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https://hdl.handle.net/11147/7597
Title: | Biotransformation of neoruscogenin by the endophytic fungus Alternaria eureka | Authors: | Özçınar, Özge Tağ, Özgür Yusufoğlu, Hasan Kıvçak, Bijen Bedir, Erdal |
Keywords: | Neoruscogenin Biotransformation Alternaria eureka Drug synthesis Sapogenins |
Publisher: | American Chemical Society | Source: | Özçınar, Ö., Tağ, Ö., Yusufoğlu, H., Kıvçak, B., and Bedir, E. (2018). Biotransformation of neoruscogenin by the endophytic fungus Alternaria eureka. Journal of Natural Products, 81(6), 1357-1367. doi:10.1021/acs.jnatprod.7b00898 | Abstract: | Biotransformation 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. | URI: | https://doi.org/10.1021/acs.jnatprod.7b00898 https://hdl.handle.net/11147/7597 |
ISSN: | 0163-3864 0163-3864 1520-6025 |
Appears in Collections: | Bioengineering / Biyomühendislik PubMed İndeksli Yayınlar Koleksiyonu / PubMed Indexed Publications Collection Scopus İndeksli Yayınlar Koleksiyonu / Scopus Indexed Publications Collection WoS İndeksli Yayınlar Koleksiyonu / WoS Indexed Publications Collection |
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acs.jnatprod.7b00898.pdf | Makale (Article) | 839 kB | Adobe PDF | View/Open |
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