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Krajowe Gatunki Rodzaju Eryngium L. W Kulturze in Vitro – Mikrorozmnażanie, Kultury Organów, Ocena Fitochemiczna I Aktywność Biologiczna

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Krajowe Gatunki Rodzaju Eryngium L. W Kulturze in Vitro – Mikrorozmnażanie, Kultury Organów, Ocena Fitochemiczna I Aktywność Biologiczna ROZPRAWA DOKTORSKA Małgorzata Kikowska Krajowe gatunki rodzaju Eryngium L. w kulturze in vitro – mikrorozmnażanie, kultury organów, ocena fitochemiczna i aktywność biologiczna Katedra i Zakład Botaniki Farmaceutycznej i Biotechnologii Roślin Wydział Farmaceutyczny Uniwersytet Medyczny im. Karola Marcinkowskiego w Poznaniu Promotor: dr hab. Barbara Thiem Badania prowadzono w ramach projektu N N405683340 na lata 2011-2014 oraz częściowo projektu N N405065334 na lata 2008-2011 finansowanych przez Ministerstwo Nauki i Szkolnictwa Wyższego Poznań, 2014 DOCTORAL THESIS Małgorzata Kikowska In vitro cultures of Polish Eryngium L. species – micropropagation, organ cultures, phytochemical investigation and biological activity Department of Pharmaceutical Botany and Plant Biotechnology Faculty of Pharmacy Poznan University of Medical Sciences Supervisor: dr hab. Barbara Thiem The study was realized as a part of the research projects N N405683340 in 2011-2014 and N N405065334 in 2008- 2011 supported by the Ministry of Science and Higher Education Poznan, 2014 2 Słowa kluczowe: Eryngium planum, Eryngium maritimum, Eryngium campestre, mikropropagacja, kultury in vitro korzeni i pędów, akumulacja metabolitów wtórnych, aktywność biologiczna Key words: Eryngium planum, Eryngium maritimum, Eryngium campestre, mikropropagation, in vitro root and shoot cultures, secondary metabolites accumulation, biological activity 3 Za możliwość wykonania części badań, pomoc w interpretacji wyników i konsultacje naukowe serdeczne podziękowania składam Dr. hab. Markowi Muriasowi Dr. hab. Adamowi Matkowskiemu Za pomoc w realizacji części badań, pomoc w interpretacji wyników i konsultacje naukowe serdeczne podziękowania składam Prof. dr hab. Elwirze Śliwińskiej Prof. dr hab. Annie Stochmal Dr Jolancie Długaszewskiej 4 Pragnę serdecznie podziękować Pani dr hab. Barbarze Thiem za włączenie do tematyki kultur in vitro polskich gatunków mikołajków cenne uwagi merytoryczne oraz pomoc w realizacji pracy doktorskiej Panu prof. dr. hab. Jaromirowi Budzianowskiemu za umożliwienie wykonania niniejszej pracy oraz cenne uwagi merytoryczne oraz Koleżankom i Kolegom z Katedry i Zakładu Botaniki Farmaceutycznej i Biotechnologii Roślin za dobrą współpracę i życzliwą atmosferę 5 Rozprawa doktorska obejmuje wyniki prac doświadczalnych dotychczas niepublikowanych oraz zawartych w następujących publikacjach: Kikowska M, Thiem B, Krawczyk A. Rosmarinic acid accumulation in the cell suspension culture of Eryngium planum L. Acta Biochim Pol 2009:56 suppl. 2:71-73 Thiem B, Kikowska M. Hairy roots and untransformed root culture of Eryngium L. species. Acta Biochim Pol 2009:56 suppl. 