PHYTOCHEMICAL PROFILING BY LC-ESI-MS/MS AND DETERMINATION OF ANTIOXIDANT, ANTI-ALZHEIMER AND ANTITYROSINASE ACTIVITIES OF TWO ASPARAGACEAE SPECIES: Scilla hyacinthoides L. AND Scilla ingridiae SPETA

Year 2024, Volume: 10 Issue: 2, 79 - 94, 30.12.2024

Alevcan Kaplan

https://doi.org/10.51477/mejs.1517732

Abstract

In this study, in vitro antioxidant, antialzheimer and antityrosinase activity, total phenolic and flavonoid components, phytochemical profiling, identified by Liquid chromatography-electrospray ionization-mass spectrometry (LC-ESI-MS/MS) analysis and also chemometric analysis, of two different parts of Scilla species (Scilla hyacinthoides L. and Scilla ingridiae Speta) were determined in detailed perspective. The highest contents of total phenolics (TPC) and total flavonoids (TFC) were determined in S1TU (S. hyacinthoides aerial parts) extract (11.72±0.00 µg GAE/mg) and S2TU (S. ingridiae aerial parts) extract (31.53±0.21 µg QE/mg). The highest ABTS and CUPRAC activities were found in S1TU and S2TU extracts. The inhibitory activities of the extracts on the enzyme acetylcholinesterase were investigated. S1TU and S2TU extracts again showed the highest activity. Although the antityrosinase enzyme inhibitory activities of the extracts were generally similar and high, the S2TA extract (S. ingridiae corm parts) showed the highest activity. LC-ESI-MS/MS was used to determine the content of phenolic components of the extracts. Fourteen different bioactive components were determined in the analyzes and their amounts were measured. The data obtained were analyzed chemometrically such as principal component analysis (PCA), hierarchical component analysis (HCA) and their relationships to each other were supported visually and numerically with Pearson correlation graphs, heat maps, etc. The research results have shown that the various components of the plant have a good effect on various biological activities, so that it can be used for various purposes in the future (especially with a good degree of antityrosinase activity), taking into account the results. The biological activities demonstrated here can rationalize the use of the plant in traditional medicine.

Keywords

Antioxidant activity, phytochemical profiling, enzyme inhibition, multivariate analysis, Pearson correlation

Thanks

The author thank to Dr. Muhammad Nauman Khan from University of Peshawar, Pakistan for the critical reading of manuscript.

