Microbial transformation of deoxyandrographolide and their inhibitory activity on LPS-induced NO production in RAW 264.7 macrophages

被引:25
作者
Deng, Sa [1 ]
Zhang, Bao Jing [1 ]
Wang, Chang Yuan [1 ]
Tian, Yan [1 ]
Yao, Ji Hong [1 ]
An, Lei [1 ]
Huang, Shan Shan [1 ]
Peng, Jin Yong [1 ]
Liu, Ke Xin [1 ]
Ma, Xiao Chi [1 ]
机构
[1] Dalian Med Univ, Sch Pharmaceut Sci, Dalian 116044, Peoples R China
基金
中国国家自然科学基金;
关键词
Deoxyandrographolide; Biotransformation; NO inhibition; Ent-labdane; ANDROGRAPHOLIDE; ANTICANCER; ALPHA;
D O I
10.1016/j.bmcl.2011.12.122
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
A series of analogues of deoxyandrographolide (1) transformed by Cunninghamella blakesleana AS 3.2004 were isolated and identified by spectral methods including 2D NMR. Among them, 3-oxo-17,19-dihydroxy-7,13-ent-labdadien-15,16-olide (9), 3-oxo-19-hydroxy-1,13-ent-labdadien-15,16-olide (16), 3-oxo-1 beta-hydroxy-14-deoxy-andrographolide (17) and 3-oxo-2 beta-hydroxy-14-deoxyandrographolide (18) are new compounds. And their structure-activity relationships (SAR) of inhibitory activity on LPS-induced NO production in RAW 264.7 macrophage cells were also discussed. (C) 2011 Elsevier Ltd. All rights reserved.
引用
收藏
页码:1615 / 1618
页数:4
相关论文
共 25 条
[1]  
Calabrese C, 2000, PHYTOTHER RES, V14, P333, DOI 10.1002/1099-1573(200008)14:5<333::AID-PTR584>3.0.CO
[2]  
2-D
[3]   Studies on the novel α-glucosidase inhibitory activity and structure-activity relationships for andrographolide analogues [J].
Dai, GF ;
Xu, HW ;
Wang, JF ;
Liu, FW ;
Liu, HM .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2006, 16 (10) :2710-2713
[4]   Synthesis, cytotoxicity, and structure-activity relationship (SAR) studies of andrographolide analogues as anti-cancer agent [J].
Das, Bimolendu ;
Chowdhury, Chinmay ;
Kumar, Deepak ;
Sen, Rupashree ;
Roy, Rajneeta ;
Das, Padma ;
Chatterjee, Mitali .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2010, 20 (23) :6947-6950
[5]  
Deng W. L., 1990, DRUGS FUTURE, V15, P809
[6]  
Gupa S., 1990, INT J CRUDE DRUG RES, V28, P273
[7]   Synthesis and antitumour activity of pyrene-linked pyrrolo [2,1-c][1,4]benzodiazepine hybrids [J].
Kamal, A ;
Ramesh, G ;
Srinivas, O ;
Ramulu, P .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2004, 14 (02) :471-474
[8]   Anticancer and immunostimulatory compounds from Andrographis paniculata [J].
Kumar, RA ;
Sridevi, K ;
Kumar, NV ;
Nanduri, S ;
Rajagopal, S .
JOURNAL OF ETHNOPHARMACOLOGY, 2004, 92 (2-3) :291-295
[9]   Microbial transformation of deoxyandrographolide by Cunninghamella echinulata [J].
Li, Feng Yun ;
Cang, Peter R. ;
Huang, Shan Shan ;
Zhang, Bao Jing ;
Xin, Xiu Lan ;
Yao, Ji Hong ;
Zhou, Qi ;
Tian, Yan ;
Deng, Sha ;
Ma, Xiao Chi .
JOURNAL OF MOLECULAR CATALYSIS B-ENZYMATIC, 2011, 68 (02) :187-191
[10]   Synthesis of andrographolide derivatives and their TNF-α and IL-6 expression inhibitory activities [J].
Li, Jing ;
Huang, Wenlong ;
Zhang, Huibin ;
Wang, Xinyang ;
Zhou, Huiping .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2007, 17 (24) :6891-6894