Peptides cyanobacteria

Diehnelt, C.W., Peterman, S.M., and Budde, W.L. (2005) Liquid chromatography-tandem mass spectrometry and accurate m/z measurements of cyclic peptide cyanobacteria toxins. Trends Anal. 

Work with European toxic cyanobacteria was partially supported by a NATO collaborative research grant between W.W. Carmichael and G.A. Codd, University of Dundee, Scotland, and O.M. Skulberg, Norwegian Water Research Institute, Oslo, Norway. Toxin structure work on European and North American peptide toxins is supported in part by U.S. AMRDC contract DAMD17-87-C-7019 to W.W. Carmichael. Portions of the work represent part of the Ph.D. dissertation research of N.A. Mahmood and E.G. Hyde. Their work was supported in part by fellowship support from the Biomedical Ph.D. Program, Wright State University. 

Moore RE (1996) Cyclic peptides and depsipeptides from cyanobacteria a review. J Ind Microbiol 16 134-143... 

In the field of fresh water plankton chemical ecology microcystins from cyanobacteria have stimulated much research and discussion. A critical reflection on the ecological function of these non-ribosomal peptides has recently been published (Babica et al. 2006). Surveys of methods for the quantification of these peptides (McElhiney and Lawton 2005 Msagati et al. 2006) and on the effects on fish (Malbrouck and Kestemont 2006) can be found as well. 

The nonprotein amino acid /3-A -methylamino-L-alanine (BMAA) is a neurotoxin found in various species of marine cyanobacteria. This nonprotein amino acid occurs both as a free amino acid and bound to proteins.Siderophores are secondary metabolites generally produced by bacteria under iron-deficient conditions. These molecules sequester and transport ferric ion via active transport in bacteria. Some known siderophores are nonribosomal peptides that contain nonprotein amino acids with terminal amines or hydroxylamine side chains, such as exochelin Many of the known nonprotein amino... 

H Fungi - Amanita phalloides and Agaricus phalloides Cyanobacteria -Lyngbya majuscula Phalloidin, phallicidin, and amanitin - toxic peptides Majusculamide D - cytotoxic peptide Microcolin A - peptide with immunosuppressive, antileukemic and protein kinase C inhibitory activity 242... 

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... 

Freshwater cyanobacteria blooms implicated in human and livestock intoxications have been extensively studied. And they have become a serious health problem in recent years. Blooms of marine cyanobacteria are also becoming an increasingly familiar occurrence within the tropical and subtropical regions of the world. Several systematic surveys within Europe and the USA have concluded that the two most commonly isolated groups of cyanotoxins are the alkaloids-neurotoxins and the cyclic peptide hepato-toxins, both of which are destructive to liver cells. Several genera... 

FFepatotoxins are the most commonly encountered toxins involving cyanobacteria, that include the cyclic peptides microcystin and nodularin (Fig. 4). Microcystins are cyclic seven amino acid peptides, and nodularins are cyclic five amino acid peptides. Over 50 different variants of microcystin have been isolated. 

Peptide toxins. Of all the toxins produced by freshwater cyanobacteria, the peptide toxins of Microcystis aeruginosa have received the most attention. All research on these peptide toxins indicates they are small, possibly cyclic, with molecular weights estimated at 1200 to 2600 (10,11). Recent work has become more definitive in the estimation of molecular weight and amino acid composition. In 1978 Elleman et al. (12) reported that they had isolated and characterized the peptide toxin of an Australian strain Microcystis which was a pentapeptide with a minimum molecular weight of 654. It consisted of equimolar amounts of alanine, tyrosine, methionine, glutamic and 3-methyl aspartic acid and methylamine. 

Other Peptide Toxin Producing Cyanobacteria. No other cyanobacteria genera have been analyzed for the presence of toxic peptides. Based on toxicity signs however it is thought that peptide toxins are present in certain isolates of Anabaena flos-aquae (J) and Oscillatorla agardhil (9,17). 

Other parts of the northeastern Atlantic are more productive indole alkaloids isolated from bryozoans, seco-steroids from a gorgonian, Gersemia fruticosa, from the White Sea, toxic peptides from brackish-water cyanobacteria, and macrolides from dinoflagellates (Chart 7.8.A/P/PO). 

The teleocidins from terrestrial actinomycetales and the lyngbyatoxins from marine cyanobacteria (Chart 8.3.P) are peptide alkaloids well known for their tumor promoting ability. 

Peptides are short chains of amino acids. By combining in various ways, two or more of the over 20 amino acids that are made by ail cells, a very large amount of chemical diversity can be generated. Some species of simple organisms such as the bacteria and the cyanobacteria make a number of distinct peptides, each species producing a different mixture. Some of these molecules have been shown to possess biological activity in certain test systems hence these peptides could be considered as NPs. Interestingly, the biosynthesis of these peptides has been compared, as has the biosynthesis of other NPs (see Chapter 5), with nature s version of the chemist s attempts to maximise the production of chemical diversity. ... 

Cyanobacteria are photosynthetic prokaryotes that are widely distributed throughout marine and terrestrial environments. Members of the marine cyanobacteria genus Lyngbya are known to produce structurally interesting and biologically active secondary metabolites. Typically, linear/cyclic peptides and depsipeptides that include various nonproteinogenic amino acids are the major groups of these metabolites (Fig. 10.11), which can exhibit potent cytotoxicity. 

Maru, N., Ohno, O., and Uemura, D. (2010c). Lyngbyacyclamides A and B, novel cytotoxic peptides from marine cyanobacteria Lyngbya sp. Tetrahedron Lett. 51,6384-6387. 

The thiazoline and thiazole rings are present in many cyclic peptides isolated from marine organisms. Most of these types of compound have been isolated from tunicates belonging to the Lissoclinum and Didemnum genus, from sponges of the genus Theonella, and from the sea hare mollusc Dolabella auricularia. The isolation of closely related compounds from cyanobacteria pointed out the symbiont origin of these metabolites. 

Certain strains of cyanobacteria produce toxins. These cyanobacterial toxins can be classified according to their chemical structure or their toxicity. Table 16.1 summarises the characteristics of the main cyanobacterial toxins. Depending on the chemical structure, there are cyclic peptides, alkaloids and lipopolysaccharides. According to the toxic effects, they are classified as ... 

W.P. Brooks and G.A. Codd, Immunoassay of hepatotoxic cultures and water blooms of cyanobacteria using Microcystis areuginosa peptide toxin polyclonal antibodies, Environ. Technol. Lett., 9 (1988) 1343-1348. 

Metabolites from cyanobacteria are generally of amino acid or polyketide origin and frequently show potent biological activity. The series of dolastatin metabolites, exemplified by dolastatin-10 (Structure 2.18), are linear peptides which show potent cytotoxic activity and are of clinical interest as anti-tumour agents. Originally isolated in very low yield from the Indian Ocean sea hare Dolabella auricularia, dolastatins are now known to be cyanobacterial products.43,44 The discovery of a microbial source for these pharmaceutically important compounds will facilitate study of their biosynthesis and could potentially lead to the production of structural analogues by provision of modified biosynthetic precursors to the cultivar. As discussed below and in Section VI, toxic secondary metabolites from cyanobacteria have often been implicated in the chemical defenses of sea hares.45"17... 

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