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au:Berlinck, Roberto G. S.

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Natural Products from Marine Invertebrates and Microorganisms in Brazil between 2004 and 2017: Still the Challenges, More Rewards
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Ióca, Laura P.

; Nicacio, Karen J.

; Berlinck, Roberto G. S.

Journal of the Brazilian Chemical Society

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may 2018, Volume 29 N. 5 Pages 998 - 1031

Abstract: En | Text: En | PDF: En

The Brazilian marine biodiversity represents a unique, yet underexplored resource of biologically active compounds. This review provides an analysis of the development of marine natural products chemistry in Brazil within the period comprised between 2004 and 2017. Emphasis is directed towards marine invertebrate and marine microorganisms metabolites, including isolation, structure analysis, biosynthesis, bioactivities and total synthesis. An overview of the research on marine natural products by Brazilian researchers is also discussed, as well as perspectives for the development of the chemistry of marine natural products in Brazil.

https://doi.org/10.21577/0103-5053.20180016 1771 downloads

A QUÍMICA DE PRODUTOS NATURAIS DO BRASIL DO SÉCULO XXI
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Berlinck, Roberto G. S.

; Borges, Warley de S.

; Scotti, Marcus T.

; Vieira, Paulo C.

Química Nova

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jul 2017, Volume 40 N. 6 Pages 706 - 710

Abstract: Pt En | Text: Pt En | PDF: Pt | PDF: En

The chemistry of natural products in Brazil has experienced a rapid development during the 21st century, with a diversification of lines of research, methodological approaches, exploration of diverse natural sources for the isolation of secondary metabolites and establishment of several multidisciplinary initiatives. These topics are critically discussed, evidencing achievements and new challenges to be faced for the future of Brazilian natural products chemistry.

https://doi.org/10.21577/0100-4042.20170070 4937 downloads

Evaluation of Chemical Defense and Chemical Diversity in the Exotic Bryozoan Amathia verticillata
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Santos, Larissa A. H. dos

; Clavico, Etiene E. G.

; Parra, Lizbeth L. L.

; Berlinck, Roberto G. S.

; Ferreira, Antonio G.

; Paul, Valerie J.

; Pereira, Renato C.

Journal of the Brazilian Chemical Society

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mar 2017, Volume 28 N. 3 Pages 435 - 442

Abstract: En | Text: En | PDF: En

The present investigation tests the effects against feeding by fishes of crude extracts obtained from eleven distinct populations of the bryozoan Amathia verticillata, an invasive species found globally in tropical to warm-temperate waters. Investigation of extracts from 11 populations of A. verticillata led to the identification and quantification of the known indole alkaloid 2,5,6-tribromo-N-methylgramine and isolation and identification of the new indole alkaloid, 2,6-dibromo-N-methylgramine. One extract of A. verticillata from Brazil significantly deterred feeding, while other extracts of A. verticillata from Florida significantly stimulated feeding by fishes, in field assays performed in Brazil. The same extracts of Florida samples showed variable effects on feeding, ranging from attraction to deterrence, in assays carried out in Florida. The absence of broad chemical defenses against feeding by fish suggests that the establishment of A. verticillata as an invasive species into new areas may be due to reasons other than defensive chemistry.

https://doi.org/10.21577/0103-5053.20160257 861 downloads

A STRATEGY FOR THE RAPID IDENTIFICATION OF FUNGAL METABOLITES AND THE DISCOVERY OF THE ANTIVIRAL ACTIVITY OF PYRENOCINE A AND HARZIANOPYRIDONE
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Ióca, Laura P.

; Romminger, Stelamar

; Santos, Mario F. C.

; Bandeira, Karin F.

; Rodrigues, Fabiana T.

; Kossuga, Miriam H.

; Nicacio, Karen J.

; Ferreira, Everton L. F.

; Morais-Urano, Raquel P.

; Passos, Messias S.

; Kohn, Luciana K.

; Arns, Clarice W.

; Sette, Lara D.

; Berlinck, Roberto G. S.

