Prodigiosin

Prodigiosin
IUPAC name

4-methoxy-5-[(Z)-(5-methyl-4-pentyl-2H-pyrrol-2-ylidene)methyl]-1H,1′H-2,2′-bipyrrole
Identifiers
CAS number 82-89-3 N
PubChem 5351169
ChemSpider 10577755 Y
MeSH Prodigiosin
ChEMBL CHEMBL275787 N
Jmol-3D images Image 1
Properties
Molecular formula C20H25N3O
Molar mass 323.432 g/mol
 N (verify) (what is: Y/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Prodigiosin is the red pigment produced by many strains of the bacterium Serratia marcescens,[1] other Gram-negative, gamma proteobacteria such as Vibrio psychroerythrus and Hahella chejuensis[2] It is in a family of compounds termed "prodiginines", which are produced in some Gram-negative gamma proteobacteria, as well as select Gram-positive Actinobacteria (e.g. Streptomyces coelicolor)[2]. The name "prodigiosin" is derived from "prodigious" (i.e. something marvelous).

Contents

Secondary Metabolite

Prodigiosin is a secondary metabolite of Serratia marcescens. Because it is easy to detect, it has been used as a model system to study secondary metabolism. Prodigiosin production ha long been known to be enhanced by phosphate limitation. In low phosphate conditions, pigmented strains have been shown to grow to a higher density than unpigmented strains.[3]

Religious function

The ability of pigmented strains of Serratia marcescens to grow on bread has led to a possible explanation of Medieval transubstantiation miracles, in which Eucharistic bread is converted into the Body of Christ. Such miracles led to Pope Urban IV instituting the Feast of Corpus Christi in 1264. This followed celebration of a Mass at Bolsena in 1263, led by a Bohemian priest who had doubts concerning transubstantiation. During the Mass, the eucharist appeared to bleed and each time the priest wiped away the blood, more would appear. This event is celebrated in a fresco in the Pontifical Palace in the Vatican City, painted by Raphael.[4]

Biological activity

Prodigiosines have recently received renewed attention[2][5] for their reported antibacterial, antifungal, antiprotozoal, antimalarial, immunosuppressive and anticancer properties.

References

  1. ^ Bennett JW, Bentley R (2000). "Seeing red: The story of prodigiosin". Adv Appl Microbiol 47: 1–32. doi:10.1016/S0065-2164(00)47000-0. PMID 12876793. 
  2. ^ a b c Williamson NR, Fineran PC, Gristwood T, Leeper FJ, Salmond GP (2006). "The biosynthesis and regulation of bacterial prodiginines". Nature Reviews Microbiology 4 (12): 887–899. doi:10.1038/nrmicro1531. PMID 17109029. http://www.nature.com/nrmicro/journal/v4/n12/abs/nrmicro1531.html. 
  3. ^ M. Todd-Guay and P.H. Demchick. 1995. Role of prodigiosin in phosphate-starved Serratia marcescens. Abstract of the Annual Meeting, American Society for Microbiology.
  4. ^ "The Mass at Bolsena by Raphael". Vatican Museums. http://mv.vatican.va/3_EN/pages/x-Schede/SDRs/SDRs_02_01_012.html. Retrieved 2006-05-03. 
  5. ^ Williamson NR, Fineran PC, Gristwood T, Chawrai SR, Leeper FJ, Salmond GP (2007). "Anticancer and immunosuppressive properties of bacterial prodiginines". Future Microbiol. 6 (6): 605–618. doi:10.2217/17460913.2.6.605. PMID 18041902.