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E234 (NISIN)

CAS No.: 1414-45-5

Molecular Formula: C143H230N42O37S7
Molar mass: 3,354.07 g/mol
Boiling point: 2,966 °C (5,371 °F; 3,239 K)
Density: 1.402 g/mL
IUPAC Name: (2S)-6-amino-2-[2-[[(2S)-2-[[(2S)-2-[[(2S,3S)-2-[[(2S)-2-[[(1R,4S,7R,11R,14S,17R)-7-[[(2S)-6-amino-2-[[(2S)-2-[[(2S)-4-amino-2-[[(3R,9S,12S,15S,21S)-21-[[(2R)-6-amino-2-[[(3R,7R,13S)-3-[[(3R,6S,12S,15R)-15-[[(E)-2-[[(2S,3S)-2-amino-3-methylpentanoyl]amino]but-2-enoyl]amino]-12-[(2S)-butan-2-yl]-9-methylidene-6-(2-methylpropyl)-5,8,11,14-tetraoxo-1-thia-4,7,10,13-tetrazacyclohexadecane-3-carbonyl]amino]-4-methyl-2,9,12-trioxo-5-thia-1,8,11-triazabicyclo[11.3.0]hexadecane-7-carbonyl]amino]hexanoyl]amino]-15,22-dimethyl-12-(2-methylpropyl)-9-(2-methylsulfanylethyl)-5,8,11,14,17,20-hexaoxo-1-thia-4,7,10,13,16,19-hexazacyclodocosane-3-carbonyl]amino]-4-oxobutanoyl]amino]-4-methylsulfanylbutanoyl]amino]hexanoyl]amino]-14-(1H-imidazol-5-ylmethyl)-4,8,20-trimethyl-3,6,12,15,21-pentaoxo-9,19-dithia-2,5,13,16,22-pentazabicyclo[9.9.2]docosane-17-carbonyl]amino]-3-hydroxypropanoyl]amino]-3-methylpentanoyl]amino]-3-(1H-imidazol-5-yl)propanoyl]amino]-3-methylbutanoyl]amino]prop-2-enoylamino]hexanoic acid

E234 (NISIN) is a polycyclic antibacterial peptide produced by the bacterium Lactococcus lactis that is used as a food preservative.
E234 (NISIN) has 34 amino acid residues, including the uncommon amino acids lanthionine (Lan), methyllanthionine (MeLan), didehydroalanine (Dha), and didehydroaminobutyric acid (Dhb).
These unusual amino acids are introduced by posttranslational modification of the precursor peptide.
In these reactions a ribosomally synthesized 57-mer is converted to the final peptide.
The unsaturated amino acids originate from serine and threonine, and the enzyme-catalysed addition of cysteine residues to the didehydro amino acids result in the multiple (5) thioether bridges.

Subtilin and epidermin are related to nisin.
All are members of a class of molecules known as lantibiotics.

In the food industry, nisin is obtained from the culturing of L. lactis on natural substrates, such as milk or dextrose, and it is not chemically synthesized.

E234 (NISIN) was originally isolated in the late 1930s, and produced since the 1950s as Nisaplin from naturally occurring sources by Aplin and Barrett in laboratories in Beaminster in Dorset (now owned by DuPont), and approved as an additive for food use in the US in the late 1960s.

While in general most bacteriocins inhibit only closely related species, nisin is a rare example of a "broad-spectrum" bacteriocin effective against many Gram-positive organisms, including lactic acid bacteria (commonly associated to avoid food spoilage), Listeria monocytogenes (a known pathogen), Staphylococcus aureus, Bacillus cereus, Clostridium botulinum, etc.
E234 (NISIN) is also particularly effective against spores. Gram-negative bacteria are protected by their outer membrane but may become susceptible to nisin action after a heat shock or when this is coupled with the chelator EDTA.
When used in combination with EDTA, nisin has the ability to inhibit E. coli O157:H7 and Salmonella enterica.
E234 (NISIN), as a class I bacteriocin, is very stable at acidic pHs and is more heat stable at lower pHs.
The mode of action of E234 (NISIN) against pathogens such as L. monocytogenes is to dissipate the membrane potential and pH gradient.

E234 (NISIN) is soluble in water and can be effective at levels nearing the parts-per-billion range.
E234 (NISIN) concentration can be measured using various techniques such as chromatography or by a simple agar diffusion bioassay.

E234 (NISIN) is a preservative and inhibitor used in dairy and meat products.

E234 (NISIN) is a polycyclic antibacterial peptide produced by the bacterium Lactococcus lactis, which is used as a food preservative.
E234 (NISIN) belongs to a class of molecules called lantibiotics and is in the same family as subtilin, epidermis duo.
E234 (NISIN) is used to destroy thermophilic bacterial species such as B. stearothermophilus (cause of flat sour spoilage) and C. thermosaccharolyticum (cause of box swelling) that cause spoilage in food.
Therefore, the addition of nisin can prevent the growth of spores of these thermophilic spoilage organisms, facilitating long-term storage of foods at normal temperatures.

