New prenylated flavonoid glycosides derived from Epimedium wushanense by β-glucosidase hydrolysis and their testosterone production-promoting effects.
10.1016/S1875-5364(22)60188-2
- Author:
Xin-Guang SUN
1
;
Xu PANG
1
;
Hai-Zhen LIANG
1
;
Jie ZHANG
1
;
Bei WANG
1
;
Qi LI
1
;
Jie WANG
1
;
Xiao-Juan CHEN
1
;
Bao-Lin GUO
2
;
Bai-Ping MA
3
Author Information
1. Department of Pharmaceutical Sciences, Beijing Institute of Radiation Medicine, Beijing 100850, China.
2. Institute of Medicinal Plant Development, Chinese Academy of Medical Sciences & Peking Union Medical College, Beijing 100193, China.
3. Department of Pharmaceutical Sciences, Beijing Institute of Radiation Medicine, Beijing 100850, China. Electronic address: mabaiping@sina.com.
- Publication Type:Journal Article
- Keywords:
Biotransformation;
Epimedium wushanense;
Prenylated flavonoids;
Regulation on testosterone production
- MeSH:
Animals;
Epimedium/chemistry*;
Flavonoids/chemistry*;
Furans;
Glycosides/chemistry*;
Hydrolysis;
Male;
Molecular Docking Simulation;
Molecular Structure;
Rats;
Testosterone;
beta-Glucosidase/metabolism*
- From:
Chinese Journal of Natural Medicines (English Ed.)
2022;20(9):712-720
- CountryChina
- Language:English
-
Abstract:
Six new prenylated flavonoid glycosides, including four new furan-flavonoid glycosides wushepimedoside A-D (1-4) and two new prenyl flavonoid derivatives wushepimedoside E-F (5-6), and one know analog epimedkoreside B (7) were isolated from biotransformation products of the aerial parts of Epimedium wushanense. Their structures were elucidated according to comprehensive analysis of HR-MS and NMR spectroscopic data, and the absolute configurations were assigned using experimental and calculated electronic circular dichroism (ECD) data. The regulatory activity of compounds 1-7 on the production of testosterone in primary rat Leydig cells were investigated, and 4 and 5 exhibited testosterone production-promoting activities. Molecular docking analysis suggested that bioactive compounds 4 and 5 showed the stable binding with 3β-HSD and 4 also had good affinity with Cyp17A1, which suggested that these compounds may regulate testosterone production through stimulating the expression of the above two key proteins.
