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Isolation and characterization of secondary metabolites from apolar fraction of Scabiosa sicula and evaluation of their antioxidant activities

Year 2021, Volume: 11 Issue: 3, 934 - 942, 15.07.2021
https://doi.org/10.17714/gumusfenbil.888739

Abstract

In this study, the identification and characterization of Scabiosa sicula dichloromethane extract constituents were discussed for the first time. Moreover, this study is also providing an overview of the phytochemistry of Mediterranean medicinal plants. The phytochemical investigation of S. sicula dichloromethane extract was performed by HPLC and resulted in isolation of six compounds and five of them were identified as phenolic compounds and one as triterpene. The structures of the isolated compounds determined as luteolin-6-C-glucoside, luteolin-7-O-glucoside, caffeic acid, ursolic acid, 4-O-caffeoylquinic acid and 3,5-O-dicaffeoylquinic acid using spectroscopic analysis, including NMR and HR-MS techniques. Moreover, TEAC and DPPH assays were performed to evaluate the antioxidant activity of S. sicula’s dichloromethane extract. TEAC value was defined as the concentration of Trolox solution with the same amount of antioxidant potential found in the 1 mg/mL solution of the tested extract resulted to be 1.21 ± 0.01 mg/mL. DPPH activity was calculated as (4.42 μg/mL) while the corresponding methanol extract antiradical activity was 3.34 ± 0.01 μg/mL. The contribution to literature with this study is to increase the depth of knowledge about S. sicula on secondary metabolites isolated from apolar fraction and the results of this study will help reveal the medical potential of these species.

