Micropeptins

Cyanobacteria -Microcystis aeruginosa Micropeptins 478-A and -B -peptide-based plasmin inhibitors Cyanopeptolins A-D -protease inhibitors Cyanopeptolin 963A-chymotrypsin inhibitor 120 6, 262 263... 

The prevalent Microcystis aeruginosa has afforded the plasmin inhibitors micropeptins 478-A (1115) and 478-B (1116) (1133). The terrestrial cyanobacterium Scytonema hofmanni PCC 7110 gives rise to scyptolins A (1117) and B (1118), which contain the 3-chloro-A-methyltyrosine residue (1134). The binding of 1117 to pancreatic elastase has been determined by X-ray crystallography (1135). Myriastramide B (1119) was isolated from the Philippine sponge Myriastra clavosa and features a novel chlorinated ether moiety (1136). 

Ishida K, Matsuda H, Murakami M, Yamaguchi K (1997) Micropeptins 478-A and -B, Plasmin Inhibitors from the Cyanobacterium Microcystis aeruginosa. J Nat Prod 60 184... 

A lot of interesting lipopeptides, both terms of biological activities and structures, have been discovered from the metabolites of marine-associated organisms. In particular, cyanobacteria produce many kinds of bioactive metabolites including toxins and enzyme inhibitors. Some cyclic lipopeptides from marine-associated organisms have unique structures, which are much different from those of their soil-associated counterparts. For example, the a-diketo structure is in cyclotheonamides 3-amino-6-hydroxy-2-piperidone is in micropeptins, scyptolins and planktopeptins and (2S, 3S, 8S,... 

Micropeptins E1992 and E1964 (Fig. 47) were isolated as protease inhibitors from the extracts of two samples of non-toxic cyanobacterium... 

Micropeptins, cyclodepsipeptides ( dep-sipeptides) isolated from cultures of cyanobacterium Microcystis aeruginosa. Mi-cropeptin 90, isolated from the cultured freshwater blue-green alga Microcystis aeru nosa (NIES-90), inhibits plas-min and trypsin, with ICsos of 0.1 and... 

Several other inhibitors of serine protease were isolated from freshwater and terrestrial cyanobacteria, such as the micropeptins (Ishida et ah, 1995,1997 Reshef and Carmeli, 2001 Ploutno, Shoshan, and Carmeli, 2002 Yamaki et ah, 2005), but these fall outside the scope of this work. 

Ishida, K., Murakami, M., Matsuda, H., and Yamaguchi, K. (1995) Micropeptin 90, a plasmin and trypsin inhibitor from the blue-green alga Microcystis aeruginosa. Tetrahedron Lett., 36, 3535-3538. 

Zafrir-Ilan, E. and Carmeli, S. (2010a) Micropeptins from an Israeli fishpond water bloom of the cyanobacterium Microcystis sp. ]. Nat. Prod., 73, 352-358. 

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