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Wei Yang – Effects of Genetic and Environmental Factors DOCTORAL THESES IN FOOD SCIENCES AT THE UNIVERSITY OF TURKU Food Chemistry Effects of Genetic and Environmental Factors on Proanthocyanidins in Sea Buckthorn (Hippophaë rhamnoides) and Flavonol Glycosides in Leaves of Currants (Ribes spp.) WEI YANG Food Chemistry and Food Development Department of Biochemistry TURKU, FINLAND – 2017 Food Chemistry and Food Development Department of Biochemistry University of Turku, Finland Supervised by Professor Baoru Yang, Ph.D. Department of Biochemistry University of Turku Turku, Finland Professor emeritus Heikki Kallio, Ph.D. Department of Biochemistry University of Turku Turku, Finland Reviewed by Professor Encarna Gómez-Plaza, Ph.D. Food Science and Technology Department University of Murcia Murcia, Spain Professor Laura Jaakola, Ph.D. Department of Arctic and Marine Biology UiT The Arctic University of Norway Tromsø, Norway Opponent Professor Marina Heinonen, Ph.D. Department of Food and Environmental Sciences University of Helsinki Helsinki, Finland Research director Professor Baoru Yang, Ph.D. Department of Biochemistry University of Turku Turku, Finland The originality of this dissertation has been checked in accordance with the University of Turku quality assurance system using the Turnitin OriginalityCheck service ISBN 978-951-29-6780-3 (print) ISBN 978-951-29-6781-0 (pdf) ISSN 2323-9395 (print) ISSN 2323-9409 (pdf) Painosalama Oy – Turku, Finland 2017 Table of Contents TABLE OF CONTENTS ABSTRACT ......................................................................................................... i SUOMENKIELINEN ABSTRAKTI .............................................................. iii LIST OF ABBREVIATIONS ........................................................................... v LIST OF ORIGINAL PUBLICATIONS ....................................................... vii 1 INTRODUCTION ......................................................................................... 1 2 REVIEW OF THE LITERATURE ............................................................. 4 2.1 Proanthocyanidins ......................................................................... 4 2.1.1 Structures and existence of proanthocyanidins .............. 4 2.1.2 Functions of proanthocyanidins in plants ....................... 7 2.1.3 Role of proanthocyanidins in sensory properties of food ........................................................................................ 8 2.1.4 Heath effects of proanthocyanidins ................................ 9 2.1.5 Absorption and metabolism of proanthocyanidins ....... 10 2.2 Flavonol glycosides ..................................................................... 11 2.2.1 Structure of flavonol glycosides ................................... 11 2.2.2 Flavonols and flavonol glycosides in food ................... 12 2.2.3 Health effects of flavonols ........................................... 12 2.2.4 Absorption and metabolism of flavonols ..................... 13 2.3 Biosynthesis of proanthocyanidins and flavonol glycosides ...... 15 2.3.1 General biosynthetic pathway of proanthocyanidins and flavonol glycosides ....................................................... 15 2.3.2 Transportation and polymerization of proanthocyanidins ...................................................................................... 17 2.4 Analysis of proanthocyanidins and flavonol glycosides ............. 17 2.4.1 Sample preparation ....................................................... 17 2.4.2 Extraction and purification ........................................... 18 2.4.3 High performance liquid chromatography ................... 19 2.4.4 Mass spectrometry ........................................................ 21 2.4.5 NMR ............................................................................. 22 2.5 Effects of growth conditions ....................................................... 23 2.5.1 Effects of latitude and altitude ...................................... 23 2.5.2 Effects of temperature .................................................. 25 2.5.3 Effect of light ................................................................ 26 2.5.4 Genome × environment interaction .............................. 27 Table of Contents 3 AIMS OF THE STUDY .............................................................................. 29 4 MATERIALS AND METHODS ................................................................ 30 4.1 Plant samples ............................................................................... 30 4.2 Sample extraction ........................................................................ 34 4.2.1 Extraction of proanthocyanidins from sea buckthorn berries ........................................................................... 