E234 (NISIN), unlike many bacteriocins, is a broad-spectrum bacteriocin with most gram-positive effects, including lactic acid bacteria.
E234 (NISIN) is also effective on sports. Gram-negative bacteria protect outer membranes but are not susceptible to light shocks etc. can be sensitized to the effects.
E234 (NISIN) is a highly preferred food preservative because it is a natural preservative that is effective on all these bacteria.

E234 (NISIN) is used in processed cheese, meat, beverage, etc. during production to extend shelf life by suppressing Gram-positive spoilage and pathogenic bacteria.
E234 (NISIN) is used in products.
The use of nisin in foods at levels ranging from ~1-25 is common.
As a food additive, nisin has an E number of E234.

Due to its naturally selective spectrum of activity, it is also used as a selective agent in the microbiological environment for the isolation of gram-negative bacteria, yeasts and molds.
E234 (NISIN) has also been used in food packaging applications and can serve as a preservative with controlled release from polymer packaging to the food surface.

In combination with miconazole, it has been studied as a possible treatment for Clostridium difficile infections.

E234 (NISIN) is a mixture of structurally related bacteriocin peptides with antimicrobial activity and some Lactococcus lactis subsp. lactis isolated from strains.
Commercial preparations consist of a concentrated mixture of nisin and sodium chloride standardized for nisin activity.

E234 (NISIN), Lactococcus lactis subsp. lactis It is a normal dietary component, as it contains many lactic acid bacteria, including fermented milk and meat products.
When consumed as part of these foods, nisins are inactivated by digestive enzymes and then hydrolyzed in the small intestine to small peptides which are then broken down into their constituent amino acids.
Like other amino acids in the diet, these will be absorbed into the bloodstream and then enter the normal metabolic pathways.
Small peptides that are not completely reduced to individual amino acids in the small intestine are expected to pass through the colon, where they will be metabolized or excreted by intestinal bacteria.
There is no known case where nisin has been identified as a trigger for an allergic reaction.

E234 (NISIN) may be effective in controlling some microorganisms, especially when used in combination with other antimicrobial technologies.
Food manufacturers using nisin or other antimicrobial technologies are responsible for ensuring that the food products they sell are microbiologically safe.

E234 (NISIN) is a bacteriocin produced by a group of Gram-positive bacteria that belongs to Lactococcus and Streptococcus species.
E234 (NISIN) is classified as a Type A (I) lantibiotic that is synthesized from mRNA and the translated peptide contains several unusual amino acids due to post-translational modifications.
Over the past few decades, nisin has been used widely as a food biopreservative.
Since then, many natural and genetically modified variants of nisin have been identified and studied for their unique antimicrobial properties.
E234 (NISIN) is an FDA approved and GRAS (generally regarded as safe) peptide with recognized potential for clinical use. Over the past two decades the application of nisin has been extended to biomedical fields.
Studies have reported that nisin can prevent the growth of drug-resistant bacterial strains, such as methicillin resistant Staphylococcus aureus, Streptococcus pneumoniae, Enterococci and Clostridium difficile.
E234 (NISIN) has now been shown to have antimicrobial activity against both Gram-positive and Gram-negative disease-associated pathogens.
E234 (NISIN) has been reported to have anti-biofilm properties and can work synergistically in combination with conventional therapeutic drugs.
In addition, like host defense peptides, nisin may activate the adaptive immune response and have an immunomodulatory role.
Increasing evidence indicates that nisin can influence the growth of tumors and exhibit selective cytotoxicity towards cancer cells.
Collectively, the application of nisin has advanced beyond its role as a food biopreservative.

E234 (NISIN) has a potential role in the production of alcoholic beverages.
E234 (NISIN) has been demonstrated that nisin is effective in controlling spoilage by lactic acid bacteria, such as Lactobacillus, Pediococcus, Leuconostoc, and Oenococcus at a level of 0.25–2.5 mg l−1 in both beer and wine.
Yeasts are completely unaffected by nisin, which allows its addition during the fermentation.
Identified applications of nisin in the brewing and wine industry include: its addition to fermenters to prevent or control contamination, increasing the shelf life of unpasteurized beers, reducing pasteurization regimes, and washing pitching yeast to eliminate contaminating bacteria (as an alternative method to acid washing, which affects yeast viability).
Formerly, nisin could not be used during wine fermentations that depend on malolactic acid fermentation.
However, this problem has been overcome by developing nisin-resistant strains of Oenococcus oenos, which can grow and maintain malolactic fermentation in the presence of nisin.
In the production of fruit brandies, the addition of nisin reduces the growth of competitive lactic acid bacteria and directly favors the growth of the fermenting yeast, to increase alcohol content by at least 10%.

E234 (NISIN) is used in pasteurized, processed cheese products to prevent outgrowth of spores such as those of Clostridium tyrobutyricum that may survive heat treatments as high as 85–105°C.
Use of nisin allows these products to be formulated with high moisture levels and low NaCl and phosphate contents, and also allows them to be stored outside chill cabinets without risk of spoilage.
The level of nisin used depends on food composition, likely spore load, required shelf life and temperatures likely to be encountered during storage.

