Yıl: 2017 Cilt: 11 Sayı: 5 Sayfa Aralığı: 462 - 505 Metin Dili: İngilizce İndeks Tarihi: 29-07-2022

Cholinesterase Inhibition and Molecular Docking Studies of Sesquiterpene Coumarin Ethers from Heptaptera cilicica

Öz:
Five sesquiterpene coumarin ethers: umbelliprenin, umbelliprenin-10',11'-monoepoxide, conferone, mogoltacin and feselol were isolated from the fruits of Heptaptera cilicica. Their structures were identified by means of spectroscopic methods. AChE and BuChE inhibitory activities of the compounds were determined by molecular docking method which were confirmed by in vitro experiments. According to molecular docking results, total score of feselol and umbelliprenin were 5.69 and 3.23 kcal/mol against acetylcholinesterase, respectively. Total score for butyrylcholinesterase inhibitory effect of them were 2.76 and 4.99 kcal/mol, respectively. Feselol and umbelliprenin exhibited significantly high inhibitory potency against acetylcholinesterase (IC50 = 1.26 ± 0.01 and 5.86 ± 0.03 μM, respectively) and butyrylcholinesterase (IC50 = 9.98 ± 0.24 and 1.10 ± 0.19 μM, respectively). This is the first report of isolation of natural bioactives obtained from the chloroform extract of Heptaptera cilicica fruits with anticholinesterase activity
Anahtar Kelime:

