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Prof. Dr. Ernani Pinto
Universidade de São Paulo - USP - Center for Nuclear Energy in Agriculture - CENA

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0 Mass Spectrometry
0 Natural Products
0 Cyanobacteria
0 cyanotoxins
0 Metabolomic Analysis

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Mass Spectrometry
Cyanobacteria
Natural Products
cyanotoxins
secondary metabolites
cyanopeptides

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Short Biography

Ernani Pinto is Pharmacist (University of São Paulo) and a professor of Environmental Toxicology at University of São Paulo (USP). He received his Ph.D. (2002) degree from Chemistry Institute - USP. He joined the School of Pharmaceutical Sciences (USP) from 2003 to 2019 and he started as a Full Professor at the Centre for Nuclear Energy in Agriculture (CENA-USP) at the ESALQ USP campus since 2019, where he has remained currently. He was a visiting scientist in Sweden (University of Uppsala) and Germany (Friedrich Schiller University Jena) through STINT and CAPES-DAAD, respectively. He has particular expertise in environmental toxicology, analytical chemistry, toxins and peptides from cyanobacteria, chromatography and mass spectrometry to develop methods and analyze relevant metabolites from different biological matrices. Additionally, his research interests include aspects of metabolomics and proteomics involved in environmental toxicology.

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Journal article
Published: 08 June 2021 in Toxins
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Combining coagulants with ballast (natural soil or modified clay) to remove cyanobacteria from the water column is a promising tool to mitigate nuisance blooms. Nevertheless, the possible effects of this technique on different toxin-producing cyanobacteria species have not been thoroughly investigated. This laboratory study evaluated the potential effects of the “Floc and Sink” technique on releasing microcystins (MC) from the precipitated biomass. A combined treatment of polyaluminium chloride (PAC) with lanthanum modified bentonite (LMB) and/or local red soil (LRS) was applied to the bloom material (mainly Dolichospermum circinalis and Microcystis aeruginosa) of a tropical reservoir. Intra and extracellular MC and biomass removal were evaluated. PAC alone was not efficient to remove the biomass, while PAC + LMB + LRS was the most efficient and removed 4.3–7.5 times more biomass than other treatments. Intracellular MC concentrations ranged between 12 and 2.180 µg L−1 independent from the biomass. PAC treatment increased extracellular MC concentrations from 3.5 to 6 times. However, when combined with ballast, extracellular MC was up to 4.2 times lower in the top of the test tubes. Nevertheless, PAC + LRS and PAC + LMB + LRS treatments showed extracellular MC concentration eight times higher than controls in the bottom. Our results showed that Floc and Sink appears to be more promising in removing cyanobacteria and extracellular MC from the water column than a sole coagulant (PAC).

ACS Style

Renan Arruda; Natália Noyma; Leonardo de Magalhães; Marcella Mesquita; Éryka de Almeida; Ernani Pinto; Miquel Lürling; Marcelo Marinho. ‘Floc and Sink’ Technique Removes Cyanobacteria and Microcystins from Tropical Reservoir Water. Toxins 2021, 13, 405 .

AMA Style

Renan Arruda, Natália Noyma, Leonardo de Magalhães, Marcella Mesquita, Éryka de Almeida, Ernani Pinto, Miquel Lürling, Marcelo Marinho. ‘Floc and Sink’ Technique Removes Cyanobacteria and Microcystins from Tropical Reservoir Water. Toxins. 2021; 13 (6):405.

Chicago/Turabian Style

Renan Arruda; Natália Noyma; Leonardo de Magalhães; Marcella Mesquita; Éryka de Almeida; Ernani Pinto; Miquel Lürling; Marcelo Marinho. 2021. "‘Floc and Sink’ Technique Removes Cyanobacteria and Microcystins from Tropical Reservoir Water." Toxins 13, no. 6: 405.

Journal article
Published: 23 May 2021 in Energies
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Cyanobacterial blooms and strains absorb carbon dioxide, drawing attention to its use as feed for animals and renewable energy sources. However, cyanobacteria can produce toxins and have a low heating value. Herein, we studied a cyanobacterial strain harvested during a bloom event and analyzed it to use as animal feed and a source of energy supply. The thermal properties and the contents of total nitrogen, protein, carbohydrate, fatty acids, lipid, and the presence of cyanotoxins were investigated in the Microcystis aeruginosa LTPNA 01 strain and in a bloom material. Microcystins (hepatotoxins) were not detected in this strain nor in the bloom material by liquid chromatography coupled to mass spectrometry. Thermogravimetric analysis showed that degradation reactions (devolatilization) initiated at around 180 °C, dropping from approximately 90% to 20% of the samples’ mass. Our work showed that despite presenting a low heating value, both biomass and non-toxic M. aeruginosa LTPNA 01 could be used as energy sources either by burning or producing biofuels. Both can be considered a protein and carbohydrate source similar to some microalgae species as well as biomass fuel. It could also be used as additive for animal feed; however, its safety and potential adverse health effects should be further investigated.

ACS Style

Larissa Passos; Éryka Almeida; Claudio de Pereira; Alessandro Casazza; Attilio Converti; Ernani Pinto. Chemical Characterization of Microcystis aeruginosa for Feed and Energy Uses. Energies 2021, 14, 3013 .

AMA Style

Larissa Passos, Éryka Almeida, Claudio de Pereira, Alessandro Casazza, Attilio Converti, Ernani Pinto. Chemical Characterization of Microcystis aeruginosa for Feed and Energy Uses. Energies. 2021; 14 (11):3013.

Chicago/Turabian Style

Larissa Passos; Éryka Almeida; Claudio de Pereira; Alessandro Casazza; Attilio Converti; Ernani Pinto. 2021. "Chemical Characterization of Microcystis aeruginosa for Feed and Energy Uses." Energies 14, no. 11: 3013.

