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Prodigiosin-like pigments.

N N Gerber

    CRC Critical Reviews in Microbiology
    |May 1, 1975
    PubMed
    Summary
    This summary is machine-generated.

    Prodigiosin and related pigments from Serratia marcescens and other bacteria exhibit diverse structures and biological activities, including antibacterial and antimalarial properties. Biosynthetic pathways and identification methods for these tripyrrole compounds are detailed.

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    Area of Science:

    • Microbiology
    • Natural Products Chemistry
    • Biochemistry

    Background:

    • Prodigiosin, a red tripyrrole pigment from Serratia marcescens, is also found in other bacteria.
    • Prodigiosin structure can be modified, leading to analogs like nor-prodigiosin and blue tetrapyrrole pigments.
    • Prodigiosin-like (prodiginine) pigments from Streptomyces and Actinomadurae have distinct structures and side chains.

    Purpose of the Study:

    • To elucidate the structures of novel prodigiosin analogs and prodiginine pigments.
    • To investigate the biosynthetic pathways of prodigiosin using labeled precursors.
    • To summarize identification methods and biological activities of these pigments.

    Main Methods:

    • Mass spectroscopy for detecting higher prodigiosin homologs.

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  • Mutant strains of S. marcescens to generate novel analogs.
  • Structure elucidation of prodiginine pigments from Streptomyces and Actinomadurae.
  • 13C-labeled precursors and NMR spectroscopy to study biosynthesis.
  • Literature review and evaluation of earlier findings.

    • Main Results:

    • Novel biosynthetic analogs of prodigiosin were obtained.
    • Structures of three prodiginine pigments from Streptomyces and six from Actinomadurae were elucidated.
    • Identification of undecylprodiginine and other unique prodiginine structures with varying side chains.
    • Incorporation patterns of acetate, proline, glycine, serine, alanine, and methionine into prodigiosin and related pigments were determined.
    • Prodigiosin and prodiginine pigments show antibacterial and antimalarial activities; prodigiosin has been tested clinically.

    Conclusions:

    • The study details the structural diversity and biosynthesis of prodigiosin and related pigments.
    • Various bacterial species produce prodigiosin and its analogs.
    • Prodiginine pigments possess significant structural variations and biological activities.
    • Understanding these pigments aids in natural product discovery and potential therapeutic applications.