title: 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.
abstract: 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-Δ3-2-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 and the SI value.
authors.affiliation: Department of Natural Product Chemistry, Shanghai Institute of Materia Medica, Chinese Academy of Sciences , Shanghai 201203, People's Republic of China.
authors.forename: Luo-Yi
authors.initials: LY
authors.lastname: Wang
authors.affiliation: Department of Natural Product Chemistry, Shanghai Institute of Materia Medica, Chinese Academy of Sciences , Shanghai 201203, People's Republic of China.|University of Chinese Academy of Sciences , No. 19A Yuquan Road, Beijing 100049, People's Republic of China.
authors.forename: Jun-Jun
authors.initials: JJ
authors.lastname: Qin
authors.affiliation: Department of Natural Product Chemistry, Shanghai Institute of Materia Medica, Chinese Academy of Sciences , Shanghai 201203, People's Republic of China.
authors.forename: Zhen-Hua
authors.initials: ZH
authors.lastname: Chen
authors.affiliation: State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences , Shanghai 201203, People's Republic of China.
authors.forename: Yu
authors.initials: Y
authors.lastname: Zhou
authors.affiliation: State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences , Shanghai 201203, People's Republic of China.
authors.forename: Wei
authors.initials: W
authors.lastname: Tang
authors.affiliation: State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences , Shanghai 201203, People's Republic of China.
authors.forename: Jian-Ping
authors.initials: JP
authors.lastname: Zuo
authors.affiliation: Department of Natural Product Chemistry, Shanghai Institute of Materia Medica, Chinese Academy of Sciences , Shanghai 201203, People's Republic of China.
authors.forename: Wei-Min
authors.identifier: 0000-0001-8879-069X
authors.initials: WM
authors.lastname: Zhao
mesh_terms: D049109:Cell Proliferation / Q000187:drug effects; D006027:Glycosides / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D007166:Immunosuppressive Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D015394:Molecular Structure; D031109:Periploca / Q000737:chemistry*; D018517:Plant Roots / Q000737:chemistry; D011278:Pregnanes / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D013601:T-Lymphocytes / Q000187:drug effects
chemical_list: D006027:Glycosides; D007166:Immunosuppressive Agents; D011278:Pregnanes; C000621398:periploside C; C000621399:periploside F; C574437:pregnane glycoside