Journal article
Published: 30 March 2021 in Free Radical Biology and Medicine
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Nitrones derived from natural antioxidants are emerging as highly specific therapeutics against various human diseases, including stroke, neurodegenerative pathologies, and cancer. However, the development of useful pseudo-natural nitrones requires the judicious choice of a secondary metabolite as the precursor. Betalains are nitrogen-containing natural pigments that exhibit marked antioxidant capacity and pharmacological properties and, hence, are ideal candidates for designing multifunctional nitrones. In this work, we describe the semisynthesis and properties of a biocompatible and antioxidant betalain-nitrone called OxiBeet. This bio-based compound is a better radical scavenger than ascorbic acid, gallic acid, and most non-phenolic antioxidants and undergoes concerted proton-coupled electron transfer. The autoxidation of OxiBeet produces a persistent nitroxide radical, which, herein, is studied via electron paramagnetic resonance spectroscopy. In addition, femtosecond transient absorption spectroscopy reveals that excited state formation is not required for the oxidation of OxiBeet. The results are compared with those obtained using betanin, a natural betalain, and pBeet, the imine analog of OxiBeet. The findings of this study will enable the development of antioxidant and spin-trap nitrones based on the novel N-oxide 1,7-diazaheptamethinium scaffold and betalain dyes with enhanced hydrolytic stability in aqueous alkaline media.

ACS Style

Amanda Capistrano Pinheiro; Rodrigo Boni Fazzi; Larissa Cerrato Esteves; Caroline Oliveira Machado; Felipe Augusto Dörr; Ernani Pinto; Yocefu Hattori; Jacinto Sa; Ana Maria Da Costa Ferreira; Erick Leite Bastos. A bioinspired nitrone precursor to a stabilized nitroxide radical. Free Radical Biology and Medicine 2021, 168, 110 -116.

AMA Style

Amanda Capistrano Pinheiro, Rodrigo Boni Fazzi, Larissa Cerrato Esteves, Caroline Oliveira Machado, Felipe Augusto Dörr, Ernani Pinto, Yocefu Hattori, Jacinto Sa, Ana Maria Da Costa Ferreira, Erick Leite Bastos. A bioinspired nitrone precursor to a stabilized nitroxide radical. Free Radical Biology and Medicine. 2021; 168 ():110-116.

Chicago/Turabian Style

Amanda Capistrano Pinheiro; Rodrigo Boni Fazzi; Larissa Cerrato Esteves; Caroline Oliveira Machado; Felipe Augusto Dörr; Ernani Pinto; Yocefu Hattori; Jacinto Sa; Ana Maria Da Costa Ferreira; Erick Leite Bastos. 2021. "A bioinspired nitrone precursor to a stabilized nitroxide radical." Free Radical Biology and Medicine 168, no. : 110-116.

Journal article
Published: 16 March 2021 in Environmental Toxicology and Pharmacology
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Female juveniles of the Neotropical fish Astyanax altiparanae were exposed for 96 h to four treatments containing the active ingredient from Imidacloprid® commercial formulation (IMI 1, IMI 2, IMI 3, and IMI 4) and to a control treatment (only dechlorinated tap water). Glutathione content, glutathione S-transferase activity, lipid peroxidation (LPO) and protein carbonylation levels, acetylcholinesterase (AChE) activity, and frequency of micronuclei and erythrocyte nuclear abnormalities (ENA) were measured in the fish. The muscle and gills were the most affected organs; their antioxidant defense was not enough to prevent oxidative damage (LPO) in the IMI 2 and IMI 4 treatment fish. IMI also inhibited AChE activity in the muscle (IMI 3 and IMI 4) and increased ENA frequency (IMI 4). IMI can affect the health of A. altiparanae in environmentally relevant concentrations, causing oxidative damage in different organs, neurotoxic effects in the muscle, and genotoxicity.

ACS Style

Éryka Costa Almeida; Larissa Souza Passos; Carlos Eduardo Delfino Vieira; Raphael Danna Acayaba; Cassiana Carolina Montagner; Ernani Pinto; Claudia Bueno Dos Reis Martinez; Ana Lúcia Fonseca. Can the insecticide Imidacloprid affect the health of the Neotropical freshwater fish Astyanax altiparanae (Teleostei: Characidae)? Environmental Toxicology and Pharmacology 2021, 85, 103634 .

AMA Style

Éryka Costa Almeida, Larissa Souza Passos, Carlos Eduardo Delfino Vieira, Raphael Danna Acayaba, Cassiana Carolina Montagner, Ernani Pinto, Claudia Bueno Dos Reis Martinez, Ana Lúcia Fonseca. Can the insecticide Imidacloprid affect the health of the Neotropical freshwater fish Astyanax altiparanae (Teleostei: Characidae)? Environmental Toxicology and Pharmacology. 2021; 85 ():103634.

Chicago/Turabian Style

Éryka Costa Almeida; Larissa Souza Passos; Carlos Eduardo Delfino Vieira; Raphael Danna Acayaba; Cassiana Carolina Montagner; Ernani Pinto; Claudia Bueno Dos Reis Martinez; Ana Lúcia Fonseca. 2021. "Can the insecticide Imidacloprid affect the health of the Neotropical freshwater fish Astyanax altiparanae (Teleostei: Characidae)?" Environmental Toxicology and Pharmacology 85, no. : 103634.

Review
Published: 14 January 2021 in Pharmaceuticals
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Mycosporines and mycosporine-like amino acids are ultra-violet-absorbing compounds produced by several organisms such as lichens, fungi, algae and cyanobacteria, especially upon exposure to solar ultraviolet radiation. These compounds have photoprotective and antioxidant functions. Mycosporine-like amino acids have been used as a natural bioactive ingredient in cosmetic products. Several reviews have already been developed on these photoprotective compounds, but they focus on specific features. Herein, an extremely complete database on mycosporines and mycosporine-like amino acids, covering the whole class of these natural sunscreen compounds known to date, is presented. Currently, this database has 74 compounds and provides information about the chemistry, absorption maxima, protonated mass, fragments and molecular structure of these UV-absorbing compounds as well as their presence in organisms. This platform completes the previous reviews and is available online for free and in the public domain. This database is a useful tool for natural product data mining, dereplication studies, research working in the field of UV-absorbing compounds mycosporines and being integrated in mass spectrometry library software.

ACS Style

Vanessa Geraldes; Ernani Pinto. Mycosporine-Like Amino Acids (MAAs): Biology, Chemistry and Identification Features. Pharmaceuticals 2021, 14, 63 .

AMA Style

Vanessa Geraldes, Ernani Pinto. Mycosporine-Like Amino Acids (MAAs): Biology, Chemistry and Identification Features. Pharmaceuticals. 2021; 14 (1):63.

Chicago/Turabian Style

Vanessa Geraldes; Ernani Pinto. 2021. "Mycosporine-Like Amino Acids (MAAs): Biology, Chemistry and Identification Features." Pharmaceuticals 14, no. 1: 63.