Supporting Institution

TUBİTAK

Project Number

1059B191700874

Thanks

The author would like to thank TUBITAK 2219 Grant number: 1059B191700874

References

  • Baykal, T., Panayir, T., Tasdemir, D., Sticher, O. And Calis, I. (1998). Triterpene saponins from Scabiosa rotata. Phytochemistry, 48, 867–873. https://doi.org/10.1016/S0031-9422(97)00982-5
  • Bendary, E., Francis, R.R., Ali, H.M.G., Sarwat, M.I. and El Hady S. (2013). Antioxidant and structure–activity relationships (SARs) of some phenolic and anilines compounds. Annals of Agricultural Science, 58, 173– 181. https://doi.org/10.1016/j.aoas.2013.07.002
  • Besbes, M., Omri A., Cheraif, I., Daami, M., Jannet, H.B., Mastouri, M., Aouni, M. and Selmi, B. (2012). Chemical composition and antimicrobial activity of essential oils from Scabiosa arenaria Forssk. growing wild in Tunisia. Chemistry & Biodiversity, 9, 829-839. https://doi.org/10.1002/cbdv.201100191
  • Bonet, M. and Valles, J. (2007). Ethnobotany of Montseny biosphere reserve (Catalonia, Iberian Peninsula): Plants used in veterinary medicine. Journal of Ethnopharmacology, 110, 130-147. https://doi.org/10.1016/j.jep.2006.09.016
  • Cerulli, A., Lauro, G., Masullo, M., Cantone, V., Olas, B., Kontek, B., Nazzaro, F., Bifulco, G. and Piacente, S. (2017). Cyclic diarylheptanoids from Corylus avellana green leafy covers: determination of their absolute configurations and evaluation of their antioxidant and antimicrobial activities. Journal of Natural Products, 80, 1703–1713. https://doi.org/10.1021/acs.jnatprod.6b00703
  • Cerulli, A., Masullo, M., Montoro, P., Hosek, J., Pizza, C., Piacente, S. (2018). Metabolite profiling of “green” extracts of Corylus avellana leaves by 1H NMR spectroscopy and multivariate statistical analysis. Journal of Pharmaceutical and Biomedical Analysis; 160, 168–178. https://doi.org/10.1016/j.jpba.2018.07.046
  • Chuppeng, W., Shanshan, L., Lin, L., Chuying, C. and Shuying, F. (2017). Caffeoylquinic acids from the aerial parts of Chrysanthemum coronorium L. Plants, 6, 10. https://doi.org/10.3390/plants6010010
  • Corradi, E., De Mieri, M., Gafner, F., Hamburger, M. and Potterat, O. (2016). A new secoiridoid glucoside and a metabolite profile of Scabiosa lucida. Natural Product Communications, 11, 887–890. https://doi.org/10.1177/1934578X1601100705
  • Davis, P.H. (1970). Flora of Turkey: Edinburg, University Press.
  • Do A.F.P., Napolitano, A., Masullo, M., dos Santos, L.C., Festa, M., Vilegas, W., Pizza, C. and Piacente, S. (2012). HPLC-ESIMSn profiling, isolation, structural elucidation, and evaluation of the antioxidant potential of phenolics from Paepalanthus geniculatus. Journal of Natural Products, 75, 547–556. https://doi.org/10.1021/np200604k
  • Elhawary, S.S., Eltantawy, M.E., Sleem, A.A., Abdallah, H.M. and Mohamed, N.M. (2011). Investigation of phenolic content and biological activities of Scabiosa atropurpurea L. World Applied Sciences Journal, 15, 311–317.
  • Garaev, E. A., Movsumov, I. S. and Isaev, M. I. (2008). Flavonoids and oleanolic acid from Scabiosa caucasica. Chemistry of Natural Compounds, 44, 4. https://doi.org/10.1007/s10600-008-9108-x
  • Gnoatto, S.C.B., Dassonville-Klimpt A., Da Nascimento, S., Gale ́ra, P., Boumediene, K., Gosmann, G., Sonnet, P. and Moslemi S. (2008). Evaluation of ursolic acid isolated from Ilex paraguariensis and derivatives on aromatase inhibition. European Journal of Medicinal Chemistry, 43, 1865-1877. https://doi.org/10.1016/j.ejmech.2007.11.021
  • Hlila, M.B., Mosbah, H., Majouli, K., Msaada, K., Ben J.H., Aouni, M. and Selmi, B. (2015). Alpha-Glucosidase inhibition by Tunisian Scabiosa arenaria Forssk. extracts. International Journal of Biological Macromolecules, 77, 383-389. https://doi.org/10.1016/j.ijbiomac.2015.03.035
  • Jeong C., Jeong H., Choi G., Kim D., Lee U. and Heo H. (2011). Neuroprotective and anti-oxidant effects of caffeic acid isolated from Erigeron annuus leaf. Chinese Medicine, 6, 25. https://doi.org/10.1186/1749-8546-6-25
