548-54-9

Usage

Uses

Used in Pharmaceutical Applications:
Violacein is used as an antimicrobial agent for its broad-spectrum activity against bacteria, protozoans (including malaria), viruses, and mammalian cell lines. It exhibits cell toxicity resembling TNF-α signal transduction.
Used in Cosmetic Applications:
Violacein is used as a colorant for natural and synthetic fabrics, functioning as a respiratory pigment and regulating tryptophan production.
Used in Environmental Applications:
Violacein is used as a standard to determine the crude violacein concentration in ethanol extracts of D. violaceinigra str. NI28 cultures and to identify violacein in the leaf samples of Nicotiana.
Used in Anticancer Applications:
Violacein is used as an anticancer agent, demonstrating synergistic effects when combined with conventional chemotherapeutic drugs, enhancing chemo-sensitivity and efficacy in resistant cases.
Used in Textile Industry:
Violacein is used as a colorant for natural and synthetic fabrics, providing a vibrant violet color to the materials.
Used in Food Industry:
Violacein is used as a natural colorant in the food industry, adding a unique violet hue to various products.
Used in Research Applications:
Violacein is used in cell culture assays and for the detection of quorum sensing mediators due to the regulation of pigment biosynthesis in Chromobacterium violaceum CV26.

Biochem/physiol Actions

Violacein, a violet pigment, is an indole derivative produced by various bacterial strains such as Chromobacterium violaceum, Janthinobacterium lividum, Chromobacterium lividum, and Pseudoalteromonas luteoviolacea. Violacein is a member of a novel class of cytotoxic drugs, which mediate apoptosis. Violacein exhibits antitumoral, antibacterial, antiulcerogenic, antileishmanial, and antiviral activities. Violacein and its β-cyclodextrin complexes trigger apoptosis and differentiation in HL60 leukemic cells. Violacein cytotoxicity is preceded by activation of caspase 8, transcription of NF-κB target genes, and p38-MAPK activation resembling TNF-α signal transduction.

InChI:InChI=1/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/h1-9,21,24H,(H,22,26)(H,23,25)/b18-13+

Upstream product

• 112349-36-7 3-[(E)-5-(5-methoxy-indol-3-yl)-2-oxo-1,2-dihydro-pyrrol-3-ylidene]-indolin-2-one 
• 73-22-3 L-Tryptophan 
• 4350-09-8 L-5-HTP 
• 1429218-35-8 (E)-3-(5-(5-(benzyloxy)-1H-indol-3-yl)-1-(4-methoxybenzyl)-2-oxo-1H-pyrrol-3(2H)-ylidene)indolin-2-one 
• 1429218-34-7 5-(5-(benzyloxy)-1H-indol-3-yl)-1-(4-methoxybenzyl)-1H-pyrrol-2-(5H)-one 
• 1429218-33-6 5-(5-(benzyloxy)-1H-indol-3-yl)-1-(4-methoxybenzyl)pyrrolidin-2-one 
• 160858-75-3 1-tert-butoxycarbonylisatin 
• 348128-39-2 3-[5-(6-Benzyloxy-1,3a-dihydrocyclohepta[b]pyrrol-3-yl)-2-oxo-1,2-dihydropyrrol-3-ylidene]-1,3-dihydroindol-2-one 
• 91-56-5 indole-2,3-dione 
• 1215-59-4 5-benzyloxy-1H-indole 
• 348128-42-7 2-(5-Benzyloxy-1-tert-butoxycarbonyl-1H-indol-3-yl)-5-oxopyrrolidine-1-carboxylic acid tert-butyl ester 
• 348128-34-7 5-(5-Benzyloxy-1H-indol-3-yl)pyrrolidin-2-one 

Downstream Products

• 112349-36-7 3-[(E)-5-(5-methoxy-indol-3-yl)-2-oxo-1,2-dihydro-pyrrol-3-ylidene]-indolin-2-one 
• 94493-20-6 tetramethylviolacein 
• 94493-21-7 Acetic acid 1-acetyl-3-{5-oxo-4-[2-oxo-1,2-dihydro-indol-(3E)-ylidene]-4,5-dihydro-1H-pyrrol-2-yl}-1H-indol-5-yl ester 

Relevant academic research and scientific papers

The violacein biosynthesis monitored by multi-wavelength fluorescence spectroscopy and by the PARAFAC method

Obtaining information about a biosynthetic pathway is a complex and laborious procedure. In this sense, this work presents a new approach for the initial analysis of the biosynthesis of fluorescent natural products using as example the violacein biosynthe

Tandem ring-closing metathesis/isomerization reactions for the total synthesis of violacein

A series of 5-substituted 2-pyrrolidinones was synthesized through a one-pot ruthenium alkylidene-catalyzed tandem RCM/isomerization/nucleophilic addition sequence. The intermediates resulting from RCM/isomerization showed reactivity toward electrophiles in aldol condensation reactions which provided a new entry for the total synthesis of the antileukemic natural product violacein.

A short synthesis of the bacterial pigments violacein and deoxyviolacein

A concise synthesis of the bacterial pigments deoxyviolacein (1a) and violacein (1b) is described in which two indole units are attached stepwise to the central pyrrolinone ring.

Biosynthesis of Violacein: Evidence for the Intermediacy of 5-Hydroxy-L-tryptophan and the Structure of a New Pigment, Oxyviolacein, Produced by the Metabolism of 5-Hydroxytryptophan

The administration of 5-hydroxy-L-tryptophan to growing cells yielded a new blue pigment.The chemical structure was determined to be 5-(5-hydroxyindol-3-yl)-3-(5-hydroxy-3-oxoindolylidene)-4-pyrroline-2-one, mainly by using proton- and carbon 13-NMR.Feeding experiments of 5-hydroxytryptophan labeled with deuterium and carbon-13 unambiguously demonstrated that the hydroxylation of tryptophan was the first step for violacein biosynthesis.No incorporation of 5-hydroxy-tryptamine suggests that decarboxylation of 5-hydroxy-L-tryptophan was not the secondreaction, but should take place at a later stage in the pathway of violacein formation. 5-Hydroxy-indole was not incorporated, indicating that an enzyme like tryptophanase was unlikely to have been involved in violacein biosynthesis.