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Research Collection Doctoral Thesis Analytical investigation on and isolation of procyanidins from Crataegus leaves and flowers Author(s): Rohr, Gabriela Elisabeth Publication Date: 1999 Permanent Link: https://doi.org/10.3929/ethz-a-002045003 Rights / License: In Copyright - Non-Commercial Use Permitted This page was generated automatically upon download from the ETH Zurich Research Collection. For more information please consult the Terms of use. ETH Library Diss. ETHNo. 13020 Analytical Investigation on and Isolation of Procyanidins from Crataegus Leaves and Flowers A dissertation submitted to the Swiss Federal Institute of Technology Zurich for the degree of Doctor of Natural Sciences Presented by Gabriela Elisabeth Rohr pharmacist born December 11, 1963 Hunzenschwil (AG) Accepted on the recommendation of Prof. Dr. O. Sticher, examiner Prof. Dr. B. Meier, co-examiner Zurich 1999 Acknowledgments I greatly would like to thank professor Dr. O. Sticher for giving me the opportunity to work in his research group, for providing extraordinary working facilities as well as for guaranteeing continuing financial support for this research. I would like to heartly thank professor Dr. B. Meier for his encouragement and interest as well as his advices and his guidance throughout the works on this project. I would like to warmly thank Dr. G. Riggio from the Institute of Pharmacology of the University of Zurich, Switzerland, for his patience with the LC-MS project and his invaluable technical support. I greatly acknowledge the preliminary works on LC-MS analysis of Dr. M. Howald and Mr. 0. Fertig from RCC Umweltchemie AG in CH- Itingen/BL and Dr. W. Wagner-Redeker from Spectronex AG in CH-Basel. I would like to thank Dr. D. Treutter from the Institute for Agriculture and Horticulture of the Technical University of Munich, Germany, for discussions, the introduction to his technique of chemical reaction detection and for analyzing fractions of extracts of hawthorn. On behalf of the structure elucidation I would like to especially thank Dr. O. Zerbe for his practical NMR support and PD Dr. M. Mirbach for discussions. I greatly acknowledge the advices on structure elucidation that I obtained from professor Dr. H. Kolodziej, Dr. L. Balas and Dr. T. de Bruyne. Thanks are also due to Dr. W. Amrein and Mr. R. Häfliger for the FAB-MS measurements as well as Dr. E. Zass for performing literature searches. The financial support provided by Lichtwer Pharma GmbH in D-Berlin during the first two years of this project is gratefully acknowledged. Special thanks are due to Mrs. A. Suter for her editorial assistance and revision of chapter one. I also wish to thank all my colleagues and the staff of the Department of Pharmacy at the ETH Zurich for the nice working atmosphere and the great time we had together. Last but not least I would like to thank my husband and my family without whose love, patience, understanding and spiritual support completion of this work would not have been possible. Contents General abbreviations 1 Abbreviations for procyanidins 3 Summary 4 Zusammenfassung 7 Objectives 11 Part I: Analytical part 1 Analysis of procyanidins (publication 1) 12 1.1 Introduction 12 1.2 Sample