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E Z G I E R Soy Ist a N B U L Ü N Ive R Sit E Si Sa Ğ . B Il. E N St EZGİ ERSOY İSTANBUL ÜNİVERSİTESİ SAĞ. BİL. ENST. DOKTORA TEZİ İSTANBUL -2019 T.C. İSTANBUL ÜNİVERSİTESİ SAĞLIK BİLİMLERİ ENSTİTÜSÜ ( DOKTORA TEZİ ) ULUDAĞ’DA YETİŞEN ÜÇ HYPERICUM TÜRÜNÜN KİMYASAL BİLEŞİKLERİ VE BİYOLOJİK AKTİVİTELERİ ÜZERİNDE ARAŞTIRMALAR EZGİ ERSOY DANIŞMAN PROF. DR. AFİFE MAT FARMAKOGNOZİ ANABİLİM DALI FARMAKOGNOZİ PROGRAMI İSTANBUL-2019 ii iii BEYAN Bu tez çalışmasının kendi çalışmam olduğunu, tezin planlanmasından yazımına kadar bütün safhalarda etik dışı davranışımın olmadığını, bu tezdeki bütün bilgileri akademik ve etik kurallar içinde elde ettiğimi, bu tez çalışmayla elde edilmeyen bütün bilgi ve yorumlara kaynak gösterdiğimi ve bu kaynakları da kaynaklar listesine aldığımı, yine bu tezin çalışılması ve yazımı sırasında patent ve telif haklarını ihlal edici bir davranışımın olmadığını beyan ederim. iv İTHAF Beni ben yapan her şeyi borçlu olduğum babam, annem, kardeşim ve çok özlediğim babanneme… v TEŞEKKÜR Doktora çalışmasına başlamamdaki en büyük sebep, sadece akademik çalışmalarımda değil, hayatın her alanında her zaman bana yol gösteren, her şeyiyle örnek aldığım hocama, Farmakognozi Anabilim Dalı Başkanı ve aynı zamanda tez danışmanım olan Prof. Dr. Afife Mat ‘a sonsuz saygılarımla teşekkür ederim. Bu tezde benim kadar emeği olan, hem hocam; artık hem de ablam, çok sevdiğim ve saydığım, benim için çok özel bir insana, Dr. Öğr. Üyesi Esra Eroğlu Özkan’a, bana yıllardır sabrettiği, ihtiyaç duyduğum her zaman yanımda olduğu ve beni desteklediği için binlerce kez teşekkür ederim. Bitkilerimin teşhisinde ve botanik açıdan incelenmesinde yardımcı olan Farmasötik Botanik Anabilim Dalı Başkanı Prof. Dr. Emine Akalın Uruşak ve Prof. Dr. Şükran Kültür’e teşekkür ederim. Tezimin antimikrobiyal aktivite çalışmalarında yardımını esirgemeyen Dr. Öğr. Üyesi Emel Mataracı Kara’ya teşekkür ederim. Dicle Üniversitesi Eczacılık Fakültesi Farmasötik Teknoloji Anabilim Dalı Başkanı Doç. Dr. Mehmet Boğa’ya, çalışmamın her aşamasında yardımcı olduğu için sonsuz teşekkür ederim. Beni her zaman en çok destekleyen kişi olan ve sahip olduğum her şeyi borçlu olduğum babam Vedat Ersoy’a, beni özgür ve bağımsız bir birey olarak yetiştiren annem Fatma Ersoy’a, hayattaki en yakınım olan biricik kardeşim Memduh Efe Ersoy’a, hayatımda oldukları için nasıl teşekkür edeceğimi bilemesem de bu vesileyle teşekkür etmek isterim. Birbirimizi tamamladığımıza inandığım canım arkadaşım Başak Cebe Şen’e, hep yanımda olan Zeynep Ersöz ve Bihter Sayan’a, ayrıca adını sayamayacağım tüm yakın arkadaşlarıma teşekkür ederim. Zorlandığım anlarda en büyük yardımcım her zaman arkadaşlarım oldu, çok şanslı olduğumu biliyor ve onları çok seviyorum. Birlikte nice elitliklere… Bu çalışmaya başladığım günden itibaren bilgisinden faydalandığım, öncelikle Hypericum üzerine çalışmış olanlar olmak üzere, farmakognozi bilimine ve insanlığa katkıda bulunmuş tüm bilim insanlarına sonsuz saygı ve teşekkürlerimi sunuyorum. Bu çalışmayı destekleyen İstanbul Üniversitesi Bilimsel Araştırma Projeleri Birimi’ne teşekkür ederim. Bu çalışma İstanbul Üniversitesi Bilimsel Araştırma Projeleri Birimi tarafından desteklenmiştir. Proje No: 58219 vi Hypericum perforatum / Uludağ – Bursa Fotoğraflar: Dr. Öğr. Üyesi Hasan Şahin vii Hypericum calycinum / Uludağ - Bursa viii Hypericum confertum / Uludağ – Bursa ix 1. İÇİNDEKİLER TEZ ONAYI ................................................................................................................... İİ BEYAN .......................................................................................................................... İİİ İTHAF ............................................................................................................................ İV TEŞEKKÜR ................................................................................................................... V İÇİNDEKİLER ............................................................................................................. İX TABLOLAR LİSTESİ .............................................................................................. Xİİİ ŞEKİLLER LİSTESİ .................................................................................................. XV SEMBOLLER / KISALTMALAR LİSTESİ ........................................................ XVİİ ÖZET ........................................................................................................................ XXİİ ABSTRACT ............................................................................................................. XXİİİ 1. GİRİŞ VE AMAÇ ....................................................................................................... 1 2. GENEL BİLGİLER .................................................................................................... 