Polycyclic polyprenylated acylphloroglucinol with an unprecedented spirocyclic core from Hypericum patulum  

作　　者：Yansong Ye Nana Jiang Xianwen Yang Gang Xu 

机构地区：[1]State Key Laboratory of Phytochemistry and Plant Resources in West China and Yunnan Key Laboratory of Natural Medicinal Chemistry,Kunming Institute of Botany,Chinese Academy of Sciences,Kunming 650201,China [2]Key Laboratory of Marine Biogenetic Resources,Third Institute of Oceanography,Xiamen 361005,China [3]University of Chinese Academy of Sciences,Beijing 100049,China

出　　处：《Chinese Chemical Letters》2020年第9期2433-2436,共4页中国化学快报（英文版）

基　　金：financially supported by the NSFC-Joint Foundation of Yunnan Province(No.U1902213);the Second Tibetan Plateau Scientific Expedition and Research(STEP)Program(No.2019QZKK0502020303);Southeast Asia Biodiversity Research Institute,CAS(No.2017CASSEABRIQG003);the Natural Sciences Foundation of Yunnan Province(No.2019FA003)。

摘　　要：Spirohypatone A(1),a spirocyclic PPAP(polycyclic polyprenylated acylphloroglucinol) bearing an unprecedented hexahydro-1’H-spiro[cyclohexane-1,2’-pentalene]-2,4,6-trione core and a new homologue(spirohypatone B,2) were isolated from Hypericum patulum together with two known biosynthetic precursors.Compound 1 represents the first spirocyclic PPAP possessing a 5/5/6 carbon ring system,biogenetically derived from the intermediate 3(attack from C-3 to C-12),which was differed from normal spirocyclic PPAPs(attack from C-3 to C-11).In addition,through extensive spectroscopic analysis,an interconversion mechanism of keto-enol of 1 was postulated and confirmed by its methylated reaction.The structures and absolute configurations of 1 and 2 were determined by comprehensive spectroscopic and chemical derivatized methods and X-ray crystallography.Compounds 1,2,and 4 were tested to exhibit cytotoxic activities against several cancer cell lines.

关 键 词：Spirocyclic PPAP Hypericum patulum Structural elucidation DERIVATIVES Cytotoxic activities 

分 类 号：R284[医药卫生—中药学]