preservation 17 1.3 Extraction 19 1.3.1 Unextractable procyanidins 22 1.4 Qualitative and quantitative analysis of procyanidins 24 1.4.1 Conventional methods 26 1.4.1.1 Colorimetric assays based on redox and complexation reactions 32 1.4.1.2 Functional group assays 32 1.4.1.2.1 Proanthocyanidin assay 32 1.4.1.2.2 Vanillin assay 37 1.4.1.2.3 Dimethylaminocinnamaldehyde assay 42 1.4.1.2.4 Conclusions 44 1.4.2 Methods based on biological effects: protein precipitation 45 1.4.3 Chromatographic methods 47 1.4.3.1 Sample clean up 47 1.4.3.1.1 Liquid-liquid extraction 48 1.4.3.1.2 Solid phase extraction 52 1.4.3.1.3 Other sample preparation techniques 56 1.4.3.1.4 Conclusions 57 1.4.3.2 Chromatography 59 1.4.3.2.1 Gas chromatography and thin layer chromatography 60 1.4.3.2.2 High-performance liquid chromatography 61 1.4.3.3 Detection 68 1.4.3.3.1 UV and diode array detection 6 8 1.4.3.3.2 Electrochemical detection 76 1.4.3.3.3 Liquid chromatography - mass spectrometry 81 1.5 References 87 2 Analysis of procyanidins in Crataegus 104 2.1 Quantitative reversed-phase high-performance liquid chromatography of procyanidins in Crataegus leaves and flowers (publication 2) 104 2.1.1 Introduction 104 2.1.2 Experimental 106 2.1.2.1 Sample preparation 108 2.1.3 Results and discussion 112 2.1.4 References 121 2.2 Additional results to publication 2 123 2.3 Analysis of Crataegus flowers and fruits 129 2.3.1 Experimental 131 2.3.2 Results and discussion 132 2.3.3 References 139 3 Solid phase extraction and addition of antioxidants to the extraction solvent in the quantitative analysis of procyanidins in Crataegus 140 3.1 Solid phase extraction of procyanidins 140 3.1.1 Experimental 140 3.1.2 Results and discussion 142 3.2 Addition of antioxidants to the extraction solvent 148 3.3 References 150 4 Evaluation of different detection modes for the analysis of procyanidins in Crataegus leaves and flowers. Part I. Diode array and electrochemical detection (publication 3) 152 4.1 Introduction 152 4.2 Experimental 153 4.3 Results and discussion 156 4.3.1 Diode array detection 156 4.3.2 Electrochemical detection 165 4.4 Conclusions 168 4.5 References 169 5 Evaluation of different detection modes for the analysis of procyanidins in Crataegus leaves and flowers. Part II. Liquid chromatography - mass spectrometry (publication 4) 172 5.1 Introduction 172 5.2 Experimental 174 5.3 Results and discussion 176 5.3.1 Flow injection analysis using the APCI interface 176 5.3.2 Flow injection analysis unsing the ESP interface 182 5.3.3 Chromatographic analysis using the ESP interface 186 5.4 Conclusions 190 5.5 References 191 Part II: Purification and structure elucidation 6 Distribution and general features of proanthocyanidins 194 6.1 Structural features of procyanidins 196 7 Procyanidins in Crataegus 199 7.1 Pharmacological activités of procyanidins from Crataegus 202 8 Purification of procyanidins from Crataegus 205 8.1 Introduction 205 8.1.1 Purification of procyanidins from plant matrices 205 8.2 Summary 207 8.3 Experimental section 208 8.3.1 Materials and instrumentation 208 8.3.2 Procedures for the characterization of extracts and procyanidins 210 8.3.3 Extraction 212 8.3.4 Fractionation of the ethyl acetate extract and isolation of pure compounds 215 8.3.5 