Violacein

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Violacein
Names
IUPAC name
(3E)-3-[5-(5-Hydroxy-1H-indol-3-yl)-2-oxo-1,2-dihydro-3H-pyrrol-3-ylidene]-1,3-dihydro-2H-indol-2-one
Other names
3-(2-(5-Hydroxyindol-3-yl)-5-oxo-2-pyrrolin-4-ylidene)-2-indolinone
Identifiers
3D model (
JSmol
)
ChEBI
ChEMBL
ChemSpider
KEGG
UNII
  • InChI=1S/C20H13N3O3/c24-10-5-6-15-12(7-10)14(9-21-15)17-8-13(19(25)23-17)18-11-3-1-2-4-16(11)22-20(18)26/h1-9,21,23-25H
    Key: SHLJIZCPRXXHHZ-UHFFFAOYSA-N
  • C1=CC=C2C(=C1)/C(=C\3/C=C(NC3=O)C4=CNC5=C4C=C(C=C5)O)/C(=O)N2
Properties
C20H13N3O3
Molar mass 343.342 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Violacein is a naturally-occurring bis-indole pigment with antibiotic (anti-bacterial, anti-viral, anti-fungal and anti-tumor) properties.[1][2][3][4] Violacein is produced by several species of bacteria, including Chromobacterium violaceum, and gives these organisms their striking purple hues. Violacein shows increasing commercially interesting uses, especially for industrial applications in cosmetics, medicines and fabrics.

Biosynthesis

Violacein is formed by enzymatic condensation of two tryptophan molecules, requiring the action of five proteins. The genes required for its production, vioABCDE, and the regulatory mechanisms employed have been studied within a small number of violacein-producing strains.[2] Production of violacein is controlled by quorum sensing using acyl-homoserine lactones (AHLs).[5]

Only a few genera of bacteria have been reported to produce violacein. These include Chromobacterium, Duganella, Pseudoalteromonas,[6] Janthinobacterium,[7] Iodobacter, Rugamonas,[8] and Massilia[5].[9]

Antibiotic activity

Violacein is known to have diverse biological activities, including as a

gram-positive pathogens.[1][3][10][11] Determining the biological roles of this pigmented molecule has been of particular interest to researchers, and understanding violacein's function and mechanism of action is relevant to potential applications. Commercial production of violacein and related compounds has proven difficult so improving fermentative yields of violacein is being pursued through genetic engineering and synthetic biology.[2]

References

  1. ^
    PMID 27288924
    .
  2. ^
    PMID 26916415
    .
  3. ^
    PMID 26339614
    .
  4. PMID 14595466
    .
  5. ^
    S2CID 232304130
    .
  6. S2CID 19143787
    .
  7. S2CID 17940699
    .
  8. PMID 34378950
    .
  9. PMID 35456753
    .
  10. PMID 16561146
    .
  11. JSTOR 30085685
    .

Further reading

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