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Bioactive Compounds in Flowers and Fruits of Sambucus Nigra L

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Bioactive Compounds in Flowers and Fruits of Sambucus Nigra L Bioactive compounds in flowers and fruits of Sambucus nigra L. Thesis for the degree of Philosophiae Doctor (Ph.D.) by Giang Thanh Thi Ho Department of Pharmaceutical Chemistry School of Pharmacy Faculty of Mathematics and Natural Sciences University of Oslo Norway 2017 PhD thesis Giang Thanh Thi Ho TABLE OF CONTENTS TABLE OF CONTENTS TABLE OF CONTENTS .....................................................................................I ACKNOWLEDGEMENTS ............................................................................. III LIST OF PUBLICATIONS .............................................................................. IV ABBREVIATIONS ........................................................................................... VI ABSTRACT ....................................................................................................... IX 1. INTRODUCTION ........................................................................................ 1 1.1 Sambucus nigra L. (black elder) ..................................................................................................... 1 1.2 Chemistry of compounds from S. nigra ......................................................................................... 4 1.2.1 Pectic polysaccharides ............................................................................................................... 4 1.2.1.1 Homogalacturonan .............................................................................................................. 5 1.2.1.2 Rhamnogalacturonan-I ....................................................................................................... 5 1.2.1.3 Substituted galacturonans ................................................................................................... 6 1.2.2 Phenolic compounds .................................................................................................................. 6 1.2.2.1 Flavonoids .......................................................................................................................... 7 1.2.2.2 Non-flavonoids ................................................................................................................. 10 1.3 Bioavailability ................................................................................................................................ 10 1.4 Immunomodulating activity ......................................................................................................... 11 1.4.1 The complement system ........................................................................................................... 12 1.4.2 Activation and inhibition of macrophages and dendritic cells ................................................. 13 1.5 Anti-diabetic activity ..................................................................................................................... 14 1.5.1 Glucose- and oleic acid uptake in skeletal muscle cells and liver cells ................................... 14 1.5.2 Inhibition of α-amylase and α-glucosidase .............................................................................. 14 1.5.3 Free radicals and antioxidant activity ...................................................................................... 15 2. AIMS OF THE STUDY ............................................................................. 18 3. SUMMARY OF PAPERS .......................................................................... 19 3.1 Paper I ............................................................................................................................................ 19 3.2 Paper II ........................................................................................................................................... 19 I PhD thesis Giang Thanh Thi Ho TABLE OF CONTENTS 3.3 Paper III ......................................................................................................................................... 20 3.4 Paper IV ......................................................................................................................................... 21 3.5 Paper V ........................................................................................................................................... 21 3.6 Paper VI ......................................................................................................................................... 22 3.7 Paper VII ........................................................................................................................................ 23 4. RESULTS AND DISCUSSION ................................................................. 24 4.1 Isolation of pectic polysaccharides ............................................................................................... 24 4.2 Structure elucidation ..................................................................................................................... 25 4.2.1 Structures of pectins from elderberries .................................................................................... 25 4.2.2 Structures of pectins from elderflowers ................................................................................... 30 4.3 Immunomodulating properties and pectin structure requirements ......................................... 36 4.3.1 Complement fixating activity ................................................................................................... 36 4.3.2 Macrophage activation ............................................................................................................. 39 4.4 Consideration regarding potential lipopolysaccharide (LPS) contamination ......................... 44 4.5 Phenolic constituents and metabolites from S. nigra ................................................................. 45 4.6 Biological activity of flavonoids, phenolic acids and metabolites from S. nigra ...................... 49 4.6.1 Glucose- and oleic acid uptake in human skeletal muscle cells and human liver cells ........... 49 4.6.2 α-Amylase and α-glucosidase inhibitory activity .................................................................... 54 4.6.3 Antioxidant activity.................................................................................................................. 56 4.6.4 Complement fixating activity ................................................................................................... 60 4.6.5 Inhibition of NO in LPS activated RAW 264.7 macrophages and dendritic D2SC/I cells ...... 62 5. CONCLUSIONS ......................................................................................... 66 REFERENCES .................................................................................................. 67 PAPERS I-VII .................................................................................................... 78 II PhD thesis Giang Thanh Thi Ho ACKNOWLEDGEMENTS ACKNOWLEDGEMENTS The present work was performed at Department of Pharmaceutical Chemistry, School of Pharmacy, University of Oslo during the years 2013-2017. I am grateful for the given opportunity to perform this Ph.D, and would like to express my gratitude to all the people that have made it possible for me. First and most importantly, I would like to thank my excellent supervisors Hilde Barsett and Helle Wangensteen for your great support and encouragement, for teaching me many things about science and especially patience, and for always being available for my questions. Without you two, this work will not have been possible. Thanks to you for letting me work independently and still giving me so much support and valuable feedbacks. You have a unique ability to see exactly what is needed to do things even better, and I have learned a lot by having you as my supervisors. A special thank and my sincere gratitude to Eili Tranheim Kase for excellent collaboration. Your positive personality and scientific insight are greatly appreciated. I further want to express my gratitude to all co-authors for their valuable contributions. Thanks to my fantastic co-workers at the Pharmacognosy group for both academic collaboration and friendship. I would like to thank you all for providing a friendly and happy environment. I would like to express my gratitude to professor emeritus Karl Egil Malterud for valuable contributions. Thank you for sharing your knowledge and passion for science. To Hoai and Suthajini, thank you for all your technical help, valuable ideas and support. The good company of my fellow PhD students, past and present, is greatly appreciated. I am grateful for my friends for always being there, especially “Fungiz”, “Team Ho” and “Knoll og Tott”. Thank you “Pumpkin” for your support and enormous patience. You are all amazing and the best! Finally, a deep thank to my family. My parents, Mẹ and Cha, you have always been the most important persons in my life. Without your unconditional belief in me, your encouragements, and support I would never have been where I am today. Oslo, March 2017 Giang Thanh Thi Ho III PhD thesis Giang Thanh Thi Ho LIST OF PUBLICATIONS LIST OF PUBLICATIONS I. Giang Thanh Thi Ho, Abeeda Ahmed, Yuan-Feng Zou, Torun Helene Aslaksen, Helle Wangensteen & Hilde Barsett. Structure-activity relationship of immunomodulating pectins from elderberries. Carbohydrate Polymers 2015, 125, 241-248. II. Giang Thanh Thi Ho, Yuan-Feng Zou, Torun Helene Aslaksen, Helle Wangensteen & Hilde Barsett. Structural characterization of bioactive
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