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ISOLATION and CHARACTERIZATION of SAPONINS from ASTRAGALUS Halicacabus and ASTRAGALUS Melanocarpus SPECIES

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ISOLATION and CHARACTERIZATION of SAPONINS from ASTRAGALUS Halicacabus and ASTRAGALUS Melanocarpus SPECIES EGE UNIVERSITY GRADUATE SCHOOL OF NATURAL AND APPLIED SCIENCES (Ph.D. THESIS) ISOLATION AND CHARACTERIZATION OF SAPONINS FROM ASTRAGALUS halicacabus AND ASTRAGALUS melanocarpus SPECIES Basile-Jimmy DJIMTOMBAYE Supervisor: Prof. Dr. Hüseyin ANIL Co-Supervisor: Prof. Dr. Özgen ALANKUŞ ÇALIŞKAN Department of Chemistry Department Code: 405.02.01 Presentation Date: 11.09.2014 Bornova-İZMİR 2014 II III Basile-Jimmy DJIMTOMBAYE tarafından Doktora tezi olarak sunulan “Isolation and Characterization of Saponins from Astragalus halicacabus and Astragalus melanocarpus species” başlıklı bu çalışma E.Ü. Lisansüstü Eğitim ve Öğretim Yönetmeliği ile E.Ü. Fen Bilimleri Enstitüsü Eğitim ve Öğretim Yönergesi’nin ilgili hükümleri uyarınca tarafımızdan değerlendirilerek savunmaya değer bulunmuş ve 11.09.2014 tarihinde yapılan tez savunma sınavında aday oybirliği/oyçokluğu ile başarılı bulunmuştur. Jüri Üyeleri : İmza Jüri Başkanı : Prof. Dr. Hüseyin ANIL ………………… Raportör : Prof. Dr. Erdal BEDİR ………………… Üye : Prof. Dr. Özgen ÇALIŞKAN ………………… Üye : Doç. Dr. Tamer KARAYILDIRIM ………………… Üye : Yrd. Doç. Dr. Kadir AY ………………… IV V EGE ÜNİVERSİTESİ FEN BİLİMLERİ ENSTİTÜSÜ ETİK KURALLARA UYGUNLUK BEYANI E.Ü. Lisansüstü Eğitim ve Öğretim Yönetmeliğinin ilgili hükümleri uyarınca Doktora Tezi olarak sunduğum “Isolation and Characterization of Saponins from Astragalus halicacabus and Astragalus melanocarpus Species.” başlıklı bu tezin kendi çalışmam olduğunu, sunduğum tüm sonuç, doküman, bilgi ve belgeleri bizzat ve bu tez çalışması kapsamında elde ettiğimi, bu tez çalışmasıyla elde edilmeyen bütün bilgi ve yorumlara atıf yaptığımı ve bunları kaynaklar listesinde usulüne uygun olarak verdiğimi, tez çalışması ve yazımı sırasında patent ve telif haklarını ihlal edici bir davranışımın olmadığını, bu tezin herhangi bir bölümünü bu üniversite veya diğer bir üniversitede başka bir tez çalışması içinde sunmadığımı, bu tezin planlanmasından yazımına kadar bütün safhalarda bilimsel etik kurallarına uygun olarak davrandığımı ve aksinin ortaya çıkması durumunda her türlü yasal sonucu kabul edeceğimi beyan ederim. 11.09.2014 Basile-Jimmy DJIMTOMBAYE VI VII ÖZET ASTRAGALUS halicacabus ve ASTRAGALUS melanocarpus TÜRLERİNDEN SAPONİNLERİN İZOLASYONU ve KARAKTERİZASYONU Basile-Jimmy DJIMTOMBAYE Doktora Tezi, Kimya Anabilim Dalı Tez Danışmanı: Prof. Dr. Hüseyin ANIL İkinci Tez Danışmanı: Prof. Dr. Özgen ALANKUŞ ÇALIŞKAN Eylül 2014, 166 sayfa Astragalus L., yaklaşık 3000 türle Leguminosae familyasındaki en geniş cinstir. Türkiye florasında 224 tanesi endemik olmak üzere toplam 445 türle temsil edilmektedir (Davis, 1970; Aytaç, 2000). Astragalus türlerinin kökleri çok eski yıllardan beri halk arasında terlemeyi önleyici, tonik ve diüretik olarak kullanılagelmektedir. Ayrıca yine şeker hastalığının, nefritin, löseminin ve rahim kanserinin tedavisinde kullanım alanı bulmaktadır (Tang and Eisenbrand, 1992). Anadolu’da, Türkiye’nin Güney- Doğusu’nda Astragalus köklerinin sulu ekstreleri geleneksel olarak lösemiye