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Izolácia Obsahových Látok Z Frakcií Získaných Z Plodov Paulownia Tomentosa

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Izolácia Obsahových Látok Z Frakcií Získaných Z Plodov Paulownia Tomentosa FARMACEUTICKÁ FAKULTA Izolácia obsahových látok z frakcií získaných z plodov Paulownia tomentosa Diplomová práca MIRIAMA DUPĽÁKOVÁ Vedúci práce: prof. PharmDr. Karel Šmejkal, Ph.D. Konzultant: PharmDr. Lenka Molčanová Ústav přírodních léčiv Program: Farmacie Brno, jar 2021 Bibliografický záznam Autorka: Miriama Dupľáková Farmaceutická fakulta Masarykova univerzita Ústav přírodních léčiv Názov práce: Izolácia obsahových látok z frakcií získaných z plodov Paulownia tomentosa Študijný program: Farmacie Vedúci práce: prof. PharmDr. Karel Šmejkal, Ph.D. Konzultant: PharmDr. Lenka Molčanová Akademický rok: 2020/2021 Počet strán: 130 Kľúčové slová: Paulownia tomentosa, Flavonoidy, Mnohopočetná lieková rezisten- cia (MDR), ABC liekové efluxné transportéry, Chromatografické metódy Anotácie Predkladaná diplomová práca sa v teoretickej časti zaoberá flavonoidmi, ktoré by mohli inhibíciou efluxných púmp zvrátiť mnohopočetnú liekovú rezistenciu a zvýšiť účinnosť chemoterapie. Medzi najvýznamnejšie efluxné pumpy, ktoré sa podieľajú na vzniku rezistencie nádorových buniek k cytostatickej liečbe patria P-gp, MRP1 a BCRP,a preto sa práca zaoberá hlavne týmito efluxnými transportérmi. V práci je priblížený rýchlorastúci strom Paulownia tomentosa (Paulowniaceae), ktorý je bohatý na obsah flavonoidov, hlavne geranylovaných. V experimentálnej časti práce je popísaná izolácia a identifikácia látok z frakcie PT3K, ktorá pochádza z chloroformového podielu etanolového extraktu plodov P. tomentosa. Frakcie boli separované pomocou rôznych chromatografických metód. Identifikácia bola prevedená pomocou UV/VIS spektrofotometrie, IČ, HRMS, NMR spektrometrie a cirkulárneho dichroizmu, pomocou ktorého bola určená absolútna konfigurácia látky. Po preparatívnej HPLC bola získaná jedna čistá látka, ktorú sanám podarilo plne identifikovať ako tomentón B. Bibliographic record Author: Miriama Dupľáková Faculty of Pharmacy Masaryk University Department of Natural Drugs Title of Thesis: Isolation of content compounds from fruits of Paulownia tomentosa Degree Programme: Pharmacy Supervisor: prof. PharmDr. Karel Šmejkal, Ph.D. Consultant: PharmDr. Lenka Molčanová Academic Year: 2020/2021 Number of Pages: 130 Keywords: Paulownia tomentosa, flavonoids, multidrug resistance, ABC drug efflux transporters, chromatographic methods Annotation The theoretical part of the diploma thesis deals with flavonoids that could reverse multidrug resistance and increase the effectiveness of chemotherapy by inhibiting efflux pumps. P-gp, MRP1 and BCRP are among the most important efflux pumps that are involved in the development of resistance of tumor cells to cytostatic treatment, therefore this thesis is mainly focused on these efflux transporters. Part of work is focused on fast growing tree Paulownia tomentosa (Paulowniaceae) rich in flavonoids, especially that geranylated. The experiment describes the isolation and identification of substances from PT3K fraction that was obtained from chloroform portion of the ethanolic extract of P. tomentosa