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Anadolu Üniversitesi HYPERICUM THYMOPSIS BOISS. (HYPERICACEAE) ÜZERİNDE FİTOKİMYASAL VE BİYOAKTİVİTE ÇALIŞMALARI Yüksek Lisans Tezi Benan OKYAY Eskişehir 2020 HYPERICUM THYMOPSIS BOISS. (HYPERICACEAE) ÜZERİNDE FİTOKİMYASAL VE BİYOAKTİVİTE ÇALIŞMALARI Benan OKYAY YÜKSEK LİSANS TEZİ Farmakognozi Anabilim Dalı Danışman: Prof. Dr. Nilgün ÖZTÜRK Eskişehir Anadolu Üniversitesi Sağlık Bilimleri Enstitüsü Temmuz 2020 Bu tez çalışması BAP Komisyonunca kabul edilen 1705S340 no.lu proje kapsamında desteklenmiştir. ÖZET HYPERICUM THYMOPSIS BOISS. (HYPERICACEAE) ÜZERİNDE FİTOKİMYASAL VE BİYOAKTİVİTE ÇALIŞMALARI Benan OKYAY Farmakognozi Anabilim Dalı Anadolu Üniversitesi Sağlık Bilimleri Enstitüsü, Temmuz 2020 Danışman: Prof. Dr. Nilgün ÖZTÜRK Bu çalışmada, Sivas-Kangal-Gürün yakınından toplanan endemik Hypericum thymopsis Boiss’in (Hypericaeae) toprak üstü kısımlarından hazırlanan farklı polaritedeki ekstrelerin ve infüzyonun toplam fenolik madde ve toplam flavonoid içerikleri spektrofotometrik metotla, hiperisin, psödohiperisin ve ayrıca fenolik asitlerinin miktarları ters-faz YBSK- DAD ile belirlenmiştir. Ayrıca, ekstrelerin antioksidan aktivitesi DPPH• serbest radikal süpürücü etki, ABTS katyon radikali süpürücü etki, metal şelatlama ve redükleyici güç tayinleri ile, asetilkolinesteraz ve butirilkolinesteraz enzim inhibisyonu aktivite tayinleri ile, antimikrobiyal aktivite tayini broth dilüsyon yöntemi ile; sitotoksitite çalışmalar ise Caco-2 kolon kanseri ve 3T3 hücre hatlarında gerçekleştirilmiştir. Sonuçlar Hypericum perforatum L. sonuçları ile karşılaştırılmıştır. YBSK ile H. thymopsis’in, H. perforatum’a kıyasla daha az miktarda hiperisin ve psödohiperisin; GK-KS/AID tekniği ile başlıca α-pinen, β-pinen, limonen gibi monoterpenler içerdiği tespit edilmiştir. En yüksek toplam fenolik madde ve toplam flavonoid miktarına sahip etil asetat ekstreleri, çalışılan diğer ekstrelerle karşılaştırıldığında, yüksek AChE enzim inhibisyonu, etil asetat ve %70 metanol ekstresi yüksek metal şelatlayıcı; %70 etanollü ekstresi yüksek serbest radikal süpürücü etki; metanol ekstresi ve infüzyonu yüksek redükleyici güç; sulu ekstresi yüksek ABTS radikal katyon renksizleştirici etki gösterdiği görülmüştür. Ayrıca etil asetat ve metanol ekstreleri çalışılan tüm suşlara karşı diğer ekstrelerden daha iyi aktivite gösterirken kloramfenikole göre belirgin antibakteriyel, Candida suşlarına karşıda yine belirgin antifungal aktivite göstermiştir. Ülkemiz endemik türlerinden biri olan H. thymopsis’in psödohiperisin içeriği ile anti-alzheimer, sitotoksik, antifungal ve antibakteriyel aktiviteleri ilk kez bu çalışmada sunulmuştur. Anahtar sözcükler: Hypericum thymopsis Boiss., Antioksidan, Anti-alzheimer, Sitotoksisite, Naftadiantronlar. iii ABSTRACT PHYTOCHEMICAL AND BIOACTIVITY STUDIES ON HYPERICUM THYMOPSIS BOISS. (HYPERICACEAE) Benan OKYAY Department of Pharmacognosy Anadolu University, Graduate School of Health Sciences, July 2020 Supervisor: Prof. Dr. Nilgün ÖZTÜRK In this study, it was determined the amounts of hypericin, pseudohypericin and also phenolic acids by reversed- phase HPLC-DAD, the total phenolic and total flavonoid contents by the spectrophotometric