  • Kılınc, H., Masullo, M., D’Urso, G., Karayildirim T., Alankus, O. and Piacente S. (2020). Phytochemical investigation of Scabiosa sicula guided by a preliminary HPLC-ESIMSn profiling. Phytochemistry, 174. https://doi.org/10.1016/j.phytochem.2020.112350
  • Lehbili, M., Magid, A.A., Kabouche, A., Voutquenne-Nazabadioko, L., Morjani, H., Harakat, D. And Kabouche, Z. (2018). Triterpenoid saponins from Scabiosa stellata collected in North-eastern Algeria. Phytochemistry ,150, 40–49. https://doi.org/10.1016/j.phytochem.2018.03.005
  • Kose, L.S., Moteetee, A. and Van Vuuren, S. (2015). Ethnobotanical survey of medicinal plants used in the Maseru district of Lesotho. Journal of Natural Products, 170, 184-200. https://doi.org/10.1016/j.jep.2015.04.047
  • Ma, J.N, Bolraa, S., Ji, M., He, Q.Q. and Ma, C.M. (2016). Quantification and antioxidant and anti-HCV activities of the constituents from the inflorescences of Scabiosa comosa and S. tschilliensis. Natural Product Research, 30, 590-594. https://doi.org/10.1080/14786419.2015.1027701
  • Panayır, T. and Baykal, T. (1997). Morphological and anatomical studies on Scabiosa rotata bieb. (Dipsacaceae). Journal of Faculty of Pharmacy of Ankara University, 26(1), 22-35. https://doi.org/10.1501/Eczfak_0000000311
  • Perdetzoglohu, D., Kaltsa, S., Tzakou, O. and Harvala, C. (1994). Comparative phytochemical and morphological study of two species of the Scabiosa L. genus. Feddes Repertorium, 105, 157 – 165. https://doi.org/10.1002/fedr.19941050305
  • Pinto, D.C.G.A., Rahmouni, N., Beghidja, N. and Silva, A.M.S. (2018). Scabiosa Genus: A rich source of bioactive metabolites. Medicines, 5, 110. https://doi.org/10.3390/medicines5040110
  • Rahmouni, N., Pinto, D.C.G.A., Beghidja, N., Benayache, S. and Silva, A.M.S. (2018a). Scabiosa stellata L. Phenolic content clarifies its antioxidant activity. Molecules; 23,6, 1285. https://doi.org/10.3390/molecules23061285
  • Rahmouni N., Pinto, D.C.G.A., Santos S.A.O., Beghidja, N. and Silva A.M.S. (2018b). Lipophilic composition of Scabiosa stellata L.: an underexploited plant from Batna (Algeria). Chemical Papers, 72, 753-762. https://doi.org/10.1007/s11696-017-0308-3
  • Reveal, J.L. and Chase, M.W. (2011). Apg III: bibliographical information and synonymy of magnoliidae. Phytotaxa, 19, 71–134. https://doi.org/10.11646/phytotaxa.19.1.4
  • Rigat, M., Bonet, M. A., Garcia, S., Garnatje, T. and Valles, J. (2007). Studies on pharmaceutical ethnobotany in the high river Ter valley (Pyrenees, Catalonia, Iberian Peninsula). Journal of Ethnopharmacology, 113, 267-277. https://doi.org/10.1016/j.jep.2007.06.004
  • Santos, C.C.D., Masullo, M., Cerulli, A., Mari, A., Estevam, C.D., Pizza, C. and Piacente, S. (2017). Isolation of antioxidant phenolics from Schinopsis brasiliensis based on a pre- liminary LC-MS profiling. Phytochemistry, 140, 45–51. https://doi.org/10.1016/j.phytochem.2017.04.008
  • Valgimigli, L., Amorati, R., Fumo M.G., Dilabio, G.A., Pedulli, G.F., Ingold, K.U. and Pratt, D. (2008). The unusual reaction of semiquinone radicals with molecular oxygen. The Journal of Organic Chemistry, 73, 1830–1841. https://doi.org/10.1021/jo7024543
  • Wang, J., Liu, K., Xu, D., Wang, Q., Bi, K., Song, Y., Li, J. and Zhang, L. (2013). Rapid micropropagation system in vitro and antioxidant activity of Scabiosa tschiliensis Grunning. Plant Growth Regulation, 69, 305–310. https://doi.org/10.1007/s10725-012-9765-4
  • Zemtsova, G.N., Bandyukova, V.A. and Shinkarenko, A.L. (1968). Quercetin diglucoside from the yellow Scabiosa. Pharmaceutical Chemistry Journal, 2, 12,180–678. https://doi.org/10.1007/BF00763332
  • Zhang, L., Cui, Z.H., Mu, Y.X., Wei, K.H., Li, Z.H., Zhu, H., Yang, D.W., Wang, Y.L., Long, P., Zhang, C.H. and Li, M.H. (2015). Ethnopharmacological investigation and rapid authentication of Mongolian patent medicines Digeda. Chinese Herbal Medicine, 7, 223-237. https://doi.org/10.1016/S1674-6384(15)60044-2
  • Zheng, Q., Koike, K., Han, L.K., Okuda, H. and Nikaido, T. (2004). New biologically active triterpenoid saponins from Scabiosa tschiliensis. Journal of Natural Products, 67, 604-613. https://doi.org/10.1021/np0304722

