:Prodiginines

Prodigiosin colour.svg|Prodigiosin

Cycloprodigiosin.svg|Cycloprodigiosin

Cyclononylprodigiosin.svg|Cyclononylprodigiosin

Undecylprodigiosin coloured.svg|Undecylprodigiosin

Butyl-meta-cycloheptylprodiginine.svg|Butyl-meta-cycloheptylprodiginine

The prodiginines are secondary metabolites originally noted in Serratia species, especially Serratia marcescens. They are also found in Actinomycetes, for example Streptomyces coelicolor and some marine bacteria, including Hahella chejuensis and Pseudoalteromonas denitrificans. Cyclononylprodigiosin was isolated from Actinomadura species.{{cite book |doi=10.1016/S0065-2164(00)47000-0 |title=Seeing red: The story of prodigiosin |series=Advances in Applied Microbiology |year=2000 |last1=Bennett |first1=J.W. |last2=Bentley |first2=Ronald |volume=47 |pages=1–32 |pmid=12876793 |isbn=9780120026470 }}

The Prodiginine family consists of primarily red-pigmented tripyrrole secondary metabolites.{{Cite journal |last1=Sakai-Kawada |first1=Francis E. |last2=Ip |first2=Courtney G. |last3=Hagiwara |first3=Kehau A. |last4=Awaya |first4=Jonathan D. |date=2019 |title=Biosynthesis and Bioactivity of Prodiginine Analogs in Marine Bacteria, Pseudoalteromonas: A Mini Review |journal=Frontiers in Microbiology |volume=10 |page=1715 |doi=10.3389/fmicb.2019.01715 |pmid=31396200 |issn=1664-302X |doi-access=free |pmc=6667630 }}

{{Main|Prodigiosin#Biosynthesis}}

Prodiginine, first extracted from terrestrial Serratia marcescens, consisted of a straight alkyl chain substituent and was named prodigiosin.{{Cite journal |last1=Rapoport |first1=Henry. |last2=Holden |first2=Kenneth G. |date=1962-02-01 |title=The Synthesis of Prodigiosin |url=https://pubs.acs.org/doi/abs/10.1021/ja00863a026 |journal=Journal of the American Chemical Society |language=en |volume=84 |issue=4 |pages=635–642 |doi=10.1021/ja00863a026 |issn=0002-7863|url-access=subscription }}

The prodiginines are produced from a common intermediate, tambjamine aldehyde (also known as MBC, from its systematic name 4-methoxy-2,2'-bipyrrole-5-carboxaldehyde). This contains two pyrrole rings built from proline and serine as shown in the blue-shaded pathway in Figure 1. The aldehyde is subsequently condensed with a third pyrrole to form prodigiosin{{cite web |url=https://biocyc.org/META/NEW-IMAGE?type=PATHWAY&object=PWY-7547&detail-level=2 |title=Pathway: prodigiosin biosynthesis |author=R. Caspi |publisher=MetaCyc Metabolic Pathway Database |date=2014-08-14 |access-date=2021-04-01 }} (compound 16 in Figure 1), which is then further elaborated to cycloprodigiosin (compound 22 in Figure 1) and the other members of the chemical family.{{cite journal |doi=10.1039/B605245M |title=Biological formation of pyrroles: Nature's logic and enzymatic machinery |year=2006 |last1=Walsh |first1=Christopher T. |last2=Garneau-Tsodikova |first2=Sylvie|author2-link= Sylvie Garneau-Tsodikova |last3=Howard-Jones |first3=Annaleise R. |journal=Natural Product Reports |volume=23 |issue=4 |pages=517–31 |pmid=16874387 }}{{cite journal | doi = 10.1021/acs.chemrev.6b00024| pmid = 27314508| pmc = 5555159| title = Structure, Chemical Synthesis, and Biosynthesis of Prodiginine Natural Products| journal = Chemical Reviews| volume = 116| issue = 14| pages = 7818–7853| year = 2016| last1 = Hu| first1 = Dennis X.| last2 = Withall| first2 = David M.| last3 = Challis| first3 = Gregory L.| last4 = Thomson| first4 = Regan J.}}

Details of the first total synthesis of the parent prodigiosin were published in 1962, confirming the chemical structure. As with the biosynthesis, the key intermediate was MBC.{{cite journal |doi=10.1021/ja00863a025 |title=The Preparation and Properties of Some Methoxypyrroles |year=1962 |last1=Rapoport |first1=Henry. |last2=Willson |first2=Clyde D. |journal=Journal of the American Chemical Society |volume=84 |issue=4 |pages=630–635 }} This aldehyde has subsequently been prepared by other methods and used to make many prodiginines.

Prodigiosin was considered for commercial production in 1823 to dye silk and wool but it has poor stability to light and the advent of synthetic alternatives cut short this application. The group has also been investigated for its pharmaceutical potential as anticancer, immunosuppressant, and antimalarial agents.{{cite journal |doi=10.1007/s00253-014-5590-1 |title=Properties and applications of undecylprodigiosin and other bacterial prodigiosins |year=2014 |last1=Stankovic |first1=Nada |last2=Senerovic |first2=Lidija |last3=Ilic-Tomic |first3=Tatjana |last4=Vasiljevic |first4=Branka |last5=Nikodinovic-Runic |first5=Jasmina |journal=Applied Microbiology and Biotechnology |volume=98 |issue=9 |pages=3841–3858 |pmid=24562326 |s2cid=16834175 }}

• Serratia marcescens, especially for the history of prodigiosin's discovery

{{Reflist}}

Category:Pyrroles

Category:Streptomyces

Category:Pseudomonadota