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Chemical Constituents from Solenostemma Argel and Their Cholinesterase Inhibitory Activity

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Chemical Constituents from Solenostemma Argel and Their Cholinesterase Inhibitory Activity Natural Product Sciences 25(2) : 115-121 (2019) https://doi.org/10.20307/nps.2019.25.2.115 Chemical Constituents from Solenostemma argel and their Cholinesterase Inhibitory Activity Rym Gouta Demmak1,2,*, Simon Bordage2, Abederrahmane Bensegueni1, Naima Boutaghane3, Thierry Hennebelle2, El Hassen Mokrani1, and Sevser Sahpaz2 1Laboratoire de Biochimie Appliquée, Département des Sciences de la Nature et de la Vie, Université Frères Mentouri-Constantine 1; 25000 Constantine, Algeria 2Laboratoire de Pharmacognosie, Univ. Lille, EA 7394 – ICV – Institut Charles Viollette; F-59000 Lille, France 3Laboratoire d’Obtention des Substances Thérapeutiques (LOST), Campus Chaabet-Ersas, Département de chimie, Université des Frères Mentouri-Constantine; 25000 Constantine, Algeria Abstract − Alzheimer’s disease is a chronic neurodegenerative disorder with no curative treatment. The commercially available drugs, which target acetylcholinesterase, are not satisfactory. The aim of this study was to investigate the cholinesterase inhibitory activity of Solenostemma argel aerial part. Eight compounds were isolated and identified by NMR: kaempferol-3-O-glucopyranoside (1), kaempferol (2), kaempferol-3-glu- copyranosyl(1→6)rhamnopyranose (3) p-hydroxybenzoic acid (4), dehydrovomifoliol (5), 14,15-dihydroxy- pregn-4-ene-3,20-dione (6), 14,15-dihydroxy-pregn-4-ene-3,20-dione-15β-D-glucopyranoside (7) and solargin I (8). Two of them (compounds 2 and 3) could inhibit over 50 % of butyrylcholinesterase activity at 100 µM. Compound (2) displayed the highest inhibitory effect against acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) with a slight selectivity towards the latter. Molecular docking studies supported the in vitro results and revealed that (2) had made several hydrogen and π-π stacking interactions which could explain the compound potency to inhibit AChE and BChE. Keywords − Alzheimer’s disease, Cholinesterase, Molecular docking, Solenostemma argel Introduction studies reported interesting antimicrobial, antiproliferative and anti-inflammatory activities of this species.6,9,10 No Alzheimer’s disease (AD) is a chronic neurodegenerative cholinesterase inhibitory activity of this plant has been disorder that is characterized by a deficient cholinergic reported. The aim of this study was to investigate the neurotransmission.1 The current treatments use acetylcho- cholinesterase inhibitory activity of the aerial parts of linesterase (AChE) inhibitors but these drugs have side Solenostemma argel by bioguided fractionation to purify effects and bioavailability issues.2,3 Therefore, better and identify active compounds and to test them in vitro cholinesterase inhibitors are needed. Work on medicinal and in silico on AChE and BChE. plants has led to the isolation of several cholinesterase (ChE) inhibitors such as galantamine and physostigmine.4 Experimental Other ChE inhibitors were found in the Apocynaceae family such as pregnane glycosides.5 Those unusual com- General experimental procedures – NMR spectra pounds were also reported in the genus Solenostemma.6 (1H, 500 MHz; 13C, 500 MHz) were recorded on a Bruker Solenostemma argel (Delile) Hayne (Apocynaceae) is a Advance 500 spectrometer. Mass spectra (HR-ESI-MS) desert plant found in the south of Algeria.7 It has been were performed on a PE Sciex API 3000 triple quadrupole used traditionally to treat various diseases including mass spectrometer equipped with an ion spray turbo bronchitis, neuralgia and sciatica.8 In addition, previous source (Thermo Fisher Scientific Extractive). The HPLC apparatus comprised a Shimadzu SCL-10 Avp pump and *Author for correspondence an SPD-M20A photodiode detector with an analytical and R. G. Demmak, Laboratoire de Biochimie Appliquée, Département a preparative RP18 column (Silica Upti-prep Strategy, des Sciences de la Nature et de la Vie, Université Frères Mentouri- Constantine 1; 25000 Constantine, Algeria 250 mm × 22 mm; particle size 5 µm, Grace, France). Tel: +213-31-92-32-22; E-mail: [email protected] 115 116 Natural Product Sciences TLC was performed on silica gel 60 F254 plates (Merck, (1 H, m, H-4′′).