Absolute Configuration of Periplosides C and F and Isolation of Minor Spiro-orthoester Group-Containing Pregnane-type Steroidal Glycosides from Periploca sepium and Their T-Lymphocyte Proliferation Inhibitory Activities

doi:10.1021/acs.jnatprod.7b00017

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	Absolute Configuration of Periplosides C and F and Isolation of Minor Spiro-orthoester Group-Containing Pregnane-type Steroidal Glycosides from Periploca sepium and Their T-Lymphocyte Proliferation Inhibitory Activities
	Wang, Luo-Yi 2; Qin, Jun-Jun 2,3; Chen, Zhen-Hua 2; Zhou, Yu1 ; Tang, Wei1 ; Zuo, Jian-Ping1 ; Zhao, Wei-Min2
刊名	JOURNAL OF NATURAL PRODUCTS
	2017-04
卷号	80 期号:4 页码:1102-1109
ISSN号	0163-3864
DOI	10.1021/acs.jnatprod.7b00017
文献子类	Article
英文摘要	Further phytochemical investigation of the root bark of Periploca sepium afforded nine new spiro-orthoester group-containing pregnane-type glycosides termed periplosides O-V and 3-O-formyl-periploside A. The structures of these glycosides along with the absolute configuration of the unique seven-membered formyl acetal-bridged spiro-orthoester function and the 4,6-dideoxy-3-O-methyl-Delta(3)-2-hexosulosyl moiety were elucidated on the basis of spectroscopic data interpretation and chemical transformation. The absolute configurations of the major compounds periplosides C and F were established by single crystal X-ray diffraction analysis. The isolated compounds were evaluated for their inhibitory activities against the proliferation of T-lymphocytes. As a result, periploside C, the most abundant glycoside containing a spiro-orthoester moiety found in the plant, exhibited the most favorite selective index value (SI = 82.5). The length and constitution of the saccharide chain in the periplosides were found to influence the inhibitory activity.
资助项目	Science and Technology Commission of Shanghai Municipality[15401901200] ; National Natural Science Foundation[81273399]
WOS关键词	CYTOSOLIC BINDING-PROTEIN ; CHEMICAL-CONSTITUENTS ; ANTITUMOR FRACTION ; CYCLOSPORINE-A ; ENCEPHALOMYELITIS ; CYCLOPHILIN ; BGE
WOS研究方向	Plant Sciences ; Pharmacology & Pharmacy
语种	英语
出版者	AMER CHEMICAL SOC
WOS记录号	WOS:000400538800040
内容类型	期刊论文
源URL	[http://119.78.100.183/handle/2S10ELR8/272715]
专题	药理学第一研究室中科院受体结构与功能重点实验室新药研究国家重点实验室天然药物化学研究室
通讯作者	Zuo, Jian-Ping; Zhao, Wei-Min
作者单位	1.Chinese Acad Sci, Shanghai Inst Mat Med, State Key Lab Drug Res, Shanghai 201203, Peoples R China 2.Chinese Acad Sci, Shanghai Inst Mat Med, Dept Nat Prod Chem, Shanghai 201203, Peoples R China; 3.Univ Chinese Acad Sci, 19A Yuquan Rd, Beijing 100049, Peoples R China;
推荐引用方式 GB/T 7714	Wang, Luo-Yi,Qin, Jun-Jun,Chen, Zhen-Hua,et al. Absolute Configuration of Periplosides C and F and Isolation of Minor Spiro-orthoester Group-Containing Pregnane-type Steroidal Glycosides from Periploca sepium and Their T-Lymphocyte Proliferation Inhibitory Activities[J]. JOURNAL OF NATURAL PRODUCTS,2017,80(4):1102-1109.
APA	Wang, Luo-Yi.,Qin, Jun-Jun.,Chen, Zhen-Hua.,Zhou, Yu.,Tang, Wei.,...&Zhao, Wei-Min.(2017).Absolute Configuration of Periplosides C and F and Isolation of Minor Spiro-orthoester Group-Containing Pregnane-type Steroidal Glycosides from Periploca sepium and Their T-Lymphocyte Proliferation Inhibitory Activities.JOURNAL OF NATURAL PRODUCTS,80(4),1102-1109.
MLA	Wang, Luo-Yi,et al."Absolute Configuration of Periplosides C and F and Isolation of Minor Spiro-orthoester Group-Containing Pregnane-type Steroidal Glycosides from Periploca sepium and Their T-Lymphocyte Proliferation Inhibitory Activities".JOURNAL OF NATURAL PRODUCTS 80.4(2017):1102-1109.