Chemistry:Violacein
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| 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
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| Other names
3-(2-(5-Hydroxyindol-3-yl)-5-oxo-2-pyrrolin-4-ylidene)-2-indolinone
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| 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). | |
 verify (what is   ?)
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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.
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 cytotoxic anticancer agent and antibacterial action against Staphylococcus aureus and other 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
- ↑ 1.0 1.1 "Advances in Chromobacterium violaceum and properties of violacein-Its main secondary metabolite: A review". Biotechnology Advances 34 (5): 1030–1045. 2016. doi:10.1016/j.biotechadv.2016.06.003. PMID 27288924.
- ↑ 2.0 2.1 2.2 "Complete genome sequence of antibiotic and anticancer agent violacein producing Massilia sp. strain NR 4-1". Journal of Biotechnology 223: 36–37. April 2016. doi:10.1016/j.jbiotec.2016.02.027. PMID 26916415.
- ↑ 3.0 3.1 "Violacein: Properties and Production of a Versatile Bacterial Pigment". BioMed Research International 2015: 465056. 2015. doi:10.1155/2015/465056. PMID 26339614.
- ↑ "Cytotoxicity and potential antiviral evaluation of violacein produced by Chromobacterium violaceum". Memórias do Instituto Oswaldo Cruz 98 (6): 843–848. September 2003. doi:10.1590/s0074-02762003000600023. PMID 14595466.
- ↑ 5.0 5.1 "Microbial synthesis of violacein pigment and its potential applications". Critical Reviews in Biotechnology 41 (6): 879–901. September 2021. doi:10.1080/07388551.2021.1892579. PMID 33730942.
- ↑ "Isolation and characterization of two groups of novel marine bacteria producing violacein". Marine Biotechnology 10 (2): 128–132. March 2008. doi:10.1007/s10126-007-9046-9. PMID 17968625. Bibcode: 2008MarBt..10..128Y.
- ↑ "Isolation and characterization of a novel violacein-like pigment producing psychrotrophic bacterial species Janthinobacterium svalbardensis sp. nov". Antonie van Leeuwenhoek 103 (4): 763–769. April 2013. doi:10.1007/s10482-012-9858-0. PMID 23192307.
- ↑ "Classification of a Violacein-Producing Psychrophilic Group of Isolates Associated with Freshwater in Antarctica and Description of Rugamonas violacea sp. nov". Microbiology Spectrum 9 (1): e0045221. September 2021. doi:10.1128/Spectrum.00452-21. PMID 34378950.
- ↑ "Characterisation of Waterborne Psychrophilic Massilia Isolates with Violacein Production and Description of Massilia antarctica sp. nov". Microorganisms 10 (4): 704. March 2022. doi:10.3390/microorganisms10040704. PMID 35456753.
- ↑ "The Antibiotic Activity of Violacein, Prodigiosin, and Phthiocol". Journal of Bacteriology 52 (1): 145–146. July 1946. doi:10.1128/JB.52.1.145-146.1946. PMID 16561146.
- ↑ "Violacein, an Antibiotic Pigment Produced by Chromobacterium violaceum". Journal of Infectious Diseases 76 (1): 47–51. 1945. doi:10.1093/infdis/76.1.47.
Further reading
- "Microbial synthesis of violacein pigment and its potential applications". Critical Reviews in Biotechnology 41 (6): 879–901. September 2021. doi:10.1080/07388551.2021.1892579. PMID 33730942.
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