Serratia marcescens Prodigiosin

McKeon, j. E. The structure of metabolic products of Serratia marcescens, prodigiosin, and prodigiosin precursor, serratamolide. Ph.D. Thesis 196I Yale Univ., New Haven, Conn. 

From the Japanese bryozoan Bugula dentata, an antimicrobial blue pigment (121) was isolated (111) and found to be identical with a tetrapyr-role previously isolated from a mutant strain of Serratia marcescens (112). The color of the bryozoan B. dentata is unusually dark blue, suggesting that the pigment 121 is ubiquitously present in the animal. Whether compound 121 is biosynthesized by the bryozoan itself or by an associated microorganism or derived from food sources such as prodigiosin-producing bacteria is still unknown. 

Streptomyces showdoensis incorporates 95% 1-[ C] or 2-[ C]acetate into showdomycin (1) in the maleimide ring only [22], and this confirms earlier C findings. The exclusive incorporation of l-[ C]acetate at C-1, and 2-[ C]acetate at C-2, C-3 and C-4 can be explained with reference to the Krebs cycle and the malic enzyme. C Spectra on 0.1 M solutions of labelled showdomycin in 13 mm tubes required 6 hr accumulation time. Furthermore, C-labelled alanine, proline, glycine and serine have been fed to the bacterium Serratia marcescens [23] to trace the origin of the carbon atoms in its tripyrrole metabolite, prodigiosin (2). The methoxy group is probably derived from methionine whereas the C-2 methyl is from alanine. 

Prodigiosin may function in air dispersal of Serratia marcescens [250]. The pigmented strain is much more able than the non-pigmented strain to adsorb onto air bubbles and enrich the drops formed on breakage of the bubbles. Also prodigiosin makes hydrophobic the normally hydrophilic cells. The pigment itself is hydrophobic. 

In this chapter, prodigiosin, obtained from the cultured broth of Serratia marcescens stachydrine, isolated from Fabaceae plants and pyrrole-2-carboxyUc acid, isolated from the culture broth of Streptomyces sp. No. 82-85 are described. Regarding these alkaloids, it was established that labeled prohne is incorporated into these alkaloids. It was also determined that alanine and glycine are incorporated into prodigiosin, in addition to proline [1]. However, intact incorporation of proline into prodigiosin as a unit retaining the nitrc en atom was observed, and consequendy this alkaloid is described in this chapter. 

Labelled prodigiosins were prepared by feeding 1- C- and 2- C-enriched sodium acetate (63%) to the bacterium Serratia marcescens. The enhanced sensitivity available by the FT mode of operation is underscored in this study since the n.m.r. spectra were recorded on 360 mg ml of natural-abundance prodigiosin in 18 minutes, on 180 mgml of the material from CHj COjNa labelling in 20 minutes, and on 17.9mgml of CHaCOjNa-labelled pigment in 6.7 hours. 

Popolophuanone F Prodigiosin marine sponges Serratia marcescens (Bacteria)... 

Goldschmidt, M. E., C. L. Gott, and R. P. Williams Coupling enzyme terminal step in biosynthesis of prodigiosin by Serratia marcescens (Abstract). Bacteriol. Proc. 92 (1965). 

Harned, R. L. The production of prodigiosin by submerged growth of Serratia marcescens. Appl. Microbiol. 2, 365 (1954). 

Hubbard, R., and C. Rimington The biosynthesis of prodigiosin, the tripyrryl-methene pigment from Bacillus prodigiosus (Serratia marcescens), Biochem. J. 46,... 

Marks, G. S., and L. Bogorad Studies on the biosynthesis of prodigiosin in Serratia marcescens. Proc. Natl. Acad. Sci. U.S. 46, 25 (i960). 

Morgan, E. N., and E.M. Tanner Prodigiosin. J. Chem. Soc. 1955, 3305. Mukherjee, P. P., M. E. Goldschmidt, and R. P. Williams Enzymic formation of prodigiosin analog by a cell-free preparation from Serratia marcescens. Biochim. et Biophys. Acta 136, 182 (1967). 

Santer, U. V., and H. J. Vogel Prodigiosin synthesis in Serratia marcescens isolation of a pyrrole-containing precursor. Biochim. et Biophys. Acta. 19, 578 (1956). 

SiDDiQUi, M. A. Q., and G. E. Peterson Streptomycin and syntrophic prodigiosin synthesis in Serratia marcescens. Antonie van Leeuwenhoek. J. Microbiol. Serol. 31, 193 (1965). 

Stavri, D., et A. Marx Recherches sur le Mecanisme de Synthese de la Prodigiosine par le Serratia marcescens. Arch, roumain. pathol. exptl. microbiol. 20, 287 (1961). 

Wasserman, H. H., J. E. McKeon, and U. V. Santer Studies related to the biosynthesis of prodigiosin in Serratia marcescens, Biochem. Biophys. Research Commun. 3, 146 (i960). 

Williams, R. P., J. A. Green, and D. A. Rappoport Studies on pigmentation of Serratia marcescens. I. Spectral and paper chromatographic properties of prodigiosin. J. Bacteriol. 71, II5 (1956a). 

Williams, R. P., and S. Krell Particulate nature of water-soluble prodigiosin from Serratia marcescens (Abstract). Texas Repts Biol, and Med. 21, 106 (1963). 

Yoshida, S. a study of a water-soluble complex of prodigiosin produced by a strain of Serratia marcescens. Can. J. Biochem. and Physiol. 40, 1019 (1962). 

Morrison, D. A. Prodigiosin synthesis in mutants of Serratia marcescens. J. Bacteriol. 91, 1599 (1966). 

Wasserman, H.H., Friedland, D.J., and Morrison, D.A. (1968) A novel dipyrrolyldipyromethene prodigiosin analog from Serratia marcescens. Tetrahedron Lett., 9, 641-644. 

In S. marcescens, AI-2-mediated quorum sensing also regulates the production of carbapenem antibiotic, prodigiosin, hemolysin, and other virulence factors. But such AI-2-mediated regulation is not for all Serratia strains, that is, it is a strain-dependent phenotype.305 321... 

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