Violacein
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| Category | Antibiotics |
| Catalog number | BBF-03469 |
| CAS | 548-54-9 |
| Molecular Weight | 343.34 |
| Molecular Formula | C20H13N3O3 |
| Purity | ≥ 95% (violacein and deoxyviolacein)，Violacein ≥ 80% |
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Description
It is a nitrogenous heterocyclic indole antibiotic produced by the strain of Chromobacterium violaceum. It has anti-gram-positive bacteria, fungi and protozoa effects. The serum has an effect on its activity.
Specification
| Synonyms | (3E)-3-[5-(5-Hydroxy-1H-indol-3-yl)-2-oxo-1,2-dihydro-3H-pyrrol-3-yliden]-1,3-dihydro-2H-indol-2-one; 2H-Indol-2-one, 3-[1,2-dihydro-5-(5-hydroxy-1H-indol-3-yl)-2-oxo-3H-pyrrol-3-ylidene]-1,3-dihydro-, (3E)- |
| Storage | Store at 2-8°C |
| IUPAC Name | 3-[2-hydroxy-5-(5-hydroxy-1H-indol-3-yl)-1H-pyrrol-3-yl]indol-2-one |
| Canonical SMILES | C1=CC2=C(C(=O)N=C2C=C1)C3=C(NC(=C3)C4=CNC5=C4C=C(C=C5)O)O |
| 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 |
| InChI Key | SHLJIZCPRXXHHZ-UHFFFAOYSA-N |
| Source | Chromobacterium violaceum |
Properties
| Appearance | Black Crystal or Acicular and Square Purplish-black Crystal |
| Antibiotic Activity Spectrum | Gram-positive bacteria; Fungi; Parasites |
| Boiling Point | 821.4±65.0°C at 760 mmHg |
| Density | 1.5±0.1 g/cm3 |
| Solubility | Soluble in Ethanol, Methanol, DMF, DMSO |
Reference Reading
1. Violacein: Properties and Production of a Versatile Bacterial Pigment
Kyoung-hye Yoon, Robert J Mitchell, Jin Il Lee, Seong Yeol Choi Biomed Res Int . 2015;2015:465056. doi: 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.
2. Violacein: properties and biological activities
Livia Cordi, Giselle Z Justo, Nelson Durán, Dorival Martins, Patrícia S Melo, Carmen V Ferreira Biotechnol Appl Biochem . 2007 Nov;48(Pt 3):127-33. doi: 10.1042/BA20070115.
The violet pigment violacein is an indole derivative, isolated mainly from bacteria of the genus Chromobacterium, which exhibits important antitumoral, antimicrobial and antiparasitary properties. Furthermore, the formulation of violacein in different polymeric carriers developed so far offers alternative approaches to overcoming physiological barriers and undesirable physicochemical properties in vivo, thus improving its efficacy.
3. Biotechnological Activities and Applications of Bacterial Pigments Violacein and Prodigiosin
Jin I Lee, Robert J Mitchell, Seong Yeol Choi, Sungbin Lim, Kyoung-Hye Yoon J Biol Eng . 2021 Mar 11;15(1):10. doi: 10.1186/s13036-021-00262-9.
In this review, we discuss violacein and prodigiosin, two chromogenic bacterial secondary metabolites that have diverse biological activities. Although both compounds were "discovered" more than seven decades ago, interest into their biological applications has grown in the last two decades, particularly driven by their antimicrobial and anticancer properties. These topics will be discussed in the first half of this review. The latter half delves into the current efforts of groups to produce these two compounds. This includes in both their native bacterial hosts and heterogeneously in other bacterial hosts, including discussing some of the caveats related to the yields reported in the literature, and some of the synthetic biology techniques employed in this pursuit.
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
