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In vitro Carbonic Anhydrase Inhibitory Effects of The Extracts of Satureja cuneifolia

Year 2021, Volume: 8 Issue: 4, 1146 - 1150, 24.10.2021
https://doi.org/10.30910/turkjans.980819

Abstract

Carbonic anhydrases catalyze the interconversion between carbon dioxide and bicarbonate. Carbonic anhydrase inhibition has therapeutic importance and there are many drugs which use this mechanism. Carbonic anhydrase inhibitors are used as diuretic, antiglaucoma, antitumor and antiepileptic agents. As an alternative for synthetic chemicals with strong side effects, natural products have gained popularity in the recent years. In this study, Satureja cuneifolia, a medicinal plant used as folk medicine, was investigated for its inhibition effects on carbonic anhydrase I and II enzymes. Four different extracts were obtained with maceration method and three different solvents were used. The results have shown that methanol extracts of Satureja cuneifolia has the strongest inhibition activity on the enzymes with the IC50 values of 31 µg/mL for hCA I and 12 µg/mL for hCA II. Further purification and analytical studies will be needed to obtain the active natural molecules and their potential for pharma and food industries.

Thanks

The authors thank Dr. İsmail ŞENKARDEŞ from Department of Pharmaceutical Botany at Marmara University for his help in plant identification.

