Prodigiosin

4-methoxy- 5-[ (Z) - (5- methyl-4 -pentyl -2H- pyrrol- 2-ylidene) methyl] -1H, 1'H -2, 2'- bipyrrole

• 82-89-3
• 56144-17-3 (hydrochloride)

Hydrochloride

Template: Infobox chemical / molecular formula search available

Prodigiosin is a secondary metabolite which is one of the Tripyrrolen. The name of this well-known since the early 20th century substance derived ( wonderful) from the English " prodigious " from.

Occurrence

Prodigiosin was first detected in Serratia marcescens. Furthermore, this compound has been proven to also be a derivative of the marine bacteria Alteromonas rubra and Vibrio gazogenes as well as a few other types of bacteria. In these bacteria, the molecule can assume a passive transmembrane transport of chloride ions.

Biosynthesis

Basic building blocks of the biosynthesis of prodigiosin are amino acids and acetate, that is towards the biosynthesis of porphyrin is replaced by succinyl-CoA acetyl -CoA. However, the biosynthesis of this molecule is not completely understood, even after decades of research.

The biosynthesis does not occur under all growth conditions of the bacteria. In the regulation of the synthesis of cAMP is involved. With decreasing pH of the growth medium, the color flips from red to green to.

Effects

The most striking characteristic of prodigiosin, the red color. Therefore, a use of the pigment biologically produced for coloring fibers has been proposed.

The substance has shown effects against microorganisms and against tumor cells as well as an immunosuppressant and therefore aroused lively research interest.

Ignorance of the ability of this substance to cause sometimes red patches on rotten bread, has also had an impact on the religious behavior of the Catholics, inasmuch as who established the Feast of Corpus Christi in the belief in miracles and blood host miracle.

Structurally related substances

The structurally related to the prodigiosin Obatoclax inhibits the protein Bcl -2 and is being developed for the treatment of cancer.