Cyanopeptolin 963A, a chymotrypsin inhibitor of Microcystis PCC 7806

被引:66
作者
Bister, B
Keller, S
Baumann, HI
Nicholson, G
Weist, S
Jung, G
Süssmuth, RD
Jüttner, F
机构
[1] Univ Tubingen, Inst Organ Chem, D-72076 Tubingen, Germany
[2] Univ Zurich, Limnol Stn, Inst Plant Biol, CH-8802 Kilchberg, Switzerland
来源
JOURNAL OF NATURAL PRODUCTS | 2004年 / 67卷 / 10期
关键词
D O I
10.1021/np049828f
中图分类号
Q94 [植物学];
学科分类号
071001 ;
摘要
A new depsipeptide, cyanopeptolin 963 A (1), was isolated from an axenic strain of the toxic freshwater cyanobacterium Microcystis PCC 7806. The structure of this compound was elucidated by chemical and spectroscopic analyses, including high-resolution ESI-FTICR-MS, 2-D NMR, and GC-MS of the hydrolysate. The major structural difference compared to previously characterized cyanopeptolins of this strain is the replacement of the basic amino acid in position 3 by L-tyrosine. Compound 1 displayed inhibitory activity against chymotrypsin with an IC50 value of 0.9 muM.
引用
收藏
页码:1755 / 1757
页数:3
相关论文
共 30 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]   Cloning, sequencing, and biochemical characterization of the nostocyclopeptide biosynthetic gene cluster: molecular basis for imine macrocyclization [J].
Becker, JE ;
Moore, RE ;
Moore, BS .
GENE, 2004, 325 :35-42
[3]   Oscillapeptin J, a new grazer toxin of the freshwater cyanobacterium Planktothrix rubescens [J].
Blom, JF ;
Bister, B ;
Bischoff, D ;
Nicholson, G ;
Jung, G ;
Süssmuth, RD ;
Jüttner, F .
JOURNAL OF NATURAL PRODUCTS, 2003, 66 (03) :431-434
[4]  
CLEMENS J, 1995, FEMS MICROBIOL LETT, V129, P129
[5]   2 CLOSELY RELATED PEPTIDE TOXINS IN AXENICALLY GROWN MICROCYSTIS-AERUGINOSA PCC-7806 [J].
DIERSTEIN, R ;
KAISER, I ;
WECKESSER, J ;
MATERN, U ;
KONIG, WA ;
KREBBER, R .
SYSTEMATIC AND APPLIED MICROBIOLOGY, 1990, 13 (01) :86-91
[6]   ENANTIOMER LABELING, A METHOD FOR THE QUANTITATIVE-ANALYSIS OF AMINO-ACIDS [J].
FRANK, H ;
NICHOLSON, GJ ;
BAYER, E .
JOURNAL OF CHROMATOGRAPHY, 1978, 167 (DEC) :187-196
[7]   Non-toxic peptides from toxic cyanobacteria, Oscillatoria agardhii [J].
Fujii, K ;
Sivonen, K ;
Naganawa, E ;
Harada, K .
TETRAHEDRON, 2000, 56 (05) :725-733
[8]   Identification of dipeptidyl nitriles as potent and selective inhibitors of cathepsin B through structure-based drug design [J].
Greenspan, PD ;
Clark, KL ;
Tommasi, RA ;
Cowen, SD ;
McQuire, LW ;
Farley, DL ;
van Duzer, JH ;
Goldberg, RL ;
Zhou, HH ;
Du, ZM ;
Fitt, JJ ;
Coppa, DE ;
Fang, Z ;
Macchia, W ;
Zhu, LJ ;
Capparelli, MP ;
Goldstein, R ;
Wigg, AM ;
Doughty, JR ;
Bohacek, RS ;
Knap, AK .
JOURNAL OF MEDICINAL CHEMISTRY, 2001, 44 (26) :4524-4534
[9]   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
[10]   Sequence analysis and biochemical characterization of the nostopeptolide A biosynthetic gene cluster from Nostoc sp GSV224 [J].
Hoffmann, D ;
Hevel, JM ;
Moore, RE ;
Moore, BS .
GENE, 2003, 311 :171-180