References

  • Abdel-Aziz, A.A-M., El-Azab, A.S., Ceruso, M., Supuran, C.T. 2014. Carbonic anhydrase inhibitory activity of sulfonamides and carboxylic acids incorporating cyclic imide scaffolds, Bioorganic and Medicinal Chemistry Letters, 24: 5185-5189.
  • Ağgül, A.G., Kuzu, M., Kandemir, F.M., Küçükler, S., Çağlayan, C. 2020. Alterations in enzyme activity of carbonic anhydrase, 6-phosphogluconate dehydrogenase and thioredoxin reductase in rats exposed to doxorubicin and morin. Clinical and Experimental Health Sciences, 10(3): 228-234.
  • Ahmad, S., Hassan, A., Rehman, T., Basit, A., Tahir, A., Adeel Arshad, M. 2019. In vitro bioactivity of extracts from seeds of Cassia absus l. growing in Pakistan. Journal of Herbal Medicine, 100258.
  • Akkemik, E., Aybek, A., Felek, I. 2019. Effects of cefan melon (Cucumıs melo l.) seed extracts on human erythrocyte carbonic anhydrase I-II enzymes, Applied Ecology and Environmental Research, 17(6): 14699-14713.
  • Almajan, G.L., Barbuceanu, S-F., Innocenti, A., Scozzafava, A., Supuran, C.T. 2008. Carbonic anhydrase inhibitors. Inhibition of the cytosolic and tumor-associated carbonic anhydrase isozymes I, II and IX with some 1,3,4-oxadiazole- and 1,2,4-triazole-thiols, Journal of Enzyme Inhibition and Medicinal Chemistry, 23: 101-107.
  • Azmir, J., Zaidul, I.S.M., Rahman, M.M., Sharif, K.M., Mohamed, A., Sahena, F., Jahurul, M.H.A., Ghafoor, K., Norulaini, N.A.N., Omar, A.K.M. 2013. Techniques for extraction of bioactive compounds from plant materials: A review, Journal of Food Engineering, 117(4): 426-436.
  • Eminagaoglu, O., Tepe, B., Yumrutas, O., Akpulat, H.A., Daferera, D., Polissiou, M., Sokmen, A. 2007. The in vitro antioxidative properties of the essential oils and methanol extracts of Satureja spicigera (K. Koch.) Boiss. and Satureja cuneifolia ten. Food Chemistry, 100(1): 339-343.
  • Gupta, A., Naraniwal, M., Kothari, V. 2012. Modern extraction methods for preparation of bioactive plant extracts, International Journal of Applied and Natural Sciences, 1(1): 8-26.
  • Güler, O.O., Supuran, C.T., Capasso, C. 2020. Carbonic anhydrase IX as a novel candidate in liquid biopsy, Journal of Enzyme Inhibition and Medicinal Chemistry, 35(1): 255-260.
  • Huie, C.W. 2002. A review of modern sample-preparation techniques for the extraction and analysis of medicinal plants, Analytical and Bioanalytical Chemistry, 373: 23-30.
  • Kan, Y, Uçan, U. 2006. GC-MS analysis and antibacterial activity of cultivated Satureja cuneifolia Ten. essential oil. Turkish Journal of Chemistry, 30 (2): 253-259.
  • Kaya, E., Erğun, B., Demir, Y., Alım, Z., Beydemir, Ş. 2019. The in vitro impacts of some plant extracts on carbonic anhydrase I, II and paraoxonase-1. Hacettepe Journal of Biology and Chemistry, 47(1): 51-59.
  • Kuzu, M., Aslan, A., Ahmed, I., Comakli, V., Demirdag, R., Uzun, N. 2016. Purification of glucose-6-phosphate dehydrogenase and glutathione reductase enzymes from the gill tissue of Lake Van fish and analyzing the effects of some chalcone derivatives on enzyme activities, Fish Physiology and Biochemistry, 42(2): 482-491.
  • Milos, M., Radonic, A., Bezic, N., Dunkic, V. 2001. Localities and seasonal variations in the chemical composition of essential oils of Satureja montana L. and S. cuneifolia Ten. Flavour and Fragrance Journal, 16(3): 157-160.
  • Nar, M., Çetinkaya, Y., Gülçin, İ., Menzek, A. 2013. (3,4-Dihydroxyphenyl) (2,3,4-trihydroxyphenyl) methanone and its derivatives as carbonic anhydrase isoenzymes inhibitors, Journal of Enzyme Inhibition and Medicinal Chemistry, 28: 402-406.
  • Nocentini, A., Vullo, D., Bartolucci, G., Supuran, C.T. 2016. N-Nitrosulfonamides: A new chemotype for carbonic anhydrase inhibition, Bioorganic and Medicinal Chemistry, 24: 3612-3617.
  • Oke, F., Aslim, B., Ozturk, S., Altundag, S. 2009. Essential oil composition, antimicrobial and antioxidant activities of Satureja cuneifolia Ten. Food Chemistry, 112(4): 874-879.
  • Orhan, F., Şentürk, M., Supuran, C.T. 2016. Interaction of anions with a newly characterized alpha carbonic anhydrase from Halomonas sp, Journal of Enzyme Inhibition and Medicinal Chemistry, 31: 1119-1123.
  • Scozzafava, A., Mastrolorenzo, A., Supuran C.T. 2004. Modulation of carbonic anhydrase activity and its applications in therapy, Expert Opinion on Therapeutic Patents, 14: 667-702.
  • Sorokina, M., Steinbeck, C. 2020. Review on natural products databases: where to find data in 2020, Journal of Cheminformatics, 13: 20.
  • Supuran, C.T. 2008. Carbonic anhydrases: novel therapeutic applications for inhibitors and activators, Nature Reviews Drug Discovery, 7: 168-181.
  • Taslimi, P., Gülçin, İ., Öztaşkın, N., Çetinkaya, Y., Göksu, S., Alwasel, S.H., Supuran, C.T. 2016. The effects of some bromophenols on human carbonic anhydrase isoenzymes. Journal of Enzyme Inhibition and Medicinal Chemistry, 31(4): 603-607.
  • Taslimi, P., Köksal, E., Gören, A.C., Bursal, E., Aras, A., Kılıç, Ö., Alwasel, S., Gülçin, İ. 2020. Anti-Alzheimer, antidiabetic and antioxidant potential of Satureja cuneifolia and analysis of its phenolic contents by LC-MS/MS. Arabian Journal of Chemistry, 13(3): 4528-4537.
  • Taşkın, T., Doğan, M., Cam, M.E., Şahin, T., Şenkardeş, İ. 2020. In vitro anti-urease, antioxidant, anticholinesterase, cytotoxic and in vivo anti-inflammatory potential of Satureja cuneifolia Ten., Natulae Scientia Biologicae, 12(2): 222-232. Türkoğlu, E.A., Kuzu, M., Ayasan, T., İnci, H., Eratak, S.V. 2019. Inhibitory effects of some flavonoids on thioredoxin reductase purified from chicken liver, Brazilian Journal of Poultry Science, 21(2): 001-008.
  • Türkoğlu, E.A., Şentürk, M., Supuran, C.T., Ekinci, D. 2017. Carbonic anhydrase inhibitory properties of some uracil derivatives, Journal of Enzyme Inhibition and Medicinal Chemistry, 32: 74-77.
  • Ucar, A., Findik, M., Kuzu, M., Pehlivanoglu, S., Sayin, U., Sayin, Z., Akgemci, E.G. 2021. Cytotoxic effects, microbiological analysis and inhibitory properties on carbonic anhydrase isozyme activities of 2-hydroxy-5-methoxyacetophenone thiosemicarbazone and its Cu (II), Co (II), Zn (II) and Mn (II) complexes. Research on Chemical Intermediates, 47(2): 533-550.
  • Verpoorte, J.A., Mehta, S., Edsall, J.T. 1967. Esterase activities of human carbonic anhydrases B and C, The Journal of Biological Chemistry, 242: 4221-4229.
  • Wang, L., Weller, C.L. 2006. Recent advances in extraction of nutraceuticals from plants, Trends in Food Science & Technology, 17(6): 300-312.