karşı ve yara iyileştirici olarak kullanılmaktadır (Çaliş et al.,2008; Bedir et al., 2000). Astragalus köklerinin bilinen biyolojik aktif bileşenleri, polisakkaritler ve saponinler olmak üzere iki temel kimyasal bileşik sınıfında toplanmıştır (Tang and Eisenbrand, 1992). Bugüne kadar 400’dan fazla sikloartan yapısında saponin tanımlanmış ve bunların arası yaklaşık 200 Astragalus cinsinden izole edilmiştir (Mamedova and Isaev, 2004; Li-Peng et al., 2013). Sikloartan yapısındaki saponinlerin en zengin kaynağını oluşturan Astragalus (Leguminosea) cinsine ait türler, bu türlerin ekstreleri ve bunlardan izole edilen bileşikler, bağışıklık uyarıcı, karaciğer koruyucu, antioksidan, antiviral, ateş düşürücü, kardiovasküler, iltihap giderici ve anti kanser etkiler göstermeleri nedeniyle giderek artan bir şekilde ilgi odağı haline gelmiştir (Rios and Waterman, 1997; Verotta El-Sebakhy, 2001). VIII Türkiye Astragalus türlerinden biyolojik olarak aktif bileşiklerin izolasyonuna ilişkin devam eden çalışmalarımız kapsamında Astragalus halicacabus Lam.ve Astragalus melanocarpus Bunge. bitkileri çalışılmıştır. Astragalus halicacabus bitkisinden 1 yeni sikloartan-tipi glikozit (halicacoside A, AHa1), 1 yeni maltol glikozit (halicacoside B, AHa2) ile birlikte 7 bilinen sikloartan-tipi glikozit (3-7) ve 1 bilinen maltol glikozit (10) izole edilmiştir. Astragalus melanocarpus bitkisinden 3 yeni saponin ile birlikte 7 bilinen saponin izole edilmiştir.. İzole edilen bu bileşiklerin yapıları, 1D- ve 2D- NMR teknikleri, ESIMS ve HRMS analizleri kullanılarak belirlenmiştir. Anahtar Sözcükler: Leguminosae, Astragalus halicacabus, Astragalus melanocarpus, sikloartan, oleanan, maltol, saponin. IX ABSTRACT ISOLATION AND CHARACTERIZATION OF SAPONINS FROM ASTRAGALUS halicacabus AND ASTRAGALUS melanocarpus SPECIES Basile-Jimmy DJIMTOMBAYE Ph.D. Thesis in Chemistry Supervisor: Prof. Dr. Hüseyin ANIL Co-Supervisor: Prof. Dr. Özgen ALANKUŞ ÇALIŞKAN September 2014, 166 pages Astragalus L. (Leguminosae), one of the largest genera of flowering plants with about 3000 species, is represented in the flora of Turkey by 445 species, 224 of which are endemic (Davis, 1970; Aytaç, 2000). The roots of Astragalus species represent a very old and well-known drug in traditional medicine for their usage as an antiperspirant, tonic and diuretic. The have also been used in the treatment of diabetes mellitus, nephritis, leukemia and uterine cancer (Tang and Eisenbrand, 1992). In the district of Anatolia, located in South Eastern Turkey, an aqueous extract of the roots of Astragalus is traditionally used against leukemia and for its wound-healing properties (Çaliş et al.,2008; Bedir et al., 2000). Modern pharmacological studies of Astragalus species indicated the multiple biological activities, such as antioxidative, immunomodulation, cardiovascular, cerebrovascular diseases, neurodegenerative diseases, liver diseases, infectious diseases and antiviral properties, etc (Li-Peng et al., 2013). Known biologically active constituents of Astragalus roots represent two major classes of chemical compounds, polysaccharides and saponins (Tang and Eisenbrand, 1992; Li-Peng et al., 2013). Up to now, more than 400 cycloartane- type saponins were determined and around 200 of them were isolated from Astragalus genus (Mamedova and