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TUOMINEN, ANU: Tannins and Other Polyphenols in Geranium Sylvaticum: Identification, Intraplant Distribution and Biological Activity

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TUOMINEN, ANU: Tannins and Other Polyphenols in Geranium Sylvaticum: Identification, Intraplant Distribution and Biological Activity ANNALES UNIVERSITATIS TURKUENSIS ANNALES UNIVERSITATIS A I 569 Anu Tuominen TANNINS AND OTHER POLYPHENOLS IN GERANIUM SYLVATICUM: Identification, intraplant distribution and biological activity Anu Tuominen ISBN 978-951-29-7049-0 (PRINT) , Finland 2017 Turku Painosalama Oy, ISBN 978-951-29-7050-6 (PDF) TURUN YLIOPISTON JULKAISUJA – ANNALES UNIVERSITATIS TURKUENSIS ISSN 0082-7002 (PRINT) | ISSN 2343-3175 (ONLINE) Sarja – ser. AI osa – tom. 569 | Astronomica – Chemica – Physica – Mathematica | Turku 2017 TANNINS AND OTHER POLYPHENOLS IN GERANIUM SYLVATICUM: Identification, intraplant distribution and biological activity Anu Tuominen TURUN YLIOPISTON JULKAISUJA – ANNALES UNIVERSITATIS TURKUENSIS Sarja - ser. A I osa - tom. 569 | Astronomica - Chemica - Physica - Mathematica | Turku 2017 University of Turku Faculty of Mathematics and Natural Sciences Department of Chemistry Laboratory of Organic Chemistry and Chemical Biology Supervised by Professor Dr Juha-Pekka Salminen Docent Dr Jari Sinkkonen Department of Chemistry Department of Chemistry University of Turku, Turku, Finland University of Turku, Turku, Finland Docent Dr Maarit Karonen Department of Chemistry University of Turku, Turku, Finland Custos Professor Dr Juha-Pekka Salminen Department of Chemistry University of Turku, Turku, Finland Reviewed by Professor Dr Herbert Kolodziej Professor Dr Anurag Agrawal Department of Biology, Chemistry, and Pharmacy Department of Ecology and Evolutionary Biology Freie Universität Berlin, Berlin, Germany Cornell University, Ithaca, NY, USA Opponent Professor Dr Kristiina Wähälä University of Helsinki, Helsinki, Finland Cover image by author The originality of this thesis has been checked in accordance with the University of Turku quality assurance system using the Turnitin OriginalityCheck service. ISBN 978-951-29-7049-0 (PRINT) ISBN 978-951-29-7050-6 (PDF) ISSN 0082-7002 (PRINT) ISSN 2343-3175 (ONLINE) Painosalama Oy - Turku, Finland 2017 ABSTRACT UNIVERSITY OF TURKU Department of Chemistry/Faculty of Mathematics and Natural Sciences TUOMINEN, ANU: Tannins and other polyphenols in Geranium sylvaticum: Identification, intraplant distribution and biological activity Doctoral thesis, 241 p. Laboratory of Organic Chemistry and Chemical Biology/ Natural Compound Chemistry December 2017 This thesis studies the phenolic compounds of Geranium sylvaticum L. It focuses especially on geraniin and related ellagitannins. The literature review covers the phytochemistry of Geranium species, the biological activity of tannins and methods for the analysis and identification of tannins. In the experimental work, methods were developed for the extraction and high- pressure liquid chromatographic analysis of polyphenols in G. sylvaticum organs and their degradation products in the alkaline pH. Using a high-resolution mass spectrometry and diode array detection, water-soluble polyphenols in the organs of G. sylvaticum were tentatively identified and studied for their seasonal variation. Moreover, the main compounds were isolated and structures further elucidated. The biological activity of organ extracts and fractions was measured with antioxidant activity and pro-oxidant activity assays. Results showed that the plant organs of G. sylvaticum have distinctive intraplant variation in their phenolic profiles. Geraniin and other ellagitannins dominated in all the green photosynthetic organs. While the pistils accumulated gallotannins, the stamens kaempferol glycosides, and seeds and roots accumulated oligomeric proanthocyanidins. Of these, galloylglucoses, gallotannins and minor ellagitannins in particular showed seasonal and ontogenic variation. The petals contained unique acetylglucosylated hydrolysable tannins. These compounds showed capacity to act as copigments for anthocyanins. Due to the high content of ellagitannins and galloyl quinic acids, the leaf, pistil and hairy root extracts showed high antioxidant and pro-oxidant activity. Hydrolyzable tannins degraded fast in the alkaline conditions used in the pro-oxidant test and produced hydrolysis, deprotonation and oxidation products. The observed intraplant distribution of the polyphenol groups, seasonal and ontogenic variation, and the various biological activities observed may reflect the different functions and importance of various types of tannins in the plants’ interaction with pollinators, herbivores and/or pathogens. Keywords: Geranium sylvaticum, tannins, biological activity TIIVISTELMÄ TURUN YLIOPISTO Kemian laitos/Matemaattis-luonnontieteellinen tiedekunta TUOMINEN, ANU: Metsäkurjenpolven (Geranium sylvaticum) tanniinit ja muut polyfenolit: