New Anabaenopeptins, Potent Carboxypeptidase-A Inhibitors from the Cyanobacterium <i>Aphanizomenon flos-aquae</i>

Murakami, Masahirô; Suzuki, Shingo; Itou, Yusai; Kodani, Shinya; Ishida, Keishi

doi:10.1021/np000120k

Cited by 79 publications

(59 citation statements)

References 9 publications

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“…Moreover, Murakami et al (2000) found that anabaenopeptins, ureido bound-containing cyclic peptides, have potent carboxypeptidase-A inhibitors (Fig. 6).…”

Section: Discussionmentioning

confidence: 97%

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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“…Moreover, Murakami et al (2000) found that anabaenopeptins, ureido bound-containing cyclic peptides, have potent carboxypeptidase-A inhibitors (Fig. 6).…”

Section: Discussionmentioning

confidence: 97%

Identification and toxigenic potential of a Nostoc sp.

Nowruzi¹,

Khavari-Nejad²,

Sivonen³

et al. 2012

ALGAE

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“…In contrast, oscillamide Y and schizopeptin have been described as effective inhibitors of serine proteases such as chymotrypsin and trypsin (38,40). Numerous variants of AP (APs G, H, T, I, and J) and brunsvicamide A have been described as potent inhibitors of carboxypeptidase A (CPD A) (21,32,46). Most recently, AP B, AP F, and the brunsvicamides were reported to inhibit porcine pancreatic elastase (PPE) and human leukocyte elastase (HLE) in the micromolar range (3,46).…”

Section: Discussionmentioning

confidence: 99%

Genetic Variation of Adenylation Domains of the Anabaenopeptin Synthesis Operon and Evolution of Substrate Promiscuity

et al. 2011

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“…In nature, anabaenopeptins appear to be at least as common as microcystins and have been found in many cyanobacterial taxa including Planktothrix, Microcystis, Anabaena, and Aphanizomenon. They have been characterised as inhibitors of carboxypeptidase, serine proteases and protein phosphatases (Murakami et al, 1997(Murakami et al, , 2000Sano & Kaya, 1995;Shin et al, 1998). The also widespread tricyclic microviridins consist of up to 14 amino acids and are known as potent protease inhibitors (Shin et al, 1996) and, at least in one case, as Daphnia toxins (Rohrlack et al, 2003).…”

Section: Introductionmentioning

confidence: 99%

Effects of nutrient and light availability on production of bioactive anabaenopeptins and microviridin by the cyanobacterium Planktothrix agardhii

Rohrlack

Utkilen

2007

Hydrobiologia

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Cyanobacteria produce a large number of bioactive oligopeptides with yet unknown functions. Here the effect of environmental factors on the production of two anabaenopeptins and a microviridin by Planktothrix agardhii was investigated. The results were compared with previous findings on the production of a third family of oligopeptides, the highly toxic microcystins, to test the hypothesis that environmental factors affect the production of different types of cyanobacterial bioactive oligopeptides in a similar manner. Despite marked changes in culture conditions, variations in the amount of cell-bound anabaenopeptins and microviridin I per biomass unit did not exceed a factor of 5. High amounts of cell-bound anabaenopeptins and microviridin I per Planktothrix biovolume were associated with a high availability of nitrogen and phosphorus.

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New Anabaenopeptins, Potent Carboxypeptidase-A Inhibitors from the Cyanobacterium Aphanizomenon flos-aquae

Cited by 79 publications

References 9 publications

Identification and toxigenic potential of a Nostoc sp.

Identification and toxigenic potential of a Nostoc sp.

Genetic Variation of Adenylation Domains of the Anabaenopeptin Synthesis Operon and Evolution of Substrate Promiscuity

Effects of nutrient and light availability on production of bioactive anabaenopeptins and microviridin by the cyanobacterium Planktothrix agardhii

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