Prodiginines

The prodiginines are a family of red tripyrrole dyestuffs produced by Gammaproteobacteria (e.g. Serratia marcescens) as well as some Actinomycetota (e.g. Streptomyces coelicolor).

They are also found in Actinomycetes, for example Streptomyces coelicolor and some marine bacteria, including Hahella chejuensis and Pseudoalteromonas denitrificans.

Prodiginine, first extracted from terrestrial Serratia marcescens, consisted of a straight alkyl chain substituent and was named prodigiosin.

[5] 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).

[8] 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.

Serratia marcescens growing on bread, showing characteristic colour of the prodiginines
Figure 1: Chemical transformations and gene clusters for prodiginine biosynthetic pathways [ 1 ]
Tambjamine aldehyde (compound 15 in Figure 1)