Undecylprodigiosin

Undecylprodigiosin is an alkaloid produced by some Actinomycetes bacteria. It is a member of the prodiginines group of natural products and has been investigated for potential antimalarial activity.

Undecylprodigiosin

Names
IUPAC name (2Z,5Z)-3-Methoxy-5-pyrrol-2-ylidene-2-[(5-undecyl-1H-pyrrol-2-yl)methylidene]pyrrole
Identifiers
CAS Number	52340-48-4 Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:29702
ChEMBL	ChEMBL83139 Y[EMBL]
ChemSpider	10481061 Y
PubChem CID	135515151
UNII	ZQ2HK5E6ZG Y
InChI InChI=1S/C25H35N3O/c1-3-4-5-6-7-8-9-10-11-13-20-15-16-21(27-20)18-24-25(29-2)19-23(28-24)22-14-12-17-26-22/h12,14-19,26-27H,3-11,13H2,1-2H3/b24-18- Y Key: HIYSWASSDOXZLC-MOHJPFBDSA-N Y
SMILES CCCCCCCCCCCC1=CC=C(N1)/C=C\2/C(=CC(=N2)C3=CC=CN3)OC
Properties
Chemical formula	C25H35N3O
Molar mass	393.575 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Natural sources

Undecylprodigiosin is a secondary metabolite found in some Actinomycetes, for example Actinomadura madurae, Streptomyces coelicolor and Streptomyces longisporus.^[1]

Production

Biosynthesis

The biosynthesis of undecylprodigiosin starts with PCP apoprotein which is transformed into the holoprotein using acetyl CoA and PPtase then adenylation occurs utilizing L-proline and ATP. The resulting molecule is then oxidized by dehydrogenase enzyme. Elongation by decarboxylative condensation with malonyl CoA is followed by another decarboxylative condensation with L-serine using α-oxamine synthase (OAS) domain. The compound is then cyclized, oxidized with dehydrogenase 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.^[2]

Biosynthesis of undecylprodigiosin

Laboratory

The first total synthesis of the undecylprodigiosin was published in 1966, confirming the chemical structure. As with the biosynthesis, the key intermediate was MBC.^[2][3]

Uses

As with other prodiginines, the compound has been investigated for its pharmaceutical potential as anticancer, immunosuppressant, or antimalarial agent.^[1][4]