2:78-79 Kikowska M, Budzianowski J, Krawczyk A, Thiem B. Accumulation of rosmarinic, chlorogenic and caffeic acids in in vitro cultures of Eryngium planum L. Acta Physiol Plant 2012:34(6):2425-2433, KBN=25.000, IF=1.305 Thiem B, Kikowska M, Krawczyk A, Więckowska B, Sliwinska E. Phenolic acids and DNA contents of micropropagated Eryngium planum L. Plant Cell Tiss Organ Cult 2013:114(2):197-206, KBN=35.00, IF=3.633 Kikowska M, Thiem B, Sliwinska E, Rewers M, Kowalczyk M, Stochmal A, Oleszek W. Micropropagation and production of phenolic acids and saponins from plantlets and adventitious root cultures of Eryngium maritimum L. (manuskrypt przyjęty do publikacji w JPGR) KBN=35.00, IF=1.990 6 Częściowe wyniki zaprezentowane zostały w postaci komunikatów i streszczeń zjazdowych: Thiem B, Kikowska M, Paluch I (2009) Accumulation of bioactive secondary metabolites in in vitro cultures of Eryngium planum L. Young Scientist Meeting – Future Trends in Phytochemistry in the Global Era of Agri-food and Health, Los Narejos, Spain, Book of Abstracts, p. 108 Kikowska M, Thiem B (2009) Characteristic of the cell suspension culture of Eryngium planum L. 12th National Conference: In vitro cultures, Poznań 2009. Acta Biol Cracov Ser Bot 51(1), p. 45 Kikowska M (2009) Kwas rozmarynowy w kulturach in vitro gatunków z rodzaju Eryngium L. Conference of Bioactive Plant Compounds – Structural and Applicative Aspects, Puławy, Poland (prezentacja ustna) Kikowska M, Thiem B (2010) Biotechnologiczna ocena kultur komórkowych Eryngium planum L. Ogólnopolska Konferencja Naukowa: Postęp w ocenie jakości substancji i produktów leczniczych; Poznań, Wydaw Nauk Uniw Med im Karola Marcinkowskiego w Poznaniu, s. 123 Thiem B, Kikowska M (2010) Ocena jakości biomasy kultur in vitro Eryngium planum L. Ogólnopolska Konferencja Naukowa: Postęp w ocenie jakości substancji i produktów leczniczych; Poznań, Wydaw Nauk Uniw Med im Karola Marcinkowskiego w Poznaniu, s. 124 Kikowska M, Thiem B (2010) Micropropagation of rare and protected species - Eryngium maritimum L. Proceedings of the 55th Meeting of the Polish Botanical Society - Planta in vivo, in vitro et in silico; Poznań, Poland; Acta Soc Bot Pol, 79, suppl. 1, p. 110 Thiem B, Kikowska M, Plauch I, Krawczyk A (2011) Effect of osmotic stress and yeast extract on accumulation of rosmarinic acid in shoot cultures of Eryngium planum L. II Conference of Bioactive Plant Compounds - Structural and Applicative Aspects. Puławy, Poland; Abstracts pp. 37-39 7 Thiem B, Budzianowski J, Kikowska M, Budzianowska A, Derda M, Hadaś E, Goślińska O, Murias Kucińska M, Piotrowska H, Ożarowski M, Mikołajczak P (2011) Eryngium planum L. - a search for biological activities. 6th Polish-German Symposium on Pharmaceutical Sciences, Perspectives for a new decade, Düsseldorf, Germany; Abstracts P035 Thiem B, Kikowska M (2012) Kultury in vitro gatunków Eryngium L. jako alternatywne źródła kwasu rozmarynowego i kompleksu triterpenowych saponin. V Krajowe Sympozjum, Naturalne i syntetyczne produkty zapachowe i kosmetyczne, Łodź, Poland; Streszczenie referatów s. 39 (prezentacja ustna) Thiem B, Kikowska M, Matkowski A, Jęderek D, Kowalczyk M (2012) UPLC-MS/MS determination of phenolic acids from selected raw material of Eryngium species. 8th International Symposium on Chromatography of Natural Products (ISCNP), The application of analytical methods for the development of natural products, Lublin, Poland, Book of Abstracts p. 170 Kikowska M, Thiem B (2013) Organ cultures of Eryngium L. as an alternative source of bioactive compounds. Interdyscyplinarne i aplikacyjne znaczenie nauk botanicznych. 