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T.C. Istanbul Üniversitesi Sağlik Bilimleri Enstitüsü T.C. İSTANBUL ÜNİVERSİTESİ SAĞLIK BİLİMLERİ ENSTİTÜSÜ (DOKTORA TEZİ ) DROSANTHE VE TAENIOCARPIUM SEKSİYONLARINA AİT BAZI ENDEMİK HYPERICUM TÜRLERİNİN KİMYASAL BİLEŞİMİ VE BİYOLOJİK AKTİVİTE YÖNÜNDEN İNCELENMESİ ESRA EROĞLU ÖZKAN DANIŞMAN PROF.DR. AFİFE MAT FARMAKOGNOZİ ANABİLİM DALI FARMAKOGNOZİ PROGRAMI İSTANBUL-2011 ii iii iv İTHAF Hayatımdaki en değerli ve en güzel insan, anneme... v TEŞEKKÜR Bu tezin hazırlanması için gerekli olanakları sağlayan Farmakognozi Anabilim Dalı Başkanı Sayın Prof.Dr. Ali H. Meriçli ve tezimin her aşamasında değerli bilgileri, deneyimleri ve güler yüzü ile bana destek olan Sayın Hocam Prof.Dr. Afife Mat’a saygı ve teşekkürlerimi sunarım. Tez çalışmalarım esnasında bana destek olan Farmakognozi Anabilim Dalı öğretim üyeleri, yardımcıları ve elemanlarına teşekkürlerimi sunarım. Bitkimin teşhisinde ve botanik açıdan incelenmesinde yardımcı olan Farmasötik Botanik Anabilim Dalı Başkanı Prof.Dr. Neriman Özhatay ve Doç.Dr. Şükran Kültür’e teşekkür ederim. Tezimin antimikrobiyal aktivite çalışmalarını yürütmeme olanak sağlayan Farmasötik Mikrobiyoloji Anabilim Dalı Başkanı Prof.Dr. Gülten Ötük’e ve çalışmalarımda yardımını esirgemeyen Doç.Dr. Berna Özbek Çelik’e teşekkür ederim. Antioksidan aktivite çalışmalarımda laboratuvar desteği sağlayan Biyokimya Anabilim Dalı Başkanı Prof.Dr. Ayşe Can’a, bilgi ve deneyimlerini paylaşmaktan kaçınmayan Yrd.Doç.Dr. Nurten Özsoy’a teşekkür ederim. Sitotoksik aktivite çalışmalarımı yürütmeme olanak sağlayan Farmasötik Toksikoloji Anabilim Dalı Başkanı Prof.Dr. Buket Alpertunga’ya, zaman ve emek sarfederek yardımlarını esirgemeyen Doç.Dr. Gül Özhan’a teşekkür ederim. YBSK ile ilgili sorularımı her zaman sabırla yanıtlayan arkadaşım Sena’ya; her türlü sıkıntımı ve sevincimi paylaşan, hep yanımda olan arkadaşlarım Elif, Mercan, Gökçe ve Serpil’e varlıkları ve dostlukları için teşekkür ederim. Uzun süren öğrencilik hayatımın bu son aşamasına kadar her daim arkamda ve yanımda olan, bana inanan ve güvenen canım annem ve babama en içten sevgi, saygı ve teşekkürlerimi sunarım. İnancı, sabrı ve desteği ile her zaman yanımda olan, bu çalışmayı gerçekleştirebilmem için fedakarlığını esirgemeyen sevgili eşim Koray Özdal Özkan’a çok teşekkür ederim. Bu çalışmayı destekleyen İstanbul Üniversitesi Bilimsel Araştırma Projeleri Birimi’ne teşekkür ederim. vi Hypericum spectabile / Arapgir – Malatya (ISTE 93192) vii Hypericum pseudolaeve / Arapgir – Malatya (ISTE 93193) Hypericum thymbrifolium / Darende – Malatya (ISTE 93194) viii Hypericum neurocalycinum / Hadim – Konya (ISTE 93195) Hypericum malatyanum / Doğanşehir – Malatya (ISTE 93196) ix Hypericum perforatum / Kemaliye – Erzincan (ISTE 93197) Fotoğraflar: Esra EROĞLU ÖZKAN x İÇİNDEKİLER TEZ ONAYI .................................................................................................................... İİ BEYAN ........................................................................................................................... İİİ İTHAF ............................................................................................................................ İV TEŞEKKÜR ..................................................................................................................... V İÇİNDEKİLER ................................................................................................................ X TABLOLAR LİSTESİ ................................................................................................ XİV ŞEKİLLER LİSTESİ ................................................................................................ XVİİİ SEMBOLLER / KISALTMALAR LİSTESİ ........................................................... XXİV ÖZET ...................................................................................................................... XXVİİ ABSTRACT ........................................................................................................... XXVİİİ 1. GİRİŞ VE AMAÇ ......................................................................................................... 1 2. GENEL BİLGİLER ...................................................................................................... 4 2.1. Botanik Bölüm ......................................................................................................... 4 2.1.1. Hypericaceae (Guttiferae, Clusiaceae) Familyası ............................................... 4 2.1.2. Hypericum L. Cinsi Genel Özellikleri ................................................................ 4 2.1.3. Drosanthe (Spach) Endl. Seksiyonu Genel Özellikleri ....................................... 5 2.1.3.1. Hypericum spectabile Jaub. & Spach. ............................................................ 