Scabiosa sicula’nın apolar fraksiyonundan ikincil metabolitlerin izolasyonu ve karakterizasyonu ve antioksidant aktivitelerinin değerlendirilmesi

Year 2021, Volume: 11 Issue: 3, 934 - 942, 15.07.2021
https://doi.org/10.17714/gumusfenbil.888739

Abstract

Bu çalışmada, Scabiosa sicula türünün diklorometan ekstresi bileşenlerinin tanımlanması ve karakterizasyonu ilk kez tartışılmıştır. Ayrıca, bu çalışma Akdeniz şifalı bitkilerinin fitokimyası hakkında genel bir bakış sunmaktadır. S. sicula diklorometan ekstresinin fitokimyasal incelenmesi HPLC ile yapılmış ve izole edilen altı bileşikten beş tanesinin fenolik bir tanesininde triterpen yapısında olduğu NMR ve HR-MS teknikleri kullanılarak luteolin-6-C-glukozit, luteolin-7-O-glukozit, kafeik asit, ursolik asit, 4-O-kafeoilkinik asit ve 3,5-O- dikaffeoilkinik asit olarak belirlenmiştir. S. sicula’nın diklorometan ekstresinin antioksidant aktivitesi TEAC ve DPPH yöntemleri ile incelenmiştir. TEAC değeri, test edilen ekstraktın 1 mg/mL solüsyonunda bulunan aynı miktarda antioksidan potansiyeline sahip Trolox solüsyonunun konsantrasyonuna bağlı olarak 1.21 ± 0.01 mg/mL tanımlandı. DPPH aktivitesi (4.42 μg / mL) olarak hesaplanırken ona karşılık gelen metanol ekstresinin antiradikal aktivitesi 3.34 ± 0.01 μg/mL olarak ölçülmüştür. Scabiosa sicula diklorometan ekstresinin ikincil metabolitlerinin tanımlandığı bu çalışmanın literatüre sağladığı katkı, bu türün tıbbi potansiyelinin ortaya çıkarılmasına yardım edecektir.

