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Tanacetum Chiliophyllum (Fisch. & Mey.)

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Tanacetum Chiliophyllum (Fisch. & Mey.) YILDIZ TEKNİK ÜNİVERSİTESİ FEN BİLİMLERİ ENSTİTÜSÜ Tanacetum chiliophyllum (Fisch. & Mey.) Schultz Bip. TÜRÜ VARYETELERİ ÜZERİNDE KARŞILAŞTIRMALI FİTOKİMYASAL VE BİYOLOJİK ARAŞTIRMALAR Kimya Müh. Kaan POLATOĞLU F.B.E. Kimya Anabilimdalı Organik Kimya Programında Hazırlanan DOKTORA TEZİ Tez Savunma Tarihi : 05 Ekim 2009 Tez Danışmanı : Prof. Dr. Nezhun GÖREN (Y.T.Ü.) Jüri Üyeleri : Prof. Dr. Ayhan ULUBELEN (İ.Ü.) : Prof. Dr. Şeniz KABAN (Y.T.Ü.) : Prof. Dr. Gülaçtı TOPÇU (İ.T.Ü.) : Prof. Dr. Belkıs BİLGİN ERAN (Y.T.Ü.) İSTANBUL, 2009 İÇİNDEKİLER Sayfa SİMGE LİSTESİ ........................................................................................................................ v KISALTMA LİSTESİ ...............................................................................................................vi ŞEKİL LİSTESİ ......................................................................................................................viii ÇİZELGE LİSTESİ .................................................................................................................xiii RESİM LiSTESİ .....................................................................................................................xvii ÖNSÖZ....................................................................................................................................xix ÖZET........................................................................................................................................ xx ABSTRACT ............................................................................................................................xxi 1 GİRİŞ..................................................................................................................... 22 1.1 Compositae Familyası ........................................................................................... 23 1.1.1 Tanacetum L. (Emend. Briq.) Cinsi ...................................................................... 24 1.1.2 Tanacetum L. (Emend. Briq.) chiliophyllum (Fisch. & Mey.) Türü ..................... 25 1.1.3 Tanacetum L. (Emend. Briq.) chiliophyllum (Fisch. & Mey.) var. monocephalum Grierson ................................................................................................................. 26 1.1.4 Tanacetum L. (Emend. Briq.) chiliophyllum (Fisch. & Mey.) var. chiliophyllum 28 1.1.5 Tanacetum L. (Emend. Briq.) chiliophyllum (Fisch. & Mey.) var. oligocephalum (D.C.) Sosn. ........................................................................................................... 32 1.1.6 Tanacetum L. (Emend. Briq.) chiliophyllum (Fisch. & Mey.) var. heimerlei (Náb.) ..............................................................................................................................36 1.2 Sekonder Metabolitler........................................................................................... 38 1.2.1 Terpenler................................................................................................................ 38 1.2.1.1 Monoterpenler ....................................................................................................... 41 1.2.1.2 Seskiterpenler ve Seskiterpen Laktonlar ............................................................... 44 1.2.1.3 Triterpenler ............................................................................................................ 50 1.2.2 Flavonoidler........................................................................................................... 54 2 Tanacetum cinsi üzerinde daha önce yapılmış araştırmalar .................................. 57 2.1 Tanacetum cinsindeki bitkilerin uçucu yağları.......................................................57 2.1.1 T. chiliophyllum varyetelerinin uçucu yağları ...................................................... .73 2.2 Tanacetum cinsindeki bitkilerden elde edilen seskiterpen laktonlar ..................... 78 2.2.1 T. chiliophyllum varyetelerinden elde edilen seskiterpen laktonlar .................... 126 2.3 Tanacetum cinsindeki bitkilerden elde edilen flavonoidler.................................. 128 2.3.1 T. chiliophyllum varyetelerinden elde edilen flavonoidler .................................. 140 2.4 Tanacetum cinsindeki bitkilerden elde edilen triterpenler .................................. 141 2.4.1 T. chiliophyllum varyetelerinden elde edilen triterpenler.................................... 143 3 Kullanılan deneysel yöntemler ............................................................................ 144 ii 3.1 Bitkisel Materyal................................................................................................. 