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Violacein

(Synonyms: 紫色杆菌素) 目录号 : GC45145

A bacterial metabolite with antibacterial and antiprotozoal activities

Violacein Chemical Structure

Cas No.:548-54-9

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1mg
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产品描述

Violacein is a bacterial metabolite originally isolated from C. violaceum that has antibacterial and antiprotozoal activities.[1] [2] It is produced by C. violaceum as a purple pigment in response to N-hexanoyl homoserine lactone , a property that has been modified to create a strain of C. violaceum used in detecting quorum-sensing molecules.[3] Violacein is active against Gram-positive bacteria, including B. subtilis and S. aureus (MICs = 0.8 and 1.6 µM, respectively). It is also active against P. falciparum, including chloroquine-susceptible and -resistant strains (IC50s = 0.85 and 0.63 µM, respectively).[2] It reduces parasitemia in a mouse model of nonlethal P. chabaudi chabaudi infection when administered at a dose of 7.5 mg/kg and increases survival in a mouse model of lethal P. chabaudi chabaudi infection. Violacein permeabilizes the cytoplasmic membrane of bacterial cells but does not affect the cell wall.[1]

Reference:
[1]. Cauz, A.C.G., Carretero, G.P.B., Saraiva, G.K.V., et al. Violacein targets the cytoplasmic membrane of bacteria. ACS Infect. Dis. 5(4), 539-549 (2019).
[2]. Lopes, S.C.P., Blanco, Y.C., Justo, G.Z., et al. Violacein extracted from Chromobacterium violaceum inhibits Plasmodium growth in vitro and in vivo. Antimicrob. Agents Chemother. 53(5), 2149-2152 (2009).
[3]. Blosser, R.S., and Gray, K.M. Extraction of violacein from Chromobacterium violaceum provides a new quantitative bioassay for N-acyl homoserine lactone autoinducers. J. Microbiol. Methods 40(1), 47-55 (2000).

Chemical Properties

Cas No. 548-54-9 SDF
别名 紫色杆菌素
化学名 (3E)-3-[1,2-dihydro-5-(5-hydroxy-1H-indol-3-yl)-2-oxo-3H-pyrrol-3-ylidene]-1,3-dihydro-2H-indol-2-one
Canonical SMILES O=C(N1)/C(C2=C1C=CC=C2)=C3C(NC(C4=CNC5=C4C=C(O)C=C5)=C/3)=O
分子式 C20H13N3O3 分子量 343.3
溶解度 Soluble in DMSO 储存条件 Store at -20°C, protect from light
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1 mM 2.9129 mL 14.5645 mL 29.129 mL
5 mM 0.5826 mL 2.9129 mL 5.8258 mL
10 mM 0.2913 mL 1.4565 mL 2.9129 mL
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Research Update

Violacein and its antifungal activity: comments and potentialities

Lett Appl Microbiol 2022 Oct;75(4):796-803.PMID:35687081DOI:10.1111/lam.13760.

Violacein is an important natural antimicrobial pigment that is mainly produced by Chromobacterium violaceum and Janthinobacterium lividum. It presents a significant range of effects against phytopathogenic and human fungi, besides being featured as having low toxicity, and by its important ecological role in protecting amphibian species and applications in dyed medical fabric. The hypothesis about Violacein's action mechanisms against mucormycosis (Rhizopus arrhizus) and candidiasis (Candida auris) is herein discussed based on data available in the scientific literature.

Microbial synthesis of Violacein pigment and its potential applications

Crit Rev Biotechnol 2021 Sep;41(6):879-901.PMID:33730942DOI:10.1080/07388551.2021.1892579.

