WoS İndeksli Yayınlar Koleksiyonu / WoS Indexed Publications Collection
Permanent URI for this collectionhttps://hdl.handle.net/11147/7150
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Conference Object Citation - WoS: 1Microbial Transformation of Ruscogenins by Cunninghamella Blakesleeana(Georg Thieme Verlag, 2016) Özçınar, Özge; Tağ, Özgür; Kıvçak, Bijen; Bedir, ErdalThe natural product drug discovery process involves the isolation of new molecules from natural sources, investigation of their biological activities, and semi-synthesis of more active analogs. Microbial transformation plays a vital role in the preparation of new oxygenated derivatives, and has frequently been used as microbial model of mammalian drug metabolism [1,2]. It has been proved that the hydroxylation of steroidal compounds is catalyzed by cytochrome P450 monoxygenase systems, which exist in all eucaryotic microorganisms [3]. Cunninghamella genus has been widely used in transformation of steroids [4,5]. The major steroidal saponins of Ruscus aculeatus, ruscogenin and neoruscogenin, has strong anti-inflammatory activities, acts as an anti-elastase, and decreases capillary permeability [6]. In the present study microbial transformation of Neoruscogenin:Ruscogenin (78:22) mixture by Cunninghamella blakesleeana fungus afforded three new compounds. The structures were elucidated by LC-MS, 1D- and 2D NMR analyses as shown below. Mainly oxydation products were obtained from neoruscogenin by C. blakesleana. As far as can be ascertained from the literature, this is the first microbial transformation study performed on neoruscogenin.Article Citation - WoS: 14Citation - Scopus: 15Biotransformation of Ruscogenins by Cunninghamella Blakesleeana Nrrl 1369 and Neoruscogenin by Endophytic Fungus Neosartorya Hiratsukae(Elsevier Ltd., 2018) Özçınar, Özge; Tağ, Özgür; Yusufoğlu, Hasan; Kıvçak, Bijen; Bedir, ErdalBiotransformation of steroidal ruscogenins (neoruscogenin and ruscogenin) was carried out with Cunninghamella blakesleeana NRRL 1369 and endophytic fungus Neosartorya hiratsukae yielding mainly P450 monooxygenase products together with a glycosylated compound. Fermentation of ruscogenins (75:25, neoruscogenin-ruscogenin mixture) with C. blakesleeana yielded 8 previously undescribed hydroxylated compounds. Furthermore, microbial transformation of neoruscogenin by endophytic fungus N. hiratsukae afforded three previously undescribed neoruscogenin derivatives. While hydroxylation at C-7, C-12, C-14, C-21 with further oxidation at C-1 and C-7 were observed with C. blakesleeana, N. hiratsukae biotransformation provided C-7 and C-12 hydroxylated compounds along with C-12 oxidized and C-1(O) glycosylated derivatives. The structures of the metabolites were elucidated by 1-D (1H, 13C and DEPT135) and 2-D NMR (COSY, HMBC, HMQC, NOESY, ROESY) as well as HR-MS analyses.Article Citation - WoS: 20Citation - Scopus: 24Biotransformation of Neoruscogenin by the Endophytic Fungus Alternaria Eureka(American Chemical Society, 2018) Özçınar, Özge; Tağ, Özgür; Yusufoğlu, Hasan; Kıvçak, Bijen; Bedir, ErdalBiotransformation of neoruscogenin (NR, 1, spirosta-5,25(27)-diene-1β,3β-diol), the major bioactive sapogenin of Ruscus preparations, was carried out with the endophytic fungus Alternaria eureka. Fourteen new biotransformation products (2-15) were isolated, and their structures were elucidated by NMR and HRESIMS data analyses. A. eureka affected mainly oxygenation, oxidation, and epoxidation reactions on the B and C rings of the sapogenin to afford compounds 8-15. In addition to these, cleavage of the spiroketal system as in compounds 2-7 and subsequent transformations provided unusual metabolites. This is the first study reporting conversion of the spirostanol skeleton to cholestane-type metabolites 2-5. Additionally, the cleavage of the C-22/C-26 oxygen bridge yielding a furostanol-type steroidal framework and subsequent formation of the epoxy bridge between C-18 and C-22 in 7 was encountered for the first time in steroid chemistry.