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Rosacea) Roots Extract: Bioactivity Guided Fractionation and Cytotoxicity Against Breast Cancer Cell Lines

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Rosacea) Roots Extract: Bioactivity Guided Fractionation and Cytotoxicity Against Breast Cancer Cell Lines ROSA HECKELIANA (ROSACEA) ROOTS EXTRACT: BIOACTIVITY GUIDED FRACTIONATION AND CYTOTOXICITY AGAINST BREAST CANCER CELL LINES A THESIS SUMMITTED TO GRADUATE SCHOOL OF NATURAL AND APPLIED SCIENCES OF MIDDLE EAST TECHNICAL UNIVERSITY BY NİZAMETTİN ÖZDOĞAN IN PARTIAL FULLFILLMENT OF THE REQUIREMENTS FOR THE DEGREE OF DOCTOR OF PHILOSOPHY IN BIOCHEMISTRY OCTOBER 2013 1 2 Approval of the thesis: ROSA HECKELIANA (ROSACEA) ROOTS EXTRACT: BIOACTIVITY GUIDED FRACTIONATION AND CYTOTOXICITY AGAINST BREAST CANCER CELL LINES submitted by NİZAMETTİN ÖZDOĞAN in partial fulfillment of the requirements for the degree of Doctor of Philosophy in Biochemistry Department, Middle East Technical University by, Prof. Dr. Canan ÖZGEN Dean, Graduate School of Natural and Applied Sciences ___________________ Prof. Dr. Orhan ADALI Head of Department, Biochemistry ___________________ _ Assoc. Prof. Dr. Nursen ÇORUH Supervisor, Chemistry Department., METU ____________________ Prof. Dr. Mesude İŞCAN Co-supervisor, Biology Dept., METU ____________________ Examining Committee Members: Prof. Dr. Orhan ADALI Biology Dept., METU ____________________ Assoc. Prof. Dr. Nursen ÇORUH Chemistry Dept., METU ____________________ Prof. Dr. İsmet Deliloğlu GÜRHAN Bioengineering Dept., Ege University ____________________ Prof. Dr. Musa DOĞAN Biology Dept., METU ____________________ Assoc. Prof. Dr. Çagdaş Devrim SON Biology Dept., METU ____________________ Date: 10.10.2013 3 I hereby declare that all information in this document has been obtained and presented in accordance with academic rules and ethical conduct. I also declare that, as required by these rules and conduct, I have fully cited and referenced all material and results that are not original to this work. Name, Last name: Nizamettin ÖZDOĞAN Signature : iv ABSTRACT ROSA HECKELIANA (ROSACEA) ROOTS EXTRACT: BIOACTIVITY GUIDED FRACTIONATION AND CYTOTOXICITY AGAINST BREAST CANCER CELL LINES ÖZDOĞAN, Nizamettin Ph.D., Deparment of Biochemistry Supervisor: Doç.Dr. Nursen ÇORUH Co-supervisor: Prof.Dr. Mesude İŞCAN October, 2013, 150 pages The genus Rosa, including about 100 species, is found to have a wide distribution throughout Europe, Asia, the Middle East and North America. Rosa heckeliana being a member of Rosa genus has been frequently used in folk medicine. Medicinal plants used in folk medicine are found to reveal their therapeutic effect due to their high content of phenolic compounds. These phenolic compounds contained in Rosacea families are located in their fruits and roots, most abundantly. This study was designed to determine the anti-oxidative and anti-proliferative properties of the roots of R. heckeliana. Roots of the plant were extracted crudely in methanol. The polyphenolic compounds of the crude extract were concentrated and separated by using bioactivity guided solvent-solvent fractionation process. All the fractions and the crude extract were subjected to antioxidant activity assays. Eventually, ethyl acetate fraction, among the others, has been found to expose the highest antioxidant properties. Therefore, the ethyl acetate fraction was further carried out for quantitative and qualitative analyses to reveal its phenolic components. Main phenolic compounds in the ethyl acetate fraction were purified by simple chromatographic methods using “Silica gel 60” and “Sephadex LH-20”. There were three major compounds isolated, they were also identified and characterized using NMR (Carbon and Proton) and HR-MS techniques. These three compounds found in the ethyl acetate fraction, in major amounts, were namely catechin, caffeic acid and ellagic acid. In the same fraction, there were also other phenolic compounds present in minor amounts, they were only subjected to identification through spectroscopic and chromatographic methods (RP-HPLC, UV-Vis spectroscopy). Identifiable compounds were epicatechin, p-coumaric acid, scopoletin and quercetin, and their structures were also confirmed by HR-MS technique. v Additionally, the anti-proliferative properties of the roots of Rosa heckeliana were examined by using XTT method. Crude extract, ethyl acetate fraction, and the isolated major phenolic components as well as matching standard compounds were all compared for their cytotoxicity on breast cancer cell lines; MCF-7 and MDA-231. The isolated major phenolic compounds were demonstrating moderate cytotoxicity, while the crude extract and ethyl acetate fraction verified only minimal cytotoxicity. Keywords: Rosa heckeliana, antioxidants, RP-HPLC, cytotoxic effects. vi ÖZ GÜL KÖK ÖZÜTLERİNİN BİYOAKTİVİTE REHBERLİ FRAKSİYONLANMASI VE MEME KANSERİ HÜCRE HATLARINA KARŞI