Bioactive polycyclic polyprenylated acylphloroglucinols from Hypericum perforatum
Guo, Yi1; Zhang, Na1; Sun, Weiguang1; Duan, Xueyan1; Zhang, Qing1; Zhou, Qun1; Chen, Chunmei1; Zhu, Hucheng1; Luo, Zengwei1; Liu, Junjun1; Li, Xiao-Nian2; Xue, Yongbo1; Zhang, Yonghui1
2018-11-21
发表期刊ORGANIC & BIOMOLECULAR CHEMISTRY
ISSN1477-0520
卷号16期号:43页码:8130-8143
摘要Fifteen new polycyclic polyprenylated acylphloroglucinols (PPAPs), hyperforatones A-O (1-15), along with 3 structurally related analogues (16-18), were isolated from the stems and leaves of Hypericum perforatum. Their structures and absolute configurations were established by a combination of NMR spectroscopic analyses, experimental and calculated electronic circular dichroism (ECD), modified Mosher's methods, Rh-2(OCOCF3)(4)- and [Mo-2(OAc)(4)]-induced ECD, X-ray crystallography, and the assistance of quantum chemical predictions (QCP) of C-13 NMR chemical shifts. Compound 5 was found to be the first PPAP decorated by a rare 2,2,4,4,5-(pentamethyltetrahydrofuran-3-yl)methanol moiety and an oxepane ring. Furthermore, the isolates were screened for their acetylcholinesterase (AChE) and -site amyloid precursor protein cleaving enzyme 1 (BACE1) inhibitory activities. Compounds 5, 10, 11, and 15 showed desirable AChE inhibitory activities (IC50 6.9-9.2 M) and simultaneously inhibited BACE1 (at a concentration of 5 M) with inhibition rates of 50.3%, 34.3%, 47.2%, and 34.6%, respectively. Interestingly, compound 5 showed the most balanced inhibitory activities against both AChE and BACE1 of all the tested compounds, which means that 5 could serve as the first valuable dual-targeted PPAP for the treatment of Alzheimer's disease. Preliminary molecular docking studies of 5 with BACE1 and AChE were also performed.
资助信息Program for Changjiang Scholars of the Ministry of Education of the People's Republic of China; National Natural Science Foundation for Distinguished Young Scholars; National Natural Science Foundation of China; Innovative Research Groups of the National Natural Science Foundation of China; Fundamental Research Funds for the Central Universities of HUST; Graduates' Innovation Fund of HUST
收录类别SCI
语种英语
资助项目Program for Changjiang Scholars of the Ministry of Education of the People's Republic of China[T2016088] ; National Natural Science Foundation for Distinguished Young Scholars[81725021] ; National Natural Science Foundation of China[31770379] ; National Natural Science Foundation of China[81641129] ; National Natural Science Foundation of China[21502057] ; Innovative Research Groups of the National Natural Science Foundation of China[81721005] ; Fundamental Research Funds for the Central Universities of HUST[5003514014] ; Fundamental Research Funds for the Central Universities of HUST[2016YXMS149] ; Fundamental Research Funds for the Central Universities of HUST[2018JYCXJJ006] ; Graduates' Innovation Fund of HUST[5003514018]
文献类型期刊论文
条目标识符http://ir.kib.ac.cn/handle/151853/63165
专题植物化学与西部植物资源持续利用国家重点实验室
通讯作者Xue, Yongbo; Zhang, Yonghui
作者单位1.Huazhong Univ Sci & Technol, Sch Pharm, Tongji Med Coll, Hubei Key Lab Nat Med Chem & Resource Evaluat, Wuhan 430030, Hubei, Peoples R China
2.Chinese Acad Sci, Kunming Inst Bot, State Key Lab Phytochem & Plant Resources West Ch, Kunming 650204, Yunnan, Peoples R China
推荐引用方式
GB/T 7714
Guo, Yi,Zhang, Na,Sun, Weiguang,et al. Bioactive polycyclic polyprenylated acylphloroglucinols from Hypericum perforatum[J]. ORGANIC & BIOMOLECULAR CHEMISTRY,2018,16(43):8130-8143.
APA Guo, Yi.,Zhang, Na.,Sun, Weiguang.,Duan, Xueyan.,Zhang, Qing.,...&Zhang, Yonghui.(2018).Bioactive polycyclic polyprenylated acylphloroglucinols from Hypericum perforatum.ORGANIC & BIOMOLECULAR CHEMISTRY,16(43),8130-8143.
MLA Guo, Yi,et al."Bioactive polycyclic polyprenylated acylphloroglucinols from Hypericum perforatum".ORGANIC & BIOMOLECULAR CHEMISTRY 16.43(2018):8130-8143.
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