7 2.1.3.2. Hypericum pseudolaeve Robson .................................................................... 7 2.1.3.3. Hypericum thymbrifolium Boiss. & Noë ........................................................ 8 2.1.4. Taeniocarpium Jaub. & Spach. Seksiyonu Genel Özellikleri ............................. 9 2.1.4.1. Hypericum neurocalycinum Boiss. & Heldr. ............................................... 10 2.1.4.2. Hypericum malatyanum Peşmen .................................................................. 10 2.1.5. Hypericum Seksiyonu Genel Özellikleri .......................................................... 11 2.1.5.1. Hypericum perforatum L. ............................................................................. 12 2.2. Kimyasal Bölüm .................................................................................................... 13 2.2.1. Naftodiantron Türevi Bileşikler ........................................................................ 13 2.2.2. Floroglusinol Türevi Bileşikler ......................................................................... 14 2.2.3. Flavonoitler ....................................................................................................... 18 2.2.4. Fenolik Asitler ................................................................................................... 20 2.2.5. Tanenler ve Proantosiyanidinler ....................................................................... 22 xi 2.2.6. Ksanton Türevleri ............................................................................................. 22 2.2.7. Uçucu Yağ Bileşikleri ....................................................................................... 24 2.3. Farmakolojik Bölüm .............................................................................................. 25 2.3.1. Antidepresan Aktivite ....................................................................................... 27 2.3.2. Antimikrobiyal Aktivite .................................................................................... 29 2.3.3. Antioksidan Aktivite ......................................................................................... 35 2.3.4. Sitotoksik Aktivite ............................................................................................ 39 2.3.5. Antienflamatuar Etkisi ...................................................................................... 41 2.3.6. Analjezik Etkisi ................................................................................................. 43 2.3.7. Yara İyileştirici Etkisi ....................................................................................... 44 2.3.8. Premenstrüal Sendrom Üzerine Etkisi .............................................................. 45 2.3.9. Bağımlılık Üzerine Etkisi .................................................................................. 46 2.3.10. Diğer Etkileri ................................................................................................... 48 2.3.11. Farmakokinetik Özellikleri ............................................................................. 48 2.3.12. Yan Etkileri ve Kontrendikasyonları .............................................................. 49 2.3.13. Gebelikte Kullanımı ........................................................................................ 51 2.3.14. İlaç Etkileşimleri ............................................................................................. 51 2.3.15. Toksisitesi ....................................................................................................... 52 3. GEREÇ VE YÖNTEM ............................................................................................... 54 3.1. Materyal ................................................................................................................. 54 3.2. Genel Metotlar ....................................................................................................... 55 3.2.1. Yüksek Basınçlı Sıvı Kromatografisi ile Miktar Tayini ................................... 55 3.2.1.1. Naftodiantron, Floroglusinol Türevi Bileşiklerin ve Fenolik Bileşiklerin Yüksek Basınçlı Sıvı Kromatografisi (YBSK) İle Analizi ....................................... 55 3.2.1.2. Ekstrelerin ve Örnek Çözeltilerin Hazırlanması .......................................... 58 3.2.1.3. Standart Çözeltilerin Hazırlanması .............................................................. 59 3.2.1.4. Ölçü Eğrisi Hazırlanması ............................................................................. 59 3.2.2. In vitro Antioksidan Aktivite Araştırması ........................................................ 59 3.2.2.1. Ekstrelerin Hazırlanması .............................................................................
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