References

• Ernst, E., “Harmless herbs? A review of the recent literature”, The American Journal of Medicine, 104(2), 170-178,1998.
• Lichterman, B.L., “Aspirin: the story of a wonder drug”, British Medical Journal, 329,1408, 2004.
• Baytop, T., “Türkiye’de Bitkiler ile Tedavi-Geçmişte ve Bugün”,second ed. Nobel Tip Kitabevleri, Istanbul, Türkiye, 1999.
• Meskin, M.S., “Phytochemicals in nutrition and health”. CRC Press, Boca Raton, FL, pp. 123, 2002.
• Springbob, K., Kutchan, T., “Introduction to the different classes of natural products”, In: Lanzotti V (ed) Plant-derived natural products: synthesis, function, and application”, Springer, New York, pp. 3, 2009.
• Ülger, T.G., Ayhan, N.Y., “Bitki sekonder metabolitlerinin sağlık üzerine fonksiyonel etkileri”, Acıbadem Üniversitesi Sağlık Bilimleri Dergisi, 3, 384-390, 2020.
• Mordak, E.V., “Scilla L.” In: Davis PH (ed.), Flora of Turkey and the East Aegean Islands, Edinburgh University Press, Edinburgh, 8, pp.214-224,1984.
• Speta, F., “Zwei neue Scilla-Arten (Hyacinthaceae) aus der S-Türkei (Two new Scilla species from South Turkey)”, Willdenowia, 21, 157-166,1991.
• Özhatay, N., “Scilla L.” In: Güner, A, Özhatay N, Ekim T, Başer, KHC, Flora of Turkey and the East Aegean Islands”, Edinburgh University Press, Edinburgh, II,pp. 233, 2000.
• Iizuka, M., Warashina, T., Noro, T., “Bufadienolides and a new lignan from the bulbs of Urginea maritime”, Chemical and Pharmaceutical Bulletin, 49, 282-286, 2001.
• Đorđević, M.R., Zlatković, D.B., and Radulović, N.S., “Scilla bifolia Wax as a Source of Diverse Long-Chain Resorcinols and Alkane-1,3-diols”, Chemistry & Biodiversity, 18,e2000811, 2021.
• Tanış K., “Scilla bifolia'nın metanolik özütünün antioksidan kapasitesi”, Yüksek Lisans Tezi, Selçuk Üniversitesi, Fen Bilimleri Enstitüsü,Konya, 2023.
• Aktepe, N., Keskin, C., Baran, A., Atalar, M. N., Baran, M. F., Akmeşe, Ş., “Biochemical components, enzyme inhibitory, antioxidant and antimicrobial activities in endemic plant Scilla mesopotamica speta”, Journal of Food Processing and Preservation,00(e15980),1-13, 2021.
• Coşkun, Z.M., “Scilla autumnalis L.'nin üreme biyolojisi”,Yüksek Lisans Tezi, Marmara Üniversitesi,Fen Bilimleri Enstitüsü, İstanbul, 2007.
• Demirtaş, İ., Özen, T., Marah, S., Mutlu, D., Arslan, Ş., Gül, F., “Functional food components and activities of Pinus nigra and Pinus sylvestris barks as food supplements”, International Journal of Chemistry and Technology, 7(2), 229-238, 2023.
• Slinkard, K., Singleton, V.L., “Total phenol analyses: automation and comparison with manual methods”, American Journal of Enology and Viticulture, 28, 49-55, 1977.
• Moreno, M.I.N., Isla, M.I., Sampietro, A.R., Vattuone, M.A., “Comparison of the free radical-scavenging activity of propolis from several regions of Argentina”, Journal of Ethnopharmacology, 71, 109-114, 2000.
• Ersoy, E., Eroğlu Özkan, E., Boğa, M., and Mat, A., “Evaluation of in vitro biological activities of three Hypericum species H. calycinum H. confertum and H. perforatum from Turkey,” South African Journal of Botany, 130, 141-147, 2020.
• Blois, M.S., “Antioxidant determinations by the use of a stable free radical”, Nature, 181, 1199-1200, 1958.
• Re, R., Pellegrini, N., Proteggente, A., Pannala, A., Yang, M., Rice-Evans, C., “Antioxidant activity applying an improved ABTS radical cation decolorization assay”, Free Radical Biology and Medicine, 26, 1231-1237, 1999.
• Ersoy, E., Özkan, E. E., Boğa, M., Yilmaz, M. A., Mat, A., “Anti-aging potential and anti-tyrosinase activity of three Hypericum species with focus on phytochemical composition by LC–MS/MS”, Industrial Crops and Products, 141, 111735, 2019.
• Apak, R., Güçlü, K., Özyürek, M., Karademir, S.E., “Novel total antioxidant capacity index for dietary polyphenols and vitamins C and E, using their cupric ion reducing capability in the presence of neocuproine: CUPRAC method”, Journal of Agricultural and Food Chemistry, 52, 7970-7981, 2004.
• Ellman, G.L., Courtney, K.D., Andres, V., Featherstone, R.M., “A new and rapid colorimetric determination of acetylcholinesterase activity”, Biochemical Pharmacology, 7, 88-95, 1961.
• Hearing, V.J., Jiménez, M., “Mammalian tyrosinase-the critical regulatory control point in melanocyte pigmentation”, International Journal of Biochemistry, 19, 1141-1147, 1987.
• Şenol, O., “Erzurum Bölgesinde Yetişen Betula pendula Yapraklarının Antioksidan Kapasitelerinin Belirlenmesi ve Kemometrik Karakterizasyonu”, Bartın Orman Fakultesi Dergisi, 21 (1), 147-154, 2019.
• Chaachouay, N.; Zidane, L., “Plant-Derived Natural Products: A Source for Drug Discovery and Development”. Drugs Drug Candidates, 3, 184-207, 2024.
• Stalikas, C.D., “Extraction, separation, and detection methods for phenolic acids and flavonoids”, Journal of Separation Science, 30(18), 3268-3295, 2007.
