Skip to main content

Thank you for visiting nature.com. You are using a browser version with limited support for CSS. To obtain the best experience, we recommend you use a more up to date browser (or turn off compatibility mode in Internet Explorer). In the meantime, to ensure continued support, we are displaying the site without styles and JavaScript.

  • Brief Communication
  • Published:

Indole alkaloid derivatives as building blocks of natural products from Bacillus thuringiensis and Bacillus velezensis and their antibacterial and antifungal activity study

Abstract

Six known indole alkaloid derivatives have been isolated for the first time from Bacillus thuringiensis and Bacillus velezensis strains, all of them as building blocks for the synthesis of larger natural products. Their structure was elucidated by a complete spectroscopy. Their biological activities were tested against some Gram-positive and Gram-negative bacteria and three phytopathogenic fungi which cause diseases in important crops, such as Moniliophthora roreri, the causal agent of cacao disease. The results indicated that some compounds had modest antibacterial activity; however, some of them had strong antifungal activity against the probed fungi. This antifungal activity of these compounds has not been reported.

This is a preview of subscription content, access via your institution

Access options

Buy this article

Prices may be subject to local taxes which are calculated during checkout

Fig. 1
Fig. 2

References

  1. Kaushik NK, Kaushik N, Attri P, Kumar N, Kim CH, Verma AK, et al. Biomedical importance of indoles. Molecules. 2013;18:6620–62.

    Article  CAS  Google Scholar 

  2. Jones RS. Tryptamine: a neuromodulator or neurotransmitter in mammalian brain? Prog Neurobiol. 1982;19:117–39.

    Article  CAS  Google Scholar 

  3. Yuwen L, Zhang F-L, Chen Q-H, Lin S-J, Zhao Y-L, Li Z-Y. The role of aromatic L-amino acid decarboxylase in bacillamide C biosynthesis by Bacillus atrophaeus C89. Sci Rep. 2013;3:1753.

    Article  Google Scholar 

  4. Williams BB, Van Benschoten AHV, Cimermancic P, Donia MS, Zimmermann M, Taketani M, et al. Discovery and characterization of gut microbiota decarboxylases that can produce the neurotransmitter tryptamine. Cell Host Microbe. 2014;16:495–503.

    Article  CAS  Google Scholar 

  5. Yu LY, Hu ZF, Ma ZJ. Production of bioactive tryptamine derivatives by co-culture of marine Streptomyces with Bacillus mycoides. Nat Prod Res. 2015;29:2087–91.

    Article  CAS  Google Scholar 

  6. Jeong S-Y, Ishida K, Ito Y, Okada S, Murakami M. Bacillamide, a novel algicide from the marine bacterium, Bacillus sp. SY-1, against the harmful dinoflagellate, Cochlodinium polykrikoides. Tetrahedron Lett. 2003;44:8005–7.

    Article  CAS  Google Scholar 

  7. Yu LL, Li ZY, Peng CS, Li ZY, Guo YW. Neobacillamide A, a novel thiazole containing alkaloid from the marine bacterium Bacillus vallismortis C89, associated with South China Sea sponge Dysidea avara. Helv Chim Acta. 2009;92:607–12.

    Article  CAS  Google Scholar 

  8. Zhang F, Mulati N, Wang Y, Li Y, Gong S, Karthik L, et al. Biosynthesis in vitro of bacillamide intermediate-heterocyclic AlaCysthiazole by heterologous expression of nonribosomal peptide synthetase (NRPS). J Biotechnol. 2019;292:5–11.

    Article  CAS  Google Scholar 

  9. Figueira VBC, Prabhakar S, Lobo AM. Synthesis of the algicide bacillamide. Arkivoc. 2005;14:14–9.

    Google Scholar 

  10. Meschwitz SM, Teasdale ME, Mozzer A, Martin N, Liu J, Forschner-Dancause S, et al. Antagonism of quorum sensing phenotypes by analogs of the marine bacterial secondary metabolite 3-methyl-N-(2′-phenylethyl)-butyramide. Mar Drugs. 2019;17:389.

    Article  CAS  Google Scholar 

  11. Mondol MAM, Shin HJ, Islam MT. Diversity of secondary metabolites from marine Bacillus species: chemistry and biological activity. Mar Drugs. 2013;11:2846–72.

    Article  Google Scholar 

  12. Netz N, Opatz T. Marine indole alkaloids. Mar Drugs. 2015;13:4814–914.

    Article  CAS  Google Scholar 

  13. MacFaddin JF. Biochemical tests for identification of medical bacteria. 3rd ed. Williams and Wilkins: Baltimore, MD; 2000.

  14. Widhalm JR, Dudareva N. A familiar ring to it: biosynthesis of plant benzoic acids. Mol Plant. 2015;8:83–97.

    Article  CAS  Google Scholar 

  15. Cuervo-Parra JA, Sanchez-Lopez V, Ramirez-Suero M, Ramirez-Lepe M. Morphological and molecular characterization of Moniliophthora roreri causal agent of frosty pod rot of cocoa tree in Tabasco, Mexico. Plant Pathol J. 2011;10:122–7.

    Article  Google Scholar 

  16. Sansinenea E, Ortiz A. Chemical compounds produced by Bacillus sp. factories and their role in nature. Mini-Rev Med Chem. 2019;19:373–80.

    Article  Google Scholar 

  17. Sansinenea E, Salazar F, Jiménez J, Mendoza A, Ortiz A. Diketopiperazines derivatives isolated from Bacillus thuringiensis and Bacillus endophyticus, establishment of their configuration by X-ray and their synthesis. Tetrahedron Lett. 2016;57:2604–7.

    Article  CAS  Google Scholar 

Download references

Acknowledgements

We thank VIEP and CONACyT (251512).

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Estibaliz Sansinenea.

Ethics declarations

Conflict of interest

The authors declare that they have no conflict of interest.

Additional information

Publisher’s note Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.

Supplementary information

41429_2020_333_MOESM1_ESM.docx

Indole Alkaloid Derivatives as Building Blocks of Natural Products from Bacillus thuringiensis and Bacillus velezensis and their antibacterial and antifungal activity study

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Vaca, J., Salazar, F., Ortiz, A. et al. Indole alkaloid derivatives as building blocks of natural products from Bacillus thuringiensis and Bacillus velezensis and their antibacterial and antifungal activity study. J Antibiot 73, 798–802 (2020). https://doi.org/10.1038/s41429-020-0333-2

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1038/s41429-020-0333-2

This article is cited by

Search

Quick links