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Title: Badania Frakcji Lotnej Metabolitów Wtórnych Wybranych Gatunków Szałwii (Salvia Sp.) Metodami Chromatograficznymi GC-MS I LC

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Title: Badania Frakcji Lotnej Metabolitów Wtórnych Wybranych Gatunków Szałwii (Salvia Sp.) Metodami Chromatograficznymi GC-MS I LC Title: Badania frakcji lotnej metabolitów wtórnych wybranych gatunków szałwii (Salvia sp.) metodami chromatograficznymi GC-MS i LC Author: Łukasz Wojtal Citation style: Wojtal Łukasz. (2011). Badania frakcji lotnej metabolitów wtórnych wybranych gatunków szałwii (Salvia sp.) metodami chromatograficznymi GC-MS i LC. Praca doktorska. Katowice : Uniwersytet Śląski Ł ukasz W ojtal Badania frakcji lotnej metabolitów wtórnych wybranych gatunków szałwii (Salvia sp.) metodami chromatograficznymi GC-MS i LC Promotorzy pracy: prof. dr hab. Teresa Kowalska Zakład Chemii Ogólnej i Chromatografii Uniwersytet Śląski w Katowicach prof. dr hab. Monika Waksmundzka-Hajnos Zakład Chemii Nieorganicznej Uniwersytet Medyczny w Lublinie Praca doktorska wykonana w Zakładzie Chemii Ogólnej i Chromatografii Uniwersytetu Śląskiego w Katowicach Katowice 2011 Spis treści: Wstęp.............................................................................................................................. 5 Cześć teoretyczna...................................................................................................... 7 1. Charakterystyka botaniczna badanych gatunków szałwii......................................8 1.1. Systematyka szałwii.........................................................................................8 1.2. Budowa morfologiczna i anatomiczna wybranych gatunków szałwii.........9 1.2.1. Salvia officinalis L. (szałwia lekarska).................................................... 9 1.2.2. Safoia lavandulifolia Vahl (szałwia lawendolistna)...............................12 1.2.3. Safoia sclarea L. (szałwia muszkatołowa)............................................. 12 1.2.4. Safoia nemorosa L. (szałwia gajowa lub szałwia omszona).................13 1.2.5. Salvia triloba L. (szałwia krzewiasta lub szałwia grecka)...................14 1.2.6. Safoia pratensis L. (szałwia łąkowa).......................................................15 2. Wybrane klasy związków zawartych w olejkach eterycznych......................... 16 2.1.1. Monoterpeny........................................................................................... 17 2.1.1.1. Monoterpeny acykliczne.................................................................. 18 2.1.1.2. Monoterpeny monocykliczne..........................................................19 2.1.1.3. Monoterpeny dicykliczne................................................................22 2.1.1.4. Monoterpeny tricykliczne...............................................................23 2.1.2. Seskwiterpeny..........................................................................................23 2.1.3. Diterpeny................................................................................................. 24 2.1.4. Triterpeny................................................................................................ 26 3. Chemotaksonomia roślin i jej znaczenie dla nowoczesnej systematyki roślin.28 4. Metody wyodrębniania lotnych substancji zawartych w materiale roślinnym29 4.1. Desorpcja z fazy nadpowierzchniowej (headspace) ....................................29 4.3. Ciśnieniowa ekstrakcja cieczowa (ASE).......................................................32 5. Chromatografia gazowa sprzężona ze spektrometrią mas (GC/MS)..............34 6. Chromatografia cienkowarstwowa sprzężona ze spektrometrem mas (TLC/MS)................................................................................................................... 39 7. Wybrane zastosowania technik chromatograficznych w analizie olejków eterycznych pochodzących z różnych gatunków szałwii (Safoia sp.) ...................42 Cel pracy...................................................................................................................... 45 Część doświadczalna................................................................................................ 46 1. Aparatura i odczynniki chemiczne...................................................................... 47 2. Metodyka przeprowadzonych badań..................................................................49 2.1. Materiał roślinny............................................................................................ 49 2.2. Destylacja w aparacie Derynga.................................................................... 49 2.3. Desorpcja z fazy nadpowierzchniowej (headspace)....................................49 2.4. Ciśnieniowa ekstrakcja cieczowa (ang. Accelerated sofoent extraction, ASE)....................................................................................................................... 