Characterization of purified compounds 225 8.3.5.1 HPLC analyses and elution order on CI8 columns 225 8.3.5.2 TLC analyses 229 8.3.5.3 Discussion on individual compounds 230 8.3.5.3.1 Monomers, dimers and trimers 230 8.3.5.3.2 Artifact I 231 8.3.5.3.3 Compounds Pc A, Pc B and Pc C 232 8.3.5.3.4 Compounds X and Y 232 8.3.5.3.5 Hypotheses on the nature of Pc B, Pc C, compounds X and Y 233 8.3.5.3.6 Higher molecular weight procyanidins 236 9 Literature overview on the structure elucidation of procyanidins 239 9.1 Spectroscopic methods 239 9.1.1 Nuclear magnetic resonance 239 9.1.1.1 Atropisomerism and conformational isomerism 241 9.1.1.2 Structure elucidation based on comparative NMR studies 243 9.1.1.3 Derivatization for structure elucidation 246 9.1.2 Circular dichroism 248 9.2 Chemical degradation methods 250 9.3 Structure elucidation of higher molecular weight compounds 254 10 Structure elucidation of isolated compounds 258 10.1 Introduction 258 10.2 Summary 258 10.3 Experimental 259 10.4 Results and discussion 265 10.4.1 (-)-Epicatechin 265 10.4.2 Procyanidin B2 270 10.4.3 Procyanidin B5 274 10.4.4 Procyanidin B4 278 10.4.5 Procyanidin Cl 282 10.4.6 Trimer I 285 10.4.7 Trimer II 287 10.4.8 Tetramer I 289 10.4.9 Artifact I 292 Part III: Stability of selected procyanidins 11 Literature overview 296 11.1 Oxidation reactions 297 11.2 Reactions of orf/zo-quinones and semiquinone radicals 300 12 Stability of selected procyanidins in solution 305 12.1 Introduction 305 12.2 Summary 305 12.3 Experimental 306 12.4 Results and discussion 307 13 References to parts II and III 328 Epilogue 344 Appendices Appendix I NMR and CD spectra of isolated compounds Appendix II List of tables Appendix III List of figures Appendix IV List of publications Appendix V List of oral presentations Curriculum vitae General abbreviations [ab specific optical rotation acetone-dö deuterated acetone ACN acetonitrile AcOH acetic acid APCI atmospheric pressure chemical ionization benzene-dö deuterated benzene C carbon atom cat (+)-catechin CD circular dichroism chloroform-di deuterated chloroform CRD chemical reaction detection d doublet S chemical shift 2D two-dimensional DAB Deutsches Arzneibuch (German Pharmacopoeia) DAC Deutscher Arzneimittel Codex (German Drug Codex) DAD diode array detector dd double doublet DEPT distortionless enhancement by polarization transfer DMACA 4-dimethylaminocinnamaldehyde DMSO-d6 deuterated dimethyl sulphoxide D20 deuterated water DQF-COSY double quantum filter correlation spectroscopy EI-MS electron impact - mass spectrometry epi (-)-epicatechin ESP electrospray EtOH ethanol FAB-MS fast atom bombardment - mass spectrometry H hydrogen atom HCl hydrochloric acid HCIO4 perchloric acid 1 H20 water HC02H formic acid HMBC heteronuclear multiple bond correlation HMQC heteronuclear multiple quantum correlation H3PO4 ort/zo-phosphoric acid HPLC high-performance liquid chromatography Hz Hertz IR infrared spectroscopy J coupling constant IV Kelvin LC-MS liquid chromatography - mass spectrometry m multiplet mAU milli absorption unit Me2CO acetone MeOH methanol methanol-d4 deuterated methanol MS mass spectrometry m/z mass-to-charge ratio nitrobenzene-d5 deuterated nitrobenzene NMR nuclear magnetic resonance nOe nuclear Overhauser effect n.s.
