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Antioxidant and Antiplasmodial Activities of Bergenin and 11-O-Galloylbergenin Isolated from Mallotus Philippensis

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Antioxidant and Antiplasmodial Activities of Bergenin and 11-O-Galloylbergenin Isolated from Mallotus Philippensis Hindawi Publishing Corporation Oxidative Medicine and Cellular Longevity Volume 2016, Article ID 1051925, 6 pages http://dx.doi.org/10.1155/2016/1051925 Research Article Antioxidant and Antiplasmodial Activities of Bergenin and 11-O-Galloylbergenin Isolated from Mallotus philippensis Hamayun Khan,1 Hazrat Amin,2 Asad Ullah,1 Sumbal Saba,2,3 Jamal Rafique,2,3 Khalid Khan,1 Nasir Ahmad,1 and Syed Lal Badshah1 1 Department of Chemistry, Islamia College University, Peshawar 25120, Pakistan 2Institute of Chemical Sciences, University of Peshawar, Peshawar 25120, Pakistan 3Departamento de Qu´ımica, Universidade Federal de Santa Catarina, 88040-900 Florianopolis, SC, Brazil Correspondence should be addressed to Hamayun Khan; [email protected] Received 23 October 2015; Revised 15 January 2016; Accepted 18 January 2016 Academic Editor: Denis Delic Copyright © 2016 Hamayun Khan et al. This is an open access article distributed under the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. Two important biologically active compounds were isolated from Mallotus philippensis. The isolated compounds were characterized using spectroanalytical techniques and found to be bergenin (1)and11-O-galloylbergenin (2). The in vitro antioxidant and antiplasmodial activities of the isolated compounds were determined. For the antioxidant potential, three standard analytical protocols, namely, DPPH radical scavenging activity (RSA), reducing power assay (RPA), and total antioxidant capacity (TAC) assay, were adopted. The results showed that compound 2 was found to be more potent antioxidant as compared to 1. Fascinatingly, compound 2 displayed better EC50 results as compared to -tocopherol while being comparable with ascorbic acid. The antiplasmodial assay data showed that both the compound exhibited good activity against chloroquine sensitive strain of Plasmodium falciparum (D10) and IC50 values were found to be less than 8 M. The in silico molecular docking analyses were also performed for the determination of binding affinity of the isolated compounds using P. falciparum proteins PfLDH and Pfg27. The results showed that compound 2 has high docking score and binding affinity to both protein receptors as compared to compound 1. The demonstrated biological potentials declared that compound 2 could be the better natural antioxidant and antiplasmodial candidate. 1. Introduction act as antioxidants. Plants are considered to be the best source of natural antioxidants [1–3, 6]. Similarly, the various Medicinal plants, their extracts, or the isolated purified con- antimalarial and antiparasitic drugs such as quinine and stituents have been used extensively as remedy for treatment artemisinin were also reported from the medicinal plants [7]. of several diseases. The flora of Pakistan is quite rich with Bergenin and 11-O-galloylbergenin are the two natural the naturally gifted medicinal plants. However, very little products. The biological and pharmacological activities of attention was given to explore the medicinal potentials of bergenin are well documented in the literature [8–21]. How- such worthy materia medica [1–3]. Various ailments such ever, very little work has been reported on the biological as Parkinson’s, Alzheimer’s, cancer, inflammation, neurode- potentials of 11-O-galloylbergenin [22, 23] which need to be generation, aging, injury to blood vessel membranes, heart, more explored. In the present study, the abovementioned and brain, and a number of other diseases may be caused naturalproductswereisolatedfromMallotus philippensis by the free radicals present in the body. Antioxidants are and their antioxidant and antiplasmodial activities were free radical scavengers that may prevent, protect, or reduce investigated. For confirmation of the experimental results, the extension of such damage [4, 5]. A number of chemical the computational study was also performed using in silico species including both synthetic and natural products may molecular docking. 