Protease inhibitors from a water bloom of the cyanobacterium Microcystis aeruginosa

被引:74
作者
Reshef, V [1 ]
Carmeli, S [1 ]
机构
[1] Tel Aviv Univ, Sch Chem, Raymond & Beverly Sackler Fac Exact Sci, IL-69978 Tel Aviv, Israel
关键词
cyanobacteria; Microcystis; protease inhibitors;
D O I
10.1016/S0040-4020(01)00141-7
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Five new protease inhibitors, micropeptins SD944 (1), SD979 (2), SD999 (3) and SD1002 (4) and microginin SD755 (5) were isolated along with two known inhibitors, micropeptin SF995 (6) and microcin SF608 (7), from the hydrophilic extract of Microcystis aeruginosa. The planar structure of compounds 1-5 was determined by homonuclear and inverse-heteronuclear 2D-NMR techniques as well as high-resolution mass spectrometry. The absolute configuration of the asymmetric centers was studied using Marfey's method for HPLC. Compounds 1-4, 6 and 7 are serine-protease inhibitors while compound 5 was found to inhibit amino-proteases. (C) 2001 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:2885 / 2894
页数:10
相关论文
共 11 条
[1]   Inhibitors of serine proteases from a waterbloom of the cyanobacterium Microcystis sp. [J].
Banker, R ;
Carmeli, S .
TETRAHEDRON, 1999, 55 (35) :10835-10844
[2]   RESEARCHES ON ACETYLENIC COMPOUNDS .1. THE PREPARATION OF ACETYLENIC KETONES BY OXIDATION OF ACETYLENIC CARBINOLS AND GLYCOLS [J].
BOWDEN, K ;
HEILBRON, IM ;
JONES, ERH ;
WEEDON, BCL .
JOURNAL OF THE CHEMICAL SOCIETY, 1946, (JAN) :39-45
[3]  
CHARMICHAEL WW, 1994, J APPL BACTERIOL, V72, P78
[4]   OCCURRENCE OF 4 DEPSIPEPTIDES, AERUGINOPEPTINS, TOGETHER WITH MICROCYSTINS FROM TOXIC CYANOBACTERIA [J].
HARADA, K ;
MAYUMI, T ;
SHIMADA, T ;
SUZUKI, M ;
KONDO, F ;
WATANABE, MF .
TETRAHEDRON LETTERS, 1993, 34 (38) :6091-6094
[5]   MICROVIRIDIN - A NOVEL TRICYCLIC DEPSIPEPTIDE FROM THE TOXIC CYANOBACTERIUM MICROCYSTIS-VIRIDIS [J].
ISHITSUKA, MO ;
KUSUMI, T ;
KAKISAWA, H ;
KAYA, K ;
WATANABE, MM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (22) :8180-8182
[6]   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
[7]   CYANOPEPTOLINS, NEW DEPSIPEPTIDES FROM THE CYANOBACTERIUM MICROCYSTIS SP PCC 7806 [J].
MARTIN, C ;
OBERER, L ;
INO, T ;
KONIG, WA ;
BUSCH, M ;
WECKESSER, J .
JOURNAL OF ANTIBIOTICS, 1993, 46 (10) :1550-1556
[8]   AERUGINOSIN 298-A, A THROMBIN AND TRYPSIN-INHIBITOR FROM THE BLUE-GREEN-ALGA MICROCYSTIS-AERUGINOSA (NIES-298) [J].
MURAKAMI, M ;
OKITA, Y ;
MATSUDA, H ;
OKINO, T ;
YAMAGUCHI, K .
TETRAHEDRON LETTERS, 1994, 35 (19) :3129-3132
[9]   MICROGININ, AN ANGIOTENSIN-CONVERTING ENZYME-INHIBITOR FROM THE BLUE-GREEN-ALGA MICROCYSTIS-AERUGINOSA [J].
OKINO, T ;
MATSUDA, H ;
MURAKAMI, M ;
YAMAGUCHI, K .
TETRAHEDRON LETTERS, 1993, 34 (03) :501-504
[10]  
RINEHART KL, 1996, J IND MICROBIOL, V17, P373