• Prasad, K.N., Kong, K.W., Ramanan, R.N., Azlan, A., Ismail, A., “Determination and optimization of flavonoid and extract yield from brown mango using response surface methodology”, Separation Science and Technology, 47(1), 73-80, 2012.
• Yaman, C., Ulukuş, D., Tugay, O., “Haplophyllum suaveolens Varyetelerinin Antioksidan Aktivitesi ve Sekonder Metabolitleri Üzerine Farklı Çözücülerin Etkisi”, Türkiye Tarımsal Araştırmalar Dergisi, 6(3), 277-284, 2019.
• Aydın, B., Yuca, H., Karakaya, S., Ekşi Bona, G., Göğer, G., Tekman, E., Acar Şahin, A., Sytar, O., Civas, A., Canlı, D., Pınar, N.M., Güvenalp, Z., “The anatomical, morphological features, and biological activity of Scilla siberica subsp. armena (Grossh.) Mordak (Asparagaceae)”, Protoplasma, 260(2),371-389, 2023.
• Mulholland, D.A., Crouch, N.R., Koorbanally, C., Moodley, N., Pohl, T., “Infraspecific chemical variation in Scilla zebrina (Hyacinthaceae)”, Biochemical Systematics and Ecology, 34 (251e255), 1-5, 2006.
• Higashi, T., Ogawa, S., “Chemical derivatization for enhancing sensitivity during LC/ESI-MS/MS quantification of steroids in biological samples: a review”, The Journal of Steroid Biochemistry and Molecular Biology, 162, 57-69, 2016.
• Walton, N.J., Mayer, M.J., Narbad, A., “Vanillin”, Phytochemistry, 63, 505-515, 2003.
• Demir, T., Akpınar, Ö., “Biological Activities of Phytochemicals in Plants”, Turkish Journal of Agriculture - Food Science and Technology, 8(8), 1734-1746, 2020.
• Lv, P.C., HQ, Li., Xue, J.Y., Shi, L., Zhu, H.L., “Synthesis and biological evaluation of novel luteolin derivatives as antibacterial agents”, European Journal of Medicinal Chemistry, 44, 908-914, 2009.
• Ullah, R., Ikram, M. , Park, T.J., Ahmad ,R., Saeed, K., Alam, S.I., Ur Rehman, I., Khan,A., Khan,I. , Jo, M.G., Ok, M.K., “Vanillic Acid, a Bioactive Phenolic Compound, Counteracts LPS-Induced Neurotoxicity by Regulating c-Jun N-Terminal Kinase in Mouse Brain”, International Journal of Molecular Sciences, 22(1),361, 2020.
• Matejczyk, M., Ofman, P., Juszczuk-Kubiak, E., Swis ´ łocka, R., Shing, W. L., Kesari, K. K., Prakash, B., Lewandowski, W., “Biological effects of vanillic acid, iso-vanillic acid, and orto-vanillic acid as environmental pollutants”, Ecotoxicology and Environmental Safety, 277 (116383),1-11, 2024.
• Park, J., Cho, S.Y., Kang, J., Park, W.Y., Lee, S., Jung, Y., Kang, M.W., Kwak, H.J., Um, J.Y., “Vanillic Acid Improves Comorbidity of Cancer and Obesity through STAT3 Regulation in High-Fat-Diet-Induced Obese and B16BL6 Melanoma-Injected Mice”, Biomolecules, 10, 1098, 2020.
• Alamri, E.S., El Rabey, H.A., Alzahrani, O.R., Almutairi, F.M., Attia, E.S., Bayomy, H.M., Albalwi, R.A., Rezk, S.M., “Enhancement of the Protective Activity of Vanillic Acid against Tetrachloro-Carbon (CCl4) Hepatotoxicity in Male Rats by the Synthesis of Silver Nanoparticles (AgNPs)”, Molecules, 27, 8308, 2022.
• Calixto-Campos, C., Carvalho, T.T., Hohmann, M.S.N., Pinho-Ribeiro, F.A., Fattori, V., Manchope, M.F., Zarpelon, A., Baracat, M.M., Georgetti, S.R., Casagrande, R., Verri Jr, W.A., “Vanillic Acid Inhibits Inflammatory Pain by Inhibiting Neutrophil Recruitment, Oxidative Stress, Cytokine Production, and NFκB Activation in Mice”, Journal of Natural Products, 78, 1799-1808, 2015.
• Yao, X., Jiao, S., Qin, M., Hu, W., Yi, B., Liu, D., “Vanillic Acid Alleviates Acute Myocardial Hypoxia/Reoxygenation Injury by Inhibiting Oxidative Stress”, Oxidative Medicine and Cellular Longevity, 2020 (8348035), 2020.
• Bai, J.R., Zhong, K., Wu, Y.P., Elena, G., Gao, H., “Antibiofilm activity of shikimic acid against Staphylococcus aureus”, Food Control, 95, 327-333, 2019.
• Chen, F. L., Hou, K. X., Li, S. Y., Zu, Y. G., & Yang, L., “Extraction and chromatographic determination of shikimic acid in Chinese conifer needles with 1-Benzyl-3- methylimidazolium bromide ionic liquid aqueous solutions”, Journal of Analytical Methods in Chemistry,3, 256473, 2014.
• Apak, R., Güçlü, K., Demirata, B., Özyürek, M., Çelik, S. E., Bektaşoğlu, B., Berker, K. I. & Özyurt, D., “Comparative evaluation of various total antioxidant capacity assays applied to phenolic compounds with the CUPRAC assay”, Molecules, 12(7), 1496-1547, 2007.
• Handique, J.G., Baruah, J.B., “Polyphenolic compounds: an overview”, Reactive and Functional Polymers, 52,163-188, 2002.
• Yasuda, S., Nishida, Y., Wada, K., Akiyama, D., Toyohisa, D., Tanaka, T., Igoshi, K., Ono, M., “Anti-inflammatory and antioxidative effects of a methanol extract from bulbs of Scilla scilloides”, Bioscience, Biotechnology, and Biochemistry, 77(1),1569-1571,2013.
• Özturk, R.B., Zengin, G., Sinan, K.I., Montesano, D., Zheleva-Dimitrova, D., Gevrenova, R., Uba, A.I., Çakılcıoğlu, U., Kaplan, A., Jugreet, S., Dall’Acqua, S., Mahomoodally, M. F., “Which Extraction Solvents and Methods Are More Effective in Terms of Chemical Composition and Biological Activity of Alcea fasciculiflora from Turkey?”, Molecules, 27, 5011, 2022.