Satureja cuneifolia Ekstraktlarının in vitro Karbonik Anhidraz İnhibitör Etkileri

Year 2021, Volume: 8 Issue: 4, 1146 - 1150, 24.10.2021
https://doi.org/10.30910/turkjans.980819

Abstract

Karbonik anhidrazlar, karbon dioksit ve bikarbonat arasındaki karşılıklı dönüşümü katalize eder. Karbonik anhidraz inhibisyonunun terapötik önemi vardır ve bu mekanizmayı kullanan birçok ilaç vardır. Karbonik anhidraz inhibitörleri diüretik, antiglokom, antitümör ve antiepileptik ajanlar olarak kullanılmaktadır. Güçlü yan etkileri olan sentetik kimyasallara alternatif olarak son yıllarda doğal ürünler popülerlik kazanmıştır. Bu çalışmada, halk ilacı olarak kullanılan tıbbi bir bitki olan Satureja cuneifolia’nın karbonik anhidraz I ve II enzimleri üzerindeki inhibisyon etkileri araştırılmıştır. Maserasyon yöntemi ile dört farklı ekstrakt elde edilmiş ve üç farklı çözücü kullanılmıştır. Sonuçlar, Satureja cuneifolia’nın metanol ekstrelerinin, hCA I için 31 µg/mL ve hCA II için 12 µg/mL IC50 değerleri ile enzimler üzerinde en güçlü inhibisyon aktivitesine sahip olduğunu göstermiştir. Aktif doğal moleküllerin elde edilebilmesi ve bunların ilaç ve gıda endüstrileri için potansiyellerini değerlendirmek için daha fazla saflaştırma ve analitik çalışmalara ihtiyaç duyulmaktadır.