SİTOTOKSİSİTESİ ÖZDOĞAN, Nizamettin Doktora, Biyokimya Bölümü Tez Yöneticisi: Doç.Dr. Nursen ÇORUH Ortak Tez Yöneticisi: Prof.Dr. Mesude İŞCAN Ekim 2013, 150 sayfa Avrupa, Asya, Orta Doğu ve Güney Amerika’da geniş bir yayılım gösteren Gülgiller, bünyesinde yaklaşık 100 tür barındırmaktadır. Bu cinsin üyelerinden olan Rosa heckeliana, halk arasında bitkisel ilaç olarak sık sık kullanılmaktadır. Halk arasında bitkisel ilaç olarak kullanılan tıbbi bitkiler, yüksek miktarda fenolik bileşik ihtiva ettiklerinden dolayı terapötik etki göstermektedirler. Rosacea familyasında bulunan bu fenolik bileşiklerin meyve ve köklerde bol miktarda bulunduğu tespit edilmiştir. Bu çalışma, R. heckeliana köklerinin antioksidatif ve antiproliferatif özelliklerini araştırmak için tasarlanmıştır. Bitkinin kökleri ham olarak metanolde özüt haline getirildi. Ham özütün fenolik bileşikleri, bioaktivite rehberli sıvı sıvı fraksiyonlama işlemi kullanılarak yoğunlaştırıldı ve ayrıldı. Tüm fraksiyonlar ve ham özüt antioksidan aktivite denemesine tabi tutuldu. Sonuç olarak, etil aseat fraksiyonu diğerlerine göre en yüksek antioksidan özellik sergiledi. Bu nedenle, etil aseat fraksiyonunun fenolik bileşiklerinin ortaya çıkarılması için ileri kantitatif ve kalitatif analizleri yapıldı. Etil asetat fraksiyonu içerisindeki büyük fenolik bileşikler, basit kromatografi metodları “Silica gel 60” ve “Sephadex LH-20” kullanılarak saflaştırıldı. NMR (Karbon ve Proton) ve HR-MS teknikleri kullanılarak tanımlanan ve karakterize edilen üç büyük bileşik izole edildi. Kateşin, kafeik asit ve ellagik asit olarak adlandırılan bu üç bileşik büyük miktarlarda etil asetat fraksiyonunda bulundu. Aynı fraksiyonda, küçük miktarlardaki diğer fenolik bileşikler sadece spektroskopik ve kromatografik metotlar (RP-HPLC, UV- Vis spectroscopy) kullanılarak tanımlamaya tabi tutuldu. Epikateşin, p-kumarik asit, skopoletin ve kersetin tanımlanabilen bileşiklerdi ve yapıları da HR-MS tekniği ile doğrulandı. vii Bunlara ek olarak, R.heckeliana’ın köklerinin antiproliferatif özellikleri XTT metodu kullanılarak incelendi. Ham özüt, etil asetat fraksiyonu, ve izole edilen büyük fenolik bileşiklerin antiproliferatif aktiviteleri, MCF-7 ve MDA-MB-231 meme kanser hücre hatlarında uygun standart bileşiklerle karşılaştırılmıştır. Ham özüt ve etil asetat fraksiyonu sadece minimal sitotoksisite gösterirken, izole edilen büyük fenolik bileşikler ılımlı sitotoksisite göstermiştir. Anahtar kelimeler: Rosa heckeliana, antioksidanlar, RP-HPLC, sitotoksisite viii To my beloved wife and daughter ix ACKNOWLEDGEMENTS This study was carried out in the Biochemistry Department, Department of Biological Sciences, The Middle East Technical University, during the years 2007-2013. I am most indebted to my guide and supervisor Dr. Nursen ÇORUH, Associate Professor, Department of Chemistry, Middle East Technical University, Ankara, for her valuable advices as well as for encouraging guidance, positive attitude and for enlightening my professional and academic vision throughout my study. I would like to gratefully thank and to express my gratitude to co-supervisor Prof.Dr.Mesude İŞCAN for her guidance and valuable advices. I have learned lots from her. I would like to also thanks to Prof. Dr. Mesude İŞCAN to give me opportunity to use her laboratory equipment. I apprecite Prof.Dr.İsmet DELİLOĞLU GÜRHAN and Assoc.Prof. Dr. Çagdaş Devrim SON for contributions to the study, for their valuable suggestions and encouragements, throughout the research. I would like to thank to our botanist Assist.Prof.Dr.Fevzi ÖZGÖKÇE for collecting our plant samples and his collaboration. I acknowledge examining committee members Prof. Dr. Orhan ADALI and Prof. Dr. Musa DOĞAN for evaluating my thesis and their contributions I am also grateful for all past and present members of Nursen Çoruh Research Group Ömer Faruk GERDAN, Burak BARUT, Can NEBİGİL, Yeşim KÜMBET, Şule ŞAHİN, Aslıgül AKSOY and Özge KAYA. I would like to express my sincere thanks to Dr.Pembegül UYAR, Dr.Can YILMAZ, Assit.Prof.Dr.Metin KONUŞ, Assit.Prof.Dr.Gökhan SADİ, Selis YILMAZ, Elif AŞIK, Bade KAYA, Elif SAKALLI, Serkan TUNA, Muhammet TEKŞAN, Dr.Kubilay YILDIRIM, Assoc. Prof. Dr Ferhat CELEP and Nermin ŞAHAN for their endless support, patience, helps, friendship, and motivation throughout this work. I am thankful Binnur ÖZKAN and METU Central Laboratory, Mass Spectroscopy Laboratory for HR-MS analyses of R. heckeliana L. I would like to also thank all my friends for everything. x The most important, I thank my beloved wife Dilek for her love, support, encouragement and patient. Finally I thank my dearest, adorable and peanut daughter Elif Ceren for being the sunshine of my life and teaching me how to live in a moment. I am very grateful to my family for their eternal love, encouragement and trust. This study was supported by the Research Fund of METU OYP Grant No: BAP-08-11- DPT-2002K120510 xi TABLE
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