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

doi:10.3389/fchem.2022.1014110

	New 8-prenylated quercetin glycosides from the flowers of Epimedium acuminatum and their testosterone production-promoting activities
	Zhang, Yixin ; Zhang, Cheng 1; Li, Zihan 2; Zeng, Cheng 3; Xue, Zhen 3; Li, Erwei 4; Li, Gang 5; Li, Juan 2; Shen, Guoan ; Xu, Chaoqun ; Wang, Yuanyue ; Ma, Baiping 5; Zhang, Hui 3; Guo, Baolin
	2022
发表期刊	FRONTIERS IN CHEMISTRY
ISSN	2296-2646
卷号	10
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.
关键词	Epimedium flavonols phytochemical investigation flowers testosterone production structure-activity relationship Epimedium acuminatum
学科领域	Chemistry, Multidisciplinary
DOI	10.3389/fchem.2022.1014110
收录类别	SCI
语种	英语
WOS关键词	FLAVONOL GLYCOSIDES ; DIFFERENT PARTS ; LEYDIG ; CELLS
WOS研究方向	Science Citation Index Expanded (SCI-EXPANDED)
WOS记录号	WOS:000876201000001
出版者	FRONTIERS MEDIA SA
文献子类	Article
出版地	LAUSANNE
资助机构	CAMS Innovation Fund for Medical Sciences (CIFMS) ; [2021-I2M-1-031]
作者邮箱	zhhui12@ibcas.ac.cn ; blguo@implad.ac.cn
作品OA属性	gold, Green Published
引用统计
文献类型	期刊论文
条目标识符	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.Beijing Normal Univ, Coll Life Sci, Key Lab Biodivers Sci & Ecol Engn, Minist Educ, Beijing, Peoples R China 3.Hubei Univ Chinese Med, Hubei Prov Key Lab Tradit Chinese Med Resource & C, Wuhan, Hubei, Peoples R China 4.Chinese Acad Sci, Inst Bot, Key Lab Plant Mol Physiol, Beijing, Peoples R China 5.Chinese Acad Sci, Inst Microbiol, State Key Lab Mycol, Beijing, Peoples R China 6.Beijing Inst Radiat Med, Dept Pharmaceut Sci, 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).

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