References

  • Abdel-Aziz, A.A-M., El-Azab, A.S., Ceruso, M., Supuran, C.T. 2014. Carbonic anhydrase inhibitory activity of sulfonamides and carboxylic acids incorporating cyclic imide scaffolds, Bioorganic and Medicinal Chemistry Letters, 24: 5185-5189.
  • Ağgül, A.G., Kuzu, M., Kandemir, F.M., Küçükler, S., Çağlayan, C. 2020. Alterations in enzyme activity of carbonic anhydrase, 6-phosphogluconate dehydrogenase and thioredoxin reductase in rats exposed to doxorubicin and morin. Clinical and Experimental Health Sciences, 10(3): 228-234.
  • Ahmad, S., Hassan, A., Rehman, T., Basit, A., Tahir, A., Adeel Arshad, M. 2019. In vitro bioactivity of extracts from seeds of Cassia absus l. growing in Pakistan. Journal of Herbal Medicine, 100258.
  • Akkemik, E., Aybek, A., Felek, I. 2019. Effects of cefan melon (Cucumıs melo l.) seed extracts on human erythrocyte carbonic anhydrase I-II enzymes, Applied Ecology and Environmental Research, 17(6): 14699-14713.
  • Almajan, G.L., Barbuceanu, S-F., Innocenti, A., Scozzafava, A., Supuran, C.T. 2008. Carbonic anhydrase inhibitors. Inhibition of the cytosolic and tumor-associated carbonic anhydrase isozymes I, II and IX with some 1,3,4-oxadiazole- and 1,2,4-triazole-thiols, Journal of Enzyme Inhibition and Medicinal Chemistry, 23: 101-107.
  • Azmir, J., Zaidul, I.S.M., Rahman, M.M., Sharif, K.M., Mohamed, A., Sahena, F., Jahurul, M.H.A., Ghafoor, K., Norulaini, N.A.N., Omar, A.K.M. 2013. Techniques for extraction of bioactive compounds from plant materials: A review, Journal of Food Engineering, 117(4): 426-436.
  • Eminagaoglu, O., Tepe, B., Yumrutas, O., Akpulat, H.A., Daferera, D., Polissiou, M., Sokmen, A. 2007. The in vitro antioxidative properties of the essential oils and methanol extracts of Satureja spicigera (K. Koch.) Boiss. and Satureja cuneifolia ten. Food Chemistry, 100(1): 339-343.
  • Gupta, A., Naraniwal, M., Kothari, V. 2012. Modern extraction methods for preparation of bioactive plant extracts, International Journal of Applied and Natural Sciences, 1(1): 8-26.
  • Güler, O.O., Supuran, C.T., Capasso, C. 2020. Carbonic anhydrase IX as a novel candidate in liquid biopsy, Journal of Enzyme Inhibition and Medicinal Chemistry, 35(1): 255-260.
  • Huie, C.W. 2002. A review of modern sample-preparation techniques for the extraction and analysis of medicinal plants, Analytical and Bioanalytical Chemistry, 373: 23-30.
  • Kan, Y, Uçan, U. 2006. GC-MS analysis and antibacterial activity of cultivated Satureja cuneifolia Ten. essential oil. Turkish Journal of Chemistry, 30 (2): 253-259.
  • Kaya, E., Erğun, B., Demir, Y., Alım, Z., Beydemir, Ş. 2019. The in vitro impacts of some plant extracts on carbonic anhydrase I, II and paraoxonase-1. Hacettepe Journal of Biology and Chemistry, 47(1): 51-59.
  • Kuzu, M., Aslan, A., Ahmed, I., Comakli, V., Demirdag, R., Uzun, N. 2016. Purification of glucose-6-phosphate dehydrogenase and glutathione reductase enzymes from the gill tissue of Lake Van fish and analyzing the effects of some chalcone derivatives on enzyme activities, Fish Physiology and Biochemistry, 42(2): 482-491.
  • Milos, M., Radonic, A., Bezic, N., Dunkic, V. 2001. Localities and seasonal variations in the chemical composition of essential oils of Satureja montana L. and S. cuneifolia Ten. Flavour and Fragrance Journal, 16(3): 157-160.
  • Nar, M., Çetinkaya, Y., Gülçin, İ., Menzek, A. 2013. (3,4-Dihydroxyphenyl) (2,3,4-trihydroxyphenyl) methanone and its derivatives as carbonic anhydrase isoenzymes inhibitors, Journal of Enzyme Inhibition and Medicinal Chemistry, 28: 402-406.
