3, 4-seco-Labdane diterpenoids from the leaves of Callicarpa nudiflora and their inhibitory effects on nitric oxide production

被引:33
作者
Zhang, Lei [1 ]
Dong, Lin [2 ]
Huang, Jian [1 ]
Liu, Mingsheng [3 ]
Li, Guoyu [4 ]
Zhang, Cui [1 ]
Zhang, Ke [4 ]
Wang, Jinhui [1 ,4 ]
机构
[1] Shenyang Pharmaceut Univ, Sch Tradit Chinese Med, Shenyang 110016, Peoples R China
[2] Hainan Med Coll, Hainan Prov Key Lab R&D Trop Med Plants, Haikou 571199, Peoples R China
[3] Acad South Med & Li Med Hainan Prov, Haikou 571199, Peoples R China
[4] Shihezi Univ, Sch Pharm, Shihezi 832023, Peoples R China
关键词
3; 4-seco-Labdane diterpenoids; Callicarpa nudiflora; Nitric oxide; RAW; 264.7; AJUGA-NIPPONENSIS; GALBANIC ACID; SESQUITERPENE; ETHERS;
D O I
10.1016/j.fitote.2013.05.022
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
As a part of our ongoing search for bioactive compounds from the leaves of Callicarpa nudiflora that inhibit nitric oxide (NO) production, the 90% EtOH fraction eluted by macroporous resin adsorption was found to show significant inhibitory activity against the production of NO in RAW 264.7 stimulated by lipopolysaccharide (U'S). Bioactivity-guided isolation of the fraction yielded three new bioactive diterpenoids, named ent-3, 4-seco-14-carbonyl-15, 16-epoxy-4(18), 8(17), 13(14)-labdatrien-3-oic acid (1), syn-3, 4-seco-12R-hydroxy-15, 16-epoxy-4(18), 8(17), 13(16), 14(15)-labdatetraen-3-oic acid (2) and syn-3, 4-seco-12S-hydroxy-15, 16-epoxy-4(18), 8(17), 13(16), 14(15)-labdatetraen-3-oic acid (3). Their structures and configurations were elucidated by comprehensive spectroscopic analysis. All the three compounds exhibited potent inhibitory activity on NO production in LPS-activated RAW 264.7 macrophage cells. (C) 2013 Elsevier B.V. All rights reserved.
引用
收藏
页码:218 / 223
页数:6
相关论文
共 18 条
[1]  
APPENDINO G, 1994, PHYTOCHEMISTRY, V35, P183, DOI 10.1016/S0031-9422(00)90530-2
[2]  
Bagirov VY, 1980, KHIM PRIR SOEDIN, V16, P620
[3]  
Calixto JB, 2004, PLANTA MED, V70, P93, DOI [10.1055/s-2004-815483, 10.1055/s-2003-45141]
[4]   Total synthesis and structural confirmation of ent-galbanic acid and marneral [J].
Corbu, Andrei ;
Perez, Manuel ;
Aquino, Maurizio ;
Retailleau, Pascal ;
Arsenlyadis, Simeon .
ORGANIC LETTERS, 2008, 10 (13) :2853-2856
[5]   Natural and Unnatural A-seco Terpenes from Pulegone: Synthesis of Galbanic Acid and Marneral Revisited [J].
Corbu, Andrei ;
Aquino, Maurizio ;
Perez, Manuel ;
Gandara, Zoila ;
Arseniyadis, Simeon .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2009, 2009 (36) :6386-6392
[6]  
[董琳 DONG Lin], 2010, [沈阳药科大学学报, Journal of Shenyang Pharmaceutical University], V27, P290
[7]  
[董琳 DONG Lin], 2009, [中国药物化学杂志, Chinese Journal of Medicinal Chemistry], V19, P371
[8]  
Freddy R, 2008, PHYTOCHEMISTRY, V69, P2406
[9]   CIRCULAR-DICHROISM .93. DETERMINATION OF THE ABSOLUTE-CONFIGURATION OF ALCOHOLS, OLEFINS, EPOXIDES, AND ETHERS FROM THE CD OF THEIR INSITU COMPLEXES WITH [RH2(O2CCF3)4] [J].
GERARDS, M ;
SNATZKE, G .
TETRAHEDRON-ASYMMETRY, 1990, 1 (04) :221-236
[10]   A sesquiterpene, dehydrocostus lactone, inhibits the expression of inducible nitric oxide synthase and TNF-α in LPS-activated macrophages [J].
Lee, HJ ;
Kim, NY ;
Jang, MK ;
Son, HJ ;
Kim, KM ;
Sohn, DH ;
Lee, SH ;
Ryu, JH .
PLANTA MEDICA, 1999, 65 (02) :104-108