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Anti-Oxidant, Anti-Malarial, and Phytochemical Studies on Muscari Inconstrictum Bulbs Distributed in Iran

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Anti-Oxidant, Anti-Malarial, and Phytochemical Studies on Muscari Inconstrictum Bulbs Distributed in Iran Corrected Proof ArchiveJundishapur of J NatSID Pharm Prod. 2020 May; 15(2):e92219. doi: 10.5812/jjnpp.92219. Published online 2019 December 24. Research Article Anti-Oxidant, Anti-Malarial, and Phytochemical Studies on Muscari inconstrictum Bulbs Distributed in Iran Fariba Heshmati Afshar 1, 2, Mohammadali Torbati 3, Sedigheh Bamdad 1 and Solmaz Asnaashari 4, * 1Drug Applied Research Center, Tabriz University of Medical Sciences, Tabriz, Iran 2Department of Pharmacognosy, Faculty of Pharmacy, Tabriz University of Medical Sciences, Tabriz, Iran 3Department of Food Sciences and Technology, Faculty of Nutrition, Tabriz University of Medical Sciences, Tabriz, Iran 4Biotechnology Research Center, Tabriz University of Medical Sciences, Tabriz, Iran *Corresponding author: Biotechnology Research Center, Tabriz University of Medical Sciences, Tabriz, Iran. Email: [email protected] Received 2019 April 13; Revised 2019 August 05; Accepted 2019 August 31. Abstract Background: Muscari inconstrictum Rech. f. is an ornamental and bulbous species with various medicinal and biological effects. Objectives: This study was designed to evaluate the anti-oxidant and anti-malarial activities of M. inconstrictum as one of the Ira- nian species of Muscari genus. Additionally, preliminary phytochemical investigation of the extracts with different polarity was performed. Methods: M. inconstrictum bulbs were extracted with n-hexane, chloroform, and methanol (MeOH) by Soxhlet apparatus, in the order of their polarity. Next, vacuum liquid chromatography (VLC) was used for the fractionation of extracts. Free radical scavenging and anti-malarial activities were investigated via DPPH (2,2-diphenyl-1-picrylhydrazyl) and cell-free β-hematin formation methods. Thin layer chromatography (TLC) and gas chromatography-mass spectrometry (GC-MS) were used for the characterization of potent fractions. Results: Among different extracts of M. inconstrictum, bulbs, chloroform, and n-hexane extracts were the most potent anti-oxidant and anti-malarial extracts, respectively. Moreover, methanolic, 80% and 100% ethyl acetate/n-hexane VLC fractions of chloroform extract showed significant anti-oxidant activities, which can be related to the presence of flavonoid and coumarin structures. Fur- thermore, 40% ethyl acetate/n-hexane VLC fraction of n-hexane extract with saponin structures is introduced as the most potent anti-malarial part. GC-MS analysis of methanol fraction of chloroform extract, 40% ethyl acetate/n-hexane VLC fraction of n-hexane extract, and the volatile oil of plant demonstrated the presence of phenolic monoterpenoid, fatty acid derivatives, and sesquiter- penoid structures as the main ingredients, respectively. Conclusions: It seems that more studies on M. inconstrictum are necessary to focus on pure compounds and their biological activi- ties. Keywords: Muscari inconstrictum, Bulb, Anti-Oxidant, Anti-Malarial, Phytochemical 1. Background which are a subclass of flavonoids and are rarely found in nature (5,8-10). In a genotoxicological study, Miadokova et Muscari Miller, from the Asparagaceae family, is repre- al. (8), suggested that homoisoflavonoids from the bulbs sented by about 50 species worldwide. These ornamental of Muscari racemosum (L.) have important pharmacologi- plants are distributed in Iran, Iraq, Anatolia, Syria, Cauca- cal effects and might be beneficial for inhibition of cancer sia, Central and East Southern of Europe, Southern Russia, owing to their anti-mutagenic and anti-clastogenic prop- and Africa (1-3). Eight bulbous species were reported in Ira- erties. nian flora (2,4,5). Previous literature offered various medicinal and bio- Approximately, 240 types of natural occurring ho- logical effects such as a diuretic, emetic, anti-oxidant, anti- moisoflavonoids were reported from the various parts of inflammatory,hypoglycemic, and stimulant effects (2,6,7). the plants from Asparagaceae, Fabaceae, Polygonaceae, Or- Moreover, earlier phytochemical studies on the plants chidaceae, Portulacaceae, and Gentianaceae families. They of genus Muscari showed the occurrence of flavonoid, alka- have an extensive variety of biological effects including loid, terpenoid, and steroid structures (4). Muscari genus anti-oxidant, anti-microbial, anti-viral, anti-mutagenic, is one of the chief sources of homoisoflavonoid structures, anti-diabetic, anti-inflammatory, anti-angiogenic, va- Copyright © 2019, Jundishapur Journal of Natural Pharmaceutical Products. This is an open-access article distributed under the terms of the Creative Commons Attribution-NonCommercial 4.0 International License (http://creativecommons.org/licenses/by-nc/4.0/) which permits copy and redistribute the material justwww.SID.ir in noncommercial usages, provided the original work is properly cited. Corrected Proof Archive of SID Heshmati Afshar F et al. sorelaxant, immunomodulatory, and cytotoxic effects methanolic extract and chloroform (for n-hexane and chlo- (5, 11). In addition, according to