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Anticholinesterase and antityrosinase activities of endemic Prangos heyniae H. Duman & M. F. Watson and its metabolites

Year 2023, Volume: 53 Issue: 1, 51 - 57, 28.04.2023

Gökay Albayrak Serdar Demir Halil Koyu Sura Baykan

https://doi.org/10.26650/IstanbulJPharm.2023.1087126

Abstract

Background and Aims: Prangos Lindl. (Apiaceae) are abundant in coumarins. Previously, along with n-hexane(HEX), chloroform(CHCl3), and methanol(MeOH) extracts, 8 molecules named osthol(1), isoimperatorin(2), oxypeucedanin(3), 7-methoxy-isoarnottinin-4'-O-β-ᴅ-glucopyranoside(4), 7-methoxy-isoarnottinin-4'-O-rutinoside(5), oxypeucedanin hydrate-3'-O-β-ᴅ-glucopyranoside(6), 1-methylethyl-6-O-D-apio-β-ᴅ-furanosyl-β-ᴅ-glucopyranoside(7), and cnidioside A(8) were obtained from the roots of endemic Prangos heyniae H. Duman & M. F. Watson. 4 and 5 were reported as novel compounds. Coumarins are known for their neuroprotective properties. Tyrosinase and cholinesterase enzymes play a key role in the course of neurodegenerative diseases such as Parkinson’s and Alzheimer’s disease(AD), respectively. Therefore, we aimed to evaluate the antityrosinase and anticholinesterase effects of the extracts and compounds 1-8 from Prangos heyniae roots.
Methods: Tyrosinase and acetylcholinesterase-butyrylcholinesterase(AChE-BChE) inhibitory activities of the samples were evaluated spectrophotometrically. The screening of the samples was carried on at 1000 μg/mL. Results of triplicate analyses of the samples were given as IC50 values obtained through linear regression analysis. Kojic acid and galantamine were used as positive controls for antityrosinase and anticholinesterase experiments, respectively.
Results: Only MeOH extract showed antityrosinase activity with an IC50 value of 543.37±7.45 μg/mL. CHCl3 extract exhibited both AChE and BChE inhibitory activities with IC50 values of 273.92 ± 32.07 and 38.68±2.56 μg/mL, respectively. Among tested compounds, 6 showed a weak BChE-specific inhibitory activity (IC50= 91.93±3.86μg/mL) and managed to possess 40 times inferior activity than galantamine(IC50= 2.25 ± 0.05μg/mL).

Conclusion: The CHCl3 extract displayed a good BChE inhibitory activity. These findings suggested that Prangos heyniae

could be a valuable natural source to develop novel BChE inhibitors with further studies against AD.

Keywords

Prangos heyniae coumarin anticholinesterase activity antityrosinase activity oxypeucedanin hydrate-3

Supporting Institution

TÜBİTAK

Project Number

219S127

Thanks

This study was supported by TUBITAK (The Scientific and Technological Research Council of Turkey) under Grant number: 219-S-127.

References

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Year 2023, Volume: 53 Issue: 1, 51 - 57, 28.04.2023