fruits. The fractions were separated by various chromatographic methods. The identification of the obtained compounds was performed by UV/VIS spectrophotometry, IR, HRMS, NMR spectrometry and circular dichroism, which determined the absolute configuration of the substance. Using preparative HPLC we isolated and identified one pure substance – tomentone B. Vyhlásenie Vyhlasujem, že som predloženú diplomovú prácu vypracovala samostatne len s použitím uvedenej literatúry a prameňov. Miriama Dupľáková Poďakovanie Touto cestou by som sa chcela poďakovať môjmu vedúcemu diplomovej práce prof. PharmDr. Karlovi Šmejkalovi, Ph.D. (Ústav přírodních léčiv, Farmaceutická fakulta, Masarykova univerzita) za jeho vedenie a cenné rady. Moja veľká vďaka patrí mojej školiteľke PharmDr. Lenke Molčanovej (Ústav přírodních léčiv, Farmaceutická fakulta, Masarykova univerzita) za jej odborné vedenie, trpezlivosť, poznatky a pripomienky, ktoré mi boli nápomocné pri tvorbe celej práce. Rada by som sa jej poďakovala tiež za meranie a vyhodnocovanie čistej látky pomocou identifikačných metód. Obsah Úvod 1 I Teoretická časť 3 1 Mnohopočetná lieková rezistencia4 1.1 Typická a atypická MDR . .6 2 ABC liekové efluxné transportéry7 2.1 P-glykoproteín (ABCB1) . .8 2.2 Proteín spojený s mnohopočetnou liekovou rezistenciou (MRP1/ ABCC1)9 2.3 Proteín rezistencie na rakovinu prsníka (BCRP/ABCG2) . 11 3 Flavonoidy, ktoré inhibujú efluxné pumpy 13 3.1 Efluxná pumpa MRP1 . 23 3.2 Efluxná pumpa P-glykoproteín . 29 3.3 Efluxná pumpa BCRP . 41 4 Paulownia tomentosa Steud. 50 4.1 Taxonomická klasifikácia . 51 4.2 Pôvod a geografický výskyt . 51 4.3 Morfológia . 52 4.4 Tradičné využitie . 53 4.5 Obsahové látky . 54 5 Cieľ práce 55 II Experimentálna časť 56 6 Materiál a metódy 57 6.1 Rastlinný materiál . 57 6.2 Chemikálie . 57 6.3 Materiál pre chromatografiu . 58 6.4 Prístroje . 58 6.5 Separačné metódy . 59 6.6 Identifikačné metódy . 62 7 Pracovný postup 64 7.1 Vzorka PT3K . 64 7.2 Určenie mobilnej fázy pre stĺpcovú chromatografiu . 64 7.3 Separácia vzorky PT3K stĺpcovou chromatografiou . 65 7.4 Spojenie frakcií stĺpcovej chromatografie . 66 7.5 Výber metódy pre preparatívnu HPLC frakcia PT3K/13-15 . 67 7.6 Výber metódy pre preparatívnu HPLC frakcia PT3K/26-28 . 68 8 Výsledky 70 8.1 Analýza získaných frakcií . 70 8.2 Identifikácia látky získanej z frakcie PT3K/13-15/2 . 73 9 Diskusia 78 10 Záver 82 Bibliografia 83 Zoznam použitých skratiek 93 Prílohy 97 A HPLC chromatogram ghost píkov zo systému 98 B Prehľad flavonoidov, ktoré boli testované na inhibíciu efluxných púmp 99 Zoznam tabuliek 2.1 Podrodiny ľudských génov ABC 8 3.1 Isoflavóny, ktoré inhibujú efluxné pumpy 15 3.2 Flavóny, ktoré inhibujú efluxné pumpy 17 3.3 Syntetizované flavóny testované na inhibíciu BCRP 18 3.4 Syntetizované deriváty chryzínu, ktoré inhibujú efluxné pumpy 19 3.5 Flavanóny, ktoré inhibujú efluxné pumpy 21 3.6 Séria flavonoidov, ktoré inhibujú MRP1 24 3.7 Účinky icaritínu (63) 30 3.8 Účinky baicaleínu (23) 32 3.9 Účinky izoprenylovaných derivátov chryzínu na akumuláciu DNM 39 3.10 Účinky derivátov 2,3-dehydrosilybínu na inhibíciu P-gp 41 3.11 Účinky flavónov na inhibíciu BCRP 43 3.12 Vzťah štruktúry a aktivity flavonoidov na inhibíciu BCRP 44 3.13 Účinky série flavonoidov na inhibíciu BCRP 46 3.14 Inhibícia efluxnej