Química Nova

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jul 2016, Volume 39 N. 6 Pages 720 - 731

Abstract: En | Text: En | PDF: En

The isolation and identification of bioactive metabolites from complex extracts obtained from microbial growth media is a time consuming, costly, and labor-intensive task. A strategy to rapidly identify secondary metabolites isolated from extracts obtained from the culture media of marine-derived and endophytic fungal strains is described. Identification was achieved by HPLC-UV-MS and 1H NMR analyses in combination with data obtained from the Dictionary of Natural Products. Among the compounds identified, (-)-naphthoquinoneimine, citreorosein, emodin, pyrenocine A and harzianopyridone displayed moderate to potent antiviral activity. (-)-Naphthoquinoneimine was isolated as the enantiomer of its previously reported dextrorotatory congener, while 6,7-dihydroxy-2,2-dimethyl-4-chromanone is herein reported for the first time as a natural product.

https://doi.org/10.5935/0100-4042.20160092 2688 downloads

Rodriguesic acids, modified diketopiperazines from the gastropod mollusc Pleurobranchus areolatus
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Pereira, Fabio R.

; Santos, Mario F. C.

; Williams, David E.

; Andersen, Raymond J.

; Padula, Vinicius

; Ferreira, Antonio G.

; Berlinck, Roberto G. S.

Journal of the Brazilian Chemical Society

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apr 2014, Volume 25 N. 4 Pages 788 - 794

Abstract: Pt En | Text: Pt En | PDF: Pt | PDF: En

O presente estudo foi realizado com dois espécimes do molusco nudipleura Pleurobranchus areolatus que demonstraram acumular derivados oxidados da rodriguesina A. O ácido rodriguêsico apresenta um grupo ácido carboxílico no lugar do grupo metila de uma cadeia alquila terminal da rodriguesina A. Um grupo hidroxamato foi observado na porção dicetopiperazínica do ácido rodriguêsico. As estruturas do ácido rodriguêsico e do hidroxamato do ácido rodriguêsico foram estabelecidas por análise de seus dados espectroscópicos, inclusive sua configuração absoluta. Dois ésteres metílicos dos ácidos rodriguêsicos foram isolados como compostos majoritários, porém considerados como artefatos de isolamento.

In the present investigation, two specimens of the nudipleuran mollusc Pleurobranchus areolatus have shown to accumulate oxidized rodriguesin A derivatives. Rodriguesic acid presents a carboxylic acid replacing the terminal methyl group of the alkyl chain of rodriguesin A. A hydroxamate group was also present on the diketopiperazine moiety of a rodriguesic acid derivative. The structures of both rodriguesic acid and of rodriguesic acid hydroxamate have been established by analysis of spectroscopic data, including their absolute configuration. Two methyl esters of the rodriguesic acids have been isolated as major compounds, but were considered to be isolation artifacts.

https://doi.org/10.5935/0103-5053.20140037 1208 downloads

Biosynthesis of two dihydropyrrole-polyketides from a marine-derived Penicillium citrinum
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Romminger, Stelamar

; Pimenta, Eli F.

; Nascimento, Eduardo S.

; Ferreira, Antonio G.

; Berlinck, Roberto G. S.

Journal of the Brazilian Chemical Society

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oct 2012, Volume 23 N. 10 Pages 1783 - 1788

Abstract: Pt En | Text: Pt En | PDF: Pt | PDF: En

Experimentos de incorporação com precursores marcados com 13C foram realizados objetivando-se estabelecer a biossíntese de dois dihidropirróis N-acilados, (8E)-1-(2,3-dihidro1H-pirrol-1-il)-2-metildec-8-eno-1,3-diona (1) e 1-(2,3-dihidro-1H-pirrol-1-il)-2-metildecano1,3-diona (2), isolados de culturas de Penicillium citrinum de origem marinha. A biossíntese de ambos, 1 e 2, procede através da incorporação de acetato, metionina e ornitina.