50 2.5. Chromatografia gazowa z detektorem masowym (GC/MS)...................... 51 2.6. Chromatografia cienkowarstwowa (TLC).................................................. 52 2.7. Chromatografia cienkowarstwowa sprzężona z detektorem mas w wariancie jednowymiarowym (TLC-MS)...........................................................52 2.8. Chromatografia cienkowarstwowa sprzężona z detektorem mas w wariancie dwuwymiarowym (TLC-LC-MS).......................................................53 2.9. Spektroskopia 13C NMR................................................................................54 2.10. Wstępne przygotowanie danych do dalszej analizy..................................54 2.10.1. Eliminacja tła sygnału analitycznego.................................................. 54 2.10.2. Usuwanie szumu z sygnału analitycznego.......................................... 55 2.10.3. Nakładanie sygnałów analitycznych....................................................56 2.11. Analiza czynników głównych (PCA)..........................................................57 3. Porównanie efektywności wyodrębniania frakcji lotnej z różnych gatunków szałwii (Safoia L.) przy użyciu czterech technik izolacyjnych...............................58 4. Analiza chromatograficzna dwudziestu gatunków szałwii (Safoia sp.) techniką HS-GC/MS.................................................................................................................75 5. Analiza olejków eterycznych zawartych w różnych gatunkach szałwii (Safoia L.) metodami niskotemperaturowej chromatografii cienkowarstwowej (LT- TLC) z detekcją densytometryczną i chromatografii gazowej z detekcją masową (GC/MS)..................................................................................................................... 91 6. Analiza olejków eterycznych szałwii przy użyciu niskotemperaturowej chromatografii cienkowarstwowej sprzężonej ze spektrometrią masową (LT- TLC-MS).................................................................................................................. 101 7. Analiza olejków eterycznych szałwii (Safoia L.) przy pomocy niskotemperaturowej chromatografii cienkowarstwowej połączonej z detekcją masową (LT-TLC-MS) w wariancie jedno- i dwuwymiarowym....................... 115 8. Analiza składu chemicznego olejków eterycznych szałwii z zastosowaniem spektroskopii magnetycznego rezonansu jądrowego (NMR) oraz chromatografii gazowej z detekcją masową (GC/MS)................................................................... 131 9. Chemometryczna analiza chromatogramów gazowych frakcji lotnej dla różnych gatunków szałwii (Safoia sp.) traktowanych jako „odciski palca”...... 143 L ist a p r a c w ł a s n y c h tematycznie z w ią z a n y c h z r o z p r a w ą d o k t o r s k ą .... 153 L is t a p u b l ik a c ji konferencyjnych tematycznie z w ią z a n y c h z r o z p r a w ą DOKTORSKĄ..................................................................................................................154 ŻYCIORYS.............................................................................................................................................157 L i t e r a t u r a : ...................................................................................................................................... 158 Tradycje ziołolecznictwa sięgają czasów prehistorycznych. Człowiek zawsze szukał w przyrodzie roślin, które przywracały mu zdrowie i siłę. Już od kilkudziesięciu wieków ludzkość zna uzdrawiające właściwości czosnku, rumianku, mięty, babki czy piołunu. Kolebką ziołolecznictwa był Egipt, gdzie uprawą i dozowaniem roślin o działaniu leczniczym zajmowali się kapłani. Chińska medycyna naturalna cieszy się zaufaniem już od ponad 5000 lat. W Indiach i Azji Południowo-Wschodniej wykorzystuje się około 1800 roślin leczniczych. Szacuje się, że na świecie istnieje około 400 tysięcy gatunków roślin, a 40 tysięcy z nich posiada właściwości farmakologiczne (z których analizie poddano zaledwie około 1,5%). Medycyna naturalna współistnieje z medycyną opartą na współczesnej nauce oraz na lekach syntetycznych i dzisiaj nie ma wątpliwości, że może wspomagać oficjalne metody stosowane przez lekarzy. Ziołolecznictwo stanowi również inspirację dla nowoczesnych metod leczenia, a obecnie obserwujemy nawrót i ponowne odkrywanie jakże bogatej i niezbadanej dotąd matki natury [1,2], Obecnie bardzo szybko rozwijającą się dziedziną (szczególnie w Europie Zachodniej, Japonii i Stanach Zjednoczonych), będącą połączeniem medycyny naturalnej i zielarstwa, jest aromaterapia. Polega ona na wprowadzeniu do organizmu pacjenta poprzez układ oddechowy (inhalacje) lub przez skórę (masaż, kąpiel lub kompresy) biologicznie czynnych substancji z olejków eterycznych pochodzenia roślinnego. Aromaterapia to dosłownie leczenie zapachami, czyli lotnymi substancjami wytwarzanymi przez rośliny, tzw. olejkami eterycznymi. Szczegółowy
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