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Structural Characterization and Biological Activity of Lactarius Scrobiculatus

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Structural Characterization and Biological Activity of Lactarius Scrobiculatus Structural characterization and biological activity of Lactarius scrobiculatus Ivana Tomic Thesis for the Master´ degree in Pharmacy 45 study points Department of Pharmaceutical Chemistry School of Pharmacy Faculty of Mathematics and Natural Sciences UNIVERSITY OF OSLO November/2018 II Structural characterization and biological activity of Lactarius scrobiculatus Thesis for Master´ degree in Pharmacy Department for Pharmaceutical chemistry School of Pharmacy Faculty of Mathematics and Natural Sciences University in Oslo Ivana Tomic November 2018 Supervisor: Anne Berit Samuelsen III © Author 2018 Structural characterization and biological activity of Lactarius scrobiculatus Ivana Tomic http://www.duo.uio.no/ Print: Reprosentralen, Universitetet i Oslo IV Acknowledgments The present thesis was carried out at the Departement of Pharmaceutical Chemistry, University of Oslo (UiO), for the Master´s degree in Pharmacy at the University of Oslo. The other institute include Norwegian Centre of Molecular Medicine, where I have performed activity assay. First and foremost, I would like to thank to my supervisor Anne Berit Samuelsen for hers support and guidance throughout my work and useful comments during the writing. Further, I also want to thank Hoai Thi Nguyen and Cristian Winther Wold for help with carrying out GC and GC-MS analysis. Also, I am very thankful to Karl Malterud for help with NMR analysis. Special thanks to Suthajini Yogarajah for her patience and lab support. I would also like to thank to Kari Inngjerdingen for good and helpful Forskningforberedende kurs. My gratitude goes also to Prebens Morth group at NMCC, special to Julia Weikum and Bojana Sredic, who were always kind and helpful. Finally, I would like to express my fabulous thanks to my wonderful parents, my husband and my four sons for their great patience, sacrifice, moral support and encouragement during my master thesis. Oslo, 19.11.2018. Ivana Tomic V Abstract Mushrooms have been reported to possess certain compounds with antibacterial activity, against both G+ and G- bacteria. The aim of this thesis was to obtain different extracts from mushroom L.scrobiculatus, isolate polysaccharides, investigate their chemical composition and eventual biological effect on activity of membrane protein MgtA, present in E.coli cell wall. Lactarius scrobiculatus, a wild non-edible mushroom, contains a milky-juice, which plays important role in protecting them from insects, animals and microorganisms. β-glucans from mushrooms cell wall are assigned as compounds which can activate macrophage. In addition, other secondary metabolites from mushrooms such as phenolic compounds, terpenoids and others showed activity against bacteria and fungi. MgtA, belongs to P-type ATP-ase, found in bacteria, E.coli, which is responsible for import Mg2+ions into the cytoplasm of bacteria using energy from ATP. The possible inhibition of MgtA might hinder bacterial homeostasis. Extraction and fractionations of Lactarius scrobiculatus were performed to obtain several crude extracts and fractions of the water extract, named LsW. Polysaccharides from L.scrobiculatus were isolated by sequential extraction, enzymatic treatment, SEC-HPLC and SEC preparative chromatography using three different preparative columns. The obtained fractions were analysed with respect to monosaccharide composition and glycosidic linkage determination by methylation and GC-MS. The results from SEC-HPLC showed that LsW contained fractions with the molecular weight range from 2985,4 kDa to 2.4 kDa which may indicate that LsW contains a mixture of several polysaccharides. The results obtained by methanolysis and methylation suggested that the water extract LsW might contain a (1 → 3) -linked-D-glucan, a (1 → 6) -linked D-galactan. The terminal unidentified 6-deoxy hexose was also detected. Determination of glycosidic linkage structure of alkali extract, named LsA suggested the presence of two different glucans mainly in the alkali extract LsA: a (1 → 3) -linked -D- glucan, a (1 → 6) -linked -D-glucan and a significant amount of amylose like (1 → 4) -linked α-D-glucan. The GC-MS and iodine-potassium iodide assay has indicated the presence of high amounts of (1 → 4)-α-D-glucan. 1H NMR spectroscopy showed the presence of mannitol in ethanol extract precipitate, LsK. The three of extracts, named LsK, LsDCM and LsEt gave about 30 % inhibition of activity of MgtA, while LsW and mannitol decreased MgtA activity by about 20 %. It was only screening test which should evaluate whether the inhibition of MgtA with extracts is possible in general. The further activity tests needed in the future. VI VII VIII IX Table of contents 1 Abberviations ....................................................................................................................2 2 Introduction ......................................................................................................................5 2.1 Mushrooms ....................................................................................................................5 2.1.1 Classification of mushrroms……………………………………………………….