Project Number

1059B191700874

References

  • Baykal, T., Panayir, T., Tasdemir, D., Sticher, O. And Calis, I. (1998). Triterpene saponins from Scabiosa rotata. Phytochemistry, 48, 867–873. https://doi.org/10.1016/S0031-9422(97)00982-5
  • Bendary, E., Francis, R.R., Ali, H.M.G., Sarwat, M.I. and El Hady S. (2013). Antioxidant and structure–activity relationships (SARs) of some phenolic and anilines compounds. Annals of Agricultural Science, 58, 173– 181. https://doi.org/10.1016/j.aoas.2013.07.002
  • Besbes, M., Omri A., Cheraif, I., Daami, M., Jannet, H.B., Mastouri, M., Aouni, M. and Selmi, B. (2012). Chemical composition and antimicrobial activity of essential oils from Scabiosa arenaria Forssk. growing wild in Tunisia. Chemistry & Biodiversity, 9, 829-839. https://doi.org/10.1002/cbdv.201100191
  • Bonet, M. and Valles, J. (2007). Ethnobotany of Montseny biosphere reserve (Catalonia, Iberian Peninsula): Plants used in veterinary medicine. Journal of Ethnopharmacology, 110, 130-147. https://doi.org/10.1016/j.jep.2006.09.016
  • Cerulli, A., Lauro, G., Masullo, M., Cantone, V., Olas, B., Kontek, B., Nazzaro, F., Bifulco, G. and Piacente, S. (2017). Cyclic diarylheptanoids from Corylus avellana green leafy covers: determination of their absolute configurations and evaluation of their antioxidant and antimicrobial activities. Journal of Natural Products, 80, 1703–1713. https://doi.org/10.1021/acs.jnatprod.6b00703
  • Cerulli, A., Masullo, M., Montoro, P., Hosek, J., Pizza, C., Piacente, S. (2018). Metabolite profiling of “green” extracts of Corylus avellana leaves by 1H NMR spectroscopy and multivariate statistical analysis. Journal of Pharmaceutical and Biomedical Analysis; 160, 168–178. https://doi.org/10.1016/j.jpba.2018.07.046
  • Chuppeng, W., Shanshan, L., Lin, L., Chuying, C. and Shuying, F. (2017). Caffeoylquinic acids from the aerial parts of Chrysanthemum coronorium L. Plants, 6, 10. https://doi.org/10.3390/plants6010010
  • Corradi, E., De Mieri, M., Gafner, F., Hamburger, M. and Potterat, O. (2016). A new secoiridoid glucoside and a metabolite profile of Scabiosa lucida. Natural Product Communications, 11, 887–890. https://doi.org/10.1177/1934578X1601100705
  • Davis, P.H. (1970). Flora of Turkey: Edinburg, University Press.
  • Do A.F.P., Napolitano, A., Masullo, M., dos Santos, L.C., Festa, M., Vilegas, W., Pizza, C. and Piacente, S. (2012). HPLC-ESIMSn profiling, isolation, structural elucidation, and evaluation of the antioxidant potential of phenolics from Paepalanthus geniculatus. Journal of Natural Products, 75, 547–556. https://doi.org/10.1021/np200604k
  • Elhawary, S.S., Eltantawy, M.E., Sleem, A.A., Abdallah, H.M. and Mohamed, N.M. (2011). Investigation of phenolic content and biological activities of Scabiosa atropurpurea L. World Applied Sciences Journal, 15, 311–317.
  • Garaev, E. A., Movsumov, I. S. and Isaev, M. I. (2008). Flavonoids and oleanolic acid from Scabiosa caucasica. Chemistry of Natural Compounds, 44, 4. https://doi.org/10.1007/s10600-008-9108-x
  • Gnoatto, S.C.B., Dassonville-Klimpt A., Da Nascimento, S., Gale ́ra, P., Boumediene, K., Gosmann, G., Sonnet, P. and Moslemi S. (2008). Evaluation of ursolic acid isolated from Ilex paraguariensis and derivatives on aromatase inhibition. European Journal of Medicinal Chemistry, 43, 1865-1877. https://doi.org/10.1016/j.ejmech.2007.11.021
  • Hlila, M.B., Mosbah, H., Majouli, K., Msaada, K., Ben J.H., Aouni, M. and Selmi, B. (2015). Alpha-Glucosidase inhibition by Tunisian Scabiosa arenaria Forssk. extracts. International Journal of Biological Macromolecules, 77, 383-389. https://doi.org/10.1016/j.ijbiomac.2015.03.035
  • Jeong C., Jeong H., Choi G., Kim D., Lee U. and Heo H. (2011). Neuroprotective and anti-oxidant effects of caffeic acid isolated from Erigeron annuus leaf. Chinese Medicine, 6, 25. https://doi.org/10.1186/1749-8546-6-25
  • Kılınc, H., Masullo, M., D’Urso, G., Karayildirim T., Alankus, O. and Piacente S. (2020). Phytochemical investigation of Scabiosa sicula guided by a preliminary HPLC-ESIMSn profiling. Phytochemistry, 174. https://doi.org/10.1016/j.phytochem.2020.112350
  • Lehbili, M., Magid, A.A., Kabouche, A., Voutquenne-Nazabadioko, L., Morjani, H., Harakat, D. And Kabouche, Z. (2018). Triterpenoid saponins from Scabiosa stellata collected in North-eastern Algeria. Phytochemistry ,150, 40–49. https://doi.org/10.1016/j.phytochem.2018.03.005