  • Nocentini, A., Vullo, D., Bartolucci, G., Supuran, C.T. 2016. N-Nitrosulfonamides: A new chemotype for carbonic anhydrase inhibition, Bioorganic and Medicinal Chemistry, 24: 3612-3617.
  • Oke, F., Aslim, B., Ozturk, S., Altundag, S. 2009. Essential oil composition, antimicrobial and antioxidant activities of Satureja cuneifolia Ten. Food Chemistry, 112(4): 874-879.
  • Orhan, F., Şentürk, M., Supuran, C.T. 2016. Interaction of anions with a newly characterized alpha carbonic anhydrase from Halomonas sp, Journal of Enzyme Inhibition and Medicinal Chemistry, 31: 1119-1123.
  • Scozzafava, A., Mastrolorenzo, A., Supuran C.T. 2004. Modulation of carbonic anhydrase activity and its applications in therapy, Expert Opinion on Therapeutic Patents, 14: 667-702.
  • Sorokina, M., Steinbeck, C. 2020. Review on natural products databases: where to find data in 2020, Journal of Cheminformatics, 13: 20.
  • Supuran, C.T. 2008. Carbonic anhydrases: novel therapeutic applications for inhibitors and activators, Nature Reviews Drug Discovery, 7: 168-181.
  • Taslimi, P., Gülçin, İ., Öztaşkın, N., Çetinkaya, Y., Göksu, S., Alwasel, S.H., Supuran, C.T. 2016. The effects of some bromophenols on human carbonic anhydrase isoenzymes. Journal of Enzyme Inhibition and Medicinal Chemistry, 31(4): 603-607.
  • Taslimi, P., Köksal, E., Gören, A.C., Bursal, E., Aras, A., Kılıç, Ö., Alwasel, S., Gülçin, İ. 2020. Anti-Alzheimer, antidiabetic and antioxidant potential of Satureja cuneifolia and analysis of its phenolic contents by LC-MS/MS. Arabian Journal of Chemistry, 13(3): 4528-4537.
  • Taşkın, T., Doğan, M., Cam, M.E., Şahin, T., Şenkardeş, İ. 2020. In vitro anti-urease, antioxidant, anticholinesterase, cytotoxic and in vivo anti-inflammatory potential of Satureja cuneifolia Ten., Natulae Scientia Biologicae, 12(2): 222-232. Türkoğlu, E.A., Kuzu, M., Ayasan, T., İnci, H., Eratak, S.V. 2019. Inhibitory effects of some flavonoids on thioredoxin reductase purified from chicken liver, Brazilian Journal of Poultry Science, 21(2): 001-008.
  • Türkoğlu, E.A., Şentürk, M., Supuran, C.T., Ekinci, D. 2017. Carbonic anhydrase inhibitory properties of some uracil derivatives, Journal of Enzyme Inhibition and Medicinal Chemistry, 32: 74-77.
  • Ucar, A., Findik, M., Kuzu, M., Pehlivanoglu, S., Sayin, U., Sayin, Z., Akgemci, E.G. 2021. Cytotoxic effects, microbiological analysis and inhibitory properties on carbonic anhydrase isozyme activities of 2-hydroxy-5-methoxyacetophenone thiosemicarbazone and its Cu (II), Co (II), Zn (II) and Mn (II) complexes. Research on Chemical Intermediates, 47(2): 533-550.
  • Verpoorte, J.A., Mehta, S., Edsall, J.T. 1967. Esterase activities of human carbonic anhydrases B and C, The Journal of Biological Chemistry, 242: 4221-4229.
  • Wang, L., Weller, C.L. 2006. Recent advances in extraction of nutraceuticals from plants, Trends in Food Science & Technology, 17(6): 300-312.
There are 28 citations in total.

Details

Primary Language English
Journal Section Research Articles
Authors

Fatma Gülruy Aydın 0000-0003-3320-8492

Emir Alper Türkoğlu 0000-0001-7850-6456

Müslüm Kuzu 0000-0002-1375-7673

Turgut Taşkın 0000-0001-8475-6478

Publication Date October 24, 2021
Submission Date August 9, 2021
Published in Issue Year 2021 Volume: 8 Issue: 4

Cite

APA Aydın, F. G., Türkoğlu, E. A., Kuzu, M., Taşkın, T. (2021). In vitro Carbonic Anhydrase Inhibitory Effects of The Extracts of Satureja cuneifolia. Türk Tarım Ve Doğa Bilimleri Dergisi, 8(4), 1146-1150. https://doi.org/10.30910/turkjans.980819