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University of Szeged Faculty of Pharmacy Graduate School of Pharmaceutical Sciences Department of Pharmacognosy University of Szeged Faculty of Pharmacy Graduate School of Pharmaceutical Sciences Department of Pharmacognosy Pharmacological screening of Polygonaceae species and isolation of biologically active compounds from Rumex aquaticus L. and Rumex thyrsiflorus Fingerh. PhD Thesis Orsolya Orbán-Gyapai Pharm.D. Supervisors: Prof. Judit Hohmann DSc Andrea Vasas PhD Szeged, Hungary 2017 LIST OF PUBLICATIONS RELATED TO THE THESIS I. Orbán-Gyapai O, Raghavan A, Vasas A, Forgo P, Hohmann J, Shah ZA. Flavonoids isolated from Rumex aquaticus exhibit neuroprotective and neurorestorative properties by enhancing neurite outgrowth and synaptophysin. CNS and Neurological Disorders. Drug Targets 2014, 13: 1458–1564. II. Orbán-Gyapai O, Lajter I, Hohmann J, Jakab G, Vasas A. Xanthine oxidase inhibitory activity of extracts prepared from Polygonaceae species. Phytotherapy Research 2015, 29: 459–465. III. Vasas A, Orbán-Gyapai O, Hohmann J. The Genus Rumex: Review of traditional uses, phytochemistry and pharmacology. Journal of Ethnopharmacology 2015, 175: 198–228. IV. Orbán-Gyapai O, Liktor-Busa E, Kúsz N, Stefkó D, Urbán E, Hohmann J, Vasas A. Antibacterial screening of Rumex species native to the Carpathian Basin and bioactivity- guided isolation of compounds from Rumex aquaticus. Fitoterapia 2017, 118: 101–106. V. Orbán-Gyapai O, Forgo P, Hohmann J, Vasas A. Phytochemical and pharmacological investigation of Rumex thyrsiflorus Fingerh. Acta Biologica Hungarica 2017, 68: 232–236. TABLE OF CONTENTS Abbreviations and symbols ............................................................................................................................. 1 1. Introduction ................................................................................................................................................. 2 2. Aims of the study ........................................................................................................................................ 4 3. Literature overview ..................................................................................................................................... 5 3.1. Botany of the genus Rumex and the investigated species .................................................................... 5 3.2. Phytochemistry of Rumex species ........................................................................................................ 6 3.2.1. Anthraquinones ............................................................................................................................. 6 3.2.2. Naphthalenes ................................................................................................................................ 7 3.2.3. Flavonoids .................................................................................................................................... 7 3.2.4. Stilbenoids .................................................................................................................................... 8 3.2.5. Tannins ......................................................................................................................................... 8 3.2.6. Other compounds .......................................................................................................................... 8 3.3. Pharmacological activities of Rumex species .................................................................................... 10 3.3.1. Traditional use of Rumex species ............................................................................................... 10 3.3.2. Antimicrobial activity ................................................................................................................. 11 3.3.3. Antioxidant activity .................................................................................................................... 13 3.3.4. Antiproliferative activity ............................................................................................................ 14 3.3.5. Other pharmacological activities ................................................................................................ 14 3.3.6. Clinical studies ........................................................................................................................... 15 3.3.7. Toxicity of Rumex species .......................................................................................................... 16 4. Materials and methods .............................................................................................................................. 17 4.1. Plant material ..................................................................................................................................... 17 4.2. Extraction........................................................................................................................................... 17 4.2.1. Preparation of extracts for pharmacological screening ............................................................... 17 4.2.2. Extraction of the plant materials for preparative phytochemical work ....................................... 17 4.3. Purification and isolation of compounds ........................................................................................... 18 4.4. Structure determination of the isolated compounds ........................................................................... 19 4.5. Pharmacological tests ........................................................................................................................ 19 4.5.1. Antimicrobial assay .................................................................................................................... 19 4.5.2. Xanthine oxidase assay ............................................................................................................... 20 4.5.3. Neuroprotective and neurorestorative assay ............................................................................... 21 5. Results ....................................................................................................................................................... 23 5.1. Pharmacological screening studies .................................................................................................... 23 5.1.1. Antibacterial activity .................................................................................................................. 23 5.1.2. XO inhibitory screening study .................................................................................................... 25 5.2. Isolation ............................................................................................................................................. 28 5.2.1. Isolation of compounds from the aerial parts of R. aquaticus .................................................... 28 5.2.2. Isolation of compounds from the roots of R. aquaticus .............................................................. 29 5.2.3. Isolation of compounds from the roots of R. thyrsiflorus ........................................................... 31 5.3. Structure elucidation .......................................................................................................................... 31 5.4. Pharmacological activity of the isolated compounds ......................................................................... 34 5.4.1. Antibacterial activity .................................................................................................................. 34 5.4.2. XO inhibitory activity ................................................................................................................. 34 5.4.3. Neuroprotective properties of flavonoids (16 and 17) ................................................................ 35 6. Discussion ................................................................................................................................................. 39 6.1. Antibacterial properties of Rumex species ......................................................................................... 39 6.2. Xanthine oxidase inhibitory properties of Rumex species ................................................................. 39 6.3. Isolation of Biologically active secondary metabolites of R. aquaticus and R. thyrsiflorus .............. 40 6.3.1. Isolated compounds .................................................................................................................... 40 6.3.2. Antimicrobial properties of the isolated compounds .................................................................. 41 6.3.3. Xanthine oxidase inhibitory properties of the isolated compounds ............................................ 41 6.3.4. Neuroprotective properties of two isolated compounds of R. aquaticus .................................... 42 7. Summary ................................................................................................................................................... 44 8. References ................................................................................................................................................. 46 9. Acknowledgements ................................................................................................................................... 52 ABBREVIATIONS AND SYMBOLS 1D one-dimensional 2D two-dimensional APCI atmospheric pressure chemical ionization CC column chromatography CFU colony-forming unit COSY correlated
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