pumpy BCRP polyfenolmi 47 3.15 Účinnosť syntetizovaných benzoflavónov na inhibíciu BCRP 48 3.16 Syntetizované flavóny a ich inhibičný potenciál voči BCRP 49 4.1 Taxonomická klasifikácia P. tomentosa 51 6.1 Metóda 1 pre analytickú HPLC 60 6.2 Metóda 2 pre analytickú HPLC 60 6.3 Metóda 3 pre analytickú HPLC 60 6.4 Metóda 4 pre preparatívnu HPLC 61 6.5 Metóda 5 pre preparatívnu HPLC 62 7.1 Hmotnosť frakcií spojených na základe TLC a HPLC 66 8.1 Hmotnosť frakcií získaných z preparatívnej HPLC 70 Zoznam obrázkov 1.1 Hlavné mechanizmy vzniku získanej MDR 5 2.1 Štruktúra transportného P-glykoproteínu 9 2.2 Štruktúra multirezistentného proteínu 1 (MRP1) 11 2.3 Štruktúra transportého proteínu BCRP 12 3.1 Všeobecná základná štruktúra flavonoidov a ich podtried 13 3.20 Inhibícia MRP1 spôsobená 8-prenylnaringenínom (106) 25 3.21 Vplyv flavonoidov na akumuláciu 3H-DNM a 3H-VBL v bunkách Panc-1 26 3.22 Účinok icaritínu (63) na akumuláciu ADR 31 3.23 Účinok baicaleínu (23) na akumuláciu rhodamínu 123 v bunkách MCF-7/ADR 32 3.24 Účinky silymarínu (112) a biochanínu A (3) na akumuláciu VBL a 3H-digoxínu v bunkách Caco-2 33 3.25 Účinky biochanínu A (3), morínu (60), silymarínu (112) a phloretínu (119) na akumuláciu daunomycínu v bunkách MDA435/LCC6 34 3.26 Účinky quercetínu (19) na akumuláciu kalceínu 35 3.27 Účinky extraktu z K. parviflora na akumuláciu rhodamínu 123 a daunorubicínu 36 3.28 Účinky 3,5,7,3´,4´-pentametoxyflavónu (41) na akumuláciu daunorubicínu 37 3.29 Účinky wogonínu (61) na akumuláciu kalceínu v bunkách HL-60 38 3.30 Súhrn štruktúrnych znakov ovlyvňujúcich inhibíciu BCRP 42 3.31 Vplyv substitúcie na inhibíciu BCRP 45 3.32 Vplyv rôznych substituentov benzoflavónov na inhibíciu BCRP 47 4.1 Paulownia tomentosa 50 4.2 Paulownia tomentosa– kvety, kôra, listy a plody 53 7.1 HPLC chromatogram vzorky PT3K 64 7.2 TLC vzorky PT3K 65 7.3 Kolóna stĺpcovej chromatografie 66 7.4 HPLC chromatogram vzorky PT3K/13-15 pri 280 nm 67 7.5 HPLC chromatogram vzorky PT3K/26-28 pri 280 nm 67 7.6 Chromatogram preparatívnej HPLC vzorky PT3K/13-15 68 7.7 Chromatogram preparatívnej HPLC vzorky PT3K/26-28 69 8.1 Chromatogram analytickej HPLC vzorky PT3K/13-15/1 71 8.2 Chromatogram analytickej HPLC vzorky PT3K/13-15/2 71 8.3 Chromatogram analytickej HPLC vzorky PT3K/26-28/2 72 8.4 Chromatogram analytickej HPLC vzoriek PT3K/26-28/3 a PT3K/26-28/4 73 8.5 Knižnica látok izolovaných z Paulownia tomentosa 74 8.6 HPLC chromatogram spoločného nástreku vzorky PT3K/13-15/2 a štandardu tomentónu B 74 8.7 IČ spektrum vzorky PT3K/13-15/2 75 8.8 HRMS spektrum látky PT3K/13-15/2 v pozitívnom móde 76 8.9 HRMS spektrum látky PT3K/13-15/2 v negatívnom móde 76 Úvod Nádorové ochorenia predstavujú globálne vážne zdravotné riziko pre populáciu na celom svete, a to potvrdzuje aj fakt, že po kardiovaskulárnych ochoreniach sú druhou najčastejšou príčinou smrti. Svetová zdravotnícka organizácia (WHO) uvádza, že v roku 2018 spôsobili nádorové ochorenia približne 9,6 milióna úmrtí. Medzi najčastejšie nádorové ochorenia patrí rakovina pľúc, prostaty, hrubého čreva, žalúdka, pečene a rakovina krčka maternice a štítnej žľazy, ktoré sú typické u žien [1], [2]. Jeden z hlavných problémov liečby nádorových ochorení (chemoterapie) sa týka nepredvídateľnosti
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