TY - JOUR T1 - Phenolic compounds and bioactivity of Scorzonera pygmaea Sibth. & Sm. aerial parts: In vitro antioxidant, anti-inflammatory and antimicrobial activities AU - Sarı, Aynur AU - Şahin, Hasan AU - Özsoy, Nurten AU - Özbek Çelik, Berna PY - 2020 DA - December JF - İstanbul Journal of Pharmacy JO - iujp PB - Istanbul University WT - DergiPark SN - 2587-2087 SP - 294 EP - 299 VL - 50 IS - 3 LA - en AB - Background and Aims: Scorzonera L. genus contains several medicinal and edible plants. Both roots and aerial parts of Scorzonera species are used. S. pygmaea is endemic to Turkey. In a previous study, nine phenolic compounds were reported from the roots of the plant alongside certain biological activities. The current study was designed to investigate the aerial parts of the plant in the same manner and compare the potentials of the two parts. Methods: Chromatographic and spectroscopic methods were used to isolate and identify the phenolics. Total phenolic contents were determined by Folin–Ciocalteu method. FRAP assay, anti-LPO, scavenging DPPH, ABTS and superoxide radicals were employed to evaluate the antioxidant activity. COX inhibition test and micro broth dilution technique were used for antiinflammatory and antimicrobial activities, respectively. Results: Seven phenolic compounds; thunberginol C (1), protocatechuic acid (2), chlorogenic acid methyl ester (3), cudrabibenzyl A (4), scorzocreticin (5), scorzocreticoside I (6) and II (7) were purified. All the compounds are new for the aerial parts of the plant and 2 is new for the genus. The aerial parts showed a high antioxidant capacity which correlated with its phenolic content. COX inhibitory activity was found to be lower compared to Indomethacin. Weak antimicrobial activity was determined against Staphylococcus aureus and S. epidermidis. Conclusion: Aerial parts possess significant/infrequent phenolics and the ethyl acetate (EtOAc) fraction of the ethanol extract is the most promising fraction for isolating these compounds. Phenolic compositions of aerial parts and roots are very similar. However, aerial parts can be a better rich source of natural antioxidants with protocatechuic acid and higher antioxidant potential. KW - Scorzonera pygmaea KW - phenolics KW - antioxidant KW - protocatechuic acid CR - • Acıkara, O. B., Çitoglu, G. S., Dall’Acqua, S., Smejkal, K., Cvacka, J., & Zemlicka, M. (2012). A new triterpene from Scorzonera latifolia (Fisch. and Mey.) DC. Natural Product Research, 26(20), 1892–1897. doi:10.1080/14786419.2011.625644 CR - • Acıkara, Ö. B., Ergene Öz, B., Bakar, F., Saltan Çitoğlu, G., & Nebioğlu, S. (2017). Evaluation of Antioxidant Activities and Phenolic Compounds of Scorzonera latifolia (Fisch. & Mey.) DC. Collected from Different Geographic Origins in Turkey. The Turkish Journal of Pharmaceutical Sciences, 14(2), 179–184. doi:10.4274/tjps.57070 CR - • Athmouni, K., Belghith, T., Bellassouad, K., Feki, A. E., & Ayadi, H. (2015). Effect of extraction solvents on the biomolecules and antioxidant properties of Scorzonera undulata (Asteraceae): Application of factorial design optimization phenolic extraction. Acta Scientiarum Polonorum, Technologia Alimentaria, 14(4), 313–330. doi:10.17306/j.afs.2015.4.32 CR - • Bader, A., De