  • Kose, L.S., Moteetee, A. and Van Vuuren, S. (2015). Ethnobotanical survey of medicinal plants used in the Maseru district of Lesotho. Journal of Natural Products, 170, 184-200. https://doi.org/10.1016/j.jep.2015.04.047
  • Ma, J.N, Bolraa, S., Ji, M., He, Q.Q. and Ma, C.M. (2016). Quantification and antioxidant and anti-HCV activities of the constituents from the inflorescences of Scabiosa comosa and S. tschilliensis. Natural Product Research, 30, 590-594. https://doi.org/10.1080/14786419.2015.1027701
  • Panayır, T. and Baykal, T. (1997). Morphological and anatomical studies on Scabiosa rotata bieb. (Dipsacaceae). Journal of Faculty of Pharmacy of Ankara University, 26(1), 22-35. https://doi.org/10.1501/Eczfak_0000000311
  • Perdetzoglohu, D., Kaltsa, S., Tzakou, O. and Harvala, C. (1994). Comparative phytochemical and morphological study of two species of the Scabiosa L. genus. Feddes Repertorium, 105, 157 – 165. https://doi.org/10.1002/fedr.19941050305
  • Pinto, D.C.G.A., Rahmouni, N., Beghidja, N. and Silva, A.M.S. (2018). Scabiosa Genus: A rich source of bioactive metabolites. Medicines, 5, 110. https://doi.org/10.3390/medicines5040110
  • Rahmouni, N., Pinto, D.C.G.A., Beghidja, N., Benayache, S. and Silva, A.M.S. (2018a). Scabiosa stellata L. Phenolic content clarifies its antioxidant activity. Molecules; 23,6, 1285. https://doi.org/10.3390/molecules23061285
  • Rahmouni N., Pinto, D.C.G.A., Santos S.A.O., Beghidja, N. and Silva A.M.S. (2018b). Lipophilic composition of Scabiosa stellata L.: an underexploited plant from Batna (Algeria). Chemical Papers, 72, 753-762. https://doi.org/10.1007/s11696-017-0308-3
  • Reveal, J.L. and Chase, M.W. (2011). Apg III: bibliographical information and synonymy of magnoliidae. Phytotaxa, 19, 71–134. https://doi.org/10.11646/phytotaxa.19.1.4
  • Rigat, M., Bonet, M. A., Garcia, S., Garnatje, T. and Valles, J. (2007). Studies on pharmaceutical ethnobotany in the high river Ter valley (Pyrenees, Catalonia, Iberian Peninsula). Journal of Ethnopharmacology, 113, 267-277. https://doi.org/10.1016/j.jep.2007.06.004
  • Santos, C.C.D., Masullo, M., Cerulli, A., Mari, A., Estevam, C.D., Pizza, C. and Piacente, S. (2017). Isolation of antioxidant phenolics from Schinopsis brasiliensis based on a pre- liminary LC-MS profiling. Phytochemistry, 140, 45–51. https://doi.org/10.1016/j.phytochem.2017.04.008
  • Valgimigli, L., Amorati, R., Fumo M.G., Dilabio, G.A., Pedulli, G.F., Ingold, K.U. and Pratt, D. (2008). The unusual reaction of semiquinone radicals with molecular oxygen. The Journal of Organic Chemistry, 73, 1830–1841. https://doi.org/10.1021/jo7024543
  • Wang, J., Liu, K., Xu, D., Wang, Q., Bi, K., Song, Y., Li, J. and Zhang, L. (2013). Rapid micropropagation system in vitro and antioxidant activity of Scabiosa tschiliensis Grunning. Plant Growth Regulation, 69, 305–310. https://doi.org/10.1007/s10725-012-9765-4
  • Zemtsova, G.N., Bandyukova, V.A. and Shinkarenko, A.L. (1968). Quercetin diglucoside from the yellow Scabiosa. Pharmaceutical Chemistry Journal, 2, 12,180–678. https://doi.org/10.1007/BF00763332
  • Zhang, L., Cui, Z.H., Mu, Y.X., Wei, K.H., Li, Z.H., Zhu, H., Yang, D.W., Wang, Y.L., Long, P., Zhang, C.H. and Li, M.H. (2015). Ethnopharmacological investigation and rapid authentication of Mongolian patent medicines Digeda. Chinese Herbal Medicine, 7, 223-237. https://doi.org/10.1016/S1674-6384(15)60044-2
  • Zheng, Q., Koike, K., Han, L.K., Okuda, H. and Nikaido, T. (2004). New biologically active triterpenoid saponins from Scabiosa tschiliensis. Journal of Natural Products, 67, 604-613. https://doi.org/10.1021/np0304722
There are 32 citations in total.

Details

Primary Language English
Journal Section Articles
Authors

Hilal Kılınç 0000-0003-3772-2691

Project Number 1059B191700874
Publication Date July 15, 2021
Submission Date March 1, 2021
Acceptance Date June 6, 2021
Published in Issue Year 2021 Volume: 11 Issue: 3

Cite

APA Kılınç, H. (2021). Isolation and characterization of secondary metabolites from apolar fraction of Scabiosa sicula and evaluation of their antioxidant activities. Gümüşhane Üniversitesi Fen Bilimleri Dergisi, 11(3), 934-942. https://doi.org/10.17714/gumusfenbil.888739