Hypermonones A-I,New Polyprenylated Acylphloroglucinols from Hypericum monogynum with Multidrug Resistance Reversal Activity  

作　　者：Yan-Rong Zeng Ya-Nan Li Jue Yang Ping Yi Lei Huang Lie-Jun Huang Wei Gu Zhan-Xing Hu Yan-Mei Li Chun-Mao Yuan Xiao-Jiang Hao 

机构地区：[1]State Key Laboratory of Functions and Applications of Medicinal Plants,Guizhou Medical University,Guiyang,Guizhou 550014,China [2]The Key Laboratory of Chemistry for Natural Products of Guizhou Province and Chinese Academy of Sciences,Guiyang,Guizhou 550014,China [3]State Key Laboratory of Phytochemistry and Plant Resources in West China,Kunming Institute of Botany,Chinese Academy of Sciences,Kunming,Yunnan 650201,China

出　　处：《Chinese Journal of Chemistry》2021年第9期2422-2432,共11页中国化学（英文版）

基　　金：supported by the National Natural Science Foundation of China(Nos.U1812403,81872772,and 81960546);the Scie nee and Tech no logy Departme nt of Guizhou Province(Nos.QKH 2020-1Z076,QKHZC[2020]4Y203z QKHJC[2018]1409,QKHZC[2019]2762,and QKHPTRC[2020]5008);the High-level Innovative Talents in Guizhou Provinee(Thousand Levels of Talent for Chunmao Yuan in 2018);the"Light of the West"Talent Cultivation Program of Chinese Academy of Sciences for Chunmao Yuan(No.RZ[2020]82);the 100 Leading Talents of Guizhou Provinee(fund for Y.M.L);the Guizhou Provincial Engineering Research Center for Natural Drugs.

摘　　要：Eleven biogenetically related polyprenylated acylphloroglucinols(PPAPs),including four novel skeletons(1-4)and five new com-pounds(5-9),were isolated from the flowers of Hypericum monogynum.Hypermonones A-D(1-4)represented the first example of a unique dilactone structure containing carbonyl bonded single 5-lactone and tricyclic γ-lactone moieties.Their structures were elucidated by NMR analysis,X-ray crystallography,and ECD calculations.Moreover,we revised the structure of hyperibrin B to hy perm on one I(9)via NMR an alysis,a qua ntum computational chemistry method,and hypothetic bios yn thetic con siderations.Three compounds(5,6,and 9)with significant MDR reversal activity(RF ranging from 61 to 223)were superior to the positive control verapamil(MCF-7/ADR,RF:53;HepG2/ADRz RF:124).Mechanism study for compound 5 indicated that this compound could inhibit the function of P-gp tran sport rather tha n its expressi on,and the possible recog nition mechanism betwee n compo und 5 and P-gp was predicted by molecular docking.

关 键 词：Hypericum monogynum PHYTOCHEMISTRY Structure elucidation Biological activity Multidrug resistance reversal activity 

分 类 号：O62[理学—有机化学]