DOCSLIB.ORG

Eth-22862-02.Pdf

Total Page：16

File Type：pdf, Size：1020Kb

Download full-text PDF Read full-text
Eth-22862-02.Pdf 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.
Load more

Recommended publications
  • Characterization and Biological Activity of Condensed Tannins from Tropical Forage Legumes
    1070 T.P. Pereira et al. Characterization and biological activity of condensed tannins from tropical forage legumes Tatiana Pires Pereira(1), Elisa Cristina Modesto(1), Delci de Deus Nepomuceno(2), Osniel Faria de Oliveira(3), Rafaela Scalise Xavier de Freitas(1), James Pierre Muir(4), José Carlos Batista Dubeux Junior(5) and João Carlos de Carvalho Almeida(1) (1)Universidade Federal Rural do Rio de Janeiro, Rodovia BR-465, Km 07, s/no, Zona Rural, CEP 23890-000 Seropédica, RJ, Brazil. E-mail: [email protected], [email protected], [email protected], [email protected] (2)In memoriam (3)Universidade Federal Rural de Pernambuco, Dois Irmãos, CEP 52171-900 Recife, PE, Brazil. E-mail: [email protected] (4)Texas AgriLife Research and Extension Center, Stephenville, TX, USA. E-mail: [email protected] (5)University of Florida, North Florida Research and Education Center, Highway, Marianna, FL, USA. E-mail: [email protected] Abstract – The objective of this work was to characterize condensed tannins (CT) from six tropical forage legumes and to determine their biological activity. The monomers propelargonidin, prodelphinidin and procyanidin were analyzed, as well as extractable condensed tannin (ECT), protein-bound CT (PBCT) and fiber-bound CT (FBCT), molecular weight, degree of polymerization, polydispersity index, and biological activity by protein precipitate by phenols (PPP) of leaves of the legumes Cajanus cajan, Gliricidia sepium, Stylosanthes capitata x Stylosanthes macrocephala (stylo), Flemingia macrophylla, Cratylia argentea, and Mimosa caesalpiniifolia, and of the bark of this latter species. Differences were observed in the concentrations of ECT, PBCT, PPP, and total condensed tannin among species, but not in that of FBCT.
    [Show full text]
  • Impact of Condensed Tannin Containing Legumes on Ruminal Fermentation, Nutrition and Performance in Ruminants: a Review
    Canadian Journal of Animal Science Impact of condensed tannin containing legumes on ruminal fermentation, nutrition and performance in ruminants: a review Journal: Canadian Journal of Animal Science ManuscriptFor ID CJAS-2020-0096.R1 Review Only Manuscript Type: Review Date Submitted by the 18-Sep-2020 Author: Complete List of Authors: Kelln, Breeanna; University of Saskatchewan, Animal and Poultry Science Penner, Gregory; University of Saskatchewan, Animal and Poultry Science Acharya, Surya; AAFC, Lethbridge Research Centre McAllister, Tim; Agriculture and Agri-Food Canada, Lethbridge Research Centre Lardner, Herbert; University of Saskatchewan College of Agriculture and Bioresources, Animal and Poultry Science Keywords: tannins, proanthocyanidins, Ruminant, legumes, bloat © The Author(s) or their Institution(s) Page 1 of 43 Canadian Journal of Animal Science Short Title: Kelln et al. Legumes with condensed tannins for cattle Impact of condensed tannin containing legumes on ruminal fermentation, nutrition and performance in ruminants: a review For Review Only B.M. Kelln*, G.B. Penner*, S.N. Acharya†, T.A. McAllister†, and H.A. Lardner*1 *Department of Animal and Poultry Science, University of Saskatchewan, Saskatoon, SK, Canada, S7N 5B5; †Agriculture and Agri-Food Canada, Lethbridge Research Centre, Lethbridge, Alberta, Canada T1J 4B1 1Correspondence should be addressed to: H.A. (Bart) Lardner Department of Animal and Poultry Science, University of Saskatchewan, Saskatoon, Saskatchewan, Canada, S7N 5A8 TEL: 1 306 966 2147 FAX: 1 306 966 4151 Email: [email protected] 1 © The Author(s) or their Institution(s) Canadian Journal of Animal Science Page 2 of 43 ABSTRACT Legume forages, such as sainfoin, and birdsfoot trefoil can increase the forage quality and quantity of western Canadian pastures, thus increasing producer profitability due to increased gains in grazing ruminants, while reducing risk of bloat in legume pastures due to the presence of proanthocyanidins.