Tommasi, N., Cotugno, R., & Braca, A. (2011). Phenolic compounds from the roots of Jordanian viper’s grass, Scorzonera judaica. Journal of Natural Products, 74(6), 1421–1426. doi:10.1021/ np200143s CR - • Baykan-Erel, S., Bedir, E., Khan, I. A., & Karaalp, C. (2010). Secondary metabolites from Centaurea ensiformis P.H. Davis. Biochemical Systematics and Ecology, 38(5), 1056–1058. doi:https://doi. org/10.1016/j.bse.2010.09.004 CR - • Baytop, T. (1999). Türkiye’de Bitkilerle Tedavi Geçmişte ve Bugün (Therapy with medicinal plants in Turkey). İstanbul: Nobel Tıp. CR - • Benzie, I. F. F., & Strain, J. J. (1996). The Ferric Reducing Ability of Plasma (FRAP) as a Measure of “Antioxidant Power”: The FRAP Assay. Analytical Biochemistry, 239(1), 70–76. doi:http://dx.doi. org/10.1006/abio.1996.0292 CR - • Brand-Williams, W., Cuvelier, M. E., & Berset, C. (1995). Use of a free radical method to evaluate antioxidant activity. Food Science Technology (London), 28(1), 25–30. doi:10.1016/S0023- 6438(95)80008-5 CR - • Chang, S. W., Kim, K. H., Lee, I. K., Choi, S. U., Ryu, S. Y., & Lee, K. R. (2009). Phytochemical constituents of Bistorta manshuriensis. Natural Products Sciences, 15(4), 234–240. • CLSI. (2000). Reference Method for Broth Dilution Antifungal Susceptbility Testing of Yeasts; Approved Standart M27-A NCCLS. Wayne, Pennsylvania: CLSI. CR - • CLSI. (2006). Methods for dilution antimicrobial susceptibility tests for bacteria that grow aerobically: Approved Standard M7- A5. Wayne, PA: CLSI. CR - • Coşkunçelebi, K., Makbul, S., Gültepe, M., Okur, S., & Güzel, M. E. (2015). A conspectus of Scorzonera s.l. in Turkey. Turkish Journal of Botany, 39, 76–87. doi:10.3906/bot-1401-10 CR - • Dalar, A., Mukemre, M., Unal, M., & Ozgokce, F. (2018). Traditional medicinal plants of Ağrı Province, Turkey. Journal of Ethnopharmacology, 226, 56–72. doi:https://doi.org/10.1016/j.jep.2018.08.004 CR - • Duh, P. D., Tu, Y. Y., & Yen, G. C. (1999). Antioxidant Activity of Water Extract of Harng Jyur (Chrysanthemum morifolium Ramat). LWT - Food Science Technology, 32(5), 269–277. doi:http://dx.doi. org/10.1006/fstl.1999.0548 CR - • Harkati, B., Akkal, S., Bayat, C., Laouer, H., & Franca, M. G. D. (2010). Secondary metabolites from Scorzonera undulata ssp. deliciosa (Guss.) Maire (Asteracae) and their antioxidant activities. Records of Natural Products, 4(3), 171–175. CR - • Kokoska, L., & Janovska, D. (2009). Chemistry and pharmacology of Rhaponticum carthamoides: A review. Phytochemistry, 70(7), 842–855. doi:https://doi.org/10.1016/j.phytochem.2009.04.008 CR - • Koyuncu, O., Yaylacı, Ö. K., & Kuş, G. (2014). Taxonomical Studies on Endemic Scorzonera pygmaea var. pygmaea and var. nutans Stat. Nov. (Asteraceae) From Turkey. Pakistan Journal of Botany, 46(2), 555–563. CR - • Lende, A. B., Kshirsagar, A. D., Deshpande, A. D., Muley, M. M., Patil, R. R., Bafna, P. A., & Naik, S. R. (2011). Anti-inflammatory and analgesic activity of protocatechuic acid in rats and mice. Inflammopharmacology, 19(5), 255. doi:10.1007/s10787-011-0086-4 CR - • Liang, N., & Kitts, D. D. (2016). Role of Chlorogenic Acids in Controlling Oxidative and Inflammatory Stress Conditions. Nutrients, 8(1), 16. doi:10.3390/nu8010016 CR - • Milella, L., Bader, A., De Tommasi, N., Russo, D., & Braca, A. (2014). Antioxidant and free