previous knowledge, roform extracts) to obtain the stock solution. Methanolic homoisoflavonoid structures can be a good source of extract was dissolved in methanol (1 mg/mL). Moreover, n- ingredients with anti-plasmodial effects (12). hexane and chloroform extracts were dissolved in chloro- form (1 mg/mL). Concentrations of 2.5 × 10-1, 1.25 × 10-1, 6.25 × 10-2, 3.13 × 10-2, and 1.56 × 10-2 mg/mL were made by di- 2. Objectives lution. About 2 mL of each dilution was mixed with DPPH The present study aimed to evaluate some biological (2 mL). Tubes were kept at room temperature for 30 min activities and phytoconstituents of Muscari inconstrictum to allow any reaction to occur. The absorbance of samples Rech. f. bulbs. To the best of our knowledge, this is the first was measured using UV/Visible Spectrophotometer (Spec- study on phytochemicals and biological effects of M. incon- tronic Genesys spectrophotometer, USA) at 517 nm. The strictum. same procedure was repeated three times and the aver- age absorbance was recorded. The reduction percentage of DPPH (R%) was calculated as below and the result was 3. Methods reported as sample concentration providing 50% DPPH re- duction (RC50). 3.1. Plant Material R% = [(Absblank − Abssample) =(Absblank)] × 100 (1) Muscari inconstrictum Rech. f. was collected from the gardens of East-Azerbaijan, the province of Iran in April Abs, absorbance of samples. 2016. After authentication, the voucher specimen (no.: 8897) was stored at the Herbarium of the East-Azarbaijan 3.5. Cell free β-Hematin Formation Assay Agricultural and Natural Resources Research and Educa- The anti-malarial activity of the three extracts was eval- tion Center, Tabriz, Iran. uated by the heme biocrystallization technique described by Afshar et al. (16). Various concentrations of extracts (0.4 - 3.2. Extraction 2 mg/mL in dimethyl sulfoxide) were mixed with 100 µL of Air-dried bulbs of M. inconstrictum were crushed and hematin (dissolved in 0.1 M NaOH), 10 mM oleic acid, and were Soxhlet-extracted with n-hexane, chloroform, and 10 µM HCl. The reaction volume was attuned to 1000 µL methanol (MeOH), continuously. Subsequent extracts by sodium acetate buffer (pH = 5). The microtubes were in- were evaporated at 50°C using a rotary evaporator. cubated at 37°C for 24 h with constant shaking. Afterward, Moreover, the 100 g of powdered bulbs of M. inconstric- samples were centrifuged (12,000 rpm for 10 min) and tum was subjected to hydro distillation for four hours us- the hemozoin sediments were washed repetitively in 2.5% ing a Clevenger device. The produced essential oil was mea- (w/v) sodium dodecyl sulfate (SDS) in phosphate buffered sured (V/W) and dried via anhydrous sodium sulfate, and saline. Finally, they were washed in sodium bicarbonate then stored in a sealed vial for further analysis. (0.1 M and pH = 9.0) until the supernatant was clear (after 4- 6 washes). In the next step, the supernatant was eliminated 3.3. Fractionation and the sediments of hemozoin were re-suspended using About 0.7 g of chloroform extract and 0.5 g of n-hexane 1 mL of NaOH (0.1 M). The absorbance of the samples was extract from M. inconstrictum bulbs were fractionated by measured at 400 nm with UV/Visible Spectrophotometer vacuum liquid chromatography (VLC) over silica gel (20 (Spectronic Genesys spectrophotometer, USA). The results g) with solvent mixtures of increasing ratios of polarities were informed as inhibition percentage (I %) of heme crys- to ethyl acetate/n-hexane (i.e., 10:90, 20:80, 40:60, 60:40, tallization calculated as follows: 80:20, and 100:0) and MeOH. All the fractions were com- I % = [(Absblank − Abssample) =(Absblank)] × 100 (2) pletely dried using a rotary evaporator at a maximum tem- perature of 45°C (13). 3.6. Identification of Components 3.6.1. GC-MS (Gas Chromatography-Mass Spectrometry) Analy- 3.4. Free Radical Scavenging Activity sis The concentrated n-hexane, chloroform, MeOH ex- GC-MS and gas chromatography with flame ionization tracts, and VLC fractions of the most potent extract were detector (GC-FID) analysis were performed on a Shimadzu objected to anti-oxidant assay test using DPPH (Sigma, Ger- QP-5050A GC-MS system (Japan) and GC-17A equipped with many) as a reagent and quercetin as a positive control (14, a DB-1 fused silica column (60 m × 0.25 mm i.d.; 0.25-µm 15). DPPH (4 mg) was dissolved in 50 mL methanol for film thickness). Helium was used as the carrier gas at a 2 Jundishapur J Nat Pharm Prod. 2020;www.SID.ir 15(2):e92219. Corrected Proof Archive of SID Heshmati Afshar F et al. flow rate of 1.3 mL/min. The sample was diluted 1:10 in n- F254 Merck (layer thickness 0.25 mm) as follows: hexane and 1 µL was injected into the column. Split ratio, Toluene:ether (l:l, saturated with 10% acetic acid) and scan time, ionization energy, and acquisition mass range chloroform:ethyl acetate (60:4) were used as a solvent sys- were 1:33, 1 s, 70 eV, and 30 - 600 amu, respectively. tem of 80% and 100% fractions of chloroform extract. Natu- The oven temperature program for essential oil was a ral products-polyethylene glycol reagent (NP/PEG) and also temperature of 50°C rising to 260°C at a rate of 3°C /min for 1% potassium hydroxide reagent was used as the reagent a total run time of 75 min.
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