TY - JOUR
T1 - Biotransformation of Neoruscogenin by the Endophytic Fungus Alternaria eureka
AU - Özçlnar, Özge
AU - Özgür Taǧ, O.
AU - Yusufoglu, Hasan
AU - Kivçak, Bijen
AU - Bedir, Erdal
N1 - Publisher Copyright:
© 2018 American Chemical Society and American Society of Pharmacognosy.
PY - 2018/6/22
Y1 - 2018/6/22
N2 - 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.
AB - 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.
UR - https://www.scopus.com/pages/publications/85049097127
U2 - 10.1021/acs.jnatprod.7b00898
DO - 10.1021/acs.jnatprod.7b00898
M3 - Article
C2 - 29893560
AN - SCOPUS:85049097127
SN - 0163-3864
VL - 81
SP - 1357
EP - 1367
JO - Journal of Natural Products
JF - Journal of Natural Products
IS - 6
ER -