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New 8-prenylated quercetin glycosides from the flowers of Epimedium acuminatum and their testosterone production-promoting activities

文献类型：期刊论文

作者Zhang, Yixin; Zhang, Cheng1; Li, Zihan6; Zeng, Cheng2; Xue, Zhen2; Li, Erwei3; Li, Gang4; Li, Juan6; Shen, Guoan; Xu, Chaoqun
刊名FRONTIERS IN CHEMISTRY
出版日期2022
卷号10
关键词Epimedium flavonols phytochemical investigation flowers testosterone production structure-activity relationship Epimedium acuminatum
ISSN号2296-2646
DOI10.3389/fchem.2022.1014110
文献子类Article
英文摘要Phytochemical investigation was carried out for the flowers of Epimedium acuminatum Franchet. by first conducting LC-MS analysis, leading to the identification of 32 compounds. Furthermore, guided by LC-MS profiling, three new 8-prenylated quercetin glycosides (3'-hydroxylikarisoside C, 3'-hydroxylepimedoside E, 3'-hydroxyldiphylloside B), one new anthocyanin (delphinidin-3-O-p-coumaroyl-sophoroside) and six known compounds were isolated from the flowers of E. acuminatum for the first time, and their structures were characterized based on spectroscopic methods including 1D and 2D NMR, and HRESIMS. Combining our discoveries and literature survey, a revised classification of Epimedium flavonols was proposed as Type A (8-prenylated kaempferol based), which was further subdivided into subtype icaritin and subtype demethylicaritin, and Type B (8-prenylated quercetin based), which was further subdivided into subtype 3'-hydroxylicaritin and subtype 3'-hydroxyldemethylicaritin. The structure-activity relationship (SAR) study was carried out by comparing testosterone production-promoting activities of all the new compounds along with nine related Epimedium flavonols, revealing that the new 8-prenylated quercetin glycosides (subtype 3'-hydroxyldemethylicaritin in Type B) exhibited lower testosterone production-promoting activities in rat primary Leydig cells than Epimedium flavonols of subtype demethylicaritin in Type A, but possessed higher activities than the Epimedium flavonols of subtype icaritin in Type A. These results suggested that either methylation at C-4' position or hydroxylation at C-3' position of ring B could significantly reduce the testosterone production-promoting activities of Epimedium flavonols.
学科主题Chemistry, Multidisciplinary
出版地LAUSANNE
WOS关键词FLAVONOL GLYCOSIDES ; DIFFERENT PARTS ; LEYDIG ; CELLS
WOS研究方向Science Citation Index Expanded (SCI-EXPANDED)
语种英语
WOS记录号WOS:000876201000001
出版者FRONTIERS MEDIA SA
资助机构CAMS Innovation Fund for Medical Sciences (CIFMS) ; [2021-I2M-1-031]
源URL[http://ir.ibcas.ac.cn/handle/2S10CLM1/28984]  
专题中科院植物分子生理学重点实验室
作者单位1.Chinese Acad Med Sci & Peking Union Med Coll, Key Lab Bioact Subst & Resources Utilizat Chinese, Minist Educ, Inst Med Plant Dev, Beijing, Peoples R China
2.Hubei Univ Chinese Med, Hubei Prov Key Lab Tradit Chinese Med Resource & C, Wuhan, Hubei, Peoples R China
3.Chinese Acad Sci, Inst Bot, Key Lab Plant Mol Physiol, Beijing, Peoples R China
4.Chinese Acad Sci, Inst Microbiol, State Key Lab Mycol, Beijing, Peoples R China
5.Beijing Inst Radiat Med, Dept Pharmaceut Sci, Beijing, Peoples R China
6.Beijing Normal Univ, Coll Life Sci, Key Lab Biodivers Sci & Ecol Engn, Minist Educ, Beijing, Peoples R China
推荐引用方式
GB/T 7714		 Zhang, Yixin,Zhang, Cheng,Li, Zihan,et al. New 8-prenylated quercetin glycosides from the flowers of Epimedium acuminatum and their testosterone production-promoting activities[J]. FRONTIERS IN CHEMISTRY,2022,10.
APA Zhang, Yixin.,Zhang, Cheng.,Li, Zihan.,Zeng, Cheng.,Xue, Zhen.,...&Guo, Baolin.(2022).New 8-prenylated quercetin glycosides from the flowers of Epimedium acuminatum and their testosterone production-promoting activities.FRONTIERS IN CHEMISTRY,10.
MLA Zhang, Yixin,et al."New 8-prenylated quercetin glycosides from the flowers of Epimedium acuminatum and their testosterone production-promoting activities".FRONTIERS IN CHEMISTRY 10(2022).

入库方式： OAI收割

来源：植物研究所

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