¹³C-NMR (CD3OD) δ: 165.0 (C-7), 161.74 Darmstadt, Germany) and the absorbance of the reaction (C-5), 157.2 (C-2), 156.9 (C-9), 131.5 (C-3), 122.6 (C- was measured using Nest 196 Microplate Spectrostar 1′), 115.2 (C-3′, C-5′). HR-ESI-MS (negative ion) m/z − Nano (BMG Labtech). 447.09430 [M-H] (Calcd for C21H19O11). Plant materials – Aerial parts of Solenostemma argel Kaempferol (2) – Yellow powder; ¹H-NMR (CD3OD) were harvested in March 2013 in the area of Djanet δ: 8.11 (1 H, d, J = 8.92 Hz, H-2′, H-6′), 6.92 (1 H, d, (Tassili of N'Ajjers massif; South-East of Algeria). The J = 8.77 Hz, H-3′, H-5′), 6.41 (1 H, s, H-8), 6.20 (1 H, s, botanical identification of the plant was done by Dr. Bazri H-6). ¹³C-NMR (CD3OD) δ: 176.1 (C-4), 164.4 (C-7), K, Department of Plant Biology, Faculty of Biology and 161.14 (C-5), 159.17 (C-9), 156.86 (C-2), 136.2 (C-3), Natural Sciences, University of Frères Mentouri, Cons- 129.2 (C-2′, C-6′), 115.1 (C-3′, C-5′), 103.4 (C-10), tantine, Algeria. A voucher specimen (Sol.2013.31) has 98.1 (C-6), 93.1 (C-8). HR-ESI-MS (negative ion) m/z − been deposited at the Herbarium of Laboratory of Applied 285.0406 [M-H] (Calcd for C15H9O6). Biochemistry, University of Frères Mentouri, Constan- Kaempferol-3-glucopyranosyl-(1→6)-rhamnopyranose tine,Algeria. (3) – Yellow powder; ¹H-NMR (CD3OD) δ: 8.07 (1 H, d, Extraction and isolation – The fresh plant was dried J = 9.00 Hz, H-2′, H-6′), 6.91 (1 H, d, J = 9.00 Hz, H-3′, in the shade and then crushed using an electric blender to H-5′), 6.40 (1 H, s, H-8), 6.20 (1 H, s, H-6), 5.78 (1 H, d, obtain a fine powder. 500 g of the powder were macerated J = 7.10 Hz, H-1′′), 5.25 (1 H, d, J = 1.3,H-1′′′), 4.01 (1 H, in MeOH/H2O (80:20). This extract was concentrated to m, H-2′′′), 3.77 (1 H,m, H-6′′a), 3.65 (1 H, m, H-2′′),3.58 dryness and the crude extract (71.4 g) was suspended in (1 H, m, H-3′′′), 3.52 (1 H, m, H-6′′b), 3.44 (1 H, m, H- H2O and partitioned successively with petroleum ether, 5′′′), 3.43 (1 H, m, H-3′′), 3.35 (1 H, m, H-4′′, H-4′′′), 3.29 CHCl3, EtOAc and n-BuOH (3 × 500 mL each), then (1 H, m, H-5′′), 3.44 (1 H, m, H-4′′), 0.99 (3 H, d, exhaustively concentrated to yield petroleum ether (1.2 g), J = 6.20, H-6′′′). ¹³C-NMR (CD3OD) δ: 179.3 (C-4), 165 CHCl3 (21.4 g), EtOAc (2.1 g) and n-BuOH (31.4 g) extracts. (C-7), 164.8 (C-5), 159.9 (C-4′), 157.2 (C-2, C-9), 133.3 After a preliminary cholinesterase inhibitory screening (C-3), 130.3 (C-2′, C-6′), 121.8 (C-1′), 104.8 (C-10), of various extracts by bioautography, the chloroform 101.23 (C-1′′′), 99.4 (C-1′′), 99.3 (C-6), 93.2 (C-8), 78.69 extract was selected for further studies and purification of (C-2′′), 77.5 (C-3′′′), 76.1 (C-4′′), 72.6 (C-4′′′), 71.0 (C- pure compounds. 3′′), 70.6 (C-2′′′), 70.38 (C-5′′), 68.9 (C-5′′′), 61.23 (C-6′′), The chloroform extract was fractionated through an 16.2 (C-6′′′). HR-ESI-MS (negative ion) m/z 593.1512 − open column chromatography on silica gel using two [M-H] (Calcd for C27H29O15). gradients: Toluene/EtOAc (0 to 100% EtOAc) and then p-Hydroxybenzoic acid (4) – White powder; ¹H-NMR EtOAc/MeOH (0 to 100% MeOH). This led to 23 fractions (CD3OD) δ: 7.88 (2 H, d, J = 8.47 Hz, H-2, H-6), 6.79 that were all tested with the TLC acetylcholinesterase (2 H, d, J = 8.47 Hz, H-3, H-5). ¹³C-NMR (CD3OD) δ: assay. Among the most active fractions (10 - 19), fraction 171.6 (COOH), 161.16 (C-4), 131.4 (C-2, C-6), 123.8 (C- 17 was submitted to another open column chromato- 1), 114.41 (C-3, C-5). HR-ESI-MS (negative ion) m/z − graphy with a gradient of Heptane/EtOAc of increasing 137.1221 [M-H] (Calcd for C7H5O3). polarity and then EtOAc/MeOH. Two of its active Dehydrovomifoliol (5) – Yellow powder; ¹H-NMR subfractions led to the isolation of two pure compounds (1 (CD3OD) δ: 7.02 (1 H, d, J = 15.92 Hz, H-7), 6.46 (1 H, and 4) by preparative HPLC. Fractions 10, 13 and 19 d, J = 15.92 Hz, H-8), 5.96 (1 H, m, H-4), 2.63 (1 H, d, were further fractionated by preparative HPLC (C18 column) J = 17.83 Hz, H-2), 2.33 (3 H, s, H-10), 1.92 (3 H, d, and eluted with mixtures of water containing 0.1% formic J = 1.41 Hz, H-13), 1.08 (3 H, s, H-12), 1.03 (3H, s, H- acid (solvent A) and acetonitrile (solvent B) at a flow rate 11). ¹³C-NMR (CD3OD) δ: 199.30 (C-9), 199.0 (C-3), of 12 mL/min. This led to the isolation of compounds 2 163.3 (C-5), 146.97 (C-7), 130.4 (C-8), 126.7 (C-4), and 5 from fraction 10, compound 6 from fraction 13 and 78.53 (C-6), 49.14 (C-2), 41.68 (C-1), 26.21 (C-10), compounds 3, 7 and 8 from fraction 19.
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