Feeding experiments with 13C-labeled precursors were performed in order to establish the biosynthesis of two N-acylated dihydropyrroles, (8E)-1-(2,3-dihydro-1H-pyrrol-1-yl)-2-methyldec8-ene-1,3-dione (1) and 1-(2,3-dihydro-1H-pyrrol-1-yl)-2-methyldecane-1,3-dione (2), isolated from the cultures of a marine-derived Penicillium citrinum. The biosynthesis of both, 1 and 2, involves the incorporation of acetate, methionine and ornithine.

2121 downloads

Evaluating methods for the isolation of marine-derived fungal strains and production of bioactive secondary metabolites
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Kossuga, Miriam H.

; Romminger, Stelamar

; Xavier, Camila

; Milanetto, Marília C.

; Valle, Milene Z. do

; Pimenta, Eli F.

; Morais, Raquel P.

; Carvalho, Erica de

; Mizuno, Carolina M.

; Coradello, Luís Fernando C.

; Barroso, Vinícius de M.

; Vacondio, Bruna

; Javaroti, Darci C. D.

; Seleghim, Mirna H. R.

; Cavalcanti, Bruno C.

; Pessoa, Claudia

; Moraes, Manoel O.

; Lima, Bruna A.

; Gonçalves, Reginaldo

; Bonugli-Santos, Rafaella C.

; Sette, Lara D.

; Berlinck, Roberto G. S.

Revista Brasileira de Farmacognosia

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apr 2012, Volume 22 N. 2 Pages 257 - 267

Abstract: En | Text: En | PDF: En

In the present investigation we evaluate methods for the isolation and growth of marine-derived fungal strains in artificial media for the production of secondary metabolites. Inoculation of marine macroorganisms fragments in Petri dishes proved to be the most convenient procedure for the isolation of the largest number of strains. Among the growth media used, 3% malt extract showed the best result for strains isolation and growth, and yielded the largest number of strains from marine macroorganisms. The percentage of strains isolated using each of the growth media which yielded cytotoxic and/or antibiotic extracts was in the range of 23-35%, regardless of the growth media used. Further investigation of extracts obtained from different marine-derived fungal strains yielded several bioactive secondary metabolites, among which (E)-4-methoxy-5-(3-methoxybut-1-enyl)-6-methyl-2H-pyran-2-one is a new metabolite isolated from the Penicillium paxilli strain Ma(G)K.

10199 downloads

Utilização de detecção por espalhamento de luz evaporativo para a análise de produtos naturais
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Urano, Raquel P. Morais

; Rodrigues, Fabiana T.

; Berlinck, Roberto G. S.

Química Nova

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2012, Volume 35 N. 6 Pages 1198 - 1208

Abstract: Pt En | Text: Pt En | PDF: Pt | PDF: En

The interest in the use of evaporative light scattering detector (ELSD) for the analysis of different classes of natural products has grown over the years. This is because this detector has become an excellent alternative compared to other types of detectors, such as the refractive index detector and the ultraviolet (UV) detector. This review describes the basic principles of ELSD functioning and discusses the advantages and disadvantages in using an ELSD for the analysis of organic compounds. Additionaly, an overview, covering the last 23 years, of ELSD applications in natural products analysis (saponins, terpenes, carbohydrates, glycosides, alkaloids, steroids, flavonoids, peptides, polyketides, coumarins and iridoids) is presented and discussed.

8838 downloads

Metabólitos secundários dos nudibrânquios Tambja stegosauriformis, Hypselodoris lajensis e Okenia zoobotryon e dos briozoários Zoobotryon verticillatum e Bugula dentata da costa do Brasil
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Pereira, Fábio R.

; Berlinck, Roberto G. S.

; Rodrigues Filho, Edson

; Veloso, Katyuscya

; Ferreira, Antonio G.