radical-scavenging activity of constituents from two Scorzonera species. Food Chemistry, 160, 298–304. doi:http://dx.doi.org/10.1016/j.foodchem.2014.03.097 CR - • Nasseri, M. A., Sharifi Bigy, S., Allahresani, A., & Malekaneh, M. (2015). Assessment of Antioxidant Activity, Chemical Characterization and Evaluation of Fatty Acid Compositions of Scorzonera paradoxa Fisch and C. A. Mey. Jundishapur Journal of Natural Pharmaceutical Products, 10(4), e19781. doi:10.17795/jjnpp-19781 CR - • Nguyen, X. H. T., Juvik, O. J., Øvstedal, D. O., & Fossen, T. (2014). 6-Carboxydihydroresveratrol 3-O-β-glucopyranoside — A novel natural product from the Cretaceous relict Metasequoia glyptostroboides. Fitoterapia, 95, 109–114. doi:https://doi.org/10.1016/j. fitote.2014.03.001 CR - • Nishikimi, M., Rao, N. A., & Yagi, K. (1972). Occurrence of superoxide anion in the reaction of reduced phenazine methosulfate and molecular oxygen. Biochemical and Biophysical Research Communications, 46(2), 849–854. doi:10.1016/S0006-291X(72)80218-3 CR - • Paraschos, S., Magiatis, P., Kalpoutzakis, E., Harvala, C., & Skaltsounis, A. L. (2001). Three new dihydroisocoumarins from the Greek endemic species Scorzonera cretica. Journal of Natural Products, 64(12), 1585–1587. doi:10.1021/np0103665 CR - • Phaniendra, A., Jestadi, D. B., & Periyasamy, L. (2015). Free radicals: properties, sources, targets, and their implication in various diseases. Indian journal of clinical biochemistry : IJCB, 30(1), 11–26. doi:10.1007/s12291-014-0446-0 CR - • Polat, R. (2019). Ethnobotanical study on medicinal plants in Bingöl (City center) (Turkey). Journal of Herbal Medicine, 16, 100211. doi:https://doi.org/10.1016/j.hermed.2018.01.007 CR - • Re, R., Pellegrini, N., Proteggente, A., Pannala, A., Yang, M., & Rice- Evans, C. (1999). Antioxidant activity applying an improved ABTS radical cation decolorization assay. Free Radical Biology and Medicine, 26(9/10), 1231–1237. doi:10.1016/S0891-5849(98)00315-3 CR - • Sarı, A. (2010). Two new 3-benzylphthalides from Scorzonera veratrifolia Fenzl. Natural Product Research, 24(1), 56–62. doi:10.1080/14786410902800699 CR - • Sarı, A. (2012). Phenolic compounds from Scorzonera latifolia (Fisch. & Mey.) DC. Natural Product Research, 26(1), 50–55. doi:10 .1080/14786419.2010.533666 CR - • Sarı, A., Özbek, B., & Özgökçe, F. (2009). Antimicrobial activities of two Scorzonera species growing in Turkey. Asian Journal of Chemistry, 21(6), 4785–4788. CR - • Sarı, A., Şahin, H., Özsoy, N., & Özbek Çelik, B. (2019). Phenolic compounds and in vitro antioxidant, anti-inflammatory, antimicrobial activities of Scorzonera hieraciifolia Hayek roots. South African Journal of Botany, 125, 116–119. doi:https://doi.org/10.1016/j. sajb.2019.07.009 CR - • Sarı, A., Zidorn, C., Ellmerer, E. P., Özgökçe, F., Ongania, K.