tunnistaminen, kasvinsisäinen jakaantuminen ja biologinen aktiivisuus Väitöskirja, 241 s. Orgaanisen kemian ja kemiallisen biologian laboratorio/ Luonnonyhdisteiden kemia Joulukuu 2017 Tutkimustyö käsittelee metsäkurjenpolven (Geranium sylvaticum L.) fenolisia yhdisteitä keskittyen erityisesti geraniiniin ja muihin ellagitanniineihin. Kirjallisuusosiossa käydään läpi kurjenpolvikasvien kemiaa, tanniinien biologista aktiivisuutta ja niiden analysointimenetelmiä. Kokeellisessa osiossa kehitettiin nestekromatografisia analyysimenetelmiä, joilla tutkittiin metsäkurjenpolven eri kasvinosien polyfenoleja sekä niiden hajoamistuotteita emäksisissä olosuhteissa. Vesiliukoiset polyfenolit tunnistettiin ja niiden kasvukauden aikainen vaihtelu metsäkurjenpolven eri kasvinosissa tutkittiin käyttäen massaspektrometriaa. Lisäksi pääyhdisteet eristettiin tarkempaa rakenteen määrittämistä varten. Kasvinosauutteiden ja fraktioiden biologista aktiivisuutta mitattiin antioksidantti- ja pro-oksidanttiaktiivisuustesteillä. Tuloksista nähtiin, että metsäkurjenpolven kasvinosien polyfenolikoostumukset erosivat merkittävästi. Geraniinia ja muita ellagitanniineja esiintyi etenkin vihreissä yhteyttävissä osissa. Emeistä löytyi korkeita pitoisuuksia gallotanniineja, heteistä kemferoliglykosideja, siemenistä ja juurista oligomeerisia proantosyanidiineja. Näistä etenkin galloyyliglukooseilla, gallotanniineilla ja ellagitanniineilla havaittiin kasvukaudenaikaista ja kasvuvaiheesta riippuvaa vaihtelua. Terälehdistä tunnistettiin aivan uusi asetyyliglykosyloituneiden hydrolysoituvien tanniinien ryhmä, joiden havaittiin toimivan antosyaanien väriä tehostavina kopigmentteinä. Korkean ellagitanniini- ja galloyylikviinihappopitoisuuden takia etenkin lehti-, emi- ja hiusjuuriuutteet osoittivat voimakasta antioksidantti- ja pro-oksidanttiaktiivisuutta. Hydrolysoituvat tanniinit hajosivat nopeasti pro-oksidanttitestissä käytetyissä emäksisissä olosuhteissa ja reaktiossa syntyi hydrolyysi-, deprotonaatio- ja hapettumistuotteita. Havaittu kasvinsisäinen jakaantuminen, kasvukauden ja kasvuvaiheen aikainen vaihtelu ja biologinen aktiivisuus kuvastavat kuinka erityyppisillä tanniineilla voi olla erilaisia tehtäviä ja merkitys kasvin ja sen pölyttäjien, kasvinsyöjien sekä patogeenien välisissä vuorovaikutuksissa. Avainsanat: Geranium sylvaticum, metsäkurjenpolvi, tanniinit, biologinen aktiivisuus TABLE OF CONTENTS PREFACE AND ACKNOWLEDGEMENTS ................................................................... 1 LIST OF ORIGINAL PUBLICATIONS ........................................................................... 4 ABBREVIATIONS ............................................................................................................ 5 1 INTRODUCTION ......................................................................................................... 7 2 LITERATURE REVIEW .............................................................................................. 9 2.1 Geranium species .................................................................................................. 9 2.1.1 Classification and abundance ..................................................................... 9 2.1.2 Commercial use in herbal medicine and gardening ................................. 10 2.1.3 Geranium sylvaticum, its herbivores and gynodiecy ............................... 12 2.2 Phytochemistry of Geranium species .................................................................. 19 2.2.1 Non-phenolic lipophilic compounds produced by glandular trichomes .. 19 2.2.2 Water-soluble phenolic acids and flavonoids .......................................... 21 2.2.3 Hydrolysable tannins and proanthocyanidins .......................................... 26 2.2.4 Intraplant and seasonal variation ............................................................. 33 2.3 Biological activity of tannins .............................................................................. 38 2.3.1 Antioxidant activity ................................................................................. 38 2.3.2 Pro-oxidant activity .................................................................................. 41 2.3.3 Activation via hydrolysis ......................................................................... 46 2.3.4 Protein precipitation capacity .................................................................. 47 2.3.5 Copigmentation ........................................................................................ 48 2.4 Analysis and identification methods of tannins .................................................. 52 2.4.1 Chromatography ...................................................................................... 53 2.4.2 UV-vis spectroscopy ................................................................................ 55 2.4.3 Mass spectrometry ..................................................................................
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