method, of the different polarity extracts and infusions prepared from the aboveground parts of the endemic Hypericum thymopsis Boiss (Hypericaeae) collected near Sivas-Kangal-Gürün. In addition, it were carried out the antioxidant activity of extracts by DPPH• free radical scavenging effect, ABTS cation radical scavenging effect, metal chelation and reductive power determinations anti- alzheimer activities by acetylcholinesterase and butyrylcholinesterase enzyme inhibition activity determinations; antimicrobial activity by broth dilution method, cytotoxicity studies on Caco2 and 3T3 cell lines. The results were compared with Hypericum perforatum L. results. It has been determined that H. thymopsis contain less amount of hypericin and pseudohypericin compared to H. perforatum by the HPLC; volatile terpenes, α-pinene, β- pinene and limonene by the GC-MS/FID technique. Ethyl acetate extracts with the highest total phenolic substance and total flavonoid amount, compared to other extracts studied, while showing high AChE enzyme inhibition, ethyl acetate and %70 methanol extract; %70 ethanol extract high free radical scavenging effect; methanol extract and infusion high reduction power; the aqueous extract has been shown to have high ABTS radical cation decolorizing effect. In addition, while ethyl acetate and methanol extracts showed better activity against all strains studied than other extracts, it showed significant antibacterial activity compared to chloramphenicol and significant antifungal activity against Candida strains. Pseudohypericin content and anti-alzheimer, cytotoxic, antifungal and antibacterial activities of H. thymopsis, one of the endemic species of our country, were presented for the first time in this study. Keywords: Hypericum thymopsis Boiss., Antioxidant, Anti-alzheimer, Cytotoxicity, Naftadiantrons. iv TEŞEKKÜR Tez çalışmam süresince büyük bir sabır ve anlayışla, desteğini benden hiç ̧ esirgemeyen, değerli bilgilerini bana aktaran, danışman hocam, Prof. Dr. Nilgün ÖZTÜRK’e Laboratuvar çalışmalarım sırasında büyük bir sabır ve anlayışla her zaman yanımda olan, bildiğim her şeyi öğreten Dr. Öğr. Hülya Tuba KIYAN hocama, Tez bitkimin teminini sağlayan Trakya Üniversitesi Eczacılık Fakültesi Farmasötik Botanik ABD öğretim üyesi Doç. Dr. Mehmet TEKİN’e Tezimin uçucu bileşenlerinin GK-KS/AID analizlerimi büyük bir özveriyle gerçekleştiren Prof. Dr. Gülmira ÖZEK hocama, Hücre kültürü çalışmalarımda bana laboratuvarını açan, bilgi ve tecrübeleri ile bana yol gösteren Farmakoloji ABD öğretim üyesiProf. Dr. Miriş DİKMEN hocama, Mikrobiyolojik Analizlerimde Bilgi ve tecrübeleri esirgemeyen Mikrobiyoloji ABD öğretim üyesi Doç. Dr. Zerrin CANTÜRK hocama, Her zaman desteğini hissettiğim sevgili anneme, babama ve kardeşim Zeynep’e teşekkürlerimi sunuyorum. Benan OKYAY v 24/07/2020 ETİK İLKE VE KURALLARA UYGUNLUK BEYANNAMESİ Bu tezin bana ait, özgün bir çalışma olduğunu; çalışmamın hazırlık, veri toplama, analiz ve bilgilerin sunumu olmak üzere tüm aşamalarında bilimsel etik ilke ve kurallara uygun davrandığımı; bu çalışma kapsamında elde edilen tüm veri ve bilgiler için kaynak gösterdiğimi ve bu kaynaklara kaynakçada yer verdiğimi; bu çalışmanın Anadolu Üniversitesi tarafından