Prodigiosin

Prodigiosin
Names
	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;
3D model (JSmol)	Interactive image;
ChEMBL	ChEMBL275787;
ChemSpider	10577755 ;
MeSH	Prodigiosin
PubChem CID	5351169;
	InChI InChI=1S/C20H25N3O/c1-4-5-6-8-15-11-16(22-14(15)2)12-19-20(24-3)13-18(23-19)17-9-7-10-21-17/h7,9-13,21,23H,4-6,8H2,1-3H3/b16-12+ Key: SZXDNGVQRDTJSD-FOWTUZBSSA-N ; InChI=1/C20H25N3O/c1-4-5-6-8-15-11-16(22-14(15)2)12-19-20(24-3)13-18(23-19)17-9-7-10-21-17/h7,9-13,21,23H,4-6,8H2,1-3H3/b16-12+ Key: SZXDNGVQRDTJSD-FOWTUZBSBS;
	SMILES C\C1=NC(\C=C1\CCCCC)=C\c2nc(cc2OC)c3cccn3;
Properties
Chemical formula	C20H25N3O
Molar mass	323.432 g/mol
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) 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<ref="Williamson">{{cite journal | author=Neil R. Williamson, Peter C. Fineran, Finian J. Leeper, George P. C. Salmond | title=The biosynthesis and regulation of bacterial prodiginines | Journal=Nature Reviews Microbiology | volume=4 | pages=887-899 | doi=10.1038/nrmicro1531</ref> 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)<ref=Williamson\>. The name "prodigiosin" is derived from "prodigious" (i.e. something marvelous).

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. It has long been known the prodigiosin production is enhanced by phosphate limitation. It has been shown that in low phosphate conditions, pigmented strains grow to a higher density than non-pigmented strains.^[2]^{[self-published source?]}

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.^[3]

Biological activity

Prodigiosines have recently received renewed attention^[4]^[5] for their reported antibacterial, antifungal, antiprotozoal, antimalarial, immunosuppressive and anticancer properties.

References

^ 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.
^ 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.
^ "The Mass at Bolsena by Raphael". Vatican Museums. Retrieved 2006-05-03.
^ 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.{{cite journal}}: CS1 maint: multiple names: authors list (link)
^ 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.{{cite journal}}: CS1 maint: multiple names: authors list (link)

[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] 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.

[Vatican_Raphael-3] "The Mass at Bolsena by Raphael". Vatican Museums. Retrieved 2006-05-03.

[4] 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.{{cite journal}}: CS1 maint: multiple names: authors list (link)

[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.{{cite journal}}: CS1 maint: multiple names: authors list (link)

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