Five new discodermolide analogues from the marine sponge Discodermia species

被引:52
作者
Gunasekera, SP [1 ]
Paul, GK [1 ]
Longley, RE [1 ]
Isbrucker, RA [1 ]
Pomponi, SA [1 ]
机构
[1] Harbor Branch Oceanog Inst Inc, Div Biomed Marine Res, Ft Pierce, FL 34946 USA
来源
JOURNAL OF NATURAL PRODUCTS | 2002年 / 65卷 / 11期
关键词
D O I
10.1021/np020219m
中图分类号
Q94 [植物学];
学科分类号
071001 ;
摘要
Discodermolide (1) and five new discodermolide analogues trivially named 2-epi-discodermolide (2), 2-desmethyldiscodermolide (3), 5-hydroxymethyldiscodermolate (4), 19-des-aminocarbonyldiscodermolide (5), and 9(13)-cyclodiscodermolide (6) have been isolated from marine sponges belonging to the genus Discodermia collected from the Caribbean Sea. The isolation, structure elucidation, and biological activities of 2-6 are described. The natural analogues, which were isolated in trace amounts, exhibited significant variation of cytotoxicity against the cultured murine P-388 leukemia and A-549 human adenocarcinoma cells and suggested the importance of the C-7 through C-17 moiety for potency against cultured tumor cell lines.
引用
收藏
页码:1643 / 1648
页数:6
相关论文
共 35 条
[1]   The potent microtubule-stabilizing agent (+)-discodermolide induces apoptosis in human breast carcinoma cells - preliminary comparisons to paclitaxel [J].
Balachandran, R ;
ter Haar, E ;
Welsh, MJ ;
Grant, SG ;
Day, BW .
ANTI-CANCER DRUGS, 1998, 9 (01) :67-76
[2]  
BALACHANDRAN R, 1998, BREAST J, V4, P409
[3]   STUDIES ON THE ALKYLATION OF CHIRAL ENOLATES - APPLICATION TOWARD THE TOTAL SYNTHESIS OF DISCODERMOLIDE [J].
CLARK, DL ;
HEATHCOCK, CH .
JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (22) :5878-5879
[4]   Chelation-controlled stannylacetylene additions to β-alkoxy aldehydes promoted by alkylaluminum halide Lewis acids [J].
Evans, DA ;
Halstead, DP ;
Allison, BD .
TETRAHEDRON LETTERS, 1999, 40 (24) :4461-4462
[5]   THE SYNTHESIS OF A C-9-C-17 FRAGMENT OF DISCODERMOLIDE [J].
EVANS, PL ;
GOLEC, JMC ;
GILLESPIE, RJ .
TETRAHEDRON LETTERS, 1993, 34 (50) :8163-8166
[6]   Synthesis of C1-C8 and C9-C24 fragments of (-)-discodermolide: use of asymmetric alkylation and stereoselective aldol reactions [J].
Filla, SA ;
Song, JJ ;
Chen, LR ;
Masamune, S .
TETRAHEDRON LETTERS, 1999, 40 (30) :5449-5453
[7]   AN APPROACH TO THE SYNTHESIS OF A C-9-C-15 FRAGMENT OF DISCODERMOLIDE [J].
GOLEC, JMC ;
GILLESPIE, RJ .
TETRAHEDRON LETTERS, 1993, 34 (50) :8167-8168
[8]   THE SYNTHESIS OF A C-1-C-8 LACTONE FRAGMENT OF DISCODERMOLIDE [J].
GOLEC, JMC ;
JONES, SD .
TETRAHEDRON LETTERS, 1993, 34 (50) :8159-8162
[9]   Acetylated analogues of the microtubule-stabilizing agent discodermolide: Preparation and biological activity [J].
Gunasekera, SP ;
Longley, RE ;
Isbrucker, RA .
JOURNAL OF NATURAL PRODUCTS, 2001, 64 (02) :171-174
[10]   CORRECTION [J].
GUNASEKERA, SP .
JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (03) :1346-1346