Journal article
Published: 01 January 2021 in Journal of the Brazilian Chemical Society
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Guanitoxin (GNT) is a natural organophosphate produced by some species of freshwater cyanobacteria, which inhibits the active site of acetylcholinesterase, preventing the hydrolysis of cholinesterases and consequently causing serious disturbances in the neuromuscular system. Despite having a chemical structure like synthetic organophosphates, there is still no analytical standard available for environmental and freshwater monitoring. Therefore, this study investigated the stability of GNT under different storage conditions, pH, and temperature. The toxin is produced by the cyanobacterium Sphaerospermopsis torques-reginae and monitored by liquid chromatography coupled to mass spectrometry (LC-MS) and LC-MS/MS for the identification and verification of its stability. The main degradation product formed is the hydroxy-amino-guanidinic derivative of the toxin. The results also indicate that GNT is stable in acidic medium (pH = 3.0), but can gradually degrade at room temperature (> 23 ºC) over a period of 96 h. Lyophilized biomass of S. torques-reginae containing GNT remained stable when stored in a refrigerator below 4 ºC. In addition, the extraction yield is higher when prepared from fresh S. torques-reginae cells than from lyophilized material. Thus, the results shown here contribute with valuable information for studies that aim at the isolation, identification, and monitoring of GNT in samples of raw water and cyanobacterial blooms.

ACS Style

Kelly Fernandes; Felipe Augusto Dörr; Ernani Pinto. Stability Analyses of Guanitoxin Isolated from Sphaerospermopsis torques-reginae by Mass Spectrometry. Journal of the Brazilian Chemical Society 2021, 1 .

AMA Style

Kelly Fernandes, Felipe Augusto Dörr, Ernani Pinto. Stability Analyses of Guanitoxin Isolated from Sphaerospermopsis torques-reginae by Mass Spectrometry. Journal of the Brazilian Chemical Society. 2021; ():1.

Chicago/Turabian Style

Kelly Fernandes; Felipe Augusto Dörr; Ernani Pinto. 2021. "Stability Analyses of Guanitoxin Isolated from Sphaerospermopsis torques-reginae by Mass Spectrometry." Journal of the Brazilian Chemical Society , no. : 1.

Journal article
Published: 26 November 2020 in FEMS Microbiology Ecology
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Interactions between climate change and ultraviolet radiation (UVR) have a substantial impact on aquatic ecosystems, especially on photosynthetic organisms. To counteract the damaging effects of UVR, cyanobacteria developed adaptive strategies such as the biosynthesis of secondary metabolites. This study aimed to evaluate the effects of UVR on the metabolomic profiles of potentially toxic cyanobacteria. Twelve strains were irradiated with ultraviolet A and ultraviolet B radiation and parabolic aluminized reflector lamps for 3 days, followed by liquid chromatography–tandem mass spectometry (LC-MS/MS) analysis to assess changes in metabolomic profiles. Matrices were used to generate principal component analysis biplots, and molecular networks were obtained using the Global Natural Products platform. Most strains showed significant changes in their metabolomic profiles after UVR exposure. On average, 7% of MS features were shown to be exclusive to metabolomic profiles before UVR exposure, while 9% were unique to metabolomic profiles after UVR exposure. The identified compounds included aeruginosins, spumigins, cyanopeptolins, microginins, namalides, pseudospumigins, anabaenopeptins, mycosporine-like amino acids, nodularins and microcystins. Data showed that cyanobacteria display broad metabolic plasticity upon UVR exposure, including the synthesis and differential expression of a variety of secondary metabolites. This could result in a competitive advantage, supporting cyanobacterial blooms under various UVR light exposures.

ACS Style

Fernanda Rios Jacinavicius; Vanessa Geraldes; Camila M Crnkovic; Endrews Delbaje; Marli F Fiore; Ernani Pinto. Effect of ultraviolet radiation on the metabolomic profiles of potentially toxic cyanobacteria. FEMS Microbiology Ecology 2020, 97 .

AMA Style

Fernanda Rios Jacinavicius, Vanessa Geraldes, Camila M Crnkovic, Endrews Delbaje, Marli F Fiore, Ernani Pinto. Effect of ultraviolet radiation on the metabolomic profiles of potentially toxic cyanobacteria. FEMS Microbiology Ecology. 2020; 97 (1):.

Chicago/Turabian Style

Fernanda Rios Jacinavicius; Vanessa Geraldes; Camila M Crnkovic; Endrews Delbaje; Marli F Fiore; Ernani Pinto. 2020. "Effect of ultraviolet radiation on the metabolomic profiles of potentially toxic cyanobacteria." FEMS Microbiology Ecology 97, no. 1: .

Journal article
Published: 19 November 2020 in Pharmaceuticals
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Guanitoxin (GNT) is a potent neurotoxin produced by freshwater cyanobacteria that can cause the deaths of wild and domestic animals. Through reports of animal intoxication by cyanobacteria cells that produce GNT, this study aimed to investigate the bio-accessibility of GNT in simulated solutions of the gastrointestinal content in order to understand the process of toxicosis promoted by GNT in vivo. Dissolution tests were conducted with a mixture of Sphaerospermopsis torques-reginae (Cyanobacteria; Nostocales) cultures (30%) and gastrointestinal solutions with and without proteolytic enzymes (70%) at a temperature of 37 °C and rotation at 100 rpm for 2 h. The identification of GNT was performed by LC-QqQ-MS/MS through the transitions [M + H]+m/z 253 > 58 and [M + H]+m/z 253 > 159, which showed high concentrations of GNT in simulated gastric fluid solutions (p-value < 0.001) in comparison to simulated solutions of intestinal content. The gastric solution with pepsin promoted the stability of GNT (p-value < 0.05) compared to the simulated solution of gastric fluid at the same pH without the enzyme. However, the results showed that GNT is also available in intestinal fluids for a period of 2 h, and solutions containing the pancreatin enzyme influenced the bio-accessibility of the toxin more compared to the intestinal medium without enzyme (p-value < 0.05). Therefore, the bio-accessibility of the toxin must be considered both in the stomach and in the intestine, and may help in the diagnosis and prediction of exposure and risk in vivo through the oral ingestion of GNT-producing cyanobacteria cells.

ACS Style

Kelly Afonsina Fernandes; Humberto Gomes Ferraz; Fanny Vereau; Ernani Pinto. Availability of Guanitoxin in Water Samples Containing Sphaerospermopsis torques-reginae Cells Submitted to Dissolution Tests. Pharmaceuticals 2020, 13, 402 .

