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3-Hydroxypropionic Acid as an Antibacterial Agent from Endophytic Fungi Diaporthe phaseolorum

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Abstract

Endophytic fungi are considered a rich source of active compounds resulting from their secondary metabolism. Fungi from marine environment grow in a habitat with unique conditions that can contribute to the activation of metabolic pathways of synthesis of different unknown molecules. The production of these compounds may support the adaptation and survival of the fungi in the marine ecosystem. Mangroves are ecosystems situated between land and sea. They are frequently found in tropical and subtropical areas and enclose approximately 18.1 million hectares of the planet. The great biodiversity found in these ecosystems shows the importance of researching them, including studies regarding new compounds derived from the endophytic fungi that inhabit these ecosystems. 3-hydroxypropionic acid (3-HPA) has been isolated from the mangrove endophytic fungus Diaporthe phaseolorum, which was obtained from branches of Laguncularia racemosa. The structure of this compound was elucidated by spectroscopic methods, mainly 1D and 2D NMR. In bioassays, 3-HPA showed antimicrobial activities against both Staphylococcus aureus and Salmonella typhi. The structure of this antibiotic was modified by the chemical reaction of Fischer-Speier esterification to evaluate the biologic activity of its chemical analog. The esterified product, 3-hydroxypropanoic ethyl ester, did not exhibit antibiotic activity, suggesting that the free carboxylic acid group is important to the pharmacological activity. The antibiotic-producing strain was identified with internal transcribed spacer sequence data. To the best of our knowledge, this is the first report of antibacterial activity by 3-HPA against the growth of medically important pathogens.

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Acknowledgments

This work was funded by the financial support from the National Council of Technological and Scientific Development (fellowship awarded to F.L.S.S.) and the Fundação de Amparo à Pesquisa do Estado de São Paulo (grant 04/13910-6 and fellowship 06/57060-1 awarded to PTL). We are grateful to Paloma Marín, Laura Moreno and Sonia Lopez.

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Authors and Affiliations

  1. Department of Genetics, Escola Superior de Agricultura “Luiz de Queiroz”, University of São Paulo, Av. Pádua Dias 11, P.O. Box 83, Piracicaba, SP, 13400-970, Brazil

    Fernanda L. S. Sebastianes, João L. Azevedo & Aline A. Pizzirani-Kleiner

  2. Centro de Ecología Química Agrícola-Instituto Agroforestal del Mediterraneo, UPV, Campus de Vera, Edificio 6C, 46022, Valencia, Spain

    Nuria Cabedo

  3. Centro de Desarrollo Farmacéutico y Alimentario Parque Tecnológico de Ciencias de la Salud, Fundación MEDINA Centro de Excelencia en Investigación de Medicamentos Innovadores en Andalucía, Avda. del Conocimiento, 3 Edif., 18100, Armilla, Granada, Spain

    Noureddine El Aouad

  4. Laboratório de Microbiologia Ambiental, Embrapa Meio Ambiente (CNPMA), Via SP 340, Km 127.5, CP 69, Jaguariúna, SP, CEP 13820-000, Brazil

    Angela M. M. P. Valente

  5. Institute of Natural Sciences, Federal University of Alfenas, Rua Gabriel Monteiro da Silva, 700, Alfenas, MG, 37130-000, Brazil

    Paulo T. Lacava

  6. Departamento de Farmacología, Facultad de Farmacia, Universidad de Valencia, 46100, Burjassot, Valencia, Spain

    Diego Cortes

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  1. Fernanda L. S. Sebastianes
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Correspondence to Fernanda L. S. Sebastianes.

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Sebastianes, F.L.S., Cabedo, N., Aouad, N.E. et al. 3-Hydroxypropionic Acid as an Antibacterial Agent from Endophytic Fungi Diaporthe phaseolorum . Curr Microbiol 65, 622–632 (2012). https://doi.org/10.1007/s00284-012-0206-4

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