….5 2.1.2 Mushrooms: structure, growth and nutrition…………………………………………7 2.1.3 Polysaccharides and chitin in the fungal cell wall……………………………….…..10 2.1.4 β-glucans………………………………………………………………………….....11 2.2 β-glucan effect on the immune system………………………………………………..13 2.2.1 β-glucan receptors……………………………………………………………… …...15 2.3 Antitumor activity of mushroom β-glucans…………………………………………....16 2.4 Antimicrobial activity of mushrooms……………………………………………… ….17 2.4.1 Mushroom extracts with antimicrobial activity………………………………… ….17 2.4.2 Antibacterial activity of mushrooms secondary metabolites…………………… ….18 2.4.3 Antimicrobial activity of β-glucans- immunomodulating activity……………… …18 2.5 Lactarius scrobitulatus.....................................................................................................20 2.5.1 Description and habitat..............................................................................................21 2.5.2 Taxonomic classification and different names….......................................................22 2.5.3 Identified compounds in L.scrobiculatus....................................................................23 2.6 Biological activity-antimicrobial activity…......................................................................24 2.6.1 Magnesium transport protein (MgtA)……………………………………………….24 3 Aims of the study……………………………………………………………………......…..27 4 Methods……………………………………………………………………………………28 4.1 List of reagents…………………………………………………………………………..28 4.2 General methods………………………………………………………………………...30 4.2.1 Weighing…........................................................................................................ ......30 4.2.2 Water quality…........................................................................................................30 4.2.3 Measurement of pH….……......................................................................................30 4.2.4 Filtration…………………………………………………………………………....30 4.2.5 Freeze drying (lyophilization)………………………………………………… …...31 4.2.6 Centrifugation…………………………………………………………………… ...31 4.2.7 Evaporation with rotary evaporator…………………………………………….......32 X 4.2.8 Degassion of solutions……………………………………………………………32 4.2.9 Mixing of solution….……………………………………………………………32 4.2.10 Storage of aqueous solutions of polysaccharides……..………………………….33 4.2.11 Acid washing of glass equipment………………………………………………..33 4.2.12 Phenol-sulfuric acid test.…………………………………………………………33 4.2.13 Dialysis…………………………………………………………………………..34 5 Isolation of polysaccharides from Lactarius scrobiculatus…………..…………………36 5.1 Extraction……………………………………………………………………………...37 5.2 Sequential solvent extraction………………………………………………………….38 5.2.1 Extraction with dichloromethane…….…..……………………………………….38 5.2.2 Extraction with 96 % ethanol-Soxhlet extraction...…………………………………..39 5.2.3 Hot water extraction….…………..………………………………………………40 5.2.4 Alkaline extraction…………………………………………………………….....41 5.3 Treatment with enzymes……………………………………………………………...42 5.3.1 Protease treatment….……………………………………………………………42 5.3.2 Enzyme treatment of β-glucan with endo-(1→3)-β-glucanase………………….42 5.3.3 Iodine-potassium iodide assay…………………………………………………...43 6 Size exclusion chromatography (SEC)…………………………………………………..44 6.1 SEC-HPLC (High Performance Liquid Chromatography)…………………………...45 6.1.2 Preparative size exclusion chromatography……....………………………………48 6.1.2.1 Sephacryl S-500-gel filtration column….…………………………………48 6.1.2.2 Sephacryl S-500 HR….……………………………………………………49 6.1.2.3 Superdex 200 HR…………………………………………………………51 7 Quantitative and qualitative monosaccharide determination............................................53 7.1 Methanolysis and TMS derivatization………………………………………………..53 7.2 TMS derivatization…………………………………………………………………...54 7.3 Gas chromatography (GC)…………………………………………………………...55 7.4 Determination of the structure………………………………………………………..57 7.4.1 Linkage analysis by methylation and identification by GC-MS………………….57 7.4.2 Methylation…………………………………………………………………….58 7.4.3 Hydrolysis……………………………………………………………………...60 7.4.4 Reduction………………………………………………………………………60 7.4.5 Acetylation…………………………………………………………………….62 XI 7.4.6 GC-MS……………………………………………………………………….…….63 8 Nuclear Magnetic resonance Spectroscopy (NMR)………………………………….…...64 9 Biological activity assay..............................................................................................…...65 9.1 MgtA activity assay..........................................................................................………..65
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