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Isolation and Characterization of Phytotoxic Compounds Produced by Streptomyces sp. AMC 23 from Red Mangrove (Rhizophora mangle)

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Abstract

Natural products produced by microorganisms have been utilized as sources of new drugs possessing a wide range of agrochemical and pharmacological activities. During our research on Actinomycetes from Brazilian mangroves, the ethyl acetate extract of Streptomyces sp. AMC 23 isolated from the red mangrove (Rhizophora mangle) rhizosphere produced a highly active compound against the microalga Chlorella vulgaris, often used to assess the phytotoxic activity. As a result, the bioassay-guided fractionation led to the isolation of the mixture of the known compounds bafilomycin B1 and bafilomycin B2. The chemical structures of bafilomycin B1 and bafilomycin B2 were established based on their spectroscopic data by infrared (IR), mass spectrometry (MS), 1H nuclear magnetic resonance (NMR), gradient-enhanced heteronuclear multiple quantum coherence (gHMQC), and gradient-enhanced heteronuclear multiple-bond connectivity (gHMBC) as well as comparison with reference data from the literature. Moreover, it was also possible to identify other bafilomycins using non-chromatographic-dependent techniques (Tandem mass spectrometry). Additionally, this is the first report on the phytotoxic activity of bafilomycin B1.

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Acknowledgments

The authors are indebted to FAPESP (Fundação de Amparo à Pesquisa do Estado de São Paulo) for providing fellowships to EJC (grant 08/53000-0), RES (grant 12/01904-8), and TDZ (grant 11/14333-6), CAPES (Coordenação de Aperfeiçoamento de Pessoal de Nível Superior) for providing fellowship to SPC, and CNPq (Conselho Nacional para Desenvolvimento Científico e Tecnológico) for providing fellowship to JBC. TDZ is also grateful to FAPESP for providing the funding for developing this research (grant 11/50243-1).

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Authors and Affiliations

  1. Laboratory of Mass Spectrometry Applied Natural Products Chemistry, Department of Chemistry, Faculty of Philosophy, Sciences and Letters of Ribeirão Preto, University of São Paulo (USP), Ribeirão Preto, SP, 14040-901, Brazil

    Eduardo José Crevelin & Luiz Alberto Beraldo Moraes

  2. Laboratory of Environmental Microbiology, Brazilian Agricultural Research Corporation (EMBRAPA), Jaguariúna, SP, Brazil

    Sarah Pigato Canova, Itamar Soares Melo, Tiago Domingues Zucchi & Rafael Eduardo da Silva

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  1. Eduardo José Crevelin
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  2. Sarah Pigato Canova
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  3. Itamar Soares Melo
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  4. Tiago Domingues Zucchi
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  5. Rafael Eduardo da Silva
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  6. Luiz Alberto Beraldo Moraes
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Correspondence to Luiz Alberto Beraldo Moraes.

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Crevelin, E.J., Canova, S.P., Melo, I.S. et al. Isolation and Characterization of Phytotoxic Compounds Produced by Streptomyces sp. AMC 23 from Red Mangrove (Rhizophora mangle). Appl Biochem Biotechnol 171, 1602–1616 (2013). https://doi.org/10.1007/s12010-013-0418-5

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