Chiral separation and absolute configurations of two pairs of racemic polyprenylated benzophenones from Hypericum sampsonii.
(±) Sampsonins A-B (1-2), two pairs of racemic polyprenylated benzophenones, were isolated from the aerial parts of Hypericum sampsonii and successfully separated by chiral HPLC column. Their structures were elucidated by spectroscopic analyses, X-ray diffraction analysis, and quantum chemical calculation of ECD method. Besides, the plausible biogenetic pathways of 1-2 were proposed, and all of them were evaluated for RXRα transcriptional-inhibitory activities and cytotoxicity against HeLa cells.
School of Pharmaceutical Science, Xiamen University, China; College of Traditional Chinese Materia Medica, Shenyang Pharmaceutical University, China.
Wen-Jing
WJ
Tian
Institute of Traditional Chinese Medicine & Natural Products, Jinan University, China.
Yu-Qin
YQ
Qiu
School of Pharmaceutical Science, Xiamen University, China.
Hai-Feng
HF
Chen
College of Chemistry and Chemical Engineering, Lanzhou University, China.
Xiao-Jie
XJ
Jin
State Key Laboratory of Quality Research in Chinese Medicine, Macau Institute for Applied Research in Medicine and Health, Macau University of Science and Technology, Taipa, Macau, China; College of Chemistry and Chemical Engineering, Lanzhou University, China.
Xiao-Jun
XJ
Yao
Institute of Traditional Chinese Medicine & Natural Products, Jinan University, China. Electronic address: daiyi1004@163.com.
Yi
Y
Dai
Institute of Traditional Chinese Medicine & Natural Products, Jinan University, China; College of Traditional Chinese Materia Medica, Shenyang Pharmaceutical University, China. Electronic address: tyaoxs@jnu.edu.cn.
Xin-Sheng
XS
Yao
D001577:Benzophenones / Q000737:chemistry* / Q000302:isolation & purification; D018360:Crystallography, X-Ray; D006367:HeLa Cells; D006801:Humans; D020902:Hypericum / Q000737:chemistry*; D015394:Molecular Structure; D035261:Plant Components, Aerial / Q000737:chemistry; D054876:Prenylation; D047490:Retinoid X Receptor alpha / Q000037:antagonists & inhibitors; D014158:Transcription, Genetic / Q000187:drug effects
D001577:Benzophenones; D047490:Retinoid X Receptor alpha; C000613487:sampsonin A
Hypericum sampsonii; PPBS; RXRα transcriptional-inhibitory activities; biogenetic pathway