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Violacein information


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
CAS Number
  • 548-54-9 ☒N
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:131914
ChEMBL
  • ChEMBL1652263 ☒N
ChemSpider
  • 8103672 checkY
KEGG
  • C21136
PubChem CID
  • 11053
UNII
  • QJH0DSQ3SG
CompTox Dashboard (EPA)
  • DTXSID001028415 Edit this at Wikidata
InChI
  • 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
SMILES
  • C1=CC=C2C(=C1)/C(=C\3/C=C(NC3=O)C4=CNC5=C4C=C(C=C5)O)/C(=O)N2
Properties
Chemical formula
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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Infobox references

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.

  1. ^ Durán N, Justo GZ, Durán M, Brocchi M, Cordi L, Tasic L, et al. (2016). "Advances in Chromobacterium violaceum and properties of violacein-Its main secondary metabolite: A review". Biotechnology Advances. 34 (5): 1030–1045. doi:10.1016/j.biotechadv.2016.06.003. PMID 27288924.
  2. ^ Myeong NR, Seong HJ, Kim HJ, Sul WJ (April 2016). "Complete genome sequence of antibiotic and anticancer agent violacein producing Massilia sp. strain NR 4-1". Journal of Biotechnology. 223: 36–37. doi:10.1016/j.jbiotec.2016.02.027. PMID 26916415.
  3. ^ Choi SY, Yoon KH, Lee JI, Mitchell RJ (2015). "Violacein: Properties and Production of a Versatile Bacterial Pigment". BioMed Research International. 2015: 465056. doi:10.1155/2015/465056. PMC 4538413. PMID 26339614.
  4. ^ Andrighetti-Fröhner CR, Antonio RV, Creczynski-Pasa TB, Barardi CR, Simões CM (September 2003). "Cytotoxicity and potential antiviral evaluation of violacein produced by Chromobacterium violaceum". Memórias do Instituto Oswaldo Cruz. 98 (6): 843–848. doi:10.1590/s0074-02762003000600023. PMID 14595466.

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Violacein

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Violacein is a naturally-occurring bis-indole pigment with antibiotic (anti-bacterial, anti-viral, anti-fungal and anti-tumor) properties. Violacein is...

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Chromobacterium violaceum

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sub-tropical regions of the world. It produces a natural antibiotic called violacein, which may be useful for the treatment of colon and other cancers. It...

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Biological pigment

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cyanobacteria. Bacteria produce pigments such as carotenoids, melanin, violacein, prodigiosin, pyocyanin, actinorhodin, and zeaxanthin. Cyanobacteria produce...

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Janthinobacterium lividum

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color, due to a compound called violacein, which is produced when glycerol is metabolized as a carbon source. Violacein has antibacterial, antiviral, and...

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Duganella

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and anti-viral. Violacein producing bacterial strains have been isolated from many different environments, Duganella producing violacein strains have been...

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Chytridiomycosis

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concerning the addition of the violacein-producing bacteria J. lividum to amphibians that lacked sufficient violacein, allowing them to inhibit infection...

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Staurosporine

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this intermediate after the loss of VioE (used in the biosynthesis of violacein – a natural product formed from a branch point in this pathway that also...

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Janthinobacterium

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produces distinct purple-violet pigments among which are jagaricin and violacein, manifests diverse energy metabolism abilities, and tolerates cold, ultraviolet...

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Chemical defense

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Pseudoalteromonas produce a toxic secondary metabolite, violacein, to deter protozoan predation. Violacein is released when bacteria are consumed, killing the...

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Indolocarbazole

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C.; Brana A. F.; Mendez C.; Salas J. A. (2006). "Reevaluation of the violacein biosynthetic pathway and its relationship to indolocarbazole biosynthesis"...

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