    [Show full text]
  • DOCTOR of the University Montpellier
    Dissertation in Co-supervision: University of Tehran-University of Montpellier To obtain the degree of DOCTOR of the University Montpellier Title Preservation of plywood against biological attack with low environmental impact using tannin-boron preservative By Davood EFHAMISISI Thesis defense planned Monday, 21 September 2015 Jury Mr. Bertrand CHARRIER University of Pau and Pays de l'Adour Reviewer Mr. Ghanbar EBRAHIMI University of Tehran Reviewer Mr. Asghar OMIDVAR Gorgan University of Agricultural Sciences Examiner and Natural Resources Mr. Saeid NEZAMABADI University of Montpellier Examiner Mr. Kambiz POURTAHMASI University of Tehran Examiner Mrs. Marie-France THEVENON CIRAD, Montpellier Thesis director Mr. Yahya HAMZEH University of Tehran Thesis director Mr. Ali-Naghi KARIMI University of Tehran Co-director Mr. Antonio PIZZI University of Lorraine Co-director i Thèse en co-tutelle: l'Université de Téhéran-l'université de Montpellier Pour obtenir le grade de DOCTEUR de l'université de Montpellier Titre Protection à faible impact environnemental des contreplaqués avec des associations tannins-bore Par Davood EFHAMISISI Soutenance de thèse prévue le lundi, 21 Septembre 2015 Jury M. Bertrand CHARRIER Université de Pau et des Pays de l'Adour Rapporteur M. Ghanbar EBRAHIMI Université de Téhéran Rapporteur M. Asghar OMIDVAR Université Gorgan des sciences agricoles et Examinateur des ressources naturelles M. Saeid NEZAMABADI Université de Montpellier Examinateur M. Kambiz POURTAHMASI Université de Téhéran Examinateur Mme. Marie-France THEVENON CIRAD, Montpellier Directeur de Thèse M. Yahya HAMZEH Université de Téhéran Directeur de Thèse M. Ali-Naghi KARIMI Université de Téhéran Co-directeur M. Antonio PIZZI Université de Lorraine Co-directeur ii Acknowledgments I would like to express my deepest gratitude and appreciation to my director, Prof.
    [Show full text]
  • Proanthocyanidin Metabolism, a Mini Review
    Nutrition and Aging 2 (2014) 111–116 111 DOI 10.3233/NUA-140038 IOS Press Proanthocyanidin Metabolism, a mini review Y.Y. Choy and A.L. Waterhouse∗ Viticulture and Enology, University of California, Davis, CA, USA Abstract. There is emerging evidence suggesting that consumption of beverage and food rich in polyphenol may offer protective effects against various neurodegenerative, cardiovascular diseases and cancers. Proanthocyanidins (PACs) are one of the most abundant polyphenol in human diets, but also one of the least absorbed polyphenol mostly due to their size and structure com- plexity. PACs or condensed tannins are oligomers and polymers of monomeric unit flavan-3-ol (+)-catechin or (−)-epicatechin. To date, the absorption and metabolism of PACs are still remains largely unknown. The aim of this mini review was to highlight the absorption and metabolism of PACs, their effect in the gut and sample preparation for analysis. Ultimately, the potential bioactivities derived from the interaction between PACs metabolites and the gut microbiota warrants further investigation. Keywords: Proanthocyanidins, phenolic acids, metabolism, colon 1. Introduction derived subunits. PACs that consists exclusively of (−)-epicatechin, (+)-catechin units, are known as pro- Polyphenols are among the ubiquitous constituents cyanidins because only cyanidin is released in acid, of foods of plant origins and are widely distributed and comprised the largest class of PACs, while those throughout the plant kingdom. Polyphenols can be with gallocatechin units release delphinidin. The size categorized into different groups such as flavonoids, or molecular weight of PACs can be expressed as phenolic acids, stilbenes and lignans. The flavonoids mean degree of polymerization (mDP).
