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Anti-Oxidative, Acetylcholinesterase and Pancreatic Lipase Inhibitory Activities of Compounds from Dasiphora Fruticosa, Myricaria Alopecuroides and Sedum Hybridum

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Anti-Oxidative, Acetylcholinesterase and Pancreatic Lipase Inhibitory Activities of Compounds from Dasiphora Fruticosa, Myricaria Alopecuroides and Sedum Hybridum Mongolian Journal of Chemistry Institute of Chemistry & Chemical Technology Mongolian Academy of Sciences Anti-oxidative, acetylcholinesterase and pancreatic lipase inhibitory activities of compounds from Dasiphora fruticosa, Myricaria alopecuroides and Sedum hybridum G.Odontuya Institute of Chemistry and Chemical Technology, Mongolian Academy of Sciences, Peace Avenue, Ulaanbaatar 13330, Mongolia ARTICLE INFO: Received: 25 Oct, 2016; Revised: 15 Dec, 2016; Accepted: 22 Dec, 2016 Abstract: Total of 35 phenolics and flavonols were isolated from flowers and leaves of Dasiphora fruticosa Rydb., from branches of Myricaria alopecuroides Schrenk. and from the herb of Sedum hybridum L. The isolated compounds were identified on the basis of spectral data and tested for their anti-oxidative, acetylcholinesterase and pancreatic lipase inhibitory activities.Quercetin glycosides, gallic acid, (-)EGCG and gossypetin-8-O-xylopyranoside tellimagrandin II exhibited strong anti-oxidative activity by the DPPH scavenging method. The acetylcholinesterase inhibitory activity of quercetin glycosides and (-)EGCG was higher than those of other compounds. Whereas, tellimagrandin II, (-)EGCG and gallic acid derivatives exhibited the most potent inhibitory activity against the pancreatic lipase enzyme among the isolated compounds. Only (-)EGCG showed a prominent activity against all assayed experiments. It was concluded that these plants could be studied further for their potential as anti-oxidative, anti-aging and lipid lowering active products. Keywords: Flavonol, gallic acid, tellimagrandin II, antioxidant, anti-aging, lipid lowering activity Copyright © 2016 Odontuya G. This is an open access article distributed under the Creative Commons Attribution 4.0 International License CC BY, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. INTRODUCTION EXPERIMENTAL Traditionally, flowers, leaves and scions of Dasiphora General experimental procedures: Thin layer chromato fruticosa Rydb. (Rosaceae) were used to cure diarrhea, chromatography (TLC) was performed on pre-coated dysentery and other digestive organs disorders, as silica gel 60 F254 plate (Merck, Darmstadt, Germany) and well as for relieving the neurological disorders [1, 2]. the spots were detected under UV radiation (366 nm) Scions and branch of Myricaria alopecuroides Schrenk. by spraying with 1% methanolic diphenylboric acid-β- (Tamaricaceae) have generally been used to neutralize ethylamino ester (NP), 5% ethanolic polyethylene glycol the incidents of poisoning from different kinds of origins, (PEG). For column chromatography (CC) Sephadex to alleviate the diffused and concealed chronic fever and LH-20 (25-100 mm, Pharmacia, Uppsala, Sweden), to treat several of diseases including rash, boils, chronic MCI gel – CHP-20P (75-150 µm, Mitsubishi Chemical ulcers, phthisis, spasms and atrophy [1, 3, 4]. The herb Corporation, Japan), SepraTM C18-E (50 μm, 65Ao), of Sedum hybridum L. (Crassulaceae) has been used for Silica gel 60 (40-60 μm, Merck, Darmstadt, Germany) the treatment of diarrhea, dysentery, sepsis, thyroid, blood were used. UV spectroscopic analysis was carried out on vessel disease and seizures related with nervous system spectrophotometer UV-160 (Shimadzu, Japan) using 5% [1, 4, 5]. AlCl3, 1 N HCl, CH3COONa and H3BO3 diagnostic reagents. Previous studies revealed the presence of quercetin All used reagents and solvents were with analytical grade. derivatives in the leaves of D.fruticosa [6, 7], gallic acid 1H (500 MHz) and 13C NMR (125 MHz) spectra were and its esterified derivatives in M.alopecuroides [8,9] and recorded on Bruker AMX-500, respectively. Quantitative some flavonols and coumarins in S.hybridum [10]. analysis was carried out on spectrophotometer UV-2550 The anti-oxidative, antibacterial activities of crude extracts, (Shimadzu, Japan). fractions and some compounds from the investigated Plant materials: All investigated plant samples were plant samples have been partly reported [11-13]. As a prepared from the Gobi-Altai aimag. Especially, flowers part of continuing work on these plants, we report herein and leaves of Dasiphora fruticosa were collected from the content of bio-active compounds in the crude drugs, the mountain Khasagt Khairkhan, in June-July, 2004, the characteristic phytochemicals and their anti-oxidative, flowered green branches of Myricaria alopecuroides from acetylcholinesterase, and pancreatic lipase inhibitory the riverside meadow, in late July, 2007 and aerial parts activities. of Sedum hybridum from the ground mountain slope, in June-July, 2006. Prof. Jamsran Ts., Department of Botany, National