kullanılan “bilimsel intihal tespit programı”yla tarandığını ve hiçbir şekilde “intihal içermediğini” beyan ederim. Herhangi bir zamanda, çalışmamla ilgili yaptığım bu beyana aykırı bir durumun saptanması durumunda, ortaya çıkacak tüm ahlaki ve hukuki sonuçları kabul ettiğimi bildiririm. vi 24/07/2020 STATEMENT OF COMPLIANCE WITH ETHICAL PRINCIPLES AND RULES I hereby truthfully declare that this thesis is an original work prepared by me; that I have behaved in accordance with the scientific ethical principles and rules throughout the stages of preparation, data collection, analysis and presentation of my work; that I have cited the sources of all the data and information that could be obtained within the scope of this study, and included these sources in the references section; and that this study has been scanned for plagiarism with “scientific plagiarism detection program” used by Anadolu University, and that “it does not have any plagiarism” whatsoever. I also declare that, if a case contrary to my declaration is detected in my work at any time, I hereby express my consent to all the ethical and legal consequences that are involved. vii İÇİNDEKİLER Sayfa JÜRİ ENSTİTÜ ONAYI………………………………………………… i FINAL APPROVAL FOR THESIS…………………………………….. ii ÖZET……………………………………………………………………... iii ABSTRACT………………………………………………………………. iv TEŞEKKÜR ……………………………………………………………… v ETİK İLKE VE KURALLARA UYGUNLUK BEYANNAMESİ……. vi STATEMENT OF COMPLIANCE WITH ETHICAL PRINCIPLES vii AND RULES……………………………………………………………… İÇİNDEKİLER…………………………………………………………… viii ÇİZELGELER DİZİNİ………………………………………………….. xi GÖRSELLER DİZİNİ…………………………………………………… xii ŞEKİLLER DİZİNİ……………………………………………………… xiii SİMGELER ve KISALTMALAR DİZİNİ……………………………... xiv 1. GİRİŞ ve AMAÇ……………………………………………………... 1 2. GENEL BİLGİLER…………………………………………………. 5 2.1. Hypericum Türlerinin Genel Özellikleri……………………… 5 2.1.1. Hypericum thymopsis Boiss…………………………….. 6 2.2. Hypericum Türlerinin Fitokimyasal Özellikleri……………… 8 2.2.1. Naftodiantronlar………………………………………... 8 2.2.2. Floroglusinoller…………………………………………. 13 2.2.3. Flavonoidler……………………………………………... 20 2.2.4. Biflavonlar………………………………………………. 28 2.2.5. Proantosiyanidinler……………………………………... 28 2.2.6. Fenolik asitler…………………………………………… 29 2.2.7. Terpenler………………………………………………... 32 2.2.8. Uçucu yağlar…………………………………………….. 33 2.3. Hypericum Türlerinin Biyolojik Aktiviteleri…………………. 36 viii Sayfa 2.3.1. Antioksidan aktivite…………………………………... 36 2.3.2. AChE ve BChE enzim inhibisyonu aktiviteleri …….. 39 2.3.3. Antimikrobiyal aktivite……………………………….. 43 2.3.4. Sitotoksik aktivite……………………………………... 47 2.3.5. Antidepresan aktivite…………………………………. 55 3. YÖNTEM……………………………………………………………. 57 3.1. Bitki Materyali…………………………………………………. 57 3.2. Kimyasal Maddeler ve Cihazlar………………………………. 58 3.2.1. Kimyasal maddeler…………………………………….. 58 3.2.2. Cihazlar…………………………………………………. 59 3.3. Bitki Ekstrelerinin Hazırlanması……………………………... 60 3.4. Toplam Fenolik Madde Miktarı………………………………. 62 3.5. Toplam Flavonoid Miktarı……………………………………. 63 3.6. YBSK ile Fenolik Asitlerin Miktar Tayini…………………… 63 3.7. YBSK ile Hiperisin ve Psödohiperisin Miktar Tayini……….. 64 3.8. GK-KS/AID ile Uçucu Yağ Bileşimi Tayini………………….. 65 3.9. Antioksidan
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