Hyperxylones A and B, two polycyclic polyprenylated acylphloroglucinols with a benzoyl substituted bicyclo[3.2.1]octane core from Hypericum beanii

被引：3
作者：
Li, Xue-Yan [1 ,2 ]
Dong, Rui-Rui [1 ,2 ]
Nan, Miao-Miao [1 ,2 ]
Wang, Xiao-Li [1 ,2 ]
Cao, Tian-Jie [1 ,2 ]
Ying, Ping [3 ]
Zheng, Qiang [3 ]
Kong, Ling-Yi [1 ,2 ]
Xu, Wen-Jun [1 ,2 ]
机构：
[1] China Pharmaceut Univ, Sch Tradit Chinese Pharm, Jiangsu Key Lab Bioact Nat Prod Res, Nanjing 210009, Peoples R China
[2] China Pharmaceut Univ, Sch Tradit Chinese Pharm, State Key Lab Nat Med, Nanjing 210009, Peoples R China
[3] Lishui Univ, Coll Tradit Chinese Med & Hlth Ind, Lishui 323000, Peoples R China
来源：
FITOTERAPIA | 2023年 / 165卷
基金：
中国国家自然科学基金;
关键词：
Hypericum beanii; Bicyclo[3; 2; 1]octane; Polyprenylated acylphloroglucinols; NASH; Anti-inflammatory activity; PHLOROGLUCINOL DERIVATIVES; BIOMIMETIC SYNTHESIS; MEROTERPENOIDS;
D O I：
10.1016/j.fitote.2022.105389
中图分类号：
R914 [药物化学];
学科分类号：
100701 ;
摘要：
Two new polycyclic polyprenylated acylphloroglucinols (PPAPs) possessing a rare benzoyl substituted bicyclo [3.2.1]octane core, hyperxylones A (1) and B (2), along with three new dearomatized isoprenylated acyl-phloroglucinols (DIAPs), hyperxylones C -E (3-5), were isolated from the roots of Hypericum beanii. The structures of 1-5 were determined by high-resolution electrospray ionization mass spectroscopy (HRESIMS) and 1D/2D nuclear magnetic resonance (NMR) spectroscopic analyses, gauge-independent atomic orbital (GIAO) NMR calculations, and electronic circular dichroism (ECD) calculations. Compounds 1 and 2 were bio-mimetically semi-synthesized starting from 5 and 4, respectively, enabling the correct stereochemical assignment of 5 and 4. Moreover, compounds 1 and 2 showed anti-nonalcoholic steatohepatitis (NASH) activity by inhibiting lipid deposition in L02 cells; compounds 3 and 5 exhibited nitric oxide (NO) inhibitory activity in lipopoly-saccharides (LPS)-induced RAW264.7 cells.
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页数：9
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