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Bioactive and Protective Polyphenolics from Roots and Stumps of Conifer Trees (Norway Spruce and Scots Pine)

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Chemistry Faculty of Science University of Helsinki Finland BIOACTIVE AND PROTECTIVE POLYPHENOLICS FROM ROOTS AND STUMPS OF CONIFER TREES (NORWAY SPRUCE AND SCOTS PINE) Harri Latva-Mäenpää ACADEMIC DISSERTATION To be presented, with the permission of the Faculty of Science of the University of Helsinki, for public examination in Lecture hall 10, University main building, on 9th June 2017, at 12 noon. Helsinki 2017 Supervisors Research Director, Professor Kristiina Wähälä Organic Chemistry Faculty of Medicine University of Helsinki Finland Docent Pekka Saranpää Principal Research Scientist New business opportunities Natural Resources Institute Finland (Luke) Finland Reviewers Professor Kumi Yoshida Organic Chemistry Graduate School of Information Science University of Nagoya Japan Professor Corrado Tringali Organic Chemistry Dipartimento di Scienze Chimiche University of Catania Italy Opponent Dr. Emerson Ferreira Queiroz Senior Lecturer School of Pharmaceutical Sciences Phytochemistry and Bioactive Natural Products University of Geneva Switzerland ISBN 978-951-51-3465-3 (paperback) ISBN 978-951-51-3466-0 (PDF) Unigrafia Oy Helsinki 2017 ABSTRACT The current era of bioeconomy strives to develop new, innovative products from natural raw materials in a sustainable way. In this PhD thesis, we have searched potential bioactive compounds from different parts of the neglected roots and stumps of conifer trees for high value products. Our aim was to establish deeper knowledge concerning chemical compositions of specified and defined biomass sources (roots and stumps of conifer trees) as well as the chemistry of certain natural polyphenolic compounds in different conditions. Using methods of natural products chemistry, such as solvent extraction and chromatographic separation and analysis techniques (GC-MS, HPLC- DAD/MS), we found that the root bark of Norway spruce is a rich source of stilbenoid glucosides (astringin, isorhapontin and piceid). These have structural similarities with the most studied stilbenoid, resveratrol. We also found that the stumps of Scots pine are a source of stilbenoids, pinosylvin and its derivatives. Stilbenoids are bioactive compounds and they have shown a variety of beneficial activities in studies related for example to human health. They have also shown antimicrobial and protective properties in trees and also in tests against micro-organisms. The highest concentrations of stilbenoid glucosides were found from the inner bark of the root zones closest to the stem of Norway spruce. This study also revealed that the root neck of Norway spruce is a new source of the bioactive lignan hydroxymatairesinol (HMR). Chromatographic and spectroscopic methods were developed to isolate pure stilbenoids from the bark of Norway spruce roots for further experiments. The complete structural elucidation of stilbenoids from Norway spruce was performed by HPLC-DAD-NMR. The HPLC-DAD method was further optimized to isolate stilbenoids in a semipreparative scale. The invividual stilbenoid molecules were isolated from the extracts and their photochemical stabilities (under fluorescent and UV light) were studied by HPLC-DAD, MS and NMR. Naturally-occurring trans stilbenoids undergo photochemical transformations to cis forms. However, the extended UV irradiation caused stilbenoids to form phenanthrene structures by intramolecular cyclisation. This is the first time that these new phenanthrene structures are reported to be derived from stilbenoids of spruce bark. Our results show that that the roots and stumps of conifer trees contain bioactive polyphenolic compounds, such as stilbenoids and lignans. These molecules and the compounds formed thereof may have commercial value and the information gained would offer a base platform for the possible new commercial high-value products developed from forest biomass. Our study has also provided new scientific knowledge of natural compounds and their properties that may lead to new findings and deeper understanding of the 3 physiology and internal protection processes of plants by their bioactive secondary metabolites. Roots and stumps of conifer trees (Norway spruce and Scots pine) are a vast source of biomass containing potentially bioactive polyphenolic extractives as shown in this work, but this biomass is currently used for low- value energy production only. With already existing harvesting techniques, roots and stumps of conifer trees could be used as a source of commercially valuable biochemicals. 4 ACKNOWLEDGEMENTS This study was carried out in a cooperation between the Laboratory of Organic Chemistry, Department of Chemistry, University of Helsinki and the Finnish Forest Research Institute, Metla (nowadays Natural Resources Institute Finland, Luke). I wish to thank both organizations and several people for contributing their resources, time and expertise to this thesis by helping and supporting me to complete this work. I am grateful to my supervisors Professor Kristiina Wähälä and Docent Pekka Saranpää to give me this opportunity to dive into the interesting world of biomass and polyphenolic compounds. A major appreciation also to Docent Tytti Sarjala for her support. This has been a long journey but all of you have kindly provided me the tools to grow up as a researcher and also as a person. Your endless support, coaching and mentoring has taken me this far. I wish to thank Professors Kumi Yoshida and Corrado Tringali for reviewing the manuscript of the thesis and Docent Emerson Ferreira Queiroz for agreeing to act as my opponent at the public defence of this dissertation. Many thanks to my co-authors, all personnel and students (especially Daniel for his great work) in the laboratories of Metla/Luke in Vantaa and Parkano and in the laboratory of Organic Chemistry, University of Helsinki. Special thanks also to Anneli, Eeva, Irmeli and three Tapios for their valuable work with our samples. I wish to thank all my colleagues for their time and support to help and discuss how to proceed in the project. During the project, I was able to start working in the natural products industry to develop and commercialize products derived from biomass. The combination of academic research and business has given me valuable perspectives for the future. I am grateful to an entrepreneur Mr. Stein Ulve for this opportunity to learn so much about the business and its reality. We Finns may still need you fearless Norwegians to carry on the risks and attack the developing markets. Thanks also to my current working colleagues. Besides the work, I wanted to highlight the brotherhood in our North Stars society. You guys have given me something that is more valuable than work, friendship. I warmly thank my parents Merja and Hannu and my sister Henna for showing the examples how hard work and continuous education of yourself will lead to great things. Finally, the most important, the love of my life, Laura. There are no words that would adequately describe the value of your support. You and your love are always available. You have always believed in me and encouraged me to success in everyday life. Without you I wouldn’t be at this point. You, our boy Noel and the future newcomer have shown to me the most presious things in life. I am so grateful to have all of you with me. 5 CONTENTS Abstract ................................................................................. 3 Acknowledgements ................................................................ 5 Contents ................................................................................ 6 List of original publications ................................................... 8 Abbreviations ........................................................................ 9 1 Introduction .................................................................. 10 1.1 Background ............................................................................. 10 1.1.1 Bioeconomy, business, politics, sustainability .................... 10 1.1.2 Roots and stumps as a raw material of the future ............... 12 1.1.3 Modern analysis methods build knowledge of natural products chemistry .......................................................................... 14 1.2 Aims of the study .................................................................... 15 2 Bioactive polyphenolics of roots and stumps of Norway spruce and Scots pine ........................................................... 16 2.1 Stilbenoids ............................................................................... 16 2.1.1 Biosynthesis of stilbenoids ................................................... 16 2.1.2 Stilbenoids in Norway spruce and Scots pine ..................... 18 2.1.3 Extraction and analysis of stilbenoids from coniferous biomass ............................................................................................ 19 2.1.4 Antioxidant activity of stilbenoids ....................................... 21 2.1.5 Medicinal properties of stilbenoids .................................... 22 2.1.6 Antimicrobial and protective properties of stilbenoids ..... 23 2.2 Stability of stilbenoids ........................................................... 26 2.3 Commercial utilisation of potential bioactive compounds .... 27 3 Experimental ................................................................ 29 3.1 Sample material ..................................................................... 29 3.2 Extraction ...............................................................................
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  • Molecular Cloning and Functional Characterization of an O-Methyltransferase Catalyzing 4 -O-Methylation of Resveratrol in Acorus