2 Oxidative Medicine and Cellular Longevity 2. Materials and Methods using the default parameters of MOE energy minimization 1 13 algorithm (gradient: 0.05, force field: MMFF94X). For the 2.1. General Experimental Procedures. H-NMR and C- 1 moleculardockingoftheisolatedcompounds,defaultparam- NMR were recorded at 400 MHz for Handat100MHz 13 eters of MOE-dock program were used. To find the correct for CusingTMSasinternalstandardwithBrukerDPX- conformations of the ligands and to obtain minimum energy 400 instrument in deuterated solutions. Mass spectra were structure, ligands were allowed to be flexible. At the end of recorded on Agilent 5973N instrument using EI mode. IR docking, the best conformations of the ligand were analyzed spectra were determined using a Jasco A-302 spectropho- for their binding interactions. tometer. UV and UV-visible spectra were recorded using U- 3200 (Hitachi, Japan) and SP-3000 PLUS (Optima, Japan) spectrophotometers. For TLC and column chromatography, 3. Results and Discussion aluminum sheets precoated with silica-gel 60 F254 (20 × 20 cm, 0.2 mm thick; E. Merck, Germany) and silica gel (200– 3.1. Characterization of the Isolated Compounds. The spectral 300 mesh), respectively, were used. The commercial solvents analyses of the two isolated compounds are summarized as were used for extraction purpose and were redistilled. For follows. the antioxidant and antiplasmodial activities, analytical grade 1 ∘ reagents and chemicals were used. Compound . White needles; mp = 237 C; UV max (log )= 279(4.28); IR (KBr) max = 3310, 3350, 1712, 1632, 1609, 1510, −1 1 1230 cm ; H-NMR (DMSO-d6,400MHz): 6.97 (1H, s, H- 2.2. Plant Material. The stem wood of M. philippensis 7),5.67(1H,d,H-10b),4.98(1H,dd,H-4a),3.89(1H,dd,H-4), (Euphorbiaceae) was collected from district Bunner located 3.81 (2H, d, H-11), 3.75 (3H, s, H-12), 3.62 (1H, m, H-2), 3.48 in the north of Pakistan in July 2006 and identified via 13 (1H, dd, H-3); C-NMR (DMSO- d6,100MHz): 60.0 (C- VoucherNumber1013(pup)byProfessorDr.AbdurRashid, 12), 61.1 (C-11), 70.7 (C-3), 72.1 (C-10b), 73.7 (C-4), 79.8 (C- Department of Botany, University of Peshawar, Peshawar, 4a), 81.7 (C-2), 109.4 (C-7), 116.0 (C-10a), 118.1 (C-6a), 140.6 Pakistan. (C-9), 148.1 (C-10), 151.0 (C-8), 163.5 (C-6); EIMS m/z (rel. int.): 328 (34), 208 (100), 237 (7), 170 (30). 2.3. Extraction and Isolation. Air dried plant material was Compound 1 was obtained as white crystals. The mass chopped, grinded, and extracted three times with commer- spectral data of compound 1 gave a molecular ion peak at m/z cial ethanol for 72 h which afforded 4.32% of the crude 328 which leads to a molecular formula of C14 H16O9.The ∘ extract. From the crude extract, -hexane soluble fraction melting point of 237 C is consistent with the published melt- ∘ 1 was removed by solvent extraction with water. The aqueous ing point of bergenin, that is, 238 C. The H-NMR spectral fraction was then dried under vacuum which was further analysis showed a signal for one aromatic proton at 6.97 (1H, 1 2 13 processed for the isolation of compounds and as depicted s) and a signal for methoxy protons at 3.8 (3H, s). In the C- in Scheme 1. The isolated compounds were characterized NMR spectrum, the signals were observed at 163.5 and 60.0 using various spectroanalytical techniques. for carbonyl and methoxy groups, respectively. Compound 1 was characterized as bergenin (Figure 1) by comparing its 2.4. Antioxidant Potential. The antioxidant potential of the physical and spectral data with previous literature [23, 29]. isolated compounds was determined using DPPH radical ∘ scavenging activity (RSA) [1–3, 24], reducing power assay Compound 2. White amorphous powder; mp = 180 C; 15 ∘ (RPA) [24, 25] and total antioxidant capacity (TAC) assay []D = +37.6 (EtOH; c 1.2), UV max (log )=277(4.22); −1 1 [26]. IR (KBr) max = 3310,1712,1632,1609,1510,1230cm ; H- NMR (90 MHz, Me2CO-d): 7.21(2H, s, gall-H), 7.10 (IH, 13 2.5. Antiplasmodial Activity. For antiplasmodial activity, the s,H-7),3.90(3H,s,OMe); C-NMR (90 MHz, CD3OD): isolated compounds were tested against chloroquine sensitive 81.2 (C-2), 72.2 (C-3), 75.7 (C-4), 81.1 (C-4a), 166.5(C-6), (CQS) strain of Plasmodium falciparum (D10). Continuous in 120.0, (C-6a), 112.0 (C-7), 153.1 (C-8), 143.3 (C-9), 150.0 (C- vitro cultures of asexual erythrocyte stages of P. fal c ip ar um 10), 117.7 (C-10a), 74.7 (C-10b), 65.1 (C-11), 61.3 (C-12), 121.8 were maintained using the reported method [27]. For the (C-1 ), 111.1 (C-2 , C-6 ), 147.4 (C-3 , C-5 ), 140.0 (C-4 ), 169.2 quantitative assessment of antiplasmodial activity, parasite (C-7 ); EIMS m/z (rel. int.): 480 (32), 328 (34), 208 (100), 237 lactate dehydrogenase assay was adopted [28]. The IC50 values (7), 170 (30). were obtained using a nonlinear dose-response curve fitting Compound 2 was interpreted and analyzed as C21H20O13 1 13 analysis via Graph Pad Prism v.4.0 software. to be monogalloyl ester of bergenin by its H-NMR, C- NMR, and EIMS spectral data and also by acid hydrolysis 2.6. Molecular Docking. For the in silico molecular docking which gave bergenin and gallic acid. The position of the 13 study, the crystal structures of receptor proteins were down- galloyl group was established by C-NMR spectrum and 2D loaded from the protein data bank, code number PfLDH (P. techniques. The carbon signals other than that of C-11 in the falciparum lactate dehydrogenase) and PFG27 (gametocyte glucose moiety of bergenin were assigned as given below. The protein) of P. fal c ip ar um .
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