Clathriamide, an hexapeptide isolated from the marine sponge Clathria (Clathria) nicoleae

Freire, Vítor F.; Slivinski, Juliano; Quintana, Jairo; Moraes, Fernando C.; Paradas, Wladimir Costa; Salgado, Leonardo T.; Pereira, Renato Crespo; Moura, Rodrigo L.; Amado‐Filho, Gilberto M.; Ferreira, Antônio G.; Berlinck, Roberto G. S.

doi:10.1016/j.bjp.2019.07.001

Cited by 7 publications

(8 citation statements)

References 13 publications

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“…S6), confirmed our hypothesis. Theabsolute configurations of all amino acids was established as l by advanced Marfeysanalysis (Figures S17-21), [24,25] thus completing the structure of 1,n amed pseudovibriamide A1 (Figure 2).…”

Section: Resultsmentioning

confidence: 74%

A Family of Nonribosomal Peptides Modulate Collective Behavior in Pseudovibrio Bacteria Isolated from Marine Sponges**

et al. 2021

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Although swarming motility and biofilms are opposed collective behaviors, both contribute to bacterial survival and host colonization. Pseudovibrio bacteria have attracted attention because they are part of the microbiome of healthy marine sponges. Two‐thirds of Pseudovibrio genomes contain a member of a nonribosomal peptide synthetase‐polyketide synthase gene cluster family, which is also found sporadically in Pseudomonas pathogens of insects and plants. After developing reverse genetics for Pseudovibrio, we isolated heptapeptides with an ureido linkage and related nonadepsipeptides we termed pseudovibriamides A and B, respectively. A combination of genetics and imaging mass spectrometry experiments showed heptapetides were excreted, promoting motility and reducing biofilm formation. In contrast to lipopeptides widely known to affect motility/biofilms, pseudovibriamides are not surfactants. Our results expand current knowledge on metabolites mediating bacterial collective behavior.

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Section: Resultsmentioning

confidence: 74%

A Family of Nonribosomal Peptides Modulate Collective Behavior in Pseudovibrio Bacteria Isolated from Marine Sponges**

et al. 2021

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“…The absolute configurations of all amino acids was established as L by advanced Marfey's analysis (Figs. S17-21) 24,25 , thus completing the structure of 1, named pseudovibriamide A1 (Fig. 4).…”

Section: Identification Of Pseudovibriamidesmentioning

confidence: 83%

“…The hydrolysate was resuspended in 1 mL of H 2 O and dried three times. Marfey's derivatization was performed using 1% 5-fluoro-2,4-dinitrophenyl-Nα-L-tryptophanamide (FDTA) in acetone, as described before 24,25 . The hydrolysate was resuspended in H 2 O, followed by the addition of 20 μL of 1 mol/L NaHCO 3 , and L-FDTA at 1.4x (which was not certified by peer review) is the author/funder.…”

Section: Uplc-hresims and Msmentioning

confidence: 99%

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A novel family of nonribosomal peptides modulate collective behavior inPseudovibriobacteria isolated from marine sponges

Ióca

Dai

Kunakom

et al. 2020

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Collective behavior is a common feature of life. Although swarming motility and biofilms are opposed collective behaviors, both contribute to bacterial survival and host colonization. We have identified a link between motility/biofilms and a nonribosomal peptide synthetase-polyketide synthase gene cluster family (ppp) conserved in Pseudovibrio and Pseudomonas Proteobacteria known to interact with diverse eukaryotes. After developing reverse genetics for Pseudovibrio, we discovered two pseudovibriamide families, heptapeptides with a reversal in chain polarity via an ureido linkage 1-6 and related nonadepsipeptides 7-12. Imaging mass spectrometry showed that 1 was excreted whereas 7 was colony-associated. Deletion of pppA abolished production of 1-12 leading to reduced motility and increased biofilm production. pppD mutants that produced only 1-6 showed motility comparable to the wild-type and reduced biofilm formation, indicating that the excreted heptapeptides play a role in promoting motility. In contrast to lipopeptides widely known to affect swarming and biofilms, pseudovibriamides are not surfactants. Our results expand current knowledge on metabolites mediating bacterial collective behavior. Moreover, the establishment of reverse genetics will enable future exploration of the ecological and biotechnological potential of Pseudovibrio bacteria which have been proposed to contribute to marine sponge health.