34 4.2.2 Extraction of flavonol glycosides from currant leaves . 34 4.3 Purification of proanthocyanidins ............................................... 34 4.4 LC and MS analysis .................................................................... 35 4.4.1 HPLC/UPLC-DAD-MS analysis of proanthocyanidins ...................................................................................... 35 4.4.2 HPLC-DAD-ESI-MS/MS analysis of flavonol glycosides ..................................................................... 36 4.4.3 Semi-Preparative HPLC isolation of unknown flavonol compounds .................................................................... 36 4.5 NMR analysis of purified flavonol compounds .......................... 36 4.6 Quantitative analysis of proanthocyanidins and flavonol glycosides .................................................................................... 37 4.6.1 Quantitative analysis of proanthocyanidins by HPLC- MS ................................................................................ 37 4.6.2 Quantitative analysis of flavonol glycosides in currant leaves by HPLC-DAD .................................................. 37 4.6.3 Determination of total proanthocyanidins content by DMAC .......................................................................... 37 4.7 Determination of dry matters of sea buckthorn berries and currant leaves ........................................................................................... 38 4.8 Weather conditions ...................................................................... 38 4.9 Statistical analyses ....................................................................... 38 5 RESULTS AND DISCUSSION .................................................................. 41 5.1 Proanthocyanidins in sea buckthorn berries ................................ 41 5.1.1 Purification of proanthocyanidins by column chromatography ............................................................ 41 5.1.2 Identification of proanthocyanidins.............................. 42 5.1.3 Quantitative profiling of oligomeric proanthocyanidins ...................................................................................... 45 5.1.4 Comparison of subspecies and varieties ....................... 45 5.1.5 Comparison of latitudes ................................................ 47 5.1.6 The impact of latitude and altitude on proanthocyanidins in Chinese berries of ssp. sinensis ................................ 48 5.1.7 Effects of weather conditions on proanthocyanidins ... 49 Table of Contents 5.1.8 Effects of over-ripening on proanthocyanidins in sea buckthorn berries .......................................................... 49 5.2 Flavonol glycosides in currant leaves (paper II) ......................... 50 5.2.1 Identification of flavonol glycosides ............................ 50 5.2.2 Comparison of cultivars ............................................... 53 5.2.3 Comparison of different time points within growth seasons .......................................................................... 53 5.2.4 Comparison of growth places ....................................... 54 5.2.5 Comparison by leaf position ......................................... 54 6 SUMMARY AND CONCLUSION ............................................................ 55 ACKNOWLEDGEMENTS............................................................................. 57 APPENDIX: ORIGINAL PUBLICATIONS ................................................ 73 Abstract i ABSTRACT Sea buckthorn (Hippophaë rhamnoides) and currants (Ribes spp.) are rich sources of flavonoids and other polyphenols. Both proanthocyanidins (PAs) in sea buckthorn and flavonol glycosides (FGs) in currant leaves have biological activity and may be effective in maintaining health. The aim of this thesis was to establish methods for qualitative and quantitative analysis of complex PAs in sea buckthorn berries and FGs in currant leaves, and to investigate the effects of genetic background and growth environment on the content and composition of these compounds. A rapid and sensitive method based on hydrophilic interaction liquid chromatography combined with electrospray ionization mass spectrometry (HILIC-ESI-MS) was established for profiling of PAs of sea buckthorn berries. B-type PAs up to degree of polymerization 11 were detected. Among them, the main monomeric units were (epi)gallocatechins. Three PA dimers, four PA trimers and five PA tetramers were quantified by HILIC-ESI-MS in selected ion recording mode (SIR) using reference compound. Sea buckthorn berries of three subspecies (H. rhamnoides ssp. rhamnoides, ssp. mongolica and ssp. sinensis) including nine varieties grown in Finland, Canada and China were collected and
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