    Molecular Cloning and Functional Characterization of an O-Methyltransferase Catalyzing 4 -O-Methylation of Resveratrol in Acorus

    Journal of Bioscience and Bioengineering VOL. 127 No. 5, 539e543, 2019 www.elsevier.com/locate/jbiosc Molecular cloning and functional characterization of an O-methyltransferase catalyzing 40-O-methylation of resveratrol in Acorus calamus Takao Koeduka,1,* Miki Hatada,1 Hideyuki Suzuki,2 Shiro Suzuki,3 and Kenji Matsui1 Graduate School of Sciences and Technology for Innovation (Agriculture), Department of Biological Chemistry, Yamaguchi University, Yamaguchi 753-8515, Japan,1 Department of Applied Genomics, Kazusa DNA Research Institute, Chiba 292-0818, Japan,2 and Research Institute for Sustainable Humanosphere, Kyoto University, Kyoto 611-0011, Japan3 Received 17 July 2018; accepted 13 October 2018 Available online 22 November 2018 Resveratrol and its methyl ethers, which belong to a class of natural polyphenol stilbenes, play important roles as biologically active compounds in plant defense as well as in human health. Although the biosynthetic pathway of resveratrol has been fully elucidated, the characterization of resveratrol-specific O-methyltransferases remains elusive. In this study, we used RNA-seq analysis to identify a putative aromatic O-methyltransferase gene, AcOMT1,inAcorus calamus. Recombinant AcOMT1 expressed in Escherichia coli showed high 40-O-methylation activity toward resveratrol and its derivative, isorhapontigenin. We purified a reaction product enzymatically formed from resveratrol by AcOMT1 and confirmed it as 40-O-methylresveratrol (deoxyrhapontigenin). Resveratrol and isorhapontigenin were the most preferred substrates with apparent Km values of 1.8 mM and 4.2 mM, respectively. Recombinant AcOMT1 exhibited reduced activity toward other resveratrol derivatives, piceatannol, oxyresveratrol, and pinostilbene. In contrast, re- combinant AcOMT1 exhibited no activity toward pterostilbene or pinosylvin. These results indicate that AcOMT1 showed high 40-O-methylation activity toward stilbenes with non-methylated phloroglucinol rings.