Nisin

Last updated
Nisin
Nisin.png
Nisin 1WCO.png
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.014.370 OOjs UI icon edit-ltr-progressive.svg
E number E234 (preservatives)
PubChem CID
UNII
  • InChI=1S/C143H246N42O45S7/c1-22-68(10)104(148)134(220)183-111(76(18)193)140(226)173-93(57-189)127(213)179-107(70(12)24-3)138(224)172-91(55-187)125(211)166-86(45-66(6)7)120(206)175-98(62-235)132(218)184-112(77(19)194)142(228)185-41-31-35-99(185)133(219)152-53-103(198)158-94(58-231)128(214)161-81(33-26-29-39-145)117(203)181-108(73(15)190)135(221)153-51-101(196)156-71(13)113(199)165-85(44-65(4)5)119(205)162-82(36-42-236-20)115(201)151-52-102(197)159-95(59-232)129(215)168-89(48-100(147)195)122(208)163-83(37-43-237-21)116(202)160-80(32-25-28-38-144)118(204)182-109(74(16)191)139(225)157-72(14)114(200)180-110(75(17)192)141(227)176-97(61-234)130(216)167-87(46-78-49-149-63-154-78)121(207)174-96(60-233)131(217)170-92(56-188)126(212)178-106(69(11)23-2)137(223)169-88(47-79-50-150-64-155-79)123(209)177-105(67(8)9)136(222)171-90(54-186)124(210)164-84(143(229)230)34-27-30-40-146/h49-50,63-77,80-99,104-112,186-194,231-235H,22-48,51-62,144-146,148H2,1-21H3,(H2,147,195)(H,149,154)(H,150,155)(H,151,201)(H,152,219)(H,153,221)(H,156,196)(H,157,225)(H,158,198)(H,159,197)(H,160,202)(H,161,214)(H,162,205)(H,163,208)(H,164,210)(H,165,199)(H,166,211)(H,167,216)(H,168,215)(H,169,223)(H,170,217)(H,171,222)(H,172,224)(H,173,226)(H,174,207)(H,175,206)(H,176,227)(H,177,209)(H,178,212)(H,179,213)(H,180,200)(H,181,203)(H,182,204)(H,183,220)(H,184,218)(H,229,230) Yes check.svgY
    Key: WAMGWAJCUSJZNI-UHFFFAOYSA-N Yes check.svgY
  • InChI=1/C143H246N42O45S7/c1-22-68(10)104(148)134(220)183-111(76(18)193)140(226)173-93(57-189)127(213)179-107(70(12)24-3)138(224)172-91(55-187)125(211)166-86(45-66(6)7)120(206)175-98(62-235)132(218)184-112(77(19)194)142(228)185-41-31-35-99(185)133(219)152-53-103(198)158-94(58-231)128(214)161-81(33-26-29-39-145)117(203)181-108(73(15)190)135(221)153-51-101(196)156-71(13)113(199)165-85(44-65(4)5)119(205)162-82(36-42-236-20)115(201)151-52-102(197)159-95(59-232)129(215)168-89(48-100(147)195)122(208)163-83(37-43-237-21)116(202)160-80(32-25-28-38-144)118(204)182-109(74(16)191)139(225)157-72(14)114(200)180-110(75(17)192)141(227)176-97(61-234)130(216)167-87(46-78-49-149-63-154-78)121(207)174-96(60-233)131(217)170-92(56-188)126(212)178-106(69(11)23-2)137(223)169-88(47-79-50-150-64-155-79)123(209)177-105(67(8)9)136(222)171-90(54-186)124(210)164-84(143(229)230)34-27-30-40-146/h49-50,63-77,80-99,104-112,186-194,231-235H,22-48,51-62,144-146,148H2,1-21H3,(H2,147,195)(H,149,154)(H,150,155)(H,151,201)(H,152,219)(H,153,221)(H,156,196)(H,157,225)(H,158,198)(H,159,197)(H,160,202)(H,161,214)(H,162,205)(H,163,208)(H,164,210)(H,165,199)(H,166,211)(H,167,216)(H,168,215)(H,169,223)(H,170,217)(H,171,222)(H,172,224)(H,173,226)(H,174,207)(H,175,206)(H,176,227)(H,177,209)(H,178,212)(H,179,213)(H,180,200)(H,181,203)(H,182,204)(H,183,220)(H,184,218)(H,229,230)
    Key: WAMGWAJCUSJZNI-UHFFFAOYAB
  • C[C@H](CC)[C@@H](N)C(N/C(C(N[C@@H]1C(N[C@@H](C(NC(C(N[C@@H](C(N[C@@H](C(N[C@H](C(N2[C@@H](C(NC3)=O)CCC2)=O)[C@@H](C)SC[C@H](C(N[C@H](CCCCN)C(N[C@H](C(NCC(N[C@@H](C(N[C@H](CC(C)C)C(N[C@H](CCSC)C(NCC(N[C@@H](C(N[C@H](CC(N)=O)C(N[C@H](CCSC)C(N[C@H](CCCCN)C(N[C@@H]([C@@H](C)SC[C@@H](N6)C(N[C@H](CC5=CN=CN5)C(N[C@@H](C(N[C@H](CO)C(N[C@H]([C@@H](CC)C)C(N[C@H](CC8=CN=CN8)C(N[C@H]([C@@H](C)C)C(NC(C(N[C@H](CCCCN)C(O)=O)=O)=C)=O)=O)=O)=O)=O)CS[C@H](C)[C@H]7C6=O)=O)=O)C(N[C@H](C)C(N7)=O)=O)=O)=O)=O)=O)CS4)=O)=O)=O)=O)C)=O)=O)[C@H]4C)=O)=O)NC3=O)=O)CSC1)=O)CC(C)C)=O)=C)=O)[C@H](C)CC)=O)=O)=C\C)=O
Properties
C143H230N42O37S7
Molar mass 3354.07 g/mol
Appearancepowder
Density 1.402 g/mL
Boiling point 2,966 °C (5,371 °F; 3,239 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Nisin is a polycyclic antibacterial peptide produced by the bacterium Lactococcus lactis that is used as a food preservative. It 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 [1] . 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.

