Cepacin A
* Please be kindly noted products are not for therapeutic use. We do not sell to patients.
| Category | Antibiotics |
| Catalog number | BBF-00504 |
| CAS | 91682-95-0 |
| Molecular Weight | 270.28 |
| Molecular Formula | C16H14O4 |
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Description
It is produced by the strain of Pseudomonas cepacia SC 11783. It has anti-gram positive and negative bacterial activity.
Specification
| Synonyms | 2(3H)-Furanone, 4,5-dihydro-5-(3-hydroxy-4-oxododeca-1,6,7-trien-9,11-diynyl)-; 2(5H)-Furanone, 5-(3-(3-(1,2-heptadiene-4,6-diynyl)oxiranyl)-3-hydroxy-1-propenyl)dihydro-; 4,5-Dihydro-5-(3-hydroxy-4-oxododeca-1,6,7-trien-9,11-diynyl)-2(3H)-furanone |
| IUPAC Name | (E)-5-(3-hydroxy-4-oxododeca-1,6,7-trien-9,11-diyn-1-yl)dihydrofuran-2(3H)-one |
Properties
| Appearance | Amorphous Powder |
| Antibiotic Activity Spectrum | Gram-positive bacteria; Gram-negative bacteria |
| Boiling Point | 534.3 °C at 760 mmHg |
| Density | 1.256 g/cm3 |
| Solubility | Insoluble in Water; Soluble in Chloroform, Ethyl Acetate |
Reference Reading
1. Cepacin A and cepacin B, two new antibiotics produced by Pseudomonas cepacia
W L Parker, M L Rathnum, V Seiner, W H Trejo, P A Principe, R B Sykes J Antibiot (Tokyo). 1984 May;37(5):431-40. doi: 10.7164/antibiotics.37.431.
Two new acetylenic antibiotics, cepacins A and B, have been isolated from the fermentation broth of Pseudomonas cepacia SC 11,783 and assigned structures 1 and 2. Cepacin A has good activity against staphylococci (MIC 0.2 micrograms/ml) but weak activity against streptococci (MIC 50 micrograms/ml) and the majority of Gram-negative organisms (MIC values 6.3 approximately greater than 50 micrograms/ml). Cepacin B has excellent activity against staphylococci (MIC less than 0.05 micrograms/ml) and some Gram-negative organisms (MIC values 0.1 approximately greater than 50 micrograms/ml).
2. Genome mining identifies cepacin as a plant-protective metabolite of the biopesticidal bacterium Burkholderia ambifaria
Alex J Mullins, James A H Murray, Matthew J Bull, Matthew Jenner, Cerith Jones, Gordon Webster, Angharad E Green, Daniel R Neill, Thomas R Connor, Julian Parkhill, Gregory L Challis, Eshwar Mahenthiralingam Nat Microbiol. 2019 Jun;4(6):996-1005. doi: 10.1038/s41564-019-0383-z. Epub 2019 Mar 4.
Beneficial microorganisms are widely used in agriculture for control of plant pathogens, but a lack of efficacy and safety information has limited the exploitation of multiple promising biopesticides. We applied phylogeny-led genome mining, metabolite analyses and biological control assays to define the efficacy of Burkholderia ambifaria, a naturally beneficial bacterium with proven biocontrol properties but potential pathogenic risk. A panel of 64 B. ambifaria strains demonstrated significant antimicrobial activity against priority plant pathogens. Genome sequencing, specialized metabolite biosynthetic gene cluster mining and metabolite analysis revealed an armoury of known and unknown pathways within B. ambifaria. The biosynthetic gene cluster responsible for the production of the metabolite cepacin was identified and directly shown to mediate protection of germinating crops against Pythium damping-off disease. B. ambifaria maintained biopesticidal protection and overall fitness in the soil after deletion of its third replicon, a non-essential plasmid associated with virulence in Burkholderia cepacia complex bacteria. Removal of the third replicon reduced B. ambifaria persistence in a murine respiratory infection model. Here, we show that by using interdisciplinary phylogenomic, metabolomic and functional approaches, the mode of action of natural biological control agents related to pathogens can be systematically established to facilitate their future exploitation.
3. Genomic Assemblies of Members of Burkholderia and Related Genera as a Resource for Natural Product Discovery
Alex J Mullins, Cerith Jones, Matthew J Bull, Gordon Webster, Julian Parkhill, Thomas R Connor, James A H Murray, Gregory L Challis, Eshwar Mahenthiralingam Microbiol Resour Announc. 2020 Oct 15;9(42):e00485-20. doi: 10.1128/MRA.00485-20.
The genomes of 450 members of Burkholderiaceae, isolated from clinical and environmental sources, were sequenced and assembled as a resource for genome mining. Genomic analysis of the collection has enabled the identification of multiple metabolites and their biosynthetic gene clusters, including the antibiotics gladiolin, icosalide A, enacyloxin, and cepacin A.
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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 ╳
