Undecylprodigiosin is an

alkaloid Alkaloids are a class of basic, naturally occurring organic compounds that contain at least one nitrogen atom. This group also includes some related compounds with neutral and even weakly acidic properties. Some synthetic compounds of similar ...

produced by some

Actinomycetes The Actinomycetales is an order of Actinomycetota. A member of the order is often called an actinomycete. Actinomycetales are generally gram-positive and anaerobic and have mycelia in a filamentous and branching growth pattern. Some actinomycete ...

bacteria. It is a member of the

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''). The group is named after prodigiosin (prodiginine) and is b ...

group of

natural products A natural product is a natural Chemical compound, compound or chemical substance, substance produced by a living organism—that is, found in nature. In the broadest sense, natural products include any substance produced by life. Natural product ...

and has been investigated for potential

antimalarial Antimalarial medications or simply antimalarials are a type of antiparasitic chemical agent, often naturally derived, that can be used to treat or to prevent malaria, in the latter case, most often aiming at two susceptible target groups, young c ...

activity.

Natural sources

Undecylprodigiosin is a

secondary metabolite Secondary metabolites, also called specialised metabolites, toxins, secondary products, or natural products, are organic compounds produced by any lifeform, e.g. bacteria, fungi, animals, or plants, which are not directly involved in the norm ...

found in some Actinomycetes, for example ''

Actinomadura madurae The genus ''Actinomadura'' is one of four genera of Actinomycetota that belong to the family Thermomonosporaceae. It contains aerobic, Gram-positive, non-acid-fast, non-motile, chemo-organotrophic actinomycetes that produce well-developed, non- ...

'', ''

Streptomyces coelicolor ''Streptomyces albidoflavus'' is a bacterium species from the genus of ''Streptomyces'' which has been isolated from soil from Poland. ''Streptomyces albidoflavus'' produces dibutyl phthalate and streptothricins. Small noncoding RNA Bacteri ...

'' and '' Streptomyces longisporus''.

Production

Biosynthesis

The

biosynthesis Biosynthesis is a multi-step, enzyme-catalyzed process where substrates are converted into more complex products in living organisms. In biosynthesis, simple compounds are modified, converted into other compounds, or joined to form macromolecules. ...

of undecylprodigiosin starts with PCP apoprotein which is transformed into the

holoprotein A holoprotein or conjugated protein is an apoprotein combined with its prosthetic group. Some enzymes do not need additional components to show full activity. Others require non-protein molecules called cofactors to be bound for activity. Cofact ...

using

acetyl CoA Acetyl-CoA (acetyl coenzyme A) is a molecule that participates in many biochemical reactions in protein, carbohydrate and lipid metabolism. Its main function is to deliver the acetyl group to the citric acid cycle (Krebs cycle) to be oxidized for ...

and PPtase then

adenylation Adenylylation, more commonly known as AMPylation, is a process in which an adenosine monophosphate (AMP) molecule is covalently attached to the amino acid side chain of a protein. This covalent addition of AMP to a hydroxyl side chain of the prote ...

occurs utilizing L-proline and ATP. The resulting molecule is then oxidized by

dehydrogenase A dehydrogenase is an enzyme belonging to the group of oxidoreductases that oxidizes a substrate by reducing an electron acceptor, usually NAD+/NADP+ or a flavin coenzyme such as FAD or FMN. Like all catalysts, they catalyze reverse as well as f ...

enzyme. Elongation by decarboxylative condensation with

malonyl CoA Malonyl-CoA is a coenzyme A derivative of malonic acid. Functions It plays a key role in chain elongation in fatty acid biosynthesis and polyketide biosynthesis. Fatty acid biosynthesis Malonyl-CoA provides 2-carbon units to fatty acids and commi ...

is followed by another decarboxylative condensation with L-serine using α-oxamine synthase (OAS) domain. The compound is then cyclized, oxidized with

and methylated with SAM to give 4-methoxy-2,2′-bipyrrole-5-carboxaldehyde (MBC) intermediate which react with 2-undecylpyrrole (2-UP) to give undecylprodigiosin. Biosynth

Laboratory

The first

total synthesis Total synthesis is the complete chemical synthesis of a complex molecule, often a natural product, from simple, commercially-available precursors. It usually refers to a process not involving the aid of biological processes, which distinguishes ...

of the undecylprodigiosin was published in 1966, confirming the chemical structure. As with the biosynthesis, the key intermediate was MBC.

Uses

As with other prodiginines, the compound has been investigated for its pharmaceutical potential as anticancer, immunosuppressant, or antimalarial agent.

References

{{reflist Streptomyces Alkaloids Pyrroles