AMA Style

Kelly Afonsina Fernandes, Humberto Gomes Ferraz, Fanny Vereau, Ernani Pinto. Availability of Guanitoxin in Water Samples Containing Sphaerospermopsis torques-reginae Cells Submitted to Dissolution Tests. Pharmaceuticals. 2020; 13 (11):402.

Chicago/Turabian Style

Kelly Afonsina Fernandes; Humberto Gomes Ferraz; Fanny Vereau; Ernani Pinto. 2020. "Availability of Guanitoxin in Water Samples Containing Sphaerospermopsis torques-reginae Cells Submitted to Dissolution Tests." Pharmaceuticals 13, no. 11: 402.

Preprint content
Published: 04 August 2020
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L-DOPA extradiol dioxygenases (DODAs) catalyze the production of betalains and hygroaurins pigments. The sequence of the DODAs found in Caryophyllales and Basidiomycetes are not conserved, although betalains are produced both by plants and fungi. Here we revise the coding region of the dodA gene of fly agaric [Amanita muscaria (L.) Lam.] and describe an alternative start codon downstream that enables the heterologous expression of AmDODA, a promiscuous L-DOPA dioxygenase. AmDODA is 43-amino acid residues shorter than the recombinant DODA previously reported but catalyzes the formation of two isomeric seco-DOPAs that are the biosynthetic precursors of betalains and hygroaurins. The putative active site of AmDODA contains two distinct His-His-Glu motifs that can explain the dual cleavage of L-DOPA according to the mechanism proposed for non-heme iron-dependent dioxygenases. Upon addition of excess L-DOPA, both the betaxanthin and hygroaurin adducts of L-DOPA are produced. The kinetic parameters of enzymatic catalysis at pH 8.5 are similar to those reported for other L-DOPA dioxygenases. The rate constants for the conversion of L-DOPA into the betalamic acid and muscaflavin were estimated by kinetic modelling allowing the proposal of a mechanism of pigment formation. These results contribute to understanding the biosynthesis of bacterial, fungal and plant pigments, for the biotechnological production of hygroaurins, and for the development of more promiscuous dioxygenases for environmental remediation.

ACS Style

Douglas M. M. Soares; Leticia C. P. Goncalves; Caroline O. Machado; Larissa Cerrato Esteves; Cassius Vinicius Stevani; Carla C. Oliveira; Felipe A. Dorr; Ernani Pinto; Flavia M. M. Adachi; Carlos T. Hotta; Erick Leite Bastos. L-DOPA dioxygenase of the fly agaric toadstool: revision of the dodA gene sequence and mechanism of enzymatic pigment production. 2020, 1 .

AMA Style

Douglas M. M. Soares, Leticia C. P. Goncalves, Caroline O. Machado, Larissa Cerrato Esteves, Cassius Vinicius Stevani, Carla C. Oliveira, Felipe A. Dorr, Ernani Pinto, Flavia M. M. Adachi, Carlos T. Hotta, Erick Leite Bastos. L-DOPA dioxygenase of the fly agaric toadstool: revision of the dodA gene sequence and mechanism of enzymatic pigment production. . 2020; ():1.

Chicago/Turabian Style

Douglas M. M. Soares; Leticia C. P. Goncalves; Caroline O. Machado; Larissa Cerrato Esteves; Cassius Vinicius Stevani; Carla C. Oliveira; Felipe A. Dorr; Ernani Pinto; Flavia M. M. Adachi; Carlos T. Hotta; Erick Leite Bastos. 2020. "L-DOPA dioxygenase of the fly agaric toadstool: revision of the dodA gene sequence and mechanism of enzymatic pigment production." , no. : 1.

Journal article
Published: 02 July 2020 in Molecules
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The term cylindrospermopsins (CYNs) refers to a structurally related class of cyanobacterial metabolites comprised of a tricyclic guanidine group and a hydroxymethyluracil moiety. Most reports in environmental aquatic samples refer to cylindrospermopsin (CYN), and reports on other CYN alkaloids are scarce, due, in part, to a lack of versatile isolation protocols. Thus, using commercially available solid phase extraction (SPE) cartridges, we optimized an isolation protocol for the complete recovery of CYN, 7-deoxy-cylindrospermopsin (7D-CYN) and 7-deoxy-desulfo-cylindrospermopsin (7D-desulfo-CYN) from the same aliquot. The isolation protocol was adaptable depending on the nature of the sample (solid biomass, culture broth or environmental water sample) and tolerates up to 4 L of dense culture broth or 400 mg of lyophilized biomass. To quantitate the CYN alkaloids, we validated an LC-DAD-MS2 method, which takes advantage of the UV absorption of the uracil group (λ 262 nm). Using electrospray ionization (ESI) in a positive ion mode, the high-resolution MS1 data confirms the presence of the protonated alkaloids, and the MS2 fragment assignment is reported as complementary proof of the molecular structure of the CYNs. We isolated three CYN alkaloids with different water solubility using the same lyophilized sample, with a purity that ranged from 95% to 99%. The biological activity of the purified CYNs, along with a synthetic degradation product of CYN (desulfo-cylindrospermopsin), was evaluated by assessing necrosis and apoptosis in vitro using flow cytometry. CYN’s lethal potency in HepG2 cells was greater than the other analogs, due to the presence of all four functional groups: guanidine, uracil, C-7 hydroxyl and the sulfate residue.

ACS Style

Carlos González-Blanco; Felipe Dörr; Renata Albuquerque; Janice Onuki; Ernani Pinto. Alternative Isolation Protocol for Desulfo and Zwitterionic Cylindrospermopsin Alkaloids and Comparison of Their Toxicity in HepG2 Cells. Molecules 2020, 25, 3027 .

AMA Style

Carlos González-Blanco, Felipe Dörr, Renata Albuquerque, Janice Onuki, Ernani Pinto. Alternative Isolation Protocol for Desulfo and Zwitterionic Cylindrospermopsin Alkaloids and Comparison of Their Toxicity in HepG2 Cells. Molecules. 2020; 25 (13):3027.

Chicago/Turabian Style

Carlos González-Blanco; Felipe Dörr; Renata Albuquerque; Janice Onuki; Ernani Pinto. 2020. "Alternative Isolation Protocol for Desulfo and Zwitterionic Cylindrospermopsin Alkaloids and Comparison of Their Toxicity in HepG2 Cells." Molecules 25, no. 13: 3027.