Gökay Albayrak Serdar Demir Halil Koyu Sura Baykan

https://doi.org/10.26650/IstanbulJPharm.2023.1087126

Abstract

Project Number

219S127

References

  • Abbas-Mohammadi, M., Farimani, M. M., Salehi, P., Ebrahimi, S. N., Sonboli, A., Kelso, C., & Skropeta, D. (2018). Acetylcholines- terase-inhibitory activity of Iranian plants: Combined HPLC/bio- assay-guided fractionation, molecular networking and docking strategies for the dereplication of active compounds. Journal of Pharmaceutical and Biomedical Analysis, 158, 471–479.
  • Ahmed, J., Güvenç, A., Küçükboyacı, N., Baldemir, A., & Coşkun, M. (2011). Total phenolic contents and antioxidant activities of Prangos Lindl.(Umbelliferae) species growing in Konya province (Turkey). Turkish Journal of Biology, 35(3), 353–360. https://doi. org/10.3906/biy-0809-23
  • Albayrak, G., Demir, S., Kose, F. A., & Baykan, S. (2021). New coumarin glycosides from endemic Prangos heyniae H. Duman & M.F. Watson. Natural Product Research, 1–13. https://doi.org/10.1080/14786419. 2021.1961138/SUPPL_FILE/GNPL_A_1961138_SM0346.DOCX
  • Albayrak, G., Demir, S., Koyu, H., & Baykan, S. (2022). Anticholinester- ase compounds from endemic Prangos uechtritzii. Chemistry & Bio- diversity, 19, e202200557. https://doi.org/10.1002/cbdv.202200557
  • Aytaç, Z., & Duman, H. (2016). Prangos abieticola (Apiaceae), a new species from south Anatolia, Turkey. Edinburgh Journal of Botany, 73(1), 125–131. https://doi.org/10.1017/S0960428615000293
  • Bahadori, M. B., Zengin, G., Bahadori, S., Maggi, F., & Dinparast, L. (2017). Chemical composition of essential oil, antioxidant, anti- diabetic, anti-obesity, and neuroprotective properties of Prangos gaubae. Natural Product Communications, 12(12), 1945–1948. https://doi.org/10.1177/1934578x1701201233
  • Başer, B., & Pehlivan, S. (2015). Türkiye’nin farklı bölgelerindeki Prangos Lindl . (Apiaceae) cinsine ait taksonların polenlerinin morfolojik farklılıkları. Bitlis Eren Üniversitesi Fen Bilimleri Dergisi, 4(2), 183–188. https://doi.org/10.17798/beufen.11965
  • Başer, K. H. C., Özek, T., Demirci, B., & Duman, H. (2000). Compo- sition of the essential oil of Prangos heyniae H. Duman et M. F. Watson, a new endemic from Turkey. Flavour and Fragrance Journal, 15(1), 47–49. https://doi.org/10.1002/(SICI)1099- 1026(200001/02)15:1<47::AID-FFJ869>3.0.CO;2-9
  • Behçet, L., Yapar, Y., & Olgun, Ş. (2019). Prangos aricakensis (Apiace- ae), a new species from eastern Turkey. Phytotaxa, 401(1), 55–63. https://doi.org/10.11646/phytotaxa.401.1.5
  • Bruno, M., Ilardi, V., Lupidi, G., Quassinti, L., Bramucci, M., Fiorini, D., … Maggi, F. (2021). Composition and biological activities of the essential oil from a Sicilian accession of Prangos ferulacea (L.) Lindl. Natural Product Research, 35(5), 733–743. https://doi.org/10.1080/14786419.2019.1598996
  • Bulut, G., Tuzlacı, E., Doğan, A., & Şenkardes, I. (2014). An ethno- pharmacological review on the Turkish Apiaceae species. Journal of Faculty Pharmacy of Istanbul University, 44(2), 163–179.
  • Chang, T. S. (2009). An updated review of tyrosinase inhibitors. International Journal of Molecular Sciences, 10(6), 2440–2475. https://doi.org/10.3390/ijms10062440
  • Dall’Acqua, S., Sut, S., Zengin, G., Peron, G., Elbasan, F., Yildiztugay, E., … Mahomoodally, M. F. (2022). Phytochemical screening, anti- oxidant, and enzyme inhibitory properties of three Prangos species (P. heyniae, P. meliocarpoides var. meliocarpoides, and P. uechtritzii) depicted by comprehensive LC-MS and multivariate data analysis. Antioxidants, 11(9), 1712. https://doi.org/10.3390/antiox11091712
  • De Souza, L. G., Renn O B, M. N., & Figueroa-Villar, J. D. (2016). Cou- marins as cholinesterase inhibitors: A review. Chemico-Biological Interactions, 254, 11–23. https://doi.org/10.1016/j.cbi.2016.05.001
  • Doković, D. D., Bulatović, V. M., Božić, B. D., Kataranovski, M. V., Zrakić, 56 T. M., & Kovačević, N. N. (2004). 3,5-nonadiyne isolated from the rhi- zome of Cachrys ferulacea inhibits endogenous nitric oxide release by rat peritoneal macrophages. Chemical and Pharmaceutical Bul- letin, 52(7), 853–854. https://doi.org/10.1248/cpb.52.853
  • Duman, H., & Watson, M. F. (1999). Ekimia, a new genus of Umbel- liferae, and two new taxa of Prangos Lindl. (Umbelliferae) from southern Turkey. Edinburgh Journal of Botany, 56(2), 199–209. https://doi.org/10.1017/s0960428600001086
  • Ellman, G. L., Courtney, K. D., Andres, V., & Featherstone, R. M. (1961). A new and rapid colorimetric determination of acetyl- cholinesterase activity. Biochemical Pharmacology, 7(2), 88–95. https://doi.org/10.1016/0006-2952(61)90145-9
  • Erdogan Orhan, I., Orhan, G., & Gurkas, E. (2011). An overview on natural cholinesterase inhibitors - a multi-targeted drug class - and their mass production. Mini-Reviews in Medicinal Chemistry, 11(10), 836–842. https://doi.org/10.2174/138955711796575434
  • Fais, A., Corda, M., Era, B., Fadda, M. B., Matos, M. J., Santana, L., … Delogu, G. (2009). Tyrosinase inhibitor activity of coumarin- resveratrol hybrids. Molecules, 14(7), 2514–2520.
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There are 53 citations in total.

