Sideritis germanicopolitana Bornm., Sideritis perfoliata L. ve Sideritis libanotica Labill. bitkilerinden sekonder metabolitlerin izolasyonu ve antiproliferatif aktivitelerinin incelenmesi
Isolation and antiproliferative activities of secondary metabolites from Sideritis germanicopolitana Bornm., Sideritis perfoliata L. and Sideritis libanotica Labill.
Yazar: HÜSEYİN AKŞİT
Danışman: PROF. DR. İBRAHİM DEMİRTAŞ
Çankırı Karatekin Üniversitesi / Fen Bilimleri Enstitüsü / Kimya Ana Bilim Dalı
Derece: Doktora, 2017
Konu: Kimya = Chemistry

Özet:
Bu çalışmada, Sideritis germanicopolitana Bornm., Sideritis perfoliata L. ve Sideritis libanotica Labill. türleri fitokimyasal olarak incelendi. Sideritis germanicopolitana bitkisinin metanol özütünden verbaskosid (M1), apigenin-7-O-(6′′-O-p-kumaroil)-β-D-glukopiranosid (M2) klorojenik asit (M3), 3′-O-metilhipolaetin-7-O-(allosil-(1→2)-glikozit) (M4), izoskutellerain-7-O-[6′′′-O-asetil-allosil-(1→2)-glikozit] (M5), 3′-O-metilhipolaetin-7-O-[6′′′-O-asetil-allosil-(1→2)-glikozit] (M6), izoskutellerain-7-O-[6′′′-O-asetil-allosil-(1→2)-6′′-O-asetil-glikozit] (M7), 3′-O-metilhipolaetin-7-O-[6′′′-O-asetil-allosil-(1→2)-6′′′-O-asetil-glikozit] (M8), sideridosid (M9), Sideritis perfoliata bitkisinin metanol özütünden 4′-O-metilizoskutellerain-7-O-[6′′′-O-asetil-allosil-(1→2)-glikozit] (M10), ajugol (M11) ve ajugosid (M12) molekülleri izole edildi. Sideritis perfoliata bitkisinin etil asetat özütünden 13-epi-manoil oksit (SP1), 2-okso-13-epi-manoil oksit (SP2), 2-β-hidroksi-13-epi-manoil oksit (SP3), 7-asetil-izofoliol (SP4), 2-β-format-13-epi-manoil oksit (SP5) ve izolinearol (SP6) molekülleri, Sideritis libanotica bitkisinin etil asetat özütünden siderol (SL1) ve sideridiol (SL2) molekülleri izole edildi. İzole edilen moleküllerin yapıları NMR, MS ve IR gibi spektroskopik yöntemlerle aydınlatıldı. Sideridosid (M9) ve 2-β-format-13-epi-manoil oksit (SP5) moleküllerinin doğal kaynaklarda bulunduğu ilk defa rapor edildi.  Bitkilerin üç farklı organının (gövde, yaprak ve çiçek) metanol özütlerinin ve izole edilen moleküllerin A549, HeLa, Hep3B ve FL hücre hatlarına karşı antiproliferatif etkisi MTT ve BrDU-Eliza yöntemleri ile incelendi. Kauren tipi terpenlerin (SP4, SP6, SL1 ve SL2) yüksek antiproliferatif aktiviteye sahip olduğu belirlendi.

Abstract:
In this study, S. germanicopolitana Bornm., S. perfoliata L. and S. libanotica Labill., plants were examined phytochemically. Verbascoside (M1), apigenin-7-O-(6′′-O-p-coumaroyl)-β-D-glycopyranoside (M2) chlorogenic acid (M3), 3′-O-methylhypolaetin-7-O-(allosyl-(1→2)-glycoside) (M4), isoscutellerain-7-O-[6′′′-O-acetyl-allosyl-(1→2)-glycoside] (M5), 3′-O-methylhypolaetin-7-O-[6′′′-O-acetyl-allosyl-(1→2)-glycoside] (M6), Isoscutellerain-7-O-[6′′′-O-acetyl-allosyl-(1→2)-6′′-O-acetyl-glycoside] (M7), 3′-O-methylhypolaetin-7-O-[6′′′-O-acetyl-allosyl-(1→2)-6′′′-O-acetyl-glycoside] (M8) and sideridoside (M9) were isolated from methanol extract of Sideritis germanicopolitana. 4′-O-methylisoscutellerain-7-O-[6′′′-O-acetyl-allosyl-(1→2)-glycoside] (M10), ajugol (M11) and ajugoside (M12) were also isolated from methanol extract of Sideritis perfoliata L. From ethyl acetate extract of Sideritis perfoliata L., 13-epi-manoyl oxide (SP1), 2-oxo-13-epi-manoyl oxide (SP2), 2-β-hydroxy-13-epi-manoyl oxide (SP3), 7-acetyl-isofoliol (SP4), 2-β-format-13-epi-manoyl oxide (SP5), isolinearol (SP6), from ethyl acetate extract of Sideritis libanotica Labill. siderol (SL1) and sideridiol (SL2) were isolated. The structures of the isolated molecules were determined by spectroscopic methods such as NMR, MS and IR. Sideridoside (M9) and 2-β-format-13-epi-manoyl oxide (SP5) have been reported for the first time. The antiproliferative effect of the methanol extracts of the three different organs of the plants (stem, leaf and flower) and the isolated molecules against the A549, HeLa, Hep3B and FL cell lines was investigated by MTT and BrDU-Elisa methods. The kauren type terpenes (SP4, SP6, SL1 and SL2) were found to have high antiproliferative activity.