; Padula, Vinicius

Química Nova

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2012, Volume 35 N. 11 Pages 2194 - 2201

Abstract: Pt En | Text: Pt En | PDF: Pt | PDF: En

The chemical investigation of the MeOH extract from the bryozoan B. dentata MeOH yielded tambjamines A (1), C (3), D (4), K (6), aldehyde 8 and the new tambjamine J1(9), while the extract of its predator, the nudibranch Tambja stegosauriformis, yielded tambjamines C and K, along with aldehyde 8. Furodisinin lactone (11) was isolated from the nudibranch Hypselodoris lajensis, a compound previously isolated from Dysidea sponges. The alkaloid 2,5,6-tribromo-N-methylgramine (12) was isolated from the nudibranch Okenia zoobotryon and from its prey, the bryozoan Zoobotryon verticillatum, the only source of 12 previously known.

3043 downloads

10.

The academic plagiarism and its punishments - a review
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Berlinck, Roberto G. S.

Revista Brasileira de Farmacognosia

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jun 2011, Volume 21 N. 3 Pages 365 - 372

Abstract: En | Text: En | PDF: En

Currently there is an increase in the occurrence of plagiarism in varied types of academic texts. Therefore, in agreement with the Brazilian Coordination of Improvement of Higher Education Personnel (CAPES) policies, Brazilian higher education institutions should establish guidelines for the detection and inhibition of academic plagiarism. However, the notion of plagiarism is extremely complex, since the ability of textual construction acquired during education is also developed using others' words. Thus, it is necessary to better know the concept of plagiarism and its implications, as well as the consequences of plagiarism and the punishments that may result from it. Consequently, rules and policies to be established will be better founded in order to address the problem of plagiarism in academic texts in a comprehensive and consistent way, not only to inhibit plagiarism but also to promote education on how is possible to create texts in an original fashion.

34412 downloads

11.

A method for dextruxin analysis by HPLC-PDA-ELSD-MS
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Morais, Raquel P.

; Lira, Simone P.

; Seleghim, Mirna H. R.

; Berlinck, Roberto G. S.

Journal of the Brazilian Chemical Society

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dec 2010, Volume 21 N. 12 Pages 2262 - 2271

Abstract: Pt En | Text: Pt En | PDF: Pt | PDF: En

Destruxinas (Dtx) são ciclodepsipetídeos produzidos por fungos entomopatogênicos, que são utilizados como controle biológico em insetos pragas em diferentes agriculturas. A presente investigação reporta uma nova abordagem para análises de destruxinas produzidas por uma linhagem do fungo Beauveria felina, utilizando-se de LC-PDA-ELSD-MS. Em comparação com os métodos anteriores, a nova abordagem utiliza-se de uma limpeza prévia da amostra em cartuchos C18 que removem efetivamente os constituintes do meio de cultura. Além disso, o uso dos solventes MeCN/MeOH 50:50, (v/v) como eluentes mais fortes no sistema de gradiente em 0,1% de H2O demonstrou fornecer a melhor resolução dos picos cromatográficos. Detecções simultâneas usando arranjo de fotodiodos (PDA), detector de espalhamento de luz evaporativa (ELSD) e espectrometria de massas (MS) indicaram praticamente uma resposta idêntica de todos os detectores na análise das destruxinas. Cinco amostras obtidas da cultura de B. felina foram analisadas, e indicaram a presença de 20 destruxinas conhecidas e de 6 ciclodepsipetídeos ainda não reportados. Considerando a redução do uso do MeCN, e a eficácia do ELSD como detector para destruxina, o método prova que pode ser de grande valia e de baixo custo operacional para controle de qualidade nas análises de destruxinas produzidas por linhagens de fungos.

Destruxins (Dtx) are cyclodepsipeptides produced by enthomopathogenic fungi, which are used in biological control of different agricultural insect plagues. The present investigation reports a new approach for analysis of destruxins produced by the fungal strain Beauveria felina, using LC-PDA-ELSD-MS. Compared to previous methods, the new approach uses a clean-up on C18 cartridges, which effectively removes growth media constituents. Moreover, the use of 50:50 (v/v) MeCN/MeOH as the strongest eluting solvent in a gradient system over 0.1% H2O proved to give a better resolution of chromatographic peaks. Simultaneous detection using photodiode array (PDA), evaporative light scattering detector (ELSD) and mass spectrometry (MS) indicated a practically identical response of all detectors for destruxins analysis. Five samples obtained from the culture media of B. felina were analysed, and indicated the presence of twenty known destruxins and six yet unreported cyclodepsipeptides. Considering the reduced use of MeCN, and the effectiveness of ELSD as a detector for destruxins, the method proved to be valuable and cost-effective for quality control analysis of destruxin-producing fungal strains.

