Undecylprodigiosin
{{Chembox
| Name =
| ImageFile = Undecylprodigiosin.svg
| OtherNames =
| IUPACName = (2Z,5Z)-3-Methoxy-5-pyrrol-2-ylidene-2-[(5-undecyl-1H-pyrrol-2-yl)methylidene]pyrrole
| SystematicName =
| Section1 = {{Chembox Identifiers
| PubChem = 135515151
| ChEMBL = 83139
| ChEMBL_Ref = {{ebicite|correct|EMBL}}
| ChEBI = 29702
| CASNo = 52340-48-4
| CASNo_Ref = {{cascite|correct|CAS}}
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = ZQ2HK5E6ZG
| ChemSpiderID = 10481061
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| StdInChI = 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-
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = HIYSWASSDOXZLC-MOHJPFBDSA-N
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| SMILES = CCCCCCCCCCCC1=CC=C(N1)/C=C\2/C(=CC(=N2)C3=CC=CN3)OC
}}
| Section2 = {{Chembox Properties
| C=25|H=35|N=3|O=1
}}
| Section3 =
| Section4 =
| Section5 =
| Section6 =
}}
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.
Natural sources
Undecylprodigiosin is a secondary metabolite found in some Actinomycetes, for example Actinomadura madurae, Streptomyces coelicolor and Streptomyces longisporus.{{cite journal | doi=10.1038/nrmicro1531 |vauthors=Williamson NR, Fineran PC, Gristwood T, Leeper FJ, Salmond GP | title=The biosynthesis and regulation of bacterial prodiginines | journal=Nature Reviews Microbiology | year=2006 | pages=887–899 | issue=12 | volume=4 | url=https://www.researchgate.net/publication/6688845 | pmid=17109029|s2cid=11649828 }}
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.{{cite journal |last1=Hu |first1=Dennis X. |last2=Withall |first2=David M. |last3=Challis |first3=Gregory L. |last4=Thomson |first4=Regan J. |title=Structure, Chemical Synthesis, and Biosynthesis of Prodiginine Natural Products |journal=Chemical Reviews |date=17 June 2016 |volume=116 |issue=14 |pages=7818–7853 |doi=10.1021/acs.chemrev.6b00024|pmc=5555159 |pmid=27314508 }}
File:Biosynth.png{{clear-left}}
= 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.{{cite journal |doi=10.1039/C19660000825 |title=The structure and synthesis of undecylprodigiosin. A prodigiosin analogue from Streptomyces |year=1966 |last1=Wasserman |first1=H. H. |last2=Rodgers |first2=G. C. |last3=Keith |first3=D. D. |journal=Chemical Communications |issue=22 |pages=825–826 }}
Uses
As with other prodiginines, the compound has been investigated for its pharmaceutical potential as anticancer, immunosuppressant, or antimalarial agent.{{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 }}