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  • The Gastroprotective Effects of Eugenia Dysenterica (Myrtaceae) Leaf Extract: the Possible Role of Condensed Tannins

    The Gastroprotective Effects of Eugenia Dysenterica (Myrtaceae) Leaf Extract: the Possible Role of Condensed Tannins

    722 Regular Article Biol. Pharm. Bull. 37(5) 722–730 (2014) Vol. 37, No. 5 The Gastroprotective Effects of Eugenia dysenterica (Myrtaceae) Leaf Extract: The Possible Role of Condensed Tannins Ligia Carolina da Silva Prado,a Denise Brentan Silva,c Grasielle Lopes de Oliveira-Silva,a Karen Renata Nakamura Hiraki,b Hudson Armando Nunes Canabrava,a and Luiz Borges Bispo-da-Silva*,a a Laboratory of Pharmacology, Institute of Biomedical Sciences, Federal University of Uberlândia; b Laboratory of Histology, Institute of Biomedical Sciences, Federal University of Uberlândia; ICBIM-UFU, Minas Gerais 38400– 902, Brazil: and c Núcleo de Pesquisas em Produtos Naturais e Sintéticos, Faculty of Pharmaceutical Science at Ribeirão Preto, University of São Paulo; NPPNS-USP, São Paulo 14040–903, Brazil. Received June 26, 2013; accepted February 6, 2014 We applied a taxonomic approach to select the Eugenia dysenterica (Myrtaceae) leaf extract, known in Brazil as “cagaita,” and evaluated its gastroprotective effect. The ability of the extract or carbenoxolone to protect the gastric mucosa from ethanol/HCl-induced lesions was evaluated in mice. The contributions of nitric oxide (NO), endogenous sulfhydryl (SH) groups and alterations in HCl production to the extract’s gastroprotective effect were investigated. We also determined the antioxidant activity of the extract and the possible contribution of tannins to the cytoprotective effect. The extract and carbenoxolone protected the gastric mucosa from ethanol/HCl-induced ulcers, and the former also decreased HCl production. The blockage of SH groups but not the inhibition of NO synthesis abolished the gastroprotective action of the extract. Tannins are present in the extract, which was analyzed by matrix assisted laser desorption/ioniza- tion (MALDI); the tannins identified by fragmentation pattern (MS/MS) were condensed type-B, coupled up to eleven flavan-3-ol units and were predominantly procyanidin and prodelphinidin units.
  • Docking Characterization and in Vitro Inhibitory Activity of Flavan-3-Ols and Dimeric Proanthocyanidins Against the Main Protease Activity of SARS-Cov-2

    Docking Characterization and in Vitro Inhibitory Activity of Flavan-3-Ols and Dimeric Proanthocyanidins Against the Main Protease Activity of SARS-Cov-2

    ORIGINAL RESEARCH published: 30 November 2020 doi: 10.3389/fpls.2020.601316 Docking Characterization and in vitro Inhibitory Activity of Flavan-3-ols and Dimeric Proanthocyanidins Against the Main Protease Activity of SARS-Cov-2 Yue Zhu and De-Yu Xie* Department of Plant and Microbial Biology, North Carolina State University, Raleigh, NC, United States We report to use the main protease (Mpro) of SARS-Cov-2 to screen plant flavan-3-ols and proanthocyanidins. Twelve compounds, (–)-afzelechin (AF), (–)-epiafzelechin (EAF), (+)-catechin (CA), (–)-epicatechin (EC), (+)-gallocatechin (GC), (–)-epigallocatechin Edited by: (EGC), (+)-catechin-3-O-gallate (CAG), (–)-epicatechin-3-O-gallate (ECG), Guodong Wang, Chinese Academy of Sciences, China (–)-gallocatechin-3-O-gallate (GCG), (–)-epigallocatechin-3-O-gallate (EGCG), Reviewed by: procyanidin A2 (PA2), and procyanidin B2 (PB2), were selected for docking simulation. pro Hiroshi Noguchi, The resulting data predicted that all 12 metabolites could bind to M . The affinity Nihon Pharmaceutical scores of PA2 and PB2 were predicted to be −9.2, followed by ECG, GCG, EGCG, University, Japan Ericsson Coy-Barrera, and CAG, −8.3 to −8.7, and then six flavan-3-ol aglycones, −7.0 to −7.7. Docking Universidad Militar Nueva characterization predicted that these compounds bound to three or four subsites (S1, Granada, Colombia S1′, S2, and S4) in the binding pocket of Mpro via different spatial ways and various *Correspondence: De-Yu Xie formation of one to four hydrogen bonds. In vitro analysis with 10 available compounds pro [email protected] showed that CAG, ECG, GCG, EGCG, and PB2 inhibited the M activity with an IC50 value, 2.98 ± 0.21, 5.21 ± 0.5, 6.38 ± 0.5, 7.51 ± 0.21, and 75.3 ± 1.29 µM, Specialty section: respectively, while CA, EC, EGC, GC, and PA2 did not have inhibitory activities.