Biotransformation 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. hiratsukaЖe 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.
Cunninghamella blakesleeana, microbial biotransformation, neoruscogenin, Neosartorya hiratsukae, ruscogenins, ruscus
NCBI PubMed ID: 29689318Publication DOI: 10.1016/j.phytochem.2018.04.002Journal NLM ID: 0151434Publisher: Elsevier
Correspondence: Bedir E
Institutions: Department of Pharmacognosy, Faculty of Pharmacy, Ege University, İzmir, Turkey, Bionorm Natural Products Production & Marketing Corp., İTOB, İzmir, Turkey, Department of Pharmacognosy, College of Pharmacy, Prince Sattam Bin Abdulaziz University, Al-Kharj, Saudi Arabia, Department of Bioengineering, Faculty of Engineering, Izmir Institute of Technology, Izmir, Turkey
Methods: 13C NMR, 1H NMR, TLC, extraction, CC, HMBC, COSY, HR-MS, optical rotation measurements
Found