Please use this identifier to cite or link to this item: 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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