University of Mongolia authenticated these plant *corresponding author: e-mail: [email protected] species. Voucher specimens (Df 0406, Ma 0708, Sh 0607) DOI: http://dx.doi.org/10.5564/mjc.v17i43.746 have been deposited in the Herbariums of Natural Product 43 Mongolian Journal of Chemistry 17 (43), 2016, 42-49 Chemistry Laboratory of ICCT, MAS. formation of acid stable complex with 2% AlCl3 at 401.5 Extraction and fractionation: Air dried and chopped and 430.0 nm. Results were expressed as rutin (Sigma crude drugs of D.fruticosa, M.alopecuroides and Inc.) and quercetin (TCI Co., Ltd) equivalents (RE and S.hybridum were extracted separately with 80% ethanol QE) from the calibration curve [16, 17]. The content of at room temperature exhaustively. Each total ethanol total tannins was determined by spectrophotometry using extract was filtered and concentrated under vacuum at a hide powder and the Folin Ciocalteu reagent in pH<10, 40oC to give the thick residue which was re-suspended at 760 nm. Results were expressed as pyrogallol (Sigma in distilled water and further fractionated successively Inc.) equivalent (PE) from the calibration curve [18]. with equal volume of dichloromethane (DCM), DPPH scavenging activity: DPPH radical (2,2-diphenyl- ethylacetate (EA) and n-butanol (n-BuOH) (Table 1). 2-picrylhydrazyl hydrate, TCI, Co., Ltd) scavenging activity Table 1. Yield of extracts and fractions, g Weight of Thick DCM n-BuOH Water Plant samples EA fraction, drugs extract fraction fraction residue D.fruticosa (Df) flowers 300.0 93.0 5.1 25.8 17.3 40.0 D.fruticosa (Df) leaves 300.0 46.0 9.1 9.5 16.3 4.0 M.alopecuroides (Ma) 3500.0 818.0 68.4 40.0 250.0 200.0 branches S.hybridum (Sh) herb 1450.0 300.0 2.0 31.5 126.0 140.0 Each crude drug (50 g) was extracted twice with distilled of the crude extracts, fractions and pure compounds was water at room temperature and evaporated to dryness in determined according to the known spectrophotometric vacuo. Then they were tested for their biological activities. assay [19]. The absorbance was measured at 517 nm and Isolation and identification: The EA fractions of Df the anti-oxidative activity (AA) was expressed in percentage: flowers (25.5 g) and Sh herb (28.0 g), the EA and n-BuOH fractions of the Ma branch (35.0 and 30.0 g) were divided АA% = 100 - { [ (Abssample - Absblank) ×100] / Abscontrol}; into several subfractions using CC with Sephadex LH 20, eluting with a mixture of 50% DCM in MeOH. Each Methanol (1.5 ml) added to plant extract solution (1.5 ml) subfraction was subjected to CC with different absorbents was used as a blank. DPPH solution (1.5 ml, 6х10-5М) plus as 75-150 μm CHP 20P, and reversed phase sepraTM methanol (1.5 ml) was used as a control and rutin was C18-E (50 μm) eluting with gradient H2O – MeOH system, used as a positive control. respectively. The final purification of substances was Acetylcholinesterase inhibiting activity: The acetyl- reached by repeated CC with Sephadex LH 20. cholinesterase (AChE) inhibiting activity of crude The DCM fractions of Ma branch (30.0 g), Df flowers extracts, fractions and isolated pure substances (3.5 g) and Sh herb (1.0 g) were divided into numerous was determined using a previously reported Ellman subfractions by CC with silica gel 60 (40-60 μm), eluting spectrophotometric method with DTNB (5,5’-dithiobis(2- with n-hexane: DCM – 7:3→6:4→5:5→3:7→1:9 v/v, nitrobenzoisc acid), TCI, Co., Ltd) color reagent [20]. and DCM: EA – 10:1→95:5→9:1 v/v, respectively. The The absorbance was measured at 412 nm and the subfractions were separated repeatedly over silica gel AChE inhibiting activity (I) was expressed in percentage: columns eluted gradiently with solvent systems such as n-hexane : EA, CHCl3 : MeOH and DCM : MeOH. I (%) = 100 x (∆Abscontrol - ∆Abssample)/∆Abscontrol From all three plant species compounds (see Fig. 2) 1 (0.34 g), 10 (0.42 g), 23 (0.39 g), 31 (0.50 g), 32 (0.17 Where, ∆Acontrol = Abspositive control - Absblank positive control g) 34 (0.44 g), from Df and Ma, compound 4 (0.45 g), from Df and Sh compound 6 (66.8 mg), from Ma and Sh ∆Asample = Abssample - Absblank sample compounds 24 (0.36 g) and 35 (0.31 g) have been isolated and identified. Only from Df compounds 2 (2.1 g), 3 (0.22 Blank solution was prepared from 0.1 ml sample (1 mg/ml) g), 5 (0.88 g), 11 (62.7 mg), 12 (0.48 g), 20 (0.20 g), 21 with DTNB prepared in Tris-HCl, while the positive control (0.34 mg) and 30 (8.0 mg), from Ma compounds 7 (7.6 was prepared from DMSO (dimethylsulfoxide) with the mg), 8 (24.0 mg), 9 (24.0 mg), 13 (0.18 g), 14 (0.19 g), 17 same amount of the sample. Eserin (physostigmine, TCI, (1.19 g), 27 (1.38 g) and 29 (0.28 g), from Sh compounds Co., Ltd) was used as a positive control. 15 (5.0 mg), 16 (26.2 mg), 18 (64.4 mg), 19 (33.7 mg), 22 Pancreatic lipase inhibiting activity: The pancreatic (0.30 g) 25 (0.22 g), 26 (60.6 mg), 28 (22.3 mg) and 33 lipase (PL) enzyme inhibiting activity of crude extracts, (67.8 mg) have been isolated and identified.
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