Hyperbenzones A and B,two 1,2-seco and rearranged polycyclic polyprenylated acylphloroglucinols from Hypericum beanii  

作　　者：Weijia Lu Yanqiu Zhang Yawei Li Shengtao Ye Jun Luo Lingyi Kong Wenjun Xu 

机构地区：[1]Jiangsu Key Laboratory of Bioactive Natural Product Research and State Key Laboratory of Natural Medicines,School of Traditional Chinese Pharmacy,China Pharmaceutical University,Nanjing 210009,China

出　　处：《Chinese Chemical Letters》2022年第8期4121-4125,共5页中国化学快报（英文版）

基　　金：supported by the National Natural Science Foundation of China(Nos.31900287 and 81773886);the 111 Project from Ministry of Education of China and the State Administration of Foreign Export Affairs of China(No.B18056);Special fund from the Central Committee for guiding local scientific and technological development of Shenzhen(No.2021Szvup161)。

摘　　要：Two novel seco-polycyclic polyprenylated acylphloroglucinols(PPAPs),hyperbenzones A(1)and B(2),were isolated from the roots of Hypericum beanii,together with one known biosynthetic congener 3.Compound 1 incorporates a 6/5/5 ring system with an unprecedented spiro[bicyclo[3.3.0]octane-3,1'-cyclohexane]-2,2'-dione motif.The structures of 1 and 2 were determined by a combination of high resolution electrospray ionization mass spectroscopy(HRESIMS),nuclear magnetic resonance(NMR)spectroscopic analyses,gage-independent atomic orbital(GIAO)NMR chemical shift calculation with DP4+analyses,electronic circular dichroism(ECD)calculation,and X-ray diffraction analysis.A 1,2-seco retroClaisen rearrangement from a bicyclo[3.3.1]nonane PPAP precursor and following chemodivergent radical cascade cyclizations are proposed as the key steps in the biosynthetic pathway to yield compounds 1 and2.Biological investigations indicated that compounds 1 and 3 could decrease intracellular lipid accumulation in a palmitic acid-induced nonalcoholic steatohepatitis(NASH)cell model.

关 键 词：seco-PPAPs Hypericum beanii Hyperbenzones A and B NASH 1 2-seco-Bicyclic derivatives 

分 类 号：TQ317[化学工程—高聚物工业]