Undecylprodigiosin Explained

Undecylprodigiosin is an alkaloid produced by some Actinomycetes bacteria. It is a member of the prodiginines group of natural products and has been investigated for potential antimalarial activity.

Natural sources

Undecylprodigiosin is a secondary metabolite found in some Actinomycetes, for example Actinomadura madurae, Streptomyces coelicolor and Streptomyces longisporus.[1]

Production

Biosynthesis

The biosynthesis of undecylprodigiosin starts with PCP apoprotein which is transformed into the holoprotein using acetyl CoA and PPtase then adenylation occurs utilizing L-proline and ATP. The resulting molecule is then oxidized by dehydrogenase enzyme. Elongation by decarboxylative condensation with malonyl CoA is followed by another decarboxylative condensation with L-serine using α-oxamine synthase (OAS) domain. The compound is then cyclized, oxidized with dehydrogenase and methylated with SAM to give 4-methoxy-2,2′-bipyrrole-5-carboxaldehyde (MBC) intermediate which react with 2-undecylpyrrole (2-UP) to give undecylprodigiosin.[2]

Laboratory

The first total synthesis of the undecylprodigiosin was published in 1966, confirming the chemical structure. As with the biosynthesis, the key intermediate was MBC.[3]

Uses

As with other prodiginines, the compound has been investigated for its pharmaceutical potential as anticancer, immunosuppressant, or antimalarial agent.[1] [4]

Notes and References

  1. 10.1038/nrmicro1531 . Williamson NR, Fineran PC, Gristwood T, Leeper FJ, Salmond GP . The biosynthesis and regulation of bacterial prodiginines . Nature Reviews Microbiology . 2006 . 887–899 . 12 . 4 . 17109029. 11649828 .
  2. Hu . Dennis X. . Withall . David M. . Challis . Gregory L. . Thomson . Regan J. . Structure, Chemical Synthesis, and Biosynthesis of Prodiginine Natural Products . Chemical Reviews . 17 June 2016 . 116 . 14 . 7818–7853 . 10.1021/acs.chemrev.6b00024. 5555159 . 27314508 .
  3. 10.1039/C19660000825 . The structure and synthesis of undecylprodigiosin. A prodigiosin analogue from Streptomyces . 1966 . Wasserman . H. H. . Rodgers . G. C. . Keith . D. D. . Chemical Communications . 22 . 825–826 .
  4. 10.1007/s00253-014-5590-1 . Properties and applications of undecylprodigiosin and other bacterial prodigiosins . 2014 . Stankovic . Nada . Senerovic . Lidija . Ilic-Tomic . Tatjana . Vasiljevic . Branka . Nikodinovic-Runic . Jasmina . Applied Microbiology and Biotechnology . 98 . 9 . 3841–3858 . 24562326 . 16834175 .