    [Show full text]
  • Optimization of the Extraction of Procyanidin B-2 Rich Extract From
    Louisiana State University LSU Digital Commons LSU Master's Theses Graduate School 2017 Optimization of the Extraction of Procyanidin B-2 Rich Extract from Unfermented Cocoa Using Response Surface Methodology and Interaction of Procyanidin B-2 Rich Cocoa Extract with Collagenase and Elastase as Biomarkers of Skin Aging Marco Eduardo Toc Sagra Louisiana State University and Agricultural and Mechanical College, [email protected] Follow this and additional works at: https://digitalcommons.lsu.edu/gradschool_theses Part of the Life Sciences Commons Recommended Citation Toc Sagra, Marco Eduardo, "Optimization of the Extraction of Procyanidin B-2 Rich Extract from Unfermented Cocoa Using Response Surface Methodology and Interaction of Procyanidin B-2 Rich Cocoa Extract with Collagenase and Elastase as Biomarkers of Skin Aging" (2017). LSU Master's Theses. 4498. https://digitalcommons.lsu.edu/gradschool_theses/4498 This Thesis is brought to you for free and open access by the Graduate School at LSU Digital Commons. It has been accepted for inclusion in LSU Master's Theses by an authorized graduate school editor of LSU Digital Commons. For more information, please contact [email protected]. OPTIMIZATION OF THE EXTRACTION OF PROCYANIDIN B-2 RICH EXTRACT FROM UNFERMENTED COCOA USING RESPONSE SURFACE METHODOLOGY AND INTERACTION OF PROCYANIDIN B-2 RICH COCOA EXTRACT WITH COLLAGENASE AND ELASTASE AS BIOMARKERS OF SKIN AGING A Thesis Submitted to the Graduate Faculty of the Louisiana State University and Agricultural and Mechanical College in partial fulfillment of the requirements for the degree of Master of Science in The School of Nutrition and Food Sciences by Marco Eduardo Toc Sagra B.S., Zamorano University, 2013 August 2017 ACKNOWLEDGMENTS I would like to thank God for always being my inspiration to work hard and with excellence during this stage of my life.
    [Show full text]
  • 2.1 Structure Elucidation 14 2.2 Synthesis 15
    , HIERDIE EKSEMPlAAR MAG ONDER University Free State GEEN OMSTANDIGHEDE UIT DIE mml~lmmMMllllllln34300000347405 Universiteit Vrystaat BIBLIOTEEK VER\VYDER WORD NIE THE STRUCTURE AND SYNTHESIS OF OLIGOFLA VANOIDS AND OLIGOSTILBENES FROM CASSIA ABBREVIATA. Dissertation submitted infulfilment of the requirements for the degree Master of Science in the Department of Chemisrty Faculty of Natural Sciences at University of Orange Free State Bloemfontein by Makhosazana Claribel Mthembu Supervisor: Prof. E. Malan Co-supervisor Dr J. C. Coetzee JANUARY 2000 ACKNOWLEDGEMENTS I wish to express my gratitude to the following people: • God the Almighty for the love and support he has shown me throughout my studies. • My supervisors Professor f. Malan and Dr j. C. Coetzee, their guidance and helpful recommendations throughout this study will always be appreciated: • • Proff. Malan for his constructive guidance, critism and invaluable support in putting this work in paper. • Dr j. C. Coetzeefor recording my NMR spectra, his encourangement and unselfish assistance. • Proff. V. Brandt ,D. Ferrdra and NRF sponsor for granting me this opportumity. • Finally the members of the fomily and [riends, Irene,jaqui, Zanele, Vusl and Busi for their love, tolerance and constant encouragement, I owe the greatest debt to them. M. C. Mthembu Table of Content Abstract LITERATURE SURVERY CHAPTER 1: MONOMERIC STILBENES 1 1.1 Nomenclature 1 1.2 Structure and Natural Occurrence 3 1.3 Structure Elucidation 5 1.4 Synthesis 5 CHAPTER 2: OLIGOMERIC STILBENES 11 2.1 Structure Elucidation 14 2.2 Synthesis 15 CHAPTER 3.: FLA VAN-3-0LS 16 3.1 Nomenclature 16 3.2 Structure and Natural Occurrence 17 3.3 Structure Elucidation 19 CHAPTER 4: LEUCOANTHOCY ANIDINS.
