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Anacyclamide D8P, a prenylated cyanobactin from a Sphaerospermopsis sp. cyanobacterium

preprint
submitted on 25.08.2017 and posted on 28.08.2017 by Joana Martins, Niina Leikoski, Matti Wahlsten, Joana Azevedo, Jorge Antunes, Jouni Jokela, Kaarina Sivonen, Vitor Vasconcelos, David P. Fewer, Pedro Leao
Cyanobactins are a family of linear and cyclic peptides produced through the post-translational modification of short precursor peptides. Anacyclamides are macrocyclic cyanobactins with a highly diverse sequence that are common in the genus Anabaena. A mass spectrometry-based screening of potential cyanobactin producers led to the discovery of a new prenylated member of this family of compounds, anacyclamide D8P (1), from Sphaerospermopsis sp. LEGE 00249. The anacyclamide biosynthetic gene cluster (acy) encoding the novel macrocyclic prenylated cyanobactin, was sequenced. Heterologous expression of the acy gene cluster in Escherichia coli established the connection between genomic and mass spectrometric data. Unambiguous establishment of the type and site of prenylation required the full structural elucidation of 1 using Nuclear Magnetic Resonance (NMR), which demonstrated that a forward prenylation occurred on the tyrosine residue. Compound 1 was tested in pharmacologically or ecologically relevant biological assays and revealed moderate antimicrobial activity towards the fouling bacterium Halomonas aquamarina CECT 5000.

Funding

Norte2020 and ERFD: NORTE-01-0145-FEDER-000035; FCT: UID/Multi/04423/2013, PTDC/MAR-BIO/2818/2013; Academy of Finland: 259505, 258827.

History

Topic

  • Microbiology
  • Bioengineering and Biotechnology
  • Drug Discovery and Drug Delivery Systems

Email Address of Submitting Author

pleao@ciimar.up.pt

Email Address(es) for Other Author(s)

david.fewer@helsinki.fi

Institution

University of Porto

Country

Portugal

ORCID For Submitting Author

0000-0001-5064-9164

Declaration of Conflict of Interest

We declare no conflict of interest.

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