| Identification | Back Directory | [Name]
Nisin | [CAS]
1414-45-5 | [Synonyms]
NISIN
MISIN
Ambicin N
Aids032124
nsc-112903
Aids-032124
NisinC143H228N42O37S7
Nisin Lactococcus lactis
nisin from lactococcus lactis
nisin from streptococcus lactis
Streptococcus element (element)
NISINSTREPTOCOCCUS LACTIS: 2.5% NISIN, 75% DENATURED MILK SOLIDS
Nisin from Lactococcus lactis Vetec(TM) reagent grade, 2.5% (balance sodium chloride and denatured milk solids)
L-Isoleucyl-(Z)-2,3-didehydro-2-aminobutanoyl-D-cysteinyl-L-isoleucyl-2,3-didehydroalanyl-L-leucyl-L-cysteinyl-threo-3-mercapto-D-2-aminobutanoyl-L-prolylglycyl-L-cysteinyl-L-lysyl-threo-3-mercapto-D-2-aminobutanoylglycyl-L-alanyl-L-leucyl-L-methionylglycyl-L-cysteinyl-L-asparaginyl-L-methionyl-L-lysyl-threo-3-mercapto-D-2-aminobutanoyl-L-alanyl-threo-3-mercapto-D-2-aminobutanoyl-L-cysteinyl-L-histidyl-L-cysteinyl-L-seryl-L-isoleucyl-L-histidyl-L-valyl-2,3-didehydroalanyl-L-lysine cyclic (3->7),(8->11),(13->19),(23->26),(25->28)-pentakis(sulfide)
L-Isoleucyl-(Z)-2,3-didehydro-2-aminobutanoyl-D-cysteinyl-L-isoleucyl-2,3-didehydroalanyl-L-leucyl-L-cysteinyl-threo-3-mercapto-D-2-aminobutanoyl-L-prolylglycyl-L-cysteinyl-L-lysyl-threo-3-mercapto-D-2-aminobutanoylglycyl-L-alanyl-L-leucyl-L-methionylglycyl-L-cysteinyl-L-asparaginyl-L-methionyl-L-lysyl-threo-3-mercapto-D-2-aminobutanoyl-L-alanyl-threo-3-mercapto-D-2-aminobutanoyl-L-cysteinyl-L-histidyl-L-cysteinyl-L-seryl-L-isoleucyl-L-histidyl-L-valyl-2,3-didehydroalanyl-L-lysine cyclic (3->7),(8->11),(13->19),(23->26),(25->28)-pentakis(sulfide) | [EINECS(EC#)]
215-807-5 | [Molecular Formula]
C143H230N42O37S7 | [MDL Number]
MFCD00131724 | [MOL File]
1414-45-5.mol | [Molecular Weight]
3354.07 |
| Chemical Properties | Back Directory | [Appearance]
Crystals from ethanol. Derived from
Streptococcus lactis Lancefield Group N. | [Boiling point ]
2967℃ | [density ]
1.02 g/mL | [Fp ]
>110°(230°F) | [storage temp. ]
2-8°C
| [solubility ]
insoluble in H2O; insoluble in EtOH; ≥5.63 mg/mL in DMSO with gentle warming and ultrasonic | [form ]
solution | [color ]
Off-white to light brown | [Water Solubility ]
Soluble in water | [Merck ]
13,6592 | [InChIKey]
NVNLLIYOARQCIX-QSXKFZIVNA-N | [Uses]
Nisin is an antimicrobial agent derived from pure culture fermenta-
tions of certain strains of streptococcus lactis lancefield group n.
nisin preparation contains nisin, a group of related peptides with
antibiotic activity. it is used to inhibit the outgrowth of clostridium
botulinum spores and toxin formation in pasteurized cheese spreads
and pasteurized process cheese spreads; pasteurized cheese spread
with fruits, vegetables, or meats; and pasteurized process cheese
spread with fruits, vegetables, or meats. | [CAS DataBase Reference]
1414-45-5 |
| Hazard Information | Back Directory | [Chemical Properties]
Crystals from ethanol. Derived from
Streptococcus lactis Lancefield Group N. | [Definition]
ChEBI: A type-A lantibiotic containing 34 amino acid residues (including lanthionine (Lan), methyllanthionine (MeLan), didehydroalanine (Dha) and didehydroaminobutyric acid (Dhb)) and five thioether bridges. It is obtained by fermentation of the bacterium L
ctococcus lactis and shows particular activity against Clostridium botulinum. It is used in the production of various processed foods to suppress Gram-positive spoilage and pathogenic bacteria and so extend shelf life. | [Biological Activity]
nisin is an antibacterial peptide.nisin is produced by the lactic acid bacterium l. lactis using uncommon amino acids, including lanthionine, and is a member of the class of antibiotics referred to as lantibiotics. | [Biochem/physiol Actions]
Nisin (Nisaplin) is produced by Lactococcus lactis. It is an effective lantibiotic peptide bactericidal agent. Nisin is a broad spectrum antimicrobial bacteriocin which affects Gram-positive bacteria, however, it has little or no effect on Gram-negative bacteria, yeasts or fungi.It was demonstrated that nisin has capability to inhibit the growth of almost all tested Gram-positive beer-spoilage bacteria. Of 122 Gram-positive bacteria strains (predominantly Lactobacilli and Pediococci), 93% were sensitive to 100 units of nisin. In contrast, out of the 32 Gram-negative strains tested, only the genus Flavobacter proved to be affected by nisin.Nisin exerts its antimicrobial activity by binding to lipid II which is a membrane-bound advanced intermediate involved in the biosynthesis of bacterial cell wall. By doing so, nisin sequesters lipid II from its functional location. In addition, the nisin-lipid II complex leads to formation of pores in the membrane causing cell death. | [Mechanism of action]
Nisin is highly effective against Gram-positive bacteria, with its MICs being at nanomolar concentrations. There are two different mechanisms by which nisin kills bacteria: pore formation in the membrane and inhibition of cell wall biosynthesis by binding to lipid II. After nisin reaches the bacterial plasma membrane, a pyrophosphate cage which involves the first two rings of nisin and the pyrophosphate moiety of lipid II is formed via hydrogen bonds. The pyrophosphate is responsible for the low levels of resistance of bacteria to nisin, since the pyrophosphate is essential and not prone to mutation and also facilitates the transmembrane orientation of nisin. Nevertheless, it is difficult for nisin to penetrate the outer membrane barrier of Gram-negative bacteria, and thus, it cannot reach its target, lipid II, in the inner membrane. This leads to the relatively low level of activity of nisin against Gram-negative bacteria. Conversely, nisin actually tends to bind to the usually anionic surface of the outer membrane and stabilizes it via electrostatic interactions. Notably, nisin can inhibit the growth of Gram-negative bacteria more efficiently, when chelating agents (EDTA, citrate monohydrate, or trisodium orthophosphate) are used to destabilize the outer membrane. Thus, the main bottleneck for nisin to be active against Gram-negative bacteria appears to be its ability to pass the outer membrane[2].