Journal article
Published: 15 June 2020 in ALGAE
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ACS Style

Vanessa Geraldes; Lívia Soman De Medeiros; Stella Lima; Danillo Alvarenga; Ranko Gacesa; Paul F. Long; Marli Fátima Fiore; Ernani Pinto. Genetic and biochemical evidence for redundant pathways leading to mycosporine-like amino acid biosynthesis in the cyanobacterium Sphaerospermopsis torques-reginae ITEP-024. ALGAE 2020, 35, 177 -187.

AMA Style

Vanessa Geraldes, Lívia Soman De Medeiros, Stella Lima, Danillo Alvarenga, Ranko Gacesa, Paul F. Long, Marli Fátima Fiore, Ernani Pinto. Genetic and biochemical evidence for redundant pathways leading to mycosporine-like amino acid biosynthesis in the cyanobacterium Sphaerospermopsis torques-reginae ITEP-024. ALGAE. 2020; 35 (2):177-187.

Chicago/Turabian Style

Vanessa Geraldes; Lívia Soman De Medeiros; Stella Lima; Danillo Alvarenga; Ranko Gacesa; Paul F. Long; Marli Fátima Fiore; Ernani Pinto. 2020. "Genetic and biochemical evidence for redundant pathways leading to mycosporine-like amino acid biosynthesis in the cyanobacterium Sphaerospermopsis torques-reginae ITEP-024." ALGAE 35, no. 2: 177-187.

Preprint content
Published: 16 April 2020
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Cyanobacteria form harmful mass blooms in freshwater and marine environments around the world. A range of secondary metabolites has been identified from cultures of cyanobacteria and biomass collected from cyanobacterial bloom events. A comprehensive database is necessary to correctly identify cyanobacterial metabolites and advance research on their abundance, persistence and toxicity in natural environments. We consolidated open access databases and manually curated missing information from the literature published between 1970 and March 2020. The result is the database CyanoMetDB, which includes more than 2000 entries based on more than 750 literature references. This effort has more than doubled the total number of entries with complete literature metadata and structural composition (SMILES codes) compared to publicly available databases to this date. Over the past decade, more than one hundred additional secondary metabolites have been identified yearly. We organized all entries into structural classes and conducted substructure searches of the provided SMILES codes. This approach demonstrated, for example, that 65% of the compounds carry at least one peptide bond, 57% are cyclic compounds, and 30% carry at least one halogen atom. Structural searches by SMILES code can be further specified to identify structural motifs that are relevant for analytical approaches, research on biosynthetic pathways, bioactivity-guided analysis, or to facilitate predictive science and modeling efforts on cyanobacterial metabolites. This database facilitates rapid identification of cyanobacterial metabolites from toxic blooms, research on the biosynthesis of cyanobacterial natural products, and the identification of novel natural products from cyanobacteria.

ACS Style

Martin R. Jones; Ernani Pinto; Mariana A. Torres; Fabiane Doerr; Hanna Mazur-Marzec; Karolina Szubert; Luciana Tartaglione; Carmela Dell’Aversano; Christopher O. Miles; Daniel G. Beach; Pearse McCarron; Kaarina Sivonen; David P. Fewer; Jouni Jokela; Elisabeth M.-L. Janssen. Comprehensive database of secondary metabolites from cyanobacteria. 2020, 1 .

AMA Style

Martin R. Jones, Ernani Pinto, Mariana A. Torres, Fabiane Doerr, Hanna Mazur-Marzec, Karolina Szubert, Luciana Tartaglione, Carmela Dell’Aversano, Christopher O. Miles, Daniel G. Beach, Pearse McCarron, Kaarina Sivonen, David P. Fewer, Jouni Jokela, Elisabeth M.-L. Janssen. Comprehensive database of secondary metabolites from cyanobacteria. . 2020; ():1.

Chicago/Turabian Style

Martin R. Jones; Ernani Pinto; Mariana A. Torres; Fabiane Doerr; Hanna Mazur-Marzec; Karolina Szubert; Luciana Tartaglione; Carmela Dell’Aversano; Christopher O. Miles; Daniel G. Beach; Pearse McCarron; Kaarina Sivonen; David P. Fewer; Jouni Jokela; Elisabeth M.-L. Janssen. 2020. "Comprehensive database of secondary metabolites from cyanobacteria." , no. : 1.

Research article
Published: 03 April 2020 in Science Advances
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Blue natural pigments are rare, especially among plants. However, flowering species that evolved to attract Hymenoptera pollinators are colored by blue anthocyanin-metal complexes. Plants lacking anthocyanins are pigmented by betalains but are unable to produce blue hues. By extending the π-system of betalains, we designed a photostable and metal-free blue dye named BeetBlue that did not show toxicity to human hepatic and retinal pigment epithelial cells and does not affect zebrafish embryonal development. This chiral dye can be conveniently synthesized from betalamic acid obtained from hydrolyzed red beetroot juice or by enzymatic oxidation of l-dopa. BeetBlue is blue in the solid form and in solution of acidified polar molecular solvents, including water. Its capacity to dye natural matrices makes BeetBlue the prototype of a new class of low-cost bioinspired chromophores suitable for a myriad of applications requiring a blue hue.

ACS Style

B. C. Freitas-Dörr; C. O. Machado; A. C. Pinheiro; A. B. Fernandes; F. A. Dörr; E. Pinto; M. Lopes-Ferreira; M. Abdellah; J. Sá; L. C. Russo; F. L. Forti; L. C. P. Gonçalves; E. L. Bastos. A metal-free blue chromophore derived from plant pigments. Science Advances 2020, 6, eaaz0421 .

AMA Style

B. C. Freitas-Dörr, C. O. Machado, A. C. Pinheiro, A. B. Fernandes, F. A. Dörr, E. Pinto, M. Lopes-Ferreira, M. Abdellah, J. Sá, L. C. Russo, F. L. Forti, L. C. P. Gonçalves, E. L. Bastos. A metal-free blue chromophore derived from plant pigments. Science Advances. 2020; 6 (14):eaaz0421.

