Aplidiopsamine A, an Antiplasmodial Alkaloid from the Temperate Australian Ascidian, Aplidiopsis confluata

被引:60
作者
Carroll, Anthony R. [1 ,2 ]
Duffy, Sandra [2 ]
Avery, Vicky M. [2 ]
机构
[1] Griffith Univ, Environm Futures Ctr, Gold Coast, Qld 4222, Australia
[2] Griffith Univ, Eskitis Inst, Brisbane, Qld 4111, Australia
关键词
NATURAL-PRODUCTS; INDOLE ALKALOIDS; A-C; PYRROLNITRIN; MARINE; DERIVATIVES;
D O I
10.1021/jo101695v
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A polyaromatic alkaloid, aplidiopsamine A was isolated from the temperate Australian ascidian, Aplidiopsis confluata, and its structure was determined from interpretation of mass, 1D and 2D NMR spectra. Aplidiopsamine A is the first alkaloid to possess the tricyclic aromatic substructure 3H-pyrrolo[2,3-c]quinoline conjugated to an adenine. Aplidiopsamine A exhibited significant inhibition of growth of chloroquine resistant and sensitive strains of the malaria parasite, Plasmodium falciparum, and minimal toxicity toward human cells.
引用
收藏
页码:8291 / 8294
页数:4
相关论文
共 20 条
[1]   A photochemical approach to pyridopyrroloquinoline derivatives as new potential anticancer agents [J].
Aragon, PJ ;
Yapi, AD ;
Pinguet, F ;
Chezal, JM ;
Teulade, JC ;
Chapat, JP ;
Blache, Y .
CHEMICAL & PHARMACEUTICAL BULLETIN, 2004, 52 (06) :659-663
[2]   Marine natural products [J].
Blunt, John W. ;
Copp, Brent R. ;
Munro, Murray H. G. ;
Northcote, Peter T. ;
Prinsep, Michele R. .
NATURAL PRODUCT REPORTS, 2010, 27 (02) :165-237
[3]   Citronamides A and B, Tetrapeptides from the Australian Sponge Citronia astra [J].
Carroll, Anthony R. ;
Duffy, Sandra ;
Avery, Vicky M. .
JOURNAL OF NATURAL PRODUCTS, 2009, 72 (04) :764-768
[4]   Leptoclinidamines A-C, Indole Alkaloids from the Australian Ascidian Leptoclinides durus [J].
Carroll, Anthony R. ;
Avery, Vicky M. .
JOURNAL OF NATURAL PRODUCTS, 2009, 72 (04) :696-699
[5]   C-13 NMR-STUDIES OF METHYLNUCLEOSIDES [J].
CHANG, CJ ;
ASHWORTH, DJ ;
CHERN, LJ ;
GOMES, JD ;
LEE, CG ;
MOU, PW ;
NARAYAN, R .
ORGANIC MAGNETIC RESONANCE, 1984, 22 (11) :671-675
[6]  
El-Banna N, 1998, J APPL MICROBIOL, V85, P69
[7]   Flinderoles A-C: Antimalarial Bis-indole Alkaloids from Flindersia Species [J].
Fernandez, Liza S. ;
Buchanan, Malcolm S. ;
Carroll, Anthony R. ;
Feng, Yun Jiang ;
Quinn, Ronald J. ;
Avery, Vicky M. .
ORGANIC LETTERS, 2009, 11 (02) :329-332
[8]   Antimalarial Natural Products of Marine and Freshwater Origin [J].
Gademann, Karl ;
Kobylinska, Joanna .
CHEMICAL RECORD, 2009, 9 (03) :187-198
[9]   PYRROLNITRIN FROM MYXOCOCCUS-FULVUS (MYXOBACTERALES) [J].
GERTH, K ;
TROWITZSCH, W ;
WRAY, V ;
HOFLE, G ;
IRSCHIK, H ;
REICHENBACH, H .
JOURNAL OF ANTIBIOTICS, 1982, 35 (08) :1101-1103
[10]   The manzamines as an example of the unique structural classes available for the discovery and optimization of infectious disease controls based on marine natural products [J].
Hamann, Mark T. .
CURRENT PHARMACEUTICAL DESIGN, 2007, 13 (06) :653-660