-H., & Stuppner, H. (2007). Phenolic Compounds from Scorzonera tomentosa L. Helvetica Chimica Acta, 90, 311–317. CR - • Singh, K. N., & Lal, B. (2008). Ethnomedicines used against four common ailments by the tribal communities of Lahaul-Spiti in western Himalaya. Journal of Ethnopharmacology, 115(1), 147– 159. doi:https://doi.org/10.1016/j.jep.2007.09.017 CR - • Slinkard, K., & Singleton, V. L. (1977). Total phenol analysis: automation and comparison with manual methods. American Journal of Enology and Viticulture, 28(1), 49–55. CR - • Şahin, H., Sarı, A., Özsoy, N., Özbek Çelik, B., & Koyuncu, O. (2020). Two new phenolic compounds and some biological activities of Scorzonera pygmaea Sibth. & Sm. subaerial parts. Natural Product Research, 34(5), 621–628. doi:10.1080/14786419.2018.1493585 CR - • Şenkardeş, İ., Bulut, G., Doğan, A., & Tuzlacı, E. (2019). An Ethnobotanical Analysis on Wild Edible Plants of the Turkish Asteraceae Taxa. Agriculturae Conspectus Scientificus, 84(1), 17–28. CR - • Toshikawa, M., Uchida, E., Chatani, N., Kobayashi, H., Naitoh, Y., Okuno, Y., . . . Murakami, N. (1992). Thunberginols C,D and E, New Antiallergic and Antimicrobial Dhiydroisocoumarins and Thunberginol G 3’-O-Glucoside and (-)-Hydrangenol 4’-O-Glucoside, New Dhydroisocoumarin Glycosides from Hydrangea dulcis Folium. Chemical and Pharmaceutical Bulletin, 40(12), 3352–3354. doi:10.1248/cpb.40.3352 CR - • Tsevegsuren, N., Edrada, R., Lin, W., Ebel, R., Torre, C., Ortlepp, S., . . . Proksch, P. (2007). Biologically active natural products from Mongolian medicinal plants Scorzonera divaricata and Scorzonera pseudodivaricata. Journal of Natural Products, 70, 962–967. CR - • Vitaglione, P., Donnarumma, G., Napolitano, A., Galvano, F., Gallo, A., Scalfi, L., & Fogliano, V. (2007). Protocatechuic Acid Is the Major Human Metabolite of Cyanidin-Glucosides. The Journal of Nutrition, 137(9), 2043–2048. doi:10.1093/jn/137.9.2043 CR - • Wang, Y., Wray, V., Tsevegsuren, N., Lin, W. H., & Proksch, P. (2012). Phenolic Compounds from the Mongolian Medicinal Plant Scorzonera radiata. Zeitschrift Fur Naturforschung Section C-a Journal of Biosciences, 67(3-4), 135–143. CR - • Yang, Y. J., Liu, X., Wu, H. R., He, X. F., Bi, Y. R., Zhu, Y., & Liu, Z. L. (2013). Radical scavenging activity and cytotoxicity of active quinic acid derivatives from Scorzonera divaricata roots. Food Chemistry, 138(2-3), 2057–2063. doi:10.1016/j.foodchem.2012.10.122 CR - • Yang, Y. J., Yao, J., Jin, X. J., Shi, Z. N., Shen, T. F., Fang, J. G., . . . Zhu, Y. (2016). Sesquiterpenoids and tirucallane triterpenoids from the roots of Scorzonera divaricata. Phytochemistry, 124, 86–98. doi:http://dx.doi.org/10.1016/j.phytochem.2016.01.015 CR - • Zhu, X., Dong, X., Wang, Y., Peng, J., & Luo, S. (2005). Phenolic compounds from Viburnum cylindricum. Helvetica Chimica Acta, 88(2), 339–342. doi:10.1002/hlca.200590017 CR - • Zidorn, C., Ellmerer-Müller, E. P., & Stuppner, H. (2000). Tyrolobibenzyls - Novel secondery metabolites from Scorzonera humilis. HeIvetica Chimica Acta, 83, 2920–2925. CR - • Zidorn, C., Lohwasser, U., Pschorr, S., Salvenmoser, D., Ongania, K.-H., Ellmerer, E. P., . . . Stuppner, H. (2005). Bibenzyls and dihydroisocoumarins from white salsify (Tragopogon porrifolius subsp. porrifolius). Phytochemistry, 66(14), 1691–1697. doi:10.1016/j.phytochem. 2005.05.004 CR - • Zidorn, C., Spitaler, R., Ellmerer-Müller, E.-P., Perry, N. B., Gerhäuser, C., & Stuppner, H. (2002). Structure of Tyrolobibenzyl D and Biological Activity of Tyrolobibenzyls from Scorzonera humilis. Zeitschrift für Naturforschung C, 57(7-8), 614–619. doi:10.1515/ znc-2002-7-811 UR - https://dergipark.org.tr/en/pub/iujp/article/850708 L1 - https://dergipark.org.tr/en/download/article-file/1479403 ER -