytotoxic Properties, and Phenolic Constituents of Anthemis tinctoria var. tinctoria (Asteraceae). The Journal of The Textile Institute. 108(9), 1489-1495.
• Gonçalves, S. ve Romano, A., 2017. Inhibitory Properties of Phenolic Compounds Against Enzymes Linked with Human Diseases, in: Soto-Hernández, M. (ed), Phenolic Compounds - Biological Activity. IntechOpen, London, pp. 99-118.
• Güner, A., Özhatay, N., Ekim, T. ve Başer, K.H.C., 2000. Flora of Turkey And The East Aegean Islands, Edinburgh University Press, Edinburgh.
• Honda, G., Yesilada, E., Tabata, M., Sezik, E., Fujita, T., Takeda, Y., Takaishi, Y. ve Tanaka, T., 1996. Traditional medicine in Turkey. VI. Folk medicine in west Anatolia: Afyon, Kütahya, Denizli, Muğla, Aydin provinces. Journal of Ethnopharmacology. 53(2), 75-87.
• Hopkins, A.L. ve Groom, C.R., 2002. The Druggable Genome. Nature Reviews Drug Discovery. 727–730.
• Karim, A., Berrabah,M., Mekhfi, H., Ziyyat, A., Legssyer, A., Bouali, A., Haloui, B., Amrani, S. ve Aziz, M., 2010. Effect of essential oil of Anthemis mauritiana Maire & Sennen flowers on intestinal smooth muscle contractility. Journal of Smooth Muscle Research. 46(1), 65-75.
• Katalinic, M., Rusak, G., Baroviç, J.D., Sinko, G., Jelic, D., Antolovic, R. ve Kovarik, Z., 2010. Structural Aspects Of Flavonoids as Inhibitors of Human Butyrylcholinesterase. European Journal of Medicinal Chemistry. 45(1), 186-192.
• Lattanzio, V., 2013. Phenolic Compounds: Introduction, In: Ramawat, K.G., Merillon, J.M. (Eds.), Handbook of Natural Products. Springer-Verlag Berlin Heidelberg, pp. 1544-1573.
• Martinez, M.V. ve Whitaker, J.R., 1995. The Biochemistry and Control of Enzymatic Browning. Trends in Food Science & Technology. 6, 195–200.
• Masuda, T., Yamashita, D., Takeda, Y. ve Yonemori, S., 2005. Screening for Tyrosinase Inhibitors Among Extracts of Seashore Plants and Identification of Potent İnhibitors From Garcinia subelliptica. Bioscience, Biotechnology, and Biochemistry. 69(1), 197–201.
• Orhan, I., Deliorman-Orhan, D. ve Özçelik, B., 2009. Antiviral Activity and Cytotoxicity of The Lipophilic Extracts of Various Edible Plants and Their Fatty Acids. Food Chemistry. 115, 701-705.
• Orlando, G., Zengin, G., Ferrante, C., Ronci, M., Recinella, L. ve Menghini, L., 2019. 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. 24, 2582.
• Özek, G., Özbek, M.U., Yur, S., Göger, F., Arslan, M. ve Özek, T., 2019. Assessment of Endemic Cota fulvida (Asteraceae) for Phytochemical Composition and Inhibitory Activities against Oxidation, α-amylase, Lipoxygenase, Xanthine Oxidase and Tyrosinase Enzymes. Records of Natural Products. 13(4), 333-345.
• Papaioannoua, P., Lazaria, D., Kariotib, A., Soulelesa, C., Heilmannc, J., Hadjipavlou-Litinad, D. ve Skaltsa, H., 2007. Phenolic Compounds with Antioxidant Activity from Anthemis tinctoria L. (Asteraceae). Zeitschrift für Naturforschung C-A Journal of Biosciences. 62c, 326-330.
• Remya, C., Dileep, K.V., Tintu, I., Variyar, E.J. ve Sadasivan, C., 2012. Design of Potent Inhibitors of Acetylcholinesterase Using Morin as the Starting Compound. Frontiers in Life Science. 6(3), 107-117.
• Shawahna, R. ve Jaradat, N.A., 2017. Ethnopharmacological survey of medicinal plants used by patients with psoriasis in the West Bank of Palestine. BMC Complementary and Alternative Medicine. 17(1), 4.
• Singleton, V.L., Orthofer, R. ve Lamuela-Raventos, R.M., 1999. Analysis of Total Phenols and Other Oxidation Substrates and Antioxidants by Means of Folin-Ciocalteu Reagent. Methods in Enzymology. 299, 152-178.
• Sut, S., Dall’Acqua, S., Zengin, G., Senkardes, I., Bulut, G., Cvetanović, A. ve Mahomoodally, F. 2019. Influence of Different Extraction Techniques on the Chemical Profile and Biological Properties of Anthemis cotula L.: Multifunctional Aspects for Potential Pharmaceutical Applications. Journal of Pharmaceutical and Biomedical Analysis. 173(May), 75–85.
• Ugurlu, E. ve Secmen, O., 2008. Medicinal plants popularly used in the villages of Yunt Mountain (Manisa-Turkey). Fitoterapia. 79(2), 126–131.
• Wang, H.M., Chou, Y.T., Hong, Z.L., Chen, H.A., Chang, Y.C., Yang, W.L., Chang, H.C., Mai, C.T. ve Chen, C.Y., 2011. Bioconstituents From Stems of Synsepalum dulcificum Daniell (Sapotaceae) Inhibit Human Melanoma Proliferation, Reduce Mushroom Tyrosinase Activity and Have Antioxidant Properties. Journal of the Taiwan Institute of Chemical Engineers. 42, 204–211.
• Weinstock, M., 1999. Selectivity of Cholinesterase Inhibition: Clinical Implications for the Treatment of Alzheimer’s Disease. CNS Drugs. 12(4), 307–323.
• Zolghadri, S., Bahrami, A., Hassan Khan, M.T., Munoz-Munoz, J., Garcia-Molina, F., Garcia-Canovas, F. ve Saboury, A.A., 2019. A Comprehensive Review on Tyrosinase Inhibitors. Journal of Enzyme Inhibition and Medicinal Chemistry. 34(1), 279–309.