15791 downloads

12.

Metabólitos secundários das esponjas Aplysina fistularis e Dysidea sp. e atividade antituberculose da 11-cetofistularina-3
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Gandolfi, Renata C.

; Medina, Marina B.

; Berlinck, Roberto G. S.

; Lira, Simone P.

; Galetti, Fabio Cícero de Sá

; Silva, Célio L.

; Veloso, Katyuscya

; Ferreira, Antonio G.

; Hajdu, Eduardo

; Peixinho, Solange

Química Nova

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2010, Volume 33 N. 9 Pages 1853 - 1858

Abstract: Pt En | Text: Pt En | PDF: Pt | PDF: En

The present investigation reports the isolation of aeroplysinin-2, 2-(3,5-dibromo-4-methoxyphenyl)-N,N,N-trimethyletanamonium, 7,9-dibromo-10-hydroxy-8-methoxy-1-oxa-2-azaspiro[4.5]deca-2,6,8-trien-3-carboxylic acid and its methyl ester, 11-oxoaerothionin, aerothionin, 11-keto-12-hydroxyaerothionin, 11-ketofistularin-3 and fistularin-3 from Aplysina fistularis, as well as of furodysinin lactone and 9α,11α-epoxicholest-7-en-3β,5α,6α,10-tetrol-6-acetate from Dysidea sp. Although the extracts of both sponges displayed antituberculosis activity, only 11-ketofistularin-3 isolated from A. fistularis displayed antimycobacterial activity against Mycobacterium tuberculosis H34Rv, with MIC at 16 μg/mL and SI of 40, a result that reinforce that fistularin-3 derivatives are interesting leads for the development of antituberculosis drugs.

3559 downloads

13.

Antibacterial modified diketopiperazines from two ascidians of the genus Didemnum
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Kossuga, Miriam H.

; Lira, Simone P.

; McHugh, Shayna

; Torres, Yohandra R.

; Lima, Bruna A.

; Gonçalves, Reginaldo

; Veloso, Katyuscya

; Ferreira, Antonio G.

; Rocha, Rosana M.

; Berlinck, Roberto G. S.

Journal of the Brazilian Chemical Society

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2009, Volume 20 N. 4 Pages 704 - 711

Abstract: Pt En | Text: Pt En | PDF: Pt | PDF: En

A investigação química do extrato bruto de uma ascidia do gênero Didemnumlevou ao isolamento das dicetopiperazinas modificadas rodriguesinas A (1) e B (2) na forma de uma mistura de homólogos, os quais puderam ser identificados pela análise de seus dados espectroscópicos inclusive experimentos MS/MS. A investigação de uma segunda ascídia do gênero Didemnumforneceu a N-acetil-rodriguesina A (3) e a N-acetil-rodriguesina B (4). A configuração absoluta dos compostos 1e 2pode ser estabelecida por hidrólise e análise de Marfey e por comparação com dados da literatura do composto 3,previamente obtido como produto de síntese. A mistura de 1e 2apresentou atividade antibiótica moderada contra um isolado clínico de Streptococcus mutans, contra S. mutans UA159 e S. aureusATCC6538.

The chemical investigation of the crude extract of an ascidian of the genus Didemnumled to the isolation of the modified diketopiperazine rodriguesines A (1) and (2) as a mixture of homologues, which could be identified by analysis of spectroscopic data including MS/MS experiments. The investigation of a second Didemnumsp. led to the isolation of N-acetyl-rodriguesine A (3) and N-acetyl-rodriguesine B (4). The absolute configuration of compounds 1and 2could be established by hydrolysis and Marfey's analysis and comparison with literature data reported for compound 3, previously obtained as a synthetic product. The mixture of 1and 2displayed moderate antibiotic activity against a clinical isolate of Streptococcus mutansand against S. mutansUA159 and Staphylococcus aureusATCC6538.