Belge Türü: Makale Makale Türü: Kısa Bildiri Erişim Türü: Erişime Açık
  • [1] I. Herrnstadt and C. C. Heyn (1972). Heptaptera Marg. & Reuter., in: P. H. Davis (Ed.), Flora of Turkey and the East Aegean Islands. University Press, Edinburgh, pp. 388-390.
  • [2] G. Appendino, H. Ç. Özen, S. Tagliapietra and M. Cisero (1992). Coumarins from Heptaptera anisoptera, Phytochemistry 31(9), 3211-3213.
  • [3] G. Appendino, H. Ç. Özen, G. M. Nano and M. Cisero (1992). Sesquiterpene coumarin ethers from the genus Heptaptera, Phytochemistry 31(12), 4223-4226.
  • [4] G. Appendino, H. C. Özen and J. Jakupovic (1993). A sesquiterpene coumarin ether and a coniferyl ester from Heptaptera anisoptera, Fitoterapia LXIV(6), 505-506.
  • [5] F. Z. Şenol, G. Yilmaz, B. Şener, M. Koyuncu and I. Orhan (2010). Preliminary screening of acetylcholinesterase inhibitory and antioxidant activities of Anatolian Heptaptera species, Pharm. Biol. 48(3), 337-341.
  • [6] G. L. Ellman, D. Courtney, V. Andies and R. M. Featherstone (1961). A new and rapid colorimetric determination of acetylcholinesterase activity, Biochem.Pharmacol. 7, 88-95.
  • [7] K. Ö. Yerdelen and E. Tosun (2015). Synthesis, docking and biological evaluation of oxamide and fumaramide analogs as potential AChE and BuChE inhibitors, Med. Chem. Res. 24, 588-602.
  • [8] Y. O. Tian, Z. X. Zhang and H. H. Xu (2013). Laboratory and field evaluations on insecticidal activity of Cicuta virosa L. var. latisecta Celak, Ind. Crop. Prod. 41, 90-93.
  • [9] K. Edegger, S. F. Mayer, A. Steinreiber and K. Faber (2004). Chemo-enzymatic enantio-convergent asymmetric synthesis of (R)-(1)-Marmin, Tetrahedron 60, 583-588.
  • [10] M. Iranshahi, R. Rezaee, A. Sahebkar, C. Bassarello, S. Piacente and C. Pizza (2009). Sesquiterpene coumarins from the fruits of Ferula badrakema, Pharm Biol. 47(4), 344-347.
  • [11] S. Dall'Acqua, F. Maggi, P. Minesso, M. Salvagno, F. Papa, S. Vittori and G. Innocenti (2010). Identification of non-alkaloid acetylcholinesterase inhibitors from Ferulago campestris (Besser) Grecescu (Apiaceae), Fitoterapia 81(8), 1208-1212.
  • [12] L. O. Demirezer, P. Gurbuz, P. Kelicen, M. Bodur, N. Özenver, A. Kuruuzum-Uz and Z. Guvenalp (2015). Molecular docking, ex vivo and in vitro anticholinesterase activity studies of Salvia sp. and highlighted rosmarinic acid, Turkish J. Med. Sci. 45(5), 1141-1148.
  • [13] I. D. Kuntz, J. M. Blaney, S. J. Oatley, R. Langridge and T. E. Ferrin (1982). A geometric approach to macromolecule-ligand interactions, J. Mol. Biol. 161, 269-288.
  • [14] I. Muegge and Y. C. Martin (1999). A general and fast scoring function for protein-ligand interactions: a simplified potential approach, J. Med. Chem. 42, 791-804.
  • [15] G. Jones, P. Willett, R. C. Glen, A. R. Leach and R. Taylor (1997). Development and validation of a genetic algorithm for flexible docking, J. Mol. Biol. 267, 727-748.
  • [16] M. D. Eldridge, C. W. Murray, T. R. Auton, G. V. Paolini and R. P. Mee (1997). Empirical scoring functions: I. the development of a fast empirical scoring function to estimate the binding affinity of ligands in receptor complexes, J. Comp. Aided. Mol. Des. 11, 425-445.
  • [17] G. Karimi, M. Iranshahi, F. Hosseinalizadeh, B. Riahi and A. Sahebkar (2010). Screening of acetylcholinesterase inhibitory activity of terpenoid and coumarin derivatives from the genus Ferula, Pharmacologyonline 1, 566-574.
APA GÜVENALP Z, ÖZBEK H, YERDELEN K, YILMAZ G, KAZAZ C, DEMIREZER L (2017). Cholinesterase Inhibition and Molecular Docking Studies of Sesquiterpene Coumarin Ethers from Heptaptera cilicica. , 462 - 505.
Chicago GÜVENALP ZÜHAL,ÖZBEK HİLAL,YERDELEN Kadir Özden,YILMAZ Gülderen,KAZAZ CAVİT,DEMIREZER LUTFIYE OMUR Cholinesterase Inhibition and Molecular Docking Studies of Sesquiterpene Coumarin Ethers from Heptaptera cilicica. (2017): 462 - 505.
MLA GÜVENALP ZÜHAL,ÖZBEK HİLAL,YERDELEN Kadir Özden,YILMAZ Gülderen,KAZAZ CAVİT,DEMIREZER LUTFIYE OMUR Cholinesterase Inhibition and Molecular Docking Studies of Sesquiterpene Coumarin Ethers from Heptaptera cilicica. , 2017, ss.462 - 505.
AMA GÜVENALP Z,ÖZBEK H,YERDELEN K,YILMAZ G,KAZAZ C,DEMIREZER L Cholinesterase Inhibition and Molecular Docking Studies of Sesquiterpene Coumarin Ethers from Heptaptera cilicica. . 2017; 462 - 505.
Vancouver GÜVENALP Z,ÖZBEK H,YERDELEN K,YILMAZ G,KAZAZ C,DEMIREZER L Cholinesterase Inhibition and Molecular Docking Studies of Sesquiterpene Coumarin Ethers from Heptaptera cilicica. . 2017; 462 - 505.
IEEE GÜVENALP Z,ÖZBEK H,YERDELEN K,YILMAZ G,KAZAZ C,DEMIREZER L "Cholinesterase Inhibition and Molecular Docking Studies of Sesquiterpene Coumarin Ethers from Heptaptera cilicica." , ss.462 - 505, 2017.
ISNAD GÜVENALP, ZÜHAL vd. "Cholinesterase Inhibition and Molecular Docking Studies of Sesquiterpene Coumarin Ethers from Heptaptera cilicica". (2017), 462-505.
APA GÜVENALP Z, ÖZBEK H, YERDELEN K, YILMAZ G, KAZAZ C, DEMIREZER L (2017). Cholinesterase Inhibition and Molecular Docking Studies of Sesquiterpene Coumarin Ethers from Heptaptera cilicica. Records of Natural Products, 11(5), 462 - 505.
Chicago GÜVENALP ZÜHAL,ÖZBEK HİLAL,YERDELEN Kadir Özden,YILMAZ Gülderen,KAZAZ CAVİT,DEMIREZER LUTFIYE OMUR Cholinesterase Inhibition and Molecular Docking Studies of Sesquiterpene Coumarin Ethers from Heptaptera cilicica. Records of Natural Products 11, no.5 (2017): 462 - 505.
MLA GÜVENALP ZÜHAL,ÖZBEK HİLAL,YERDELEN Kadir Özden,YILMAZ Gülderen,KAZAZ CAVİT,DEMIREZER LUTFIYE OMUR Cholinesterase Inhibition and Molecular Docking Studies of Sesquiterpene Coumarin Ethers from Heptaptera cilicica. Records of Natural Products, vol.11, no.5, 2017, ss.462 - 505.
AMA GÜVENALP Z,ÖZBEK H,YERDELEN K,YILMAZ G,KAZAZ C,DEMIREZER L Cholinesterase Inhibition and Molecular Docking Studies of Sesquiterpene Coumarin Ethers from Heptaptera cilicica. Records of Natural Products. 2017; 11(5): 462 - 505.
Vancouver GÜVENALP Z,ÖZBEK H,YERDELEN K,YILMAZ G,KAZAZ C,DEMIREZER L Cholinesterase Inhibition and Molecular Docking Studies of Sesquiterpene Coumarin Ethers from Heptaptera cilicica. Records of Natural Products. 2017; 11(5): 462 - 505.
IEEE GÜVENALP Z,ÖZBEK H,YERDELEN K,YILMAZ G,KAZAZ C,DEMIREZER L "Cholinesterase Inhibition and Molecular Docking Studies of Sesquiterpene Coumarin Ethers from Heptaptera cilicica." Records of Natural Products, 11, ss.462 - 505, 2017.
ISNAD GÜVENALP, ZÜHAL vd. "Cholinesterase Inhibition and Molecular Docking Studies of Sesquiterpene Coumarin Ethers from Heptaptera cilicica". Records of Natural Products 11/5 (2017), 462-505.