144 3.2 Kullanılan Kimyasal Materyal............................................................................. 147 3.3 İzolasyon ve yapı tayininde kullanılan yöntemler............................................... 149 3.3.1 Hidro Distilasyon................................................................................................. 149 3.3.2 Kromatografik Yöntemler ................................................................................... 149 3.3.2.1 Kolon kromatografisi (CC).................................................................................. 149 3.3.2.2 Vakum sıvı kromatografisi (VLC) ...................................................................... 150 3.3.2.3 İnce tabaka kromatografisi (TLC) ....................................................................... 150 3.3.2.4 Orta basınçlı sıvı kromatografisi (MPLC)........................................................... 151 3.3.2.5 Yüksek basınçlı sıvı kromatografisi (HPLC) ...................................................... 152 3.3.2.6 Yüksek performanslı ince tabaka kromatografisi (HPTLC)................................ 153 3.3.2.7 Gaz Kromatografisi (GC) .................................................................................... 155 3.3.2.7.1 Gaz Kromatografisi Kütle Spektrometresi Analizi (GC-MS) ............................. 155 3.3.2.7.2 Gaz Kromatografisi (GC-FID) ............................................................................ 155 3.3.2.7.3 Uçucu yağ bileşenlerinin belirlenmesi ................................................................ 155 3.3.3 Spektroskopik yöntemler..................................................................................... 156 3.3.3.1 Infra-Red spektroskopisi (IR).............................................................................. 156 3.3.3.2 UV/VIS. spektroskopisi....................................................................................... 156 3.3.3.3 Nükleer manyetik rezonans spektroskopisi (NMR) ............................................ 157 3.3.3.4 Kütle spektroskopisi (MS)................................................................................... 157 3.4 Yapılan Biyolojik Aktivite Çalışmaları............................................................... 158 3.4.1 Antimikrobiyal Aktivite...................................................................................... 158 3.4.2 Sitotoksik Aktivite............................................................................................... 158 3.4.3 Antioksidan Özellik............................................................................................. 159 3.4.4 İnsektisidal Aktivite............................................................................................. 160 3.5 Erime noktası tayini............................................................................................. 161 3.6 Kullanılan programlar.......................................................................................... 162 4. Elde edilen sonuçlar............................................................................................. 163 4.1 Uçucu Yağlar....................................................................................................... 163 4.1.1 T. chiliophyllum var. monocephalum’un uçucu yağları...................................... 164 4.1.2 T. chiliophyllum var. chiliophyllum’un uçucu yağları........................................ 164 4.1.3 Uçucu yağların birbirleriyle karşılaştırılması ...................................................... 165 4.2 İzole edilen maddeler........................................................................................... 193 4.2.1 T. chiliophyllum var. monocephalum’dan izole edilen maddeler........................ 193 4.2.1.1 TCVM 1 - 1-epi-Chiliophyllin ............................................................................ 197 4.2.1.2 TCVM 2 – Olean-12,13-en-3β,10β-olid.............................................................. 223 4.2.1.3 TCVM 3 – Lup-12,13-en-3β-asetat (Neolupenil asetat) ..................................... 240 4.2.1.4 TCVM 4 – 4',5,7-Trihidroksi-3’8-dimetoksiflavon............................................. 243 4.2.1.5 TCVM 5 – 4',5,7-Trihidroksi-8-metoksiflavon ................................................... 245 4.2.2 T. chiliophyllum var. oligocephalum’dan izole edilen maddeler......................... 247 4.2.2.1 TCVO 1 - 5-Hidroksi-3΄,4΄,6,7-tetrametoksiflavon ........................................... 252 4.2.2.2 TCVO 2 - 5,7-Dihidroksi-3΄,4΄,6-trimetoksiflavon............................................. 254 4.2.2.3 TCVO 3 – 4'5-Dihidroksi-6,7-dimetoksiflavon................................................... 256 4.2.2.4 TCVO 4 - 4',5-Dihidroksi-3΄,6,7-trimetoksiflavon ............................................. 258
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