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
Issue Date: Jun-2018
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

Files in This Item:
File Description SizeFormat 
acs.jnatprod.7b00898.pdfMakale (Article)839 kBAdobe PDFThumbnail
View/Open
Show full item record

CORE Recommender

SCOPUSTM   
Citations

4
checked on Nov 26, 2022

WEB OF SCIENCETM
Citations

12
checked on Nov 26, 2022

Page view(s)

520
checked on Nov 21, 2022

Download(s)

148
checked on Nov 21, 2022

Google ScholarTM

Check

Altmetric


Items in GCRIS Repository are protected by copyright, with all rights reserved, unless otherwise indicated.