4 2.1. Botanik Özellikler ................................................................................................. 4 2.1.1. Hypericaceae Familyası ............................................................................. 4 2.1.2. Hypericum L. Cinsi ..................................................................................... 5 2.1.2.1. Hypericum perforatum L……………...…………………………11 2.1.2.2. Hypericum calycinum L................................................................ 12 2.1.2.3. Hypericum confertum Choisy ....................................................... 13 2.2. Etimoloji .............................................................................................................. 14 2.3. Hypericum Türlerinin Ekonomik Açıdan Önemi ................................................ 15 2.4. Arazi Çalışmalarının Yapıldığı Uludağ Bölgesi’nin Özellikleri ......................... 17 2.5. Kimyasal Özellikler ............................................................................................ 19 2.5.1. Naftodiantron Türevi Bileşikler ................................................................ 22 2.5.2. Floroglusinol Türevi Bileşikler ................................................................. 25 2.5.3. Flavonoitler ............................................................................................... 34 2.5.4. Fenolik Asitler........................................................................................... 38 2.5.5. Tanenler ve Proantosiyanidinler ............................................................... 41 2.5.6. Ksanton Bileşikleri .................................................................................... 42 2.5.7. Uçucu Yağ Bileşikleri ............................................................................... 44 2.6. Farmakolojik Etkiler ........................................................................................... 46 x 2.6.1. Antidepresan Etki ...................................................................................... 48 2.6.2. Yara İyileştirici Etki .................................................................................. 54 2.6.3. Antimikrobiyal Etki .................................................................................. 56 2.6.4. Antioksidan Etki ....................................................................................... 63 2.6.5. Sitotoksik Etki ........................................................................................... 66 2.6.6. Antienflamatuar Etki ................................................................................. 68 2.6.7. Analjezik ve Antinosiseptif Etki ............................................................... 70 2.6.8. Premenstrual Sendrom Üzerine Etki ......................................................... 73 2.6.9. Menopoz Semptomları Üzerine Etki ......................................................... 74 2.6.10. Bağımlılık Üzerine Etki .......................................................................... 76 2.6.11. Nörodejeneratif Hastalıklar Üzerine Etki ............................................... 77 2.6.12. Diğer Etkiler ............................................................................................ 79 2.6.13. Farmakokinetik Özellikleri ..................................................................... 82 2.6.14. Yan Etkileri ve Kontrendikasyonları ...................................................... 83 2.6.15. Gebelik ve Laktasyonda Kullanımı......................................................... 85 2.6.16. İlaç Etkileşimleri ..................................................................................... 85 2.6.17. Toksisitesi ............................................................................................... 87 3. GEREÇ VE YÖNTEM ............................................................................................. 90 3.1. Materyal .............................................................................................................. 90 3.2. Genel Metotlar .................................................................................................... 91 3.2.1. Ekstrelerin Hazırlanması ........................................................................... 91 3.2.2. LC-MS/MS ile 37 Fitokimyasal Maddenin Tanımlanması ve Kantitatif Analizi ....................................................................................................... 91 3.2.2.1. LC-MS/MS Cihazı ve Kromatografik Şartlar .............................. 91 3.2.3. Antioksidan Aktivite Tayini...................................................................... 92 3.2.3.1. Antioksidan Aktivite Tayin Yöntemleri ....................................... 94 3.2.3.1.1. Toplam
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