E234 (NISIN) is also used to extend the shelf life of dairy desserts which cannot be fully sterilized without damaging appearance, taste or texture.
E234 (NISIN) can significantly increase the limited shelf life of such pasteurized products.

E234 (NISIN) is added to milk in the Middle East where shelf-life problems occur owing to the warm climate, the necessity to transport milk over long distances and poor refrigeration facilities.
E234 (NISIN) can double the shelf life at chilled, ambient and elevated temperatures and prevent outgrowth of thermophilic heat-resistant spores that can survive pasteurization.
E234 (NISIN) can also be used in canned evaporated milk.

E234 (NISIN) is a polypeptide (molecular weight 3500) that usually exists as a dimer.
E234 (NISIN) is produced by Lactococcus lactis and may be formed naturally in cheese. The polypeptide chain contains l-amino acids and the unusual sulfur-amino acids lanthionine and β-methyl-lanthionine.
A specific enzyme, nisinase, has been widely reported, and its formation is possibly one reason why many lactic acid bacteria inactivate nisin.
The peptide is also susceptible to α-chymotrypsin but not to pepsin, trypsin, and carboxypeptidase A, among other proteolytic enzymes.

E234 (NISIN) binds to cell wall precursor lipid components of bacteria and disrupts cell wall production.
E234 (NISIN) alters the cell membrane which results in the leakage of cytoplasmic components and destruction of the proton motive force.
E234 (NISIN) is an antibiotic with bactericidal action.
E234 (NISIN) binds to the lipid A portion of bacterial lipopolysaccharides and induces pore formation in the membranes of cortex cells from excised sorghum roots.

Mode of Action: Binds to and interferes with the permeability of the cytoplasmic membrane.
Antimicrobial spectrum: Gram-negative and Gram-positive bacteria (requires chelator such as EDTA).

E234 (NISIN) is a polycylic antibacterial peptide, with 34 amino acid residues used as a food preservative.
E234 (NISIN) is produced by fermentation using the bacterium Lactococcus lactis.

While in general most bacteriocins inhibit only closely related species, nisin is a rare example of a "broad-spectrum" bacteriocin effective against many Gram-positive organisms, including lactic acid bacteria (commonly associated with spoilage), Listeria monocytogenes (a known pathogen), Staphylococcus aureus, Bacillus cereus, Clostridium botulinum, etc.
E234 (NISIN) is also particularly effective against spores.
Gram-negative bacteria are protected by their outer membrane but may become susceptible to nisin action after a heat shock or when this is coupled with the chelator EDTA.
E234 (NISIN) is soluble in water and can be effective at levels nearing the parts-per-billion range.

In the food industry, it is obtained from the culturing of L. lactis on natural substrates, such as milk or dextrose, and is not chemically synthesized.
E234 (NISIN) is studied as a novel antibiotic due to its antimicrobial activity and as a therapeutic against neck and head squamous cell carcinoma.

Applications

Food production
E234 (NISIN) is used in processed cheese, meats, beverages, etc. during production to extend shelf life by suppressing Gram-positive spoilage and pathogenic bacteria.
In foods, E234 (NISIN) is common to use nisin at levels ranging from ~1-25 ppm, depending on the food type and regulatory approval.
As a food additive, nisin has an E number of E234.

Other
Due to its naturally selective spectrum of activity, it is also employed as a selective agent in microbiological media for the isolation of gram-negative bacteria, yeast, and moulds.

E234 (NISIN) has also been used in food packaging applications and can serve as a preservative by controlled release onto the food surface from the polymer packaging.

In combination with miconazole it has been studied as a possible treatment for infections of Clostridium difficile.

E234 (NISIN) can be used in a wide range of heat-processed foods

These include: fresh milk, processed cheese and other dairy products, pasteurized liquid eggs, processed meat, seafood, canned food, fruit drinks, plant protein drinks, baked products, instant food, beer, and wine

E234 (NISIN) can also be used as a preservative in gelatin processing, cosmetics, drugs and health products.

E234 (NISIN) is a polycyclic lantibiotic produced by Lactococcus lactis.
E234 (NISIN) is commonly used as a food preservative.
E234 (NISIN) is also used as a selective agent in cell culture for the isolation of gram-negative bacteria, yeast, and molds.
E234 (NISIN) has been used in bioassays to study posttranslational modification.
Used to form targeted pores in cell membranes that are mediated by lipid II.
Used to study the assembly and stability of nisin-lipid II pore complexes.

Expiration: two years in cool (0°C - 10°C., dry conditions, away from direct sunlight in original unopened packs.

SYNONYMS:

AKOS024418746

E234 (NISIN) from Lactococcus lactis, 2.5% (balance sodium chloride and denatured milk solids)

E234 (NISIN) from Lactococcus lactis, Vetec(TM) reagent grade, 2.5% (balance sodium chloride and denatured milk solids)