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Phytochemical and Biological Investigations on Scutellaria Hastifolia L

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Phytochemical and Biological Investigations on Scutellaria Hastifolia L T.C. YEDİTEPE UNIVERSITY INSTITUTE OF HEALTH SCIENCES DEPARTMENT OF PHARMACOGNOSY PHYTOCHEMICAL AND BIOLOGICAL INVESTIGATIONS ON SCUTELLARIA HASTIFOLIA L. IN THE PARTIAL FULFILMENT OF THE REQUIREMENTS FOR THE DEGREE OF DOCTOR OF PHILOSOPHY Hilal Bardakcı Altan, Pharm. Advisor Prof. Dr. Hasan Kırmızıbekmez ISTANBUL JUNE 2014 1 T.C. YEDİTEPE UNIVERSITY INSTITUTE OF HEALTH SCIENCES DEPARTMENT OF PHARMACOGNOSY PHYTOCHEMICAL AND BIOLOGICAL INVESTIGATIONS ON SCUTELLARIA HASTIFOLIA L. IN THE PARTIAL FULFILMENT OF THE REQUIREMENTS FOR THE DEGREE OF DOCTOR OF PHILOSOPHY Hilal Bardakcı Altan, Pharm. Advisor Prof. Dr. Hasan Kırmızıbekmez ISTANBUL JUNE 2014 2 3 Dedication Dedicated to my grandmother and grandfather, Muradiye and Mehmet Emin I love you i Acknowledgements There are moments as a milestone in life, and there are persons, make those moments alive. By coming to end of this thesis, first of all, I would like to express my gratitude to the man who makes this moment happen; my advisor, Prof. Dr. Hasan Kırmızıbekmez. His guidance and wisdom enlighted the way of this study in every aspect. I have been extremely lucky to have a supervisor who cared so much about my work, and who responded to my questions and queries so promptly. I would also express my deep appreciation to Prof. Dr. Erdem Yeşilada for providing me the assistantship and for his continous advice during this study. The joy and enthusiasm he has for every research was contagious and motivational for me, even during tough times in the PhD. pursuit. Both of their precious contributions will continue to guide me not only for this study, but also for my life. I woulds also like to thank Assoc. Prof. Dr. Ebru Türköz Acar for helping me during my HPLC studies. She never hesitated to share her knowledge with me, and always motivated me during my studies. I will always be greatly indebted to her. My dear friend Tanja Milosevic who took my NMRs while she was pregnant, thank you, and I should also thank to the little girl, Evangelia, for letting her mom to help me. Prof. Dr. Helen Skaltsa, Prof. Dr. Dimitra Hadjipavlou Litina and Dr. Diamanto Lazari; I would like to thank all of you for carrying out not only my NMR studies also my antioxidant ve antiinflammatory activity assays. Moreover you all are always understanding, gentle and loving to me. Greece was the best part of this thesis, I will always be thankful to you all. I wish to thank everyone that I have worked with over the years, Derya Algül, Ece Gürdal, Etil Güzelmeriç, Burcu Şen, İrem Atay and Engin Celep, you are not only my collegues, all of you are also my friends forever. Thanks all to you for your patience, sincere help and kindness to me for years. I would like to thank Yeditepe University, Faculty of Pharmacy and its valuable members. This place is not only my workplace; it is also my second home. I came here when I was 17, just a confused teenage for her future, and now I am 28 and I can stand on my own feet now, owing that to you. I would also like to thank Assoc. Prof. Dr. Çiğdem Kaspar for performing the statistical analyses of my biological activity studies without any doubt. The people who inspire, care, understand and always stand with me; my beloved mother, Güzide Bardakcı, super father, Zafer Bardakcı and lovely sister, Gülen Bardakcı. Thank you for believing and supporting me. And of course my husband, Soner Altan, the man who I shared my thoughts, laughed and dreamt for ten years together. Thank you for all those good memories. Furthermore, TUBITAK and GSRT is greatly acknowledged for financial support. This study was partially funded by TUBITAK-SBAG (Project no: 109S480) and GSRT. ii Abstract Scutellaria L. (Lamiaceae) species have long been the subject of many phytochemical, analytical and biological studies. In the context of this thesis, four Scutellaria taxa, S. hastifolia L., S. velenovskyi Rech., S. orientalis L. subsp. pinnatifida and S. albida L. subsp. albida from Turkey were screened for their antioxidant profiles by calculating their total antioxidant capacities as well as total phenol and total flavonoid contents. Based on the preliminary data, S. hastifolia was selected for the detailed phytochemical and biological investigations. From the acetone and MeOH extracts, 17 compounds were isolated, including a new one, by using several chromatographic techniques. Isolated compounds were categorized as ethylcyclohexane derivatives (isorengyol, isorengyoside, cleroindicin B, cleroindicin F), phenylethanoid glycosides (cornoside, calceolarioside D, hastifolioside, neocalceolarioside D, calceolarioside B, verbascoside), flavonoids (apigenin 7-O-β-D-glucopyranoside, scutellarein 