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

 Zühal Güvenalp, Hilal Özbek , Kadir Özden Yerdelen, Gülderen Yılmaz, Cavit Kazaz and Lütfiye Ömür Demirezer

Department of Pharmacognosy, Faculty of Pharmacy, Atatürk University, Erzurum 25240, Türkiye

Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Atatürk University, Erzurum 25240, Türkiye

Department of Pharmaceutical Botany, Faculty of Pharmacy, Ankara University, Ankara 06100, Türkiye

Department of Chemistry, Faculty of Science, Atatürk University, Erzurum 25240, Türkiye

Department of Pharmacognosy, Faculty of Pharmacy, Hacettepe University, Ankara 06100, Türkiye

Abstract: 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 (IC 50 = 1.26 ± 0.01 and 5.86 ± 0.03 μM, respectively) and butyrylcholinesterase (IC 50 = 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.

Keywords: Heptaptera cilicica ; sesquiterpene coumarin ether; acetylcholinesterase; butyrylcholinesterase. 2017 ACG Publications. All rights reserved.