Isaev, 2004; Li-Peng et al., 2013). X Furthermore, the species of Astragalus genus (Leguminosae) which are the richest source of cycloartane type saponins have attracted increasing interest because of their extract’s and isolated compound’s wide range of biological activities known as anti-inflammatory, hepatoprotective, antipyretic, immunostimulant and anti cancer (Rios and Waterman, 1997; Verotta El-Sebakhy, 2001) . In our ongoing research for new bioactive compounds from Turkish Astragalus species, we carried out a study on two Astragalus species, namely Astragalus halicacabus.Lam. and Astragalus melanocarpus Bunge. One new cycloartane-type triterpene glycoside (halicacoside A, AHa1) , one new maltol glycosides (halicacoside B, AHa2), were isolated from Astragalus halicacabus along with seven known cycloartane-type glycosides (3-7) and one known maltol glycosides (10). Moreover, three new saponins were isolated from Astragalus melanocarpus along with five known compounds. Their structures were established by the extensive use of 1D and 2D-NMR experiments along with ESIMS and HRMS analysis. Keywords: Leguminosae, Astragalus halicacabus, Astragalus melanocarpus, cycloartane, oleanane, maltol, saponin. XI ACKNOWLEDGMENT This study was carried out at the Department of Chemistry, Ege University, Science Faculty, İzmir from 2008 to 2014 I am deeply grateful to Prof. Dr. Hüseyin ANIL, to Prof. Dr. Özgen ALANKUŞ ÇALIŞKAN and to Prof. Dr. Erdal BEDİR for their noble availability and precious suggestion, support, patience and for enlightening me via their deep knowledge during long years their experience, despite their heavy responsibility helped us in this study. I am also very grateful to Assoc. Prof. Dr Tamer KARAYILDIRIM for his all valuable advice, help, suggestion and support during this study. Our discussions on the completion of the thesis have been of great value. All my gratitude to him. The major credit for this scientific merit goes especially to them for their efficiency and help. My thanks to the Turkish governmet for this fellowship which allowed me to complete this doctoral study. I owe my special thanks to Prof. Dr. Sonia PIACENTE and her group for running my compounds spectra. I am grateful to Assoc Prof. Dr. Fevzi Özgökçe for the identification of Astragalus halicacabus and Astragalus melanocarpus. This project was granted by TUBITAK (109T425), Ege University Science and Technology Center (EBİLTEM) (2010 Bil 008) and Ege University Research Foundation (2009 FEN 090). I would like to thank them for their financial support. I also would like to thank TUBITAK for ( Ph.D). fellowship. My deep gratitude and special thanks goes to Mireille and Richard PARIENTE to whom I dedicate this scientific work to testify their noble friendship during my studies and my stay in Turkey. XII I am grateful to Juan Gabriel FERRONE, Priest of Göztepe for his help, supports and the long time of sharing with all parishioners during my study. I’m very thankful to my unforgettable constant companion ATILE and DJIBATI for showing patience and tolerance supported my long absence from them (during my working-times). Finally, I would thank all my family, all my teachers and friends in Ege University for their good intention. Specially
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