关键词: Biotransformation Epimedium wushanense Prenylated flavonoids Regulation on testosterone production 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

来  源:   DOI:10.1016/S1875-5364(22)60188-2

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.
摘要:
六种新的异戊烯化黄酮苷,包括4种新的呋喃-黄酮苷乌斯皮米多苷A-D(1-4)和2种新的异戊二烯类黄酮衍生物乌斯皮米多苷E-F(5-6),从乌山淫羊藿地上部分的生物转化产物中分离出一种已知的模拟淫羊藿苷B(7)。根据HR-MS和NMR光谱数据的综合分析,阐明了它们的结构,使用实验和计算的电子圆二色性(ECD)数据分配绝对构型。研究了化合物1-7对原代大鼠睾丸间质细胞产生睾酮的调节活性,4和5表现出促进睾酮产生的活性。分子对接分析表明,生物活性化合物4和5显示出与3β-HSD的稳定结合,4与Cyp17A1也具有良好的亲和力,这表明这些化合物可能通过刺激上述两种关键蛋白的表达来调节睾酮的产生。
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