Violacein is a pigment synthesized by Gram-negative bacteria such as Chromobacterium violaceum. It has garnered significant interest owing to its unique physiological and biological activities along with its synergistic effects with various antibiotics. In addition to C. violaceum, several microorganisms, including: Duganella sp., Pseudoalteromonas sp., Iodobacter sp., and Massilia sp., are known to produce Violacein. Along with the identification of violacein-producing strains, the genetic regulation, quorum sensing mechanism, and sequence of the vio-operon involved in the biosynthesis of Violacein have been elucidated. From an engineering perspective, the heterologous production of Violacein using the genetically engineered Escherichia coli or Citrobacter freundii host has also been attempted. Genetic engineering of host cells involves the heterologous expression of genes involved in the vio operon and the optimization of metabolic pathways and gene regulation. Further, the crystallography of VioD and VioE was revealed, and mass production by enzyme engineering has been accelerated. In this review, we highlight the biologically assisted end-use applications of Violacein (such as functional fabric development, nanoparticles, functional polymer composites, and sunscreen ingredients) and Violacein activation mechanisms, production strains, and the results of mass production with engineered methods. The prospects for Violacein research and engineering applications have also been discussed.

Multi-target drug with potential applications: Violacein in the spotlight

World J Microbiol Biotechnol 2021 Aug 16;37(9):151.PMID:34398340DOI:10.1007/s11274-021-03120-4.

The aim of the current review is to address updated research on a natural pigment called Violacein, with emphasis on its production, biological activity and applications. New information about Violacein's action mechanisms as antitumor agent and about its synergistic action in drug delivery systems has brought new alternatives for anticancer therapy. Thus, Violacein is introduced as reliable drug capable of overcoming at least three cancer hallmarks, namely: proliferative signaling, cell death resistance and metastasis. In addition, antimicrobial effects on several microorganisms affecting humans and other animals turn Violacein into an attractive drug to combat resistant pathogens. Emphasis is given to effects of Violacein combined with different agents, such as antibiotics, anticancer agents and nanoparticles. Although Violacein is well-known for many decades, it remains an attractive compound. Thus, research groups have been making continuous effort to help improving its production in recent years, which can surely enable its pharmaceutical and chemical application as multi-task compound, even in the cosmetics and food industries.

Violacein: Properties and Production of a Versatile Bacterial Pigment

Biomed Res Int 2015;2015:465056.PMID:26339614DOI:10.1155/2015/465056.

Violacein-producing bacteria, with their striking purple hues, have undoubtedly piqued the curiosity of scientists since their first discovery. The bisindole Violacein is formed by the condensation of two tryptophan molecules through 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. As a compound, Violacein is known to have diverse biological activities, including being an anticancer agent and being an antibiotic against Staphylococcus aureus and other Gram-positive pathogens. Identifying the biological roles of this pigmented molecule is of particular interest, and understanding Violacein's function and mechanism of action has relevance to those unmasking any of its commercial or therapeutic benefits. Unfortunately, the production of Violacein and its related derivatives is not easy and so various groups are also seeking to improve the fermentative yields of Violacein through genetic engineering and synthetic biology. This review discusses the recent trends in the research and production of Violacein by both natural and genetically modified bacterial strains.

Patents on Violacein: A Compound with Great Diversity of Biological Activities and Industrial Potential

Recent Pat Biotechnol 2021 Oct 4;15(2):102-111.PMID:33349223DOI:10.2174/2213476X07666201221111655.

Background: This review outlines the current impact of violacein-derivative materials in several technological areas through patents. Methods: A comprehensive examination of patent databases on Violacein demonstrated the relevance of this pigment, as well as the pertinent topics related to its technological development in order to obtain adaptable new pharmaceuticals, cosmetics, and new quality fiber materials, together with other applications of Violacein in different areas. Results: At present, there is no efficient and economical technique for Violacein preparation at the industrial scale. Many attempts have been made, but none have overcome the challenge of being an effective and inexpensive process. However, some potential applications of Violacein in fields such as biomedicine make the pigment worthy of continuous investigation. In particular, Violacein patents covering biosynthesis for different applications have been reported recently. Conclusion: Violacein has been used as a unique pigment in distinct specialty areas, such as in medical and industrial fields. This review of patents provides an update on Violacein innovations that are useful for researchers working in the expanding and interesting field of biotechnology with natural pigments.