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“…57 -Comparação dos cromatogramas obtidos em análise de UPLC-QTOF-MS da hidrólise dos compostos presentes na fração C23C1C e derivatizados com + L-FDTA (A), e padrões dos aminoácidos L-Ile+ L-FDTA (B), L-allo-Ile + L-FDTA (C) e L-Leu + L-FDTA (D).Fonte: Autoria própria. Condições de análises realizadas como descrito anteriormente porFreire et al (2019).Os demais resíduos de aminoácidos, Tyr, Dhb, Ala, Arg, Pro-thz e Gln, também foram confirmados de estereoquímica L por análise avançada de Marfey (Figuras S52-56).5.16 Determinação da estrutural da pseudovibriamida B4O composto presente na fração C23C1A(2,7 mg) apresentou um íon [M + H] + em m/z 1142,4929 (calculado para 1142,4941, erro de -1,1 ppm) e íon [M + 2H] ++ em m/z 571,7513 (calculado para 571,7504, erro de 1,5 ppm), em análises por HRMS-ESI + (Figura 5.58A), sugerindo a fórmula molecular C50H71N13O16S, a qual concorda com o íon [M -H]em m/z 1140,4781 (calculado para 1140,4684, erro de -0,3 ppm) observado no espectro de HRMS-ESI -(Figura 5.58B). A fórmula molecular indica a perda de uma metila (-Δ14) quando comparado com a pseudovibriamida B1 (7).…”

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Descoberta e estudos de biossíntese de peptídeos não-ribossomais envolvidos na motilidade de >i<Pseudovibrio brasiliensis>/i< Ab134

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pelas oportunidades, orientação e apoio, ao longo dos últimos 10 anos, responsável pela minha formação acadêmico-científica. À Profa. Dra. Alessandra S. Eustáquio (The University of Illinois at Chicago, UIC), por me receber em seu grupo de pesquisa, sempre disponível para discussões e guiando cada tomada de decisão. Obrigada pela orientação, paciência e conselhos. A todos os colegas do Grupo de Química Orgânica de Sistemas Biológicos pela amizade, sugestões e companhia nas longas semanas de HPLC e desenvolvimento de experimentos de cultivos intermináveis. Em especial, à Dra. Fabiana T. R. Martinelli e Dra. Karin F. B. Camargo pelo apoio técnico. Aos Prof. Dr. Alekej Krunic (UIC), Profa. Dra. Laura M. Sanchez (UIC) e Prof. Dr. Antônio G. Ferreira (Universidade Federal de São Carlos, UFSCar) pelo apoio técnico na aquisição de dados de ressonância magnética nuclear e espectrometria de massas. Aos amigos, antigos e novos, que fizeram essa caminhada mais acolhedora, principalmente a Carol

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Clathriamide, an hexapeptide isolated from the marine sponge Clathria (Clathria) nicoleae

Cited by 7 publications

References 13 publications

A Family of Nonribosomal Peptides Modulate Collective Behavior in Pseudovibrio Bacteria Isolated from Marine Sponges**

A Family of Nonribosomal Peptides Modulate Collective Behavior in Pseudovibrio Bacteria Isolated from Marine Sponges**

A novel family of nonribosomal peptides modulate collective behavior inPseudovibriobacteria isolated from marine sponges

Descoberta e estudos de biossíntese de peptídeos não-ribossomais envolvidos na motilidade de >i<Pseudovibrio brasiliensis>/i< Ab134

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