Dendroamides, new cyclic hexapeptides from a blue-green alga. Multidrug-resistance reversing activity of dendroamide A

被引:133
作者
Ogino, J
Moore, RE
Patterson, GML
Smith, CD
机构
[1] UNIV HAWAII MANOA,DEPT CHEM,HONOLULU,HI 96822
[2] FOX CHASE CANC CTR,DEPT PHARMACOL,PHILADELPHIA,PA 19111
来源
JOURNAL OF NATURAL PRODUCTS | 1996年 / 59卷 / 06期
关键词
D O I
10.1021/np960178s
中图分类号
Q94 [植物学];
学科分类号
071001 ;
摘要
Dendroamide A (1), one of three new bistratamide-type cyclic hexapeptides from the terrestrial blue-green alga (cyanobacterium) Stigonema dendroideum Fremy, exhibits multidrug-resistance reversing activity. The gross structures of the three compounds, dendroamides A-C, were determined by NMR and mass spectral analyses. Their absolute stereochemistries were determined by Marfey and chiral GC/MS analyses of derivatives formed from acid hydrolysis of the intact and ozonized peptides.
引用
收藏
页码:581 / 586
页数:6
相关论文
共 38 条
[11]   BISTRATAMIDE-C AND BISTRATAMIDE-D - 2 NEW OXAZOLE-CONTAINING CYCLIC HEXAPEPTIDES ISOLATED FROM A PHILIPPINE LISSOCLINUM-BISTRATUM ASCIDIAN [J].
FOSTER, MP ;
CONCEPCION, GP ;
CARAAN, GB ;
IRELAND, CM .
JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (24) :6671-6675
[12]   RAPID GAS-CHROMATOGRAPHIC SEPARATION OF AMINO-ACID ENANTIOMERS WITH A NOVEL CHIRAL STATIONARY PHASE [J].
FRANK, H ;
NICHOLSON, GJ ;
BAYER, E .
JOURNAL OF CHROMATOGRAPHIC SCIENCE, 1977, 15 (05) :174-176
[13]   BIOACTIVE MARINE METABOLITES SERIES .36. ORBICULAMIDE-A - A NOVEL CYTOTOXIC CYCLIC PEPTIDE FROM A MARINE SPONGE THEONELLA SP [J].
FUSETANI, N ;
SUGAWARA, T ;
MATSUNAGA, S ;
HIROTA, H .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (20) :7811-7812
[14]  
GOLAKOTI T, 1994, J AM CHEM SOC, V0116, P04729
[15]   CYCLOXAZOLINE - A CYTOTOXIC CYCLIC HEXAPEPTIDE FROM THE ASCIDIAN LISSOCLINUM-BISTRATUM [J].
HAMBLEY, TW ;
HAWKINS, CJ ;
LAVIN, MF ;
VANDENBRENK, A ;
WATTERS, DJ .
TETRAHEDRON, 1992, 48 (02) :341-348
[16]   STRUCTURE-ACTIVITY-RELATIONSHIPS OF THE LISSOCLINAMIDES - CYTOTOXIC CYCLIC-PEPTIDES FROM THE ASCIDIAN LISSOCLINUM-PATELLA [J].
HAWKINS, CJ ;
LAVIN, MF ;
MARSHALL, KA ;
VANDENBRENK, AL ;
WATTERS, DJ .
JOURNAL OF MEDICINAL CHEMISTRY, 1990, 33 (06) :1634-1638
[17]   ULICYCLAMIDE AND ULITHIACYCLAMIDE, 2 NEW SMALL PEPTIDES FROM A MARINE TUNICATE [J].
IRELAND, C ;
SCHEUER, PJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1980, 102 (17) :5688-5691
[18]   ANTI-NEOPLASTIC CYCLIC-PEPTIDES FROM THE MARINE TUNICATE LISSOCLINUM-PATELLA [J].
IRELAND, CM ;
DURSO, AR ;
NEWMAN, RA ;
HACKER, MP .
JOURNAL OF ORGANIC CHEMISTRY, 1982, 47 (10) :1807-1811
[19]   DETERMINATION OF D-AMINO ACIDS .2. USE OF A BIFUNCTIONAL REAGENT, 1,5-DIFLUORO-2,4-DINITROBENZENE [J].
MARFEY, P .
CARLSBERG RESEARCH COMMUNICATIONS, 1984, 49 (06) :591-596
[20]   PATELLAMIDE-E - A NEW CYCLIC PEPTIDE FROM THE ASCIDIAN LISSOCLINUM-PATELLA [J].
MCDONALD, LA ;
IRELAND, CM .
JOURNAL OF NATURAL PRODUCTS, 1992, 55 (03) :376-379