56. Zjazd Polskiego Towarzystwa Botanicznego; Olsztyn, Poland. Streszczenia wystąpień ustnych i plakatów, str. 304 8 SPIS TREŚCI WSTĘP I ZAŁOŻENIA PRACY 14 CZĘŚĆ TEORETYCZNA 17 1. Charakterystyka botaniczna i występowanie krajowych gatunków 17 z rodzaju Eryngium L. 1.1. Klasyfikacja taksonomiczna 17 1.2. Charakterystyka botaniczna rodzaju Eryngium 21 1.3. Rozmieszczenie geograficzne i warunki siedliskowe 23 1.4. Szczegółowa charakterystyka gatunków z rodzaju Eryngium 24 1.4.1. Eryngium planum L. 24 1.4.2. Eryngium maritimum L. 26 1.4.3. Eryngium campestre L. 29 2. Związki chemiczne występujące w gatunkach z rodzaju Eryngium L. 32 2.1. Saponiny triterpenowe 32 2.1.1. Występowanie i struktura chemiczna 32 2.1.2. Saponiny triterpenowe w rodzaju Eryngium 33 2.1.3. Właściwości biologiczne i farmakologiczne saponin triterpenowych 37 2.1.4. Zastosowanie saponin w lecznictwie 41 2.2. Kwasy fenolowe 42 2.2.1. Kwas rozmarynowy 42 2.2.1.1. Występowanie i struktura chemiczna 42 2.2.1.2. Kwas rozmarynowy w rodzaju Eryngium 43 2.2.1.3. Właściwości biologiczne i farmakologiczne kwasu rozmarynowego 44 2.2.2. Kwas chlorogenowy 46 2.2.2.1. Występowanie i struktura chemiczna 46 2.2.2.2. Kwas chlorogenowy w rodzaju Eryngium 46 2.2.2.3. Właściwości biologiczne i farmakologiczne kwasu chlorogenowego 46 2.2.3. Kwas kawowy 48 2.2.3.1. Występowanie i struktura chemiczna 48 2.2.3.2. Właściwości biologiczne i farmakologiczne kwasu kawowego 48 2.3. Flawonoidy 50 2.3.1. Występowanie i struktura chemiczna 50 9 2.3.2. Flawonoidy w rodzaju Eryngium 50 2.3.3. Właściwości biologiczne i farmakologiczne wybranych flawonoidów 51 2.4. Inne związki chemiczne 54 2.4.1. Olejki eteryczne 54 2.4.1.1. Występowanie i struktura chemiczna 54 2.4.1.2. Olejki eteryczne w rodzaju Eryngium 55 2.4.1.3. Właściwości biologiczne i farmakologiczne olejków eterycznych 56 2.4.2. Kumaryny 57 2.4.2.1. Występowanie i struktura chemiczna 57 2.4.2.2. Kumaryny w rodzaju Eryngium 58 2.4.2.3. Właściwości biologiczne i farmakologiczne wybranych kumaryn 58 2.4.3. Poliacetyleny 60 2.4.3.1. Występowanie i struktura chemiczna 60 2.4.3.2. Poliacetyleny w rodzaju Eryngium 60 2.4.3.3. Właściwości biologiczne i farmakologiczne poliacetylenów 61 2.4.4. Fitosterole 62 2.4.4.1. Występowanie i struktura chemiczna 62 2.4.4.2. Fitosterole w rodzaju Eryngium 62 2.4.4.3. Właściwości biologiczne i farmakologiczne fitosteroli 62 2.4.5. Ekdysteroidy 63 2.4.6. Betainy 64 3. Właściwości, działanie lecznicze i zastosowanie surowców Eryngium L 65 4. Wybrane roślinne kultury in vitro 72 4.1. Mikrorozmnażanie roślin leczniczych 73 4.2. Kultury organów normalnych (nietransformowanych) 75 4.2.1. Kultury korzeniowe 76 4.2.2. Kultury pędowe 79 4.3. Kultury komórkowe 81 5. Zabiegi biotechnologiczne stosowane w celu zwiększenia akumulacji 82 metabolitów wtórnych w kulturach in vitro SKRÓTY STOSOWANE W PRACY 86 CZĘŚĆ DOŚWIADCZALNA 89 1. Materiał i metody badawcze stosowane w kulturach in vitro 89 10 1.1. Materiał badawczy 89 1.2. Pożywki i roztwory 90 1.3. Zabiegi biotechnologiczne stosowane w kulturach in vitro 95 1.4. Warunki sterylizacji i pracy w warunkach aseptycznych 96 1.5. Warunki prowadzenia kultur in vitro 96 1.6. Metody badawcze 97 1.6.1. Indukcja sterylnych siewek 97 1.6.2. Namnażanie pędów i optymalizacja warunków kultur
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