Cloning, sequencing, and biochemical characterization of the nostocyclopeptide biosynthetic gene cluster: molecular basis for imine macrocyclization

Becker, Julia E.; Moore, Richard E.; Moore, Bradley S.

doi:10.1016/j.gene.2003.09.034

Cited by 95 publications

(106 citation statements)

References 33 publications

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“…NosF showed strong homology to ∆1-pyrroline-5-carboxylic acid (P5C) reductases (Luesch et al 2003). Several studies have performed similar screening of these genes in chemical structures of the nostopeptolides (Golakoti et al 2000, Becker et al 2004, Hunsucker et al 2004. It has been emphasized that some of the genes responsible for the biosynthesis of this unusual amino acid appeared to be embedded in the 3' end of the nostopeptolide gene cluster.…”

Section: Discussionmentioning

confidence: 99%

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Identification and toxigenic potential of a Nostoc sp.

Nowruzi¹,

Khavari-Nejad²,

Sivonen³

et al. 2012

ALGAE

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Cyanobacteria are well known for their production of a multitude of highly toxic and / or allelopathic compounds. Among the photosynthetic microorganisms, cyanobacteria, belonging to the genus Nostoc are regarded as good candidate for producing biologically active secondary metabolites which are highly toxic to humans and other animals. Since so many reports have been published on the poisoning of different animals from drinking water contaminated with cyanobacteria toxins, it might be assumed that bioactive compounds are found only in aquatic species causes toxicity. However, the discovery of several dead dogs, mice, ducks, and fish around paddy fields, prompted us to study the toxic compounds in a strain of Nostoc which is most abundant in the paddy fields of Iran, using polymerase chain reaction and liquid chromatography coupled with a diode array detector and mass spectrophotometer. Results of molecular analysis demonstrated that the ASN_M strain contains the nosF gene. Also, the result of ion chromatograms and MS 2 fragmentation patterns showed that while there were three different peptidic compound classes (anabaenopeptin, cryptophycin, and nostocyclopeptides), there were no signs of the presence of anatoxin-a, homoanatoxin-a, hassallidin or microcystins. Moreover, a remarkable antifungal activity was identified in the methanolic extracts. Based on the results, this study suggests that three diverse groups of potentially bioactive compounds might account for the death of these animals. This case is the first documented incident of toxicity from aquatic cyanobacteria related intoxication in dogs, mice, and aquatic organisms in Iran.Key Words: cyanobacteria; natural bioactive compound; Nostoc; toxicity INTRODUCTIONThe genus Nostoc is an ecologically, morphologically, and physiologically diverse genus of microorganisms inhabiting soils, and represents large reservoir of potentially valuable natural compounds (Dembitsky and Řezanka 2005). The ecological significance of the Nostoc species extends beyond the compounds which they primarily known to produce, as many of these organisms are capable of modifying their habitats through the synthesis of biologically active products (Ehrenreich et al. 2005). These compounds demonstrate a diverse range of biological activities and chemical structures, including novel cyclic and linear lipopeptides, fatty acids, alkaloids, and other organic chemicals (Dittmann et al. 2001). A large number of novel antimicrobial agents have been identiReceived September 16, 2012, Accepted November 20, 2012 *Corresponding Author E-mail: bahare77biol@yahoo.com Tel: +98-91-1371-0956, Fax: +98-21-8884-8940 This is an Open Access article distributed under the terms of the Creative Commons Attribution Non-Commercial License (http://creativecommons.org/licenses/by-nc/3.0/) which permits unrestricted non-commercial use, distribution, and reproduction in any medium, provided the original work is properly cited. 304 1,500-2,000 lux for two weeks (Kaushik 1987). Three small fragments of growing co...

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Section: Discussionmentioning

confidence: 99%

“…7). Nostocyclopeptides, a cyclic hexapeptide, showed weak cytotoxicity against KB (a human nasopharyngeal carcinoma) and LoVo (a human colorectal adenocarcinoma) cell lines and were devoid of antifungal and antibacterial activities (Golakoti et al 2001, Becker et al 2004, Jokela et al 2010.…”

Section: Discussionmentioning

confidence: 99%

Identification and toxigenic potential of a Nostoc sp.