Chicago/Turabian Style

B. C. Freitas-Dörr; C. O. Machado; A. C. Pinheiro; A. B. Fernandes; F. A. Dörr; E. Pinto; M. Lopes-Ferreira; M. Abdellah; J. Sá; L. C. Russo; F. L. Forti; L. C. P. Gonçalves; E. L. Bastos. 2020. "A metal-free blue chromophore derived from plant pigments." Science Advances 6, no. 14: eaaz0421.

Journal article
Published: 25 February 2020 in Toxins
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The bloom-forming cyanobacterium Nodularia spumigena CENA596 encodes the biosynthetic gene clusters (BGCs) of the known natural products nodularins, spumigins, anabaenopeptins/namalides, aeruginosins, mycosporin-like amino acids, and scytonemin, along with the terpenoid geosmin. Targeted metabolomics confirmed the production of these metabolic compounds, except for the alkaloid scytonemin. Genome mining of N. spumigena CENA596 and its three closely related Nodularia strains—two planktonic strains from the Baltic Sea and one benthic strain from Japanese marine sediment—revealed that the number of BGCs in planktonic strains was higher than in benthic one. Geosmin—a volatile compound with unpleasant taste and odor—was unique to the Brazilian strain CENA596. Automatic annotation of the genomes using subsystems technology revealed a related number of coding sequences and functional roles. Orthologs from the Nodularia genomes are involved in the primary and secondary metabolisms. Phylogenomic analysis of N. spumigena CENA596 based on 120 conserved protein sequences positioned this strain close to the Baltic Nodularia. Phylogeny of the 16S rRNA genes separated the Brazilian CENA596 strain from those of the Baltic Sea, despite their high sequence identities (99% identity, 100% coverage). The comparative analysis among planktic Nodularia strains showed that their genomes were considerably similar despite their geographically distant origin.

ACS Style

Rafael Vicentini Popin; Endrews Delbaje; Vinicius Augusto Carvalho De Abreu; Janaina Rigonato; Felipe Augusto Dörr; Ernani Pinto; Kaarina Sivonen; Marli Fatima Fiore. Genomic and Metabolomic Analyses of Natural Products in Nodularia spumigena Isolated from a Shrimp Culture Pond. Toxins 2020, 12, 141 .

AMA Style

Rafael Vicentini Popin, Endrews Delbaje, Vinicius Augusto Carvalho De Abreu, Janaina Rigonato, Felipe Augusto Dörr, Ernani Pinto, Kaarina Sivonen, Marli Fatima Fiore. Genomic and Metabolomic Analyses of Natural Products in Nodularia spumigena Isolated from a Shrimp Culture Pond. Toxins. 2020; 12 (3):141.

Chicago/Turabian Style

Rafael Vicentini Popin; Endrews Delbaje; Vinicius Augusto Carvalho De Abreu; Janaina Rigonato; Felipe Augusto Dörr; Ernani Pinto; Kaarina Sivonen; Marli Fatima Fiore. 2020. "Genomic and Metabolomic Analyses of Natural Products in Nodularia spumigena Isolated from a Shrimp Culture Pond." Toxins 12, no. 3: 141.

Journal article
Published: 17 January 2020 in Algal Research
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Mycosporines and mycosporine-like amino acids are ultra-violet radiation absorbing compounds produced by lichens, fungi, algae and cyanobacterial species, especially upon exposure to solar ultraviolet radiation. These compounds are photoprotective and some have additional antioxidant functions. Thus, mycosporine-like amino acids may be used as an active ingredient in cosmetic products. Analysis is generally achieved by separation using reverse-phase chromatography and, detection and quantification based upon characteristic absorption spectra and extremely high molar extinction coefficients. Herein, a validated liquid chromatography coupled with tandem mass spectrometry (LC-MS/MS) quantification method for mycosporine-like amino acids is presented. Additionally, an easy-to-handle and rapid extraction procedure was developed, which uses only water and volatile additives as the extractor solvents. The LC-MS/MS method was performed with an electrospray ionization source in positive mode using multiple reaction monitoring with a reverse-phase column. The method enabled the accurate determination and quantification of the mycosporine-like amino acids porphyra-334, shinorine and mycosporine-glycine-alanine in a 6 min running time, with detection limits of 0.002 μg mg−1, 0.001 μgmg−1 and 0.005 μg mg−1, respectively. These methods provided a simple extraction and rapid analysis procedure that efficiently identified and quantified these three mycosporine-like amino acids produced by a collection of 29 cyanobacteria. Although more mycosporine-like amino acids have also been identified, the validated method was developed focusing on the most abundant mycosporine-like amino acids produced by the investigated cyanobacteria. Mycosporine-like amino acids could be detected at levels well above the limits of detection for the LC-MS/MS method in 12 strains, irrespective of whether the cultures had been exposed to ultra-violet radiation. High levels of constitutive expression of mycosporine-like amino acids in cyanobacteria has rarely been reported and provides an opportunity to study mechanisms that regulate ultra-violet radiation induced mycosporine-like amino acids biosynthesis in the future.

ACS Style

Vanessa Geraldes; Lívia S. de Medeiros; Fernanda R. Jacinavicius; Paul F. Long; Ernani Pinto. Development and validation of a rapid LC-MS/MS method for the quantification of mycosporines and mycosporine-like amino acids (MAAs) from cyanobacteria. Algal Research 2020, 46, 101796 .

AMA Style

Vanessa Geraldes, Lívia S. de Medeiros, Fernanda R. Jacinavicius, Paul F. Long, Ernani Pinto. Development and validation of a rapid LC-MS/MS method for the quantification of mycosporines and mycosporine-like amino acids (MAAs) from cyanobacteria. Algal Research. 2020; 46 ():101796.

Chicago/Turabian Style

Vanessa Geraldes; Lívia S. de Medeiros; Fernanda R. Jacinavicius; Paul F. Long; Ernani Pinto. 2020. "Development and validation of a rapid LC-MS/MS method for the quantification of mycosporines and mycosporine-like amino acids (MAAs) from cyanobacteria." Algal Research 46, no. : 101796.

Journal article
Published: 29 November 2019 in Molecules
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Aminopeptidase M (AMP) inhibition is of interest for several diseases, such as highly vascularized cancer types. AMP can be inhibited by linear pentapeptides isolated from Microcystis aeruginosa LTPNA08 (MG7XX). Porcine AMP inhibition—a model for human AMP—activity was spectrophotometrically measured by the formation of p-nitroanilide from L-leucine-p-nitroanilide substrate by AMP. AMP inhibition by MG770 exhibited comparable inhibition levels to amastatin (IC50 values: 1.20 ± 0.1 μM and 0.98 ± 0.1 μM, respectively), while MG756 was slightly less potent (with IC50 values of 3.26 ± 0.5 μM). Molecular modelling suggests a potential binding mode, based on the interaction with the Zn2+ cofactor, where MG770′s extra methyl group contributes to the disturbance of the Zn2+ cofactor complex and highlights the importance of hydrophobicity for the site.