| [Side effects]
Although Nisin E234 generally regarded as a very safe and effective supplement, there can be some minor side effects. Possible side effects: pruritus, nausea, and flushing. Other side effects include: pruritus, skin rash, and vomiting. | [in vitro]
previous study showed that the sperm motility could be completely inhibited with nisin the minimum effective concentration of nisin required to immobilize sperm in vitro within 20 s was found to be 50 μg in rat, 200 μg in rabbit and 300-400 μg in monkey and human. such inhibitory effect on sperm motility was found to be dose- and time-dependent [1]. | [in vivo]
intravaginal administration of nisin before mating during proestrus-estrous transition phase caused complete arrest of sperm motility and blockage of conception. subacute toxicity studies in rats showed that, repetitive intravaginal application of nisin at the dose of 200 microg for 14 days caused no abnormalities either in the length of estrous cycle or in the morphology of vaginal epithelial cells. moreover, no histopathological abnormalities in vaginal tissue or any change in blood and serum biochemical profiles were seen. in addition, no adverse effects were found on subsequent reproductive performance, development of pups and neonate survival [1]. | [storage]
-20°C, protect from light | [Purification Methods]
This polypeptide from S. lactis is purified by crystallisation from 80% (v/v) EtOH and by countercurrent distribution. The synthetic polypeptide antibiotic can also be purified by preparative HPLC and assayed by HPLC on a Nucleosil 3007C18 (6 x 250mm) column using a MeCN—0.01M HCl gradient (30-50%), at 2%/minute, and flow rate of 1.5mL/minute to give a retention time of 8.1 minutes; or MeCN—0.3M guanidine-HCl gradient (30-50%), at 2%/minute, and flow rate of 1.5ml/minute to give a retention time of 10.9minutes. FAB-MS gave the pseudomolecular ion m/z at 3352.7 (M + H)+. It is soluble in dilute acid and is stable even on boiling. [Berridge et al. Biochem J 52 529 1952, synthesis by Fukase et al. Tetrahedron Lett 29 795 1988.] |
| Safety Data | Back Directory | [Hazard Codes ]
Xn | [Risk Statements ]
22-36/37/38 | [Safety Statements ]
22-24/25-36-26 | [WGK Germany ]
3
| [RTECS ]
QU3340000
| [F ]
10 | [Toxicity]
mouse,LD50,intravenous,100mg/kg (100mg/kg),"CRC Handbook of Antibiotic Compounds," Vols.1- , Berdy, J., Boca Raton, FL, CRC Press, 1980Vol. 4(2), Pg. 228, 1980. |
| Questions And Answer | Back Directory | [Description]
As a ribosomally synthesized peptide, Nisin has broad-spectrum antibacterial activity that is produced by the Lactococcus lactis. In the food industry, Nisin is obtained from the cultivating of Lactococcus lactis on natural substrates, such as milk or dextrose. It serves as a natural, antibacterial, and toxicologically safe food preservative which is protect against many bacteria that are food-spoilage pathogens. As a food additive, Nisin is popularly used in food production, such as milk, meats, fast food, beverages, health care products and medicines, etc. It is effective to decrease sterilization time, lower temperature during food sterilization, improve food quality, lessen damage to nutrition, and extend shelf life by suppressing Gram-positive spoilage and pathogenic bacteria. Besides, it has been studied as a possible treatment for infections of Clostridium difficile combined with miconazole. It was originally isolated in the late 1930s and approved as an additive for food use in the USA in the late 1960s.
Nisin functions by binding to cell wall precursor lipid components of bacteria and disrupts cell wall production. Once introduced Nisin initially blends with Lipid II, a precursor molecule used to form bacterial cell wall, to create a complex. The complex penetrates the cell wall and breaks into the cytoplasmic membrane and form pores, through which the internal cytoplasmic content oozes out leading to bacterial inhibition or death. | [References]
https://en.wikipedia.org/wiki/Nisin
http://www.innovateus.net/food/natural-preservative-nisin
http://www.sigmaaldrich.com/catalog/product/sigma/n5764?lang=en®ion=US&
gclid=CPu1xf6aq9MCFcSOfgodvmcHZA
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