Details

Primary Language English
Subjects Pharmacology and Pharmaceutical Sciences
Journal Section Original Article
Authors

Gökay Albayrak 0000-0002-5729-0796

Serdar Demir This is me 0000-0001-6572-8818

Halil Koyu 0000-0002-5491-9894

Sura Baykan This is me 0000-0002-3624-4811

Project Number 219S127
Publication Date April 28, 2023
Submission Date March 13, 2022
Published in Issue Year 2023 Volume: 53 Issue: 1

Cite

APA Albayrak, G., Demir, S., Koyu, H., Baykan, S. (2023). Anticholinesterase and antityrosinase activities of endemic Prangos heyniae H. Duman & M. F. Watson and its metabolites. İstanbul Journal of Pharmacy, 53(1), 51-57. https://doi.org/10.26650/IstanbulJPharm.2023.1087126
AMA Albayrak G, Demir S, Koyu H, Baykan S. Anticholinesterase and antityrosinase activities of endemic Prangos heyniae H. Duman & M. F. Watson and its metabolites. iujp. April 2023;53(1):51-57. doi:10.26650/IstanbulJPharm.2023.1087126
Chicago Albayrak, Gökay, Serdar Demir, Halil Koyu, and Sura Baykan. “Anticholinesterase and Antityrosinase Activities of Endemic Prangos Heyniae H. Duman & M. F. Watson and Its Metabolites”. İstanbul Journal of Pharmacy 53, no. 1 (April 2023): 51-57. https://doi.org/10.26650/IstanbulJPharm.2023.1087126.
EndNote Albayrak G, Demir S, Koyu H, Baykan S (April 1, 2023) Anticholinesterase and antityrosinase activities of endemic Prangos heyniae H. Duman & M. F. Watson and its metabolites. İstanbul Journal of Pharmacy 53 1 51–57.
IEEE G. Albayrak, S. Demir, H. Koyu, and S. Baykan, “Anticholinesterase and antityrosinase activities of endemic Prangos heyniae H. Duman & M. F. Watson and its metabolites”, iujp, vol. 53, no. 1, pp. 51–57, 2023, doi: 10.26650/IstanbulJPharm.2023.1087126.
ISNAD Albayrak, Gökay et al. “Anticholinesterase and Antityrosinase Activities of Endemic Prangos Heyniae H. Duman & M. F. Watson and Its Metabolites”. İstanbul Journal of Pharmacy 53/1 (April 2023), 51-57. https://doi.org/10.26650/IstanbulJPharm.2023.1087126.
JAMA Albayrak G, Demir S, Koyu H, Baykan S. Anticholinesterase and antityrosinase activities of endemic Prangos heyniae H. Duman & M. F. Watson and its metabolites. iujp. 2023;53:51–57.
MLA Albayrak, Gökay et al. “Anticholinesterase and Antityrosinase Activities of Endemic Prangos Heyniae H. Duman & M. F. Watson and Its Metabolites”. İstanbul Journal of Pharmacy, vol. 53, no. 1, 2023, pp. 51-57, doi:10.26650/IstanbulJPharm.2023.1087126.
Vancouver Albayrak G, Demir S, Koyu H, Baykan S. Anticholinesterase and antityrosinase activities of endemic Prangos heyniae H. Duman & M. F. Watson and its metabolites. iujp. 2023;53(1):51-7.
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