Discovery of bioactive polycyclic polyprenylated acylphloroglucinols from Hypericum wilsonii

被引：16

作者：

Duan, Yulin ^{[1
]}

Deng, Yanfang ^{[1
]}

Bu, Pengfei ^{[1
]}

Guo, Yi ^{[1
]}

Shi, Zhengyi ^{[1
]}

Cao, Yunfang ^{[1
]}

Zhang, Yeting ^{[1
]}

Hu, Hong ^{[1
]}

Hu, Zhengxi ^{[1
]}

Qi, Changxing ^{[1
]}

Zhang, Yonghui ^{[1
]}

机构：

[1] Huazhong Univ Sci & Technol, Tongji Med Coll, Sch Pharm, Hubei Key Lab Nat Med Chem & Resource Evaluat, Wuhan 430030, Peoples R China

来源：

BIOORGANIC CHEMISTRY | 2021年 / 115卷

基金：

中国国家自然科学基金;

关键词：

Hypericum wilsonii; Polycyclic polyprenylated acylphloroglucinols; Anti-inflammatory activities; Cytotoxic activities; PHLOROGLUCINOL DERIVATIVES; PRODUCT;

D O I：

10.1016/j.bioorg.2021.105246

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

Eleven new polycyclic polyprenylated acylphloroglucinols (PPAPs), hyperwilsones A-K (1-11), along with five known PPAPs (12-16), were isolated from Hypericum wilsonii. Their structures were established via spectroscopic methods, the careful analysis of calculated and experimental electronic circular dichroism (ECD) spectra, singlecrystal X-ray diffraction, the modified Mosher's method, and [Rh2(OCOCF3)4]-induced ECD. Hyperwilsone A (1) and hyperwilsone B (2) possessed the unique acetal functionality. Hyperwilsone C (3) was a rare example of [3.3.1]-type PPAP possessing a 3-isopropylfuran moiety. In bioassay, compounds 9 and 10 showed potent antiinflammatory activity against LPS-induced NO production by inhibiting the nuclear translocation of NF-KB p65 and thus reducing the production of proinflammatory cytokines. Compounds 5, 8, 11, and 14 exhibited moderate inhibitory activity against SUDHL-4 and HL60 cancer cells with IC50 values in the range of 5.74-19.82 mu M.

引用

页数：11

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