ACS Style

Glaucio Monteiro Ferreira; Thales Kronenberger; Éryka Costa De Almeida; Joseane Sampaio; Clélia Ferreira Terra; Ernani Pinto; Gustavo Henrique Goulart Trossini. Inhibition of Porcine Aminopeptidase M (pAMP) by the Pentapeptide Microginins. Molecules 2019, 24, 4369 .

AMA Style

Glaucio Monteiro Ferreira, Thales Kronenberger, Éryka Costa De Almeida, Joseane Sampaio, Clélia Ferreira Terra, Ernani Pinto, Gustavo Henrique Goulart Trossini. Inhibition of Porcine Aminopeptidase M (pAMP) by the Pentapeptide Microginins. Molecules. 2019; 24 (23):4369.

Chicago/Turabian Style

Glaucio Monteiro Ferreira; Thales Kronenberger; Éryka Costa De Almeida; Joseane Sampaio; Clélia Ferreira Terra; Ernani Pinto; Gustavo Henrique Goulart Trossini. 2019. "Inhibition of Porcine Aminopeptidase M (pAMP) by the Pentapeptide Microginins." Molecules 24, no. 23: 4369.

Original paper
Published: 26 November 2019 in Chemical Papers
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Piper species are commonly used by indigenous communities to treat several gastrointestinal diseases. In China, they are also used as an active ingredient in formulae to treat cancer. The objective of the study was to perform a large-scale metabolite profiling analysis to identify bioactive compounds in Piper anisum. Antioxidant capacity was assessed by the DPPH assay and total phenolics were assessed by Folin–Ciocalteu’s method. Antimicrobial activity was assessed against several Gram-positive and Gram-negative bacteria, whereas cytotoxicity was assessed against tumor cell lines MCF-7, HCT116, HepG2 and HL-60, and non-tumor cell line MRC-5. The multiplatform metabolite profiling approach encompassed NMR, GC–MS and LC–MS analyses. P. anisum root extract showed the greatest antioxidant capacity and total phenolic content, followed by the stem and leaf extracts. P. anisum extracts showed a highly selective antimicrobial profile, being specifically active against C. albicans (MIC of 500 μg mL−1). Additionally, the root extract (50 μg mL−1) showed the highest cell inhibition percentages against tumor cell lines MCF-7 (59.5%), HCT116 (49.2%), and HepG2 (61.0%). Forty-eight metabolites were annotated by GC–MS and 27 by LC–MS. These included alkaloids, carbohydrates, fatty acids, hydrocarbons, organic acids, phenolic compounds, and terpenes. Taken together, these results showed that P. anisum root extract is a promising source of bioactive compounds.

ACS Style

Danilo Batista; Patrícia Campos; Valdenizia R. Silva; Luciano De S. Santos; Daniel P. Bezerra; Milena B. P. Soares; Pio Colepicolo; Leonardo Zambotti-Villela; Ernani Pinto; Floricea M. Araújo; Dirceu Martins; Luzimar G. Fernandez; Wilco Ligterink; Gisele A B Canuto; Martins Dias De Cerqueira; Paulo R. Ribeiro. Piper anisum as a promising new source of bioactive metabolites. Chemical Papers 2019, 74, 1505 -1515.

AMA Style

Danilo Batista, Patrícia Campos, Valdenizia R. Silva, Luciano De S. Santos, Daniel P. Bezerra, Milena B. P. Soares, Pio Colepicolo, Leonardo Zambotti-Villela, Ernani Pinto, Floricea M. Araújo, Dirceu Martins, Luzimar G. Fernandez, Wilco Ligterink, Gisele A B Canuto, Martins Dias De Cerqueira, Paulo R. Ribeiro. Piper anisum as a promising new source of bioactive metabolites. Chemical Papers. 2019; 74 (5):1505-1515.

Chicago/Turabian Style

Danilo Batista; Patrícia Campos; Valdenizia R. Silva; Luciano De S. Santos; Daniel P. Bezerra; Milena B. P. Soares; Pio Colepicolo; Leonardo Zambotti-Villela; Ernani Pinto; Floricea M. Araújo; Dirceu Martins; Luzimar G. Fernandez; Wilco Ligterink; Gisele A B Canuto; Martins Dias De Cerqueira; Paulo R. Ribeiro. 2019. "Piper anisum as a promising new source of bioactive metabolites." Chemical Papers 74, no. 5: 1505-1515.

Special issue research article
Published: 02 November 2019 in Rapid Communications in Mass Spectrometry
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RATIONALE Mycosporine‐like amino acids (MAAs) are UV‐absorbing compounds produced by fungi, algae, lichens, and cyanobacteria when exposed to ultra‐violet radiation (UVR). These compounds have a photoprotective and an antioxidant function and have been widely studied for possible use in sunscreens and anti‐aging products. This study aims to identify MAAs‑producing cyanobacteria with potential application in cosmetics. METHODS A method for the identification of MAAs was developed using ultra‐high‐performance liquid chromatography ‐ diode array detection ‐ quadrupole time of flight mass spectrometry (UHPLC‐DAD‐QTOFMS). Chromatographic separation was carried out using a Synergi 4μ Hydro‐RP 80 A column (150 x 2,0 mm) at 30 °C with 0.1% formic acid aqueous solution + 2 mM ammonium formate and acetonitrile/water (8:2) + 0.1 % formic acid as a mobile phase. RESULTS Out of the sixty‐nine cyanobacteria studied, twenty‐six strains (37%) synthesized MAAs. Nine different MAAs were identified in the UHPLC‑DAD‐HRMS. Imino‐mycosporines were the major group detected (7 in 9 MAAs). In terms of abundance, the most representative genera for MAAs production were heterocyte‐forming groups. Oscilatoria sp. CMMA 1600, from homocyte type, produced the greatest diversity of MAAs. CONCLUSIONS The UHPLC‐DAD‐QTOFMS method is a powerful tool for identification and screening of MAAs in cyanobacteria strains as well as in other organisms such as dinoflagellates, macroalgae, and microalgae. The different cyanobacteria genera isolated from diverse Brazilian biomes and environments are prolific source of MAA.