    [Show full text]
  • Total Phenolic Content, Free Radical Scavenging Capacity, and Anti- Cancer Activity of Silymarin
    Journal of International Society for Food Bioactives Nutraceuticals and Functional Foods Review J. Food Bioact. 2020;10:53–63 Total phenolic content, free radical scavenging capacity, and anti- cancer activity of silymarin Uyory Choea, Monica Whenta*, Yinghua Luob and Liangli Yua aDepartment of Nutrition and Food Science, University of Maryland, College Park, MD 20742, USA bCollege of Food Science and Engineering, National Engineering Research Center for Fruit and Vegetable Processing, Ministry of Educa- tion, China Agricultural University, Beijing, China *Corresponding author: Monica Whent, Department of Nutrition and Food Science, University of Maryland, College Park, MD 20742, USA. Tel: +1 301 4054521; E-mail: [email protected] DOI: 10.31665/JFB.2020.10227 Received: June 19, 2020; Revised received & accepted: June 29, 2020 Citation: Choe, U., Whent, M., Luo, Y., and Yu, L. (2020). Total phenolic content, free radical scavenging capacity, and anti-cancer activity of silymarin. J. Food Bioact. 10: 53–63. Abstract Milk thistle (Silybum marianum) seeds are a good source of dietary polyphenols. The bioactive component of milk thistle seeds, silymarin, contains flavonolignans including silybin A, silybin B, isosilybin A, isosilybin B, sily- christin, isosilychristin, and silydiain along with the flavonol taxifolin. Silymarin is used traditionally as a natural herbal medicine with minimal side effects. Structurally, each silymarin component possesses phenolic hydroxyl groups and thus works as an antioxidant. In addition to free radical scavenging capacities, silymarin’s anti-cancer activities were reported for many different types of cancers including bladder, breast, colon, gastric, kidney, lung, oral, ovarian, prostate, and skin. The current review will discuss silymarin’s chemical components, total phenolic content, free radical scavenging capacities, and anti-cancer activities.
    [Show full text]
  • Anti-Inflammatory Activity of Sambucus Plant Bioactive
    Natural Product Sciences 25(3) : 215-221 (2019) https://doi.org/10.20307/nps.2019.25.3.215 Anti-inflammatory Activity of Sambucus Plant Bioactive Compounds against TNF-α and TRAIL as Solution to Overcome Inflammation Associated Diseases: The Insight from Bioinformatics Study Wira Eka Putra1, Wa Ode Salma2, Muhaimin Rifa'i3,* 1Department of Biology, Faculty of Mathematics and Natural Sciences, Universitas Negeri Malang, Indonesia 2Department of Nutrition, Faculty of Medicine, Halu Oleo University, Indonesia 3Department of Biology, Faculty of Mathematics and Natural Sciences, Brawijaya University, Indonesia Abstract − Inflammation is the crucial biological process of immune system which acts as body’s defense and protective response against the injuries or infection. However, the systemic inflammation devotes the adverse effects such as multiple inflammation associated diseases. One of the best ways to treat this entity is by blocking the tumor necrosis factor alpha (TNF-α) and TNF-related apoptosis-inducing ligand (TRAIL) to avoid the pro- inflammation cytokines production. Thus, this study aims to evaluate the potency of Sambucus bioactive compounds as anti-inflammation through in silico approach. In order to assess that, molecular docking was performed to evaluate the interaction properties between the TNF-α or TRAIL with the ligands. The 2D structure of ligands were retrieved online via PubChem and the 3D protein modeling was done by using SWISS Model. The prediction results of the study showed that caffeic acid (-6.4 kcal/mol) and homovanillic acid (-6.6 kcal/mol) have the greatest binding affinity against the TNF-α and TRAIL respectively. This evidence suggests that caffeic acid and homovanillic acid may potent as anti-inflammatory agent against the inflammation associated diseases.