7-O-β-D- glucopyranoside, hispidulin 7-O-β-D-glucopyranoside, hispidulin 7-O-β-D- glucuronopyranoside), sugar ester (6-O-caffeoylglucopyranose) and sugar molecules (glucose, saccharose). The pure compounds were then investigated for their effects on DPPH, LP and LOX inhibition similarly as crude extracts of S. hastifolia. All crude extracts of S. hastifolia, highly interacted with DPPH, while in LP inhibition assay the acetone extract showed remarkable activity. In LOX inhibition assay, only MeOH extract showed significant inhibition while other extracts did not. Furthermore, all of the isolates highly reacted with DPPH while only glycosides of apigenin and scutellarein along with calceolarioside D showed moderate LP inhibition. Moreover, all of the isolates showed weak soybean LOX inhibition at the tested concentration. Additionally, the qualitative and quantitative analysis of several phenylethanoid glycosides and flavonoids in all Scutellaria species were performed comparatively by using HPLC-DAD in order to characterize their main phenolic constituents. Keywords: Scutellaria hastifolia, antioxidant and antiinflammatory activities, secondary metabolites, hastifolioside, HPLC-DAD iii Özet S. hastifolia Bitkisi Üzerinde Fitokimya ve Biyolojik Aktivite Araştırmaları Scutellaria L. (Lamiaceae) türleri günümüze kadar pek çok fitokimyasal, analitik ve biyolojik aktivite çalışmalarına konu olmuştur. Bu tez kapsamında, Türkiye florasında yetişen dört Scutellaria taksonu (S. hastifolia L., S. velenovskyi Rech., S. orientalis L. subsp. pinnatifida ve S. albida L. subsp. albida) seçilerek ana ekstrelerin total antioksidan kapasiteleri, total fenol ve flavonoid miktarları hesaplanmıştır. Yapılan ön çalışmalar neticesinde, S. hastifolia fitokimyasal ve ileri aktivite çalışmaları için seçilmiştir. S. hastifolia bitkisinin aseton ve MeOH ekstrelerinden çeşitli kromatografik teknikler kullanılarak bir tane yeni olmak üzere toplam 17 bileşik saflaştırılmıştır. Bu bileşikler etilsiklohekzan türevi bileşikler (izorengyol, izorengyozit, kleroindisin B, kleroindisin F), feniletanoit glikozitleri (kornozit, kalkeolariozit D, hastifoliozit, neokalkeolariozit D, kalkeolariozit B, verbaskozit), flavonoitler (apigenin 7-O-β-D-glukopiranozit, skutellarein 7-O-β-D-glukopiranozit, hispidulin 7-O-β-D- glukopiranozit, hispidulin 7-O-β-D-glukuronopiranozit), şeker esteri (6-O-kafeoil-α/β- glukopiranoz) ve şeker molekülleri (glikoz ve sakkaroz) olarak sınıflandırılmıştır. S. hastifolia ana ekstrelerinde olduğu gibi, saf bileşiklerin de DPPH radikal süpürme, LP ve soya LOX inhibisyonu araştırılmıştır. S. hastifolia bitkisinin tüm ekstreleri önemli DPPH radikal süpürücü etki gösterirken sadece aseton ekstresi referansa yakın LP inhibisyonu göstermiştir. LOX inhibisyonu deneyinde sadece MeOH ekstresinde kuvvetli aktivite gözlenmiştir. İzole edilen tüm bileşikler yüksek DPPH radikal süpürücü etki gösterirken, apigenin ve skutellarein glikozitleri ile kalkeolariozit D bileşiği ortalama değerlerde LP inhibisyonu göstermiştir. Bunun dışında tüm bileşikler düşük LOX inhibisyonu göstermişlerdir. Bunlara ilaveten, ekstrelerin temel fenolik bileşiklerinin karakterizasyonu için, bu dört Scutellaria türünde bazı feniletanoit glikozitlerin ve flavonoitlerin HPLC-DAD ile kalitatif ve kantitatif analizleri gerçekleştirilmiştir. Anahtar Kelimeler: Scutellaria hastifolia, antioksidan ve antienflamatuvar aktivite, sekonder metabolitler, hastifoliozit, YPSK-DAD iv Contents Dedication .................................................................................................................................. i Acknowledgements ................................................................................................................... ii Abstract .................................................................................................................................... iii Özet .......................................................................................................................................... iv Contents .................................................................................................................................... v Abbreviations ........................................................................................................................... ix List of Figures ........................................................................................................................... x List of Spectra ......................................................................................................................... xii List of Tables ......................................................................................................................... xiv 1. INTRODUCTION and AIM ................................................................................................. 1 2. GENERAL DESCRIPTION
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