ACS Style

Vanessa Geraldes; Fernanda Rios Jacinavicius; Diego Bonaldo Genuário; Ernani Pinto. Identification and distribution of mycosporine‐like amino acids in Brazilian cyanobacteria using ultrahigh‐performance liquid chromatography with diode array detection coupled to quadrupole time‐of‐flight mass spectrometry. Rapid Communications in Mass Spectrometry 2019, e8634 .

AMA Style

Vanessa Geraldes, Fernanda Rios Jacinavicius, Diego Bonaldo Genuário, Ernani Pinto. Identification and distribution of mycosporine‐like amino acids in Brazilian cyanobacteria using ultrahigh‐performance liquid chromatography with diode array detection coupled to quadrupole time‐of‐flight mass spectrometry. Rapid Communications in Mass Spectrometry. 2019; ():e8634.

Chicago/Turabian Style

Vanessa Geraldes; Fernanda Rios Jacinavicius; Diego Bonaldo Genuário; Ernani Pinto. 2019. "Identification and distribution of mycosporine‐like amino acids in Brazilian cyanobacteria using ultrahigh‐performance liquid chromatography with diode array detection coupled to quadrupole time‐of‐flight mass spectrometry." Rapid Communications in Mass Spectrometry , no. : e8634.

Erratum
Published: 17 June 2019 in Ecotoxicology and Environmental Safety
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Douglas Silva Dos Santos; Maria Eduarda Rosa; Ana Paula Zanatta; Raquel Soares Oliveira; Carlos Gabriel Moreira De Almeida; Allan Pinto Leal; Miriam Sanz; Kelly Afonsina Fernandes; Velci Queiroz De Souza; Denis Reis De Assis; Ernani Pinto; Cháriston André Dal Belo. Corrigendum to "neurotoxic effects of sublethal concentrations of cyanobacterial extractcontaining anatoxin-a(s) onNauphoeta cinereacockroaches" [Ecotoxicol. Environ. Saf. 171 (2019) 138-145]. Ecotoxicology and Environmental Safety 2019, 183, 109312 .

AMA Style

Douglas Silva Dos Santos, Maria Eduarda Rosa, Ana Paula Zanatta, Raquel Soares Oliveira, Carlos Gabriel Moreira De Almeida, Allan Pinto Leal, Miriam Sanz, Kelly Afonsina Fernandes, Velci Queiroz De Souza, Denis Reis De Assis, Ernani Pinto, Cháriston André Dal Belo. Corrigendum to "neurotoxic effects of sublethal concentrations of cyanobacterial extractcontaining anatoxin-a(s) onNauphoeta cinereacockroaches" [Ecotoxicol. Environ. Saf. 171 (2019) 138-145]. Ecotoxicology and Environmental Safety. 2019; 183 ():109312.

Chicago/Turabian Style

Douglas Silva Dos Santos; Maria Eduarda Rosa; Ana Paula Zanatta; Raquel Soares Oliveira; Carlos Gabriel Moreira De Almeida; Allan Pinto Leal; Miriam Sanz; Kelly Afonsina Fernandes; Velci Queiroz De Souza; Denis Reis De Assis; Ernani Pinto; Cháriston André Dal Belo. 2019. "Corrigendum to "neurotoxic effects of sublethal concentrations of cyanobacterial extractcontaining anatoxin-a(s) onNauphoeta cinereacockroaches" [Ecotoxicol. Environ. Saf. 171 (2019) 138-145]." Ecotoxicology and Environmental Safety 183, no. : 109312.

Journal article
Published: 13 April 2019 in Toxins
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Absorption and accumulation of bioavailable cyanobacterial metabolites (including cyanotoxins) are likely in fish after senescence and the rupturing of cells during bloom episodes. We determined the toxicity of cyanopeptides identified from two strains of Microcystis (M. panniformis MIRS-04 and M. aeruginosa NPDC-01) in a freshwater tropical fish, Astyanax altiparanae (yellowtail tetra, lambari). Aqueous extracts of both Microcystis strains were prepared in order to simulate realistic fish exposure to these substances in a freshwater environment. Both strains were selected because previous assays evidenced the presence of microcystins (MCs) in MIRS-04 and lack of cyanotoxins in NPDC-01. Identification of cyanobacterial secondary metabolites was performed by LC-HR-QTOF-MS and quantification of the MC-LR was carried out by LC-QqQ-MS/MS. MIRS-04 produces the MCs MC-LR, MC-LY and MC-HilR as well as micropeptins B, 973, 959 and k139. NPCD-01 biosynthetizes microginins FR1, FR2/FR4 and SD-755, but does not produce MCs. Larval fish survival and changes in morphology were assessed for 96 h exposure to aqueous extracts of both strains at environmentally relevant concentrations from 0.1 to 0.5 mg (dry weight)/mL, corresponding to 0.15 to 0.74 μg/mL of MC-LR (considering dried amounts of MIRS-04 for comparison). Fish mortality increased with concentration and time of exposure for both strains of Microcystis. The frequencies of morphological abnormalities increased with concentration in both strains, and included abdominal and pericardial oedema, and spinal curvature. Results demonstrate that toxicity was not solely caused by MCs, other classes of cyanobacterial secondary metabolites contributed to the observed toxicity.

ACS Style

Kelly Fernandes; Andreia Gomes; Leonardo Calado; George Yasui; Diego Assis; Theodore Henry; Ana Fonseca; Ernani Pinto. Toxicity of Cyanopeptides from Two Microcystis Strains on Larval Development of Astyanax altiparanae. Toxins 2019, 11, 220 .

AMA Style

Kelly Fernandes, Andreia Gomes, Leonardo Calado, George Yasui, Diego Assis, Theodore Henry, Ana Fonseca, Ernani Pinto. Toxicity of Cyanopeptides from Two Microcystis Strains on Larval Development of Astyanax altiparanae. Toxins. 2019; 11 (4):220.

Chicago/Turabian Style

Kelly Fernandes; Andreia Gomes; Leonardo Calado; George Yasui; Diego Assis; Theodore Henry; Ana Fonseca; Ernani Pinto. 2019. "Toxicity of Cyanopeptides from Two Microcystis Strains on Larval Development of Astyanax altiparanae." Toxins 11, no. 4: 220.