Nowruzi¹,

Khavari-Nejad²,

Sivonen³

et al. 2012

ALGAE

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“…GSV224 (Hoffmann et al, 2003); Ncp, nostocyclopeptide synthetase from Nostoc sp. ATCC 53789 (Becker et al, 2004); Mcy, microcystin synthetase from M. aeruginosa PCC 7806 (Tillett et al, 2000); and Nda, the nodularin synthetase from N. spumigena (Moffitt & Neilan, 2004). For example, McnC2-Ahp denotes the A-domain in the second module of McnC activating Ahp precursor.…”

Section: Discussion Correlation Between Peptide and Operonmentioning

confidence: 99%

“…GSV224 (Hoffmann et al, 2003), nostocyclopeptide synthetase (Ncp) from Nostoc sp. ATCC 53789 (Becker et al, 2004) and nodularin synthetase (Nda) from N. spumigena (Moffitt & Neilan, 2004).…”

Section: Phylogeny Of the Different Cyanopeptolin Domainsmentioning

confidence: 99%

“…Other examples of hybrid biosynthesis between NRPS and PKS are nostopeptolide and nostocyclopeptide synthetases from Nostoc spp. (Becker et al, 2004;Hoffmann et al, 2003). Many cyanobacterial groups, particularly Microcystis strains, produce other cyclic and linear peptides, including cyanopeptolins, microviridins and aeruginosins (Birk et al, 1989;Ishitsuka et al, 1990;Murakami et al, 1997).…”

Section: Introductionmentioning

confidence: 99%

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Structural analysis of a non-ribosomal halogenated cyclic peptide and its putative operon from Microcystis: implications for evolution of cyanopeptolins

et al. 2007

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The structure of the major peptide produced by Microcystis cf. wesenbergii NIVA-CYA 172/5, the halogenated heptapeptide cyanopeptolin-984, was determined using LC/MS/MS. A gene cluster encoding a peptide synthetase putatively producing a cyanopeptolin was cloned from the same strain and sequenced. The cluster consists of four genes encoding peptide synthetases and one gene encoding a halogenase. Two additional ORFs transcribed in the opposite direction were found in the 59 flanking sequence; one of these encodes an ABC transporter. The overall organization of the cyanopeptolin synthetase operon (mcn) resembles a previously analysed anabaenopeptilide synthetase operon (apd) from Anabaena strain 90. Phylogenetic analyses of the individual domains from Mcn, Apd and other cyanobacterial peptide synthetases showed clustering of the adenylation domains according to function irrespective of operon origin -indicating strong functional constraints across peptide synthetases. In contrast, the condensation and thiolation domains to a large extent grouped according to operon affiliation or position in the respective operons. Phylogenetic analyses of condensation domains indicated that N-terminal domains and domains that condense L-amino acids and D-amino acids, respectively, form three separate groups. Although recombination events are likely to be involved in the evolution of mcn, no clear evidence of genetic recombination between the two cyanopeptolin gene clusters was found. Within the genus Microcystis, microcystin and cyanopeptolin synthetases have an evolutionary history of genomic coexistence. However, the data indicated that the two classes of peptide synthetase gene clusters have evolved independently.

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Multimodular Synthases and Supporting Enzymes for Chemical Production

Burkart

Tao

2009

Biocatalysis for the Pharmaceutical Industry

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Cloning, sequencing, and biochemical characterization of the nostocyclopeptide biosynthetic gene cluster: molecular basis for imine macrocyclization

Cited by 95 publications

References 33 publications

Identification and toxigenic potential of a Nostoc sp.

Identification and toxigenic potential of a Nostoc sp.

Structural analysis of a non-ribosomal halogenated cyclic peptide and its putative operon from Microcystis: implications for evolution of cyanopeptolins

Multimodular Synthases and Supporting Enzymes for Chemical Production

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