Prenylated phloroglucinol derivatives from Hypericum sampsonii

被引:28
作者
Xin, Wen-bo [1 ]
Man, Xiao-hua [2 ]
Zheng, Cheng-jian [1 ]
Jia, Min [1 ]
Jiang, Yi-ping [1 ]
Zhao, Xiang-xiang [1 ]
Jin, Gui-lin [1 ]
Mao, Zhu-jun
Huang, Hai-qiu [3 ]
Qin, Lu-ping [1 ]
机构
[1] Second Mil Med Univ, Sch Pharm, Dept Pharmacognosy, Shanghai 200433, Peoples R China
[2] Second Mil Med Univ, Changhai Hosp, Dept Gastroenterol, Shanghai 200433, Peoples R China
[3] Univ Maryland, Dept Nutr & Food Sci, College Pk, MD 20742 USA
关键词
Hypericum sampsonii; Phloroglucinol; Sampsonol; Cytotoxicity; Anti-inflammatory activity; BENZOYLPHLOROGLUCINOL DERIVATIVES; BENZOPHENONE DERIVATIVES; UNIQUE FAMILY; XANTHONES;
D O I
10.1016/j.fitote.2012.08.022
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
Six new acylphloroglucinol derivatives, sampsonols A-F (1-6), were isolated from the petroleum ether extract of the aerial parts of Hypericum sampsonii. The structures and relative configurations of sampsonols A-F were elucidated by extensive spectroscopic analyses. All these compounds were tested for their in vitro cytotoxic and anti-inflammatory activities. Sampsonols A and B (1 and 2) showed significant cytotoxicity against four human tumor cell lines with IC50 values in the range of 13-28 mu M, whereas sampsonols C and F (3 and 6) showed potent inhibitory activities against LPS-induced NO production in RAW 264.7 macrophages with IC50 values of 27.3 and 293 mu M, respectively. (C) 2012 Elsevier B.V. All rights reserved.
引用
收藏
页码:1540 / 1547
页数:8
相关论文
共 18 条
[1]   Prenylated Acylphloroglucinols, Chipericumins A-D, from Hypericum chinense [J].
Abe, Shuhei ;
Tanaka, Naonobu ;
Kobayashi, Jun'ichi .
JOURNAL OF NATURAL PRODUCTS, 2012, 75 (03) :484-488
[2]  
Avato P, 2005, STUD NAT PROD CHEM, V30, P603
[3]  
CHEN M-T, 1985, Heterocycles (Tokyo), V23, P2543
[4]   New phenolic principles from Hypericum sampsonii [J].
Don, MJ ;
Huang, YJ ;
Huang, RL ;
Lin, YL .
CHEMICAL & PHARMACEUTICAL BULLETIN, 2004, 52 (07) :866-869
[5]  
Guo C., 2005, Pharm. Care Res, V5, P341
[6]   Tomoeones A-H, cytotoxic phloroglucinol derivatives from Hypericum ascyron [J].
Hashida, Waka ;
Tanaka, Naonobu ;
Kashiwada, Yoshiki ;
Sekiya, Michiko ;
Ikeshiro, Yasumasa ;
Takaishi, Yoshihisa .
PHYTOCHEMISTRY, 2008, 69 (11) :2225-2230
[7]   Sulfonated xanthones from Hypericum sampsonii [J].
Hong, D ;
Yin, F ;
Hu, LH ;
Lu, P .
PHYTOCHEMISTRY, 2004, 65 (18) :2595-2598
[8]   Sampsoniones A-M, a unique family of caged polyprenylated benzoylphloroglucinol derivatives, from Hypericum sampsonii [J].
Hu, LH ;
Sim, KY .
TETRAHEDRON, 2000, 56 (10) :1379-1386
[9]   Complex caged polyisoprenylated benzophenone derivatives, sampsoniones A and B, from Hypericum sampsonii [J].
Hu, LH ;
Sim, KY .
TETRAHEDRON LETTERS, 1998, 39 (43) :7999-8002
[10]   Sampsoniones C-H, a unique family of polyprenylated benzophenone derivatives with the novel tetracyclo[7.3.1.13,11.03,7]tetradecane-2,12,14-trione skeleton, from Hypericum sampsonii (Guttiferae) [J].
Hu, LH ;
Sim, KY .
TETRAHEDRON LETTERS, 1999, 40 (04) :759-762