2094 downloads

14.

A multi-screening approach for marine-derived fungal metabolites and the isolation of cyclodepsipeptides from Beauveria felina
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Vita-Marques, Aline Maria de

; Lira, Simone P.

; Berlinck, Roberto G. S.

; Seleghim, Mirna H. R.

; Sponchiado, Sandra R. P.

; Tauk-Tornisielo, Sâmia M.

; Barata, Margarida

; Pessoa, Claudia

; Moraes, Manoel O. de

; Cavalcanti, Bruno Coêlho

; Nascimento, Gislene G. F.

; Souza, Ana O. de

; Galetti, Fabio C. S.

; Silva, Célio L.

; Silva, Marcio

; Pimenta, Eli F.

; Thiemann, Otavio

; Passarini, Michel R. Z.

; Sette, Lara D.

Química Nova

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2008, Volume 31 N. 5 Pages 1099 - 1103

Abstract: En | Text: En | PDF: En

Extracts obtained from 57 marine-derived fungal strains were analyzed by HPLC-PDA, TLC and ¹H NMR. The analyses showed that the growth conditions affected the chemical profile of crude extracts. Furthermore, the majority of fungal strains which produced either bioactive of chemically distinctive crude extracts have been isolated from sediments or marine algae. The chemical investigation of the antimycobacterial and cytotoxic crude extract obtained from two strains of the fungus Beauveria felina have yielded cyclodepsipeptides related to destruxins. The present approach constitutes a valuable tool for the selection of fungal strains that produce chemically interesting or biologically active secondary metabolites.

4321 downloads Cited 1 time in SciELO

15.

Isolamento e atividades biológicas de produtos naturais das esponjas monanchora arbuscula, aplysina sp. petromica ciocalyptoides e topsentia ophiraphidites, da ascídia didemnum ligulum e do octocoral carijoa riisei
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Kossuga, Miriam H.

; Lira, Simone P. de

; Nascimento, Andréa M.

; Gambardella, Maria Teresa P.

; Berlinck, Roberto G. S.

; Torres, Yohandra R.

; Nascimento, Gislene G. F.

; Pimenta, Eli F.

; Silva, Marcio

; Thiemann, Otávio H.

; Oliva, Glaucius

; Tempone, André G.

; Melhem, Márcia S. C.

; Souza, Ana O. de

; Galetti, Fabio C. S.

; Silva, Célio L.

; Cavalcanti, Bruno

; Pessoa, Claudia O.

; Moraes, Manoel O.

; Hajdu, Eduardo

; Peixinho, Solange

; Rocha, Rosana M.

Química Nova

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oct 2007, Volume 30 N. 5 Pages 1194 - 1202

Abstract: Pt En | Text: Pt En | PDF: Pt | PDF: En

The investigation of extracts from six species of marine invertebrates yielded one new and several known natural products. Isoptilocaulin from the sponge Monanchora aff. arbuscula displayed antimicrobial activity at 1.3 mg/mL against an oxacillin-resistant strain of Staphylococcus aureus. Five inactive known dibromotyrosine derivatives, 2 6, were isolated from a new species of marine sponge, Aplysina sp. The sponges Petromica ciocalyptoides and Topsentia ophiraphidites yielded the known halistanol sulfate A (7) as an inhibitor of the antileishmanial target adenosine phosphoribosyl transferase. The ascidian Didemnum ligulum yielded asterubin (10) and the new N,N-dimethyl-O-methylethanolamine (11). The octocoral Carijoa riisei yielded the known 18-acetoxypregna-1,4,20-trien-3-one (12), which displayed cytotoxic activity against the cancer cell lines SF295, MDA-MB435, HCT8 and HL60.

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