    [Show full text]
  • Different Approaches to Evaluate Tannin Content and Structure of Selected Plant Extracts – Review and New Aspects M
    View metadata, citation and similar papers at core.ac.uk brought to you by CORE provided by JKI Open Journal Systems (Julius Kühn-Institut) Journal of Applied Botany and Food Quality 86, 154 - 166 (2013), DOI:10.5073/JABFQ.2013.086.021 1University of Kiel, Institute of Crop Science and Plant Breeding – Grass and Forage Science / Organic Agriculture, Kiel, Germany 2Institute of Ecological Chemistry, Plant Analysis and Stored Product Protection; Julius Kühn-Institute, Quedlinburg, Germany Different approaches to evaluate tannin content and structure of selected plant extracts – review and new aspects M. Kardel1*, F. Taube1, H. Schulz2, W. Schütze2, M. Gierus1 (Received July 2, 2013) Summary extracts, tannins, salts and derivates was imported to the EU in the year 2011, mainly from Argentina, with a trade value of nearly Tannins occur in many field herbs and legumes, providing an im- 63.5 mio. US Dollar (UN-COMTRADE, 2013). These extracts are pro- mense variability in structure and molecular weight. This leads to duced industrially on a large scale. They could therefore maintain complications when measuring tannin content; comparability of a relatively constant quality and thus provide an advantage in rumi- different methods is problematic. The present investigations aimed at nant feeding. characterizing four different tannin extracts: quebracho (Schinopsis Tannins from different sources can react very diverse regarding lorentzii), mimosa (Acacia mearnsii), tara (Caesalpinia spinosa), protein affinity (MCNABB et al., 1998; BUENO et al., 2008). Diffe- and gambier (Uncaria gambir) and impact of storage conditions. rences in tannin structure can occur even between similar plant Using photometrical methods as well as HPLC-ESI-MS, fundamen- species (OSBORNE and MCNEILL, 2001; HATTAS et al., 2011) and a tal differences could be determined.
    [Show full text]
  • A Review on Stems Composition and Their Impact on Wine Quality
    molecules Review A Review on Stems Composition and Their Impact on Wine Quality Marie Blackford 1,2,* , Montaine Comby 1,2, Liming Zeng 2, Ágnes Dienes-Nagy 1, Gilles Bourdin 1, Fabrice Lorenzini 1 and Benoit Bach 2 1 Agroscope, Route de Duillier 50, 1260 Nyon, Switzerland; [email protected] (M.C.); [email protected] (Á.D.-N.); [email protected] (G.B.); [email protected] (F.L.) 2 Changins, Viticulture and Enology, HES-SO University of Applied Sciences and Arts Western Switzerland, Route de Duillier 50, 1260 Nyon, Switzerland; [email protected] (L.Z.); [email protected] (B.B.) * Correspondence: [email protected] Abstract: Often blamed for bringing green aromas and astringency to wines, the use of stems is also empirically known to improve the aromatic complexity and freshness of some wines. Although applied in different wine-growing regions, stems use remains mainly experimental at a cellar level. Few studies have specifically focused on the compounds extracted from stems during fermentation and maceration and their potential impact on the must and wine matrices. We identified current knowledge on stem chemical composition and inventoried the compounds likely to be released during maceration to consider their theoretical impact. In addition, we investigated existing studies that examined the impact of either single stems or whole clusters on the wine quality. Many parameters influence stems’ effect on the wine, especially grape variety, stem state, how stems are incorporated, Citation: Blackford, M.; Comby, M.; when they are added, and contact duration. Other rarely considered factors may also have an impact, Zeng, L.; Dienes-Nagy, Á.; Bourdin, G.; Lorenzini, F.; Bach, B.
    [Show full text]
  • 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.
    [Show full text]
  • 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.
    [Show full text]