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V9389

Sigma-Aldrich

Violacein

from Janthinobacterium lividum, >98% (violacein (minimum 85% violacein) and deoxyviolacein, HPLC), powder, bacterial metabolite

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About This Item

Empirical Formula (Hill Notation):
C20H13N3O3
CAS Number:
548-54-9
Molecular Weight:
343.34
UNSPSC Code:
12352200
NACRES:
NA.77

Product Name

Violacein from Janthinobacterium lividum, >98% (violacein (minimum 85% violacein) and deoxyviolacein, HPLC)

Quality Level

200

assay

>98% (violacein (minimum 85% violacein) and deoxyviolacein, HPLC)

solubility

H2O: insoluble
acetone: soluble
ethanol: soluble
methanol: soluble

storage temp.

2-8°C

SMILES string

N1C(=C\C(=C4/c5c(cccc5)NC/4=O)\C1=O)c2c3c([nH]c2)ccc(c3)O

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/h1-9,21,24H,(H,22,26)(H,23,25)/b18-13-

InChI key

XAPNKXIRQFHCHN-AQTBWJFISA-N

General description

Violacein from Janthinobacterium lividum is used as a colorant for natural and synthetic fabrics. It functions as a respiratory pigment and regulates tryptophan production. Violacein exhibits anti-protozoal activity.

Application

Violacein from Janthinobacterium lividum has been used:
  • for cell culture assays
  • as a standard to determine the crude violacein concentration in ethanol extracts of D. violaceinigra str. NI28 cultures
  • as a standard to identify violacein in the leaf samples of Nicotiana

Biochem/physiol Actions

Violacein is a member of a novel class of cytotoxic drugs, which mediate apoptosis. Violacein exhibits antitumoral, antibacterial, antiulcerogenic, antileishmanial, and antiviral activities.
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.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificates of Analysis (COA)

Lot/Batch Number
069M4159V
14181109
12080904
038M4067V
027M4083V

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Yee Meng Chong et al.
Journal of natural products, 74(10), 2261-2264 (2011-09-14)
A methanol-soluble extract of the bark of Myristica cinnamomea was found to exhibit anti-quorum sensing activity, and subsequent bioassay-guided isolation led to the identification of the active compound malabaricone C (1). Compound 1 inhibited violacein production by Chromobacterium violaceum CV026
Adnan Ahmetagic et al.
Plasmid, 66(3), 152-158 (2011-08-16)
Bacterial plasmids and phages encode the synthesis of toxic molecules that inhibit protozoan predation. One such toxic molecule is violacein, a purple pigmented, anti-tumour antibiotic produced by the Gram-negative soil bacterium Chromobacterium violaceum. In the current experiments a range of
High-level production of violacein by the newly isolated Duganella violaceinigra str. NI28 and its impact on Staphylococcus aureus
Choi SY, et al.
Scientific reports, 5, 15598-15598 (2015)
Wan Azlina Ahmad et al.
Applied biochemistry and biotechnology, 167(5), 1220-1234 (2012-01-27)
The present work highlighted the production of violacein by the locally isolated Chromobacterium violaceum (GenBank accession no. HM132057) in various agricultural waste materials (sugarcane bagasse, solid pineapple waste, molasses, brown sugar), as an alternative to the conventional rich medium. The
Sybiya Vasantha Packiavathy Issac Abraham et al.
Archives of medical research, 42(8), 658-668 (2012-01-10)
Emergence of antibiotic resistance among bacterial pathogens often leads to the failure of existing antibiotics to treat bacterial infections; thus, there is a need to seek alternative treatment measures. The aim of this study was to evaluate the anti-quorum sensing
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