Contents

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 dextrose, and it is not chemically synthesized.

It 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 International Flavors & Fragrances), and approved as an additive for food use in the US in the late 1960s. [2]

Properties

While most bacteriocins generally 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 avoiding food spoilage), Listeria monocytogenes (a known pathogen), Staphylococcus aureus , Bacillus cereus , Clostridium botulinum , etc. [3] It 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 can inhibit E. coli O157:H7 and Salmonella enterica . [3] Nisin, as a class I bacteriocin, is very stable at acidic pHs and is more heat stable at lower pHs. [3] The mode of action of Nisin against pathogens such as Listeria monocytogenes is to dissipate the membrane potential and pH gradient. [3]

Nisin is soluble in water and effective at levels nearing the parts-per-billion range. Nisin concentration can be measured using various techniques such as chromatography or by a simple agar diffusion bioassay. [4]

Applications

Food production

Nisin is used in processed cheese, meats, beverages, etc. during production to extend shelf life by suppressing Gram-positive spoilage and pathogenic bacteria.[ citation needed ] In foods, it 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 to isolate gram-negative bacteria, yeast, and moulds.

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. [5]

In combination with miconazole, it has been studied as a possible treatment for infections of Clostridioides difficile .[ citation needed ]

Further reading

Related Research Articles

<span class="mw-page-title-main">Food preservation</span> Inhibition of microbial growth in food

Food preservation includes processes that make food more resistant to microorganism growth and slow the oxidation of fats. This slows down the decomposition and rancidification process. Food preservation may also include processes that inhibit visual deterioration, such as the enzymatic browning reaction in apples after they are cut during food preparation. By preserving food, food waste can be reduced, which is an important way to decrease production costs and increase the efficiency of food systems, improve food security and nutrition and contribute towards environmental sustainability. For instance, it can reduce the environmental impact of food production.

<span class="mw-page-title-main">Bacteriocin</span> Class of bacterially produced peptide antibiotics

Bacteriocins are proteinaceous or peptidic toxins produced by bacteria to inhibit the growth of similar or closely related bacterial strain(s). They are similar to yeast and paramecium killing factors, and are structurally, functionally, and ecologically diverse. Applications of bacteriocins are being tested to assess their application as narrow-spectrum antibiotics.

<i>Listeria monocytogenes</i> Species of pathogenic bacteria that causes the infection listeriosis

Listeria monocytogenes is the species of pathogenic bacteria that causes the infection listeriosis. It is a facultative anaerobic bacterium, capable of surviving in the presence or absence of oxygen. It can grow and reproduce inside the host's cells and is one of the most virulent foodborne pathogens. Twenty to thirty percent of foodborne listeriosis infections in high-risk individuals may be fatal. In the European Union, listeriosis continues an upward trend that began in 2008, causing 2,161 confirmed cases and 210 reported deaths in 2014, 16% more than in 2013. In the EU, listeriosis mortality rates also are higher than those of other foodborne pathogens. Responsible for an estimated 1,600 illnesses and 260 deaths in the United States annually, listeriosis ranks third in total number of deaths among foodborne bacterial pathogens, with fatality rates exceeding even Salmonella spp. and Clostridium botulinum.

Lantibiotics are a class of polycyclic peptide antibiotics that contain the characteristic thioether amino acids lanthionine or methyllanthionine, as well as the unsaturated amino acids dehydroalanine, and 2-aminoisobutyric acid. They belong to ribosomally synthesized and post-translationally modified peptides.

<i>Lactobacillus acidophilus</i> Species of bacterium

Lactobacillus acidophilus is a rod-shaped, Gram-positive, homofermentative, anaerobic microbe first isolated from infant feces in the year 1900. The species is commonly found in humans, specifically the gastrointestinal tract and oral cavity as well as some speciality fermented foods such as fermented milk or yogurt, though it is not the most common species for this. The species most readily grows at low pH levels, and has an optimum growth temperature of 37 °C. Certain strains of L. acidophilus show strong probiotic effects, and are commercially used in dairy production. The genome of L. acidophilus has been sequenced.

<span class="mw-page-title-main">Lactic acid bacteria</span> Order of bacteria

Lactobacillales are an order of gram-positive, low-GC, acid-tolerant, generally nonsporulating, nonrespiring, either rod-shaped (bacilli) or spherical (cocci) bacteria that share common metabolic and physiological characteristics. These bacteria, usually found in decomposing plants and milk products, produce lactic acid as the major metabolic end product of carbohydrate fermentation, giving them the common name lactic acid bacteria (LAB).

<span class="mw-page-title-main">Food microbiology</span> Study of the microorganisms that inhibit, create, or contaminate food

Food microbiology is the study of the microorganisms that inhabit, create, or contaminate food. This includes the study of microorganisms causing food spoilage; pathogens that may cause disease ; microbes used to produce fermented foods such as cheese, yogurt, bread, beer, and wine; and microbes with other useful roles, such as producing probiotics.

<span class="mw-page-title-main">Class II bacteriocin</span>

Class II bacteriocins are a class of small peptides that inhibit the growth of various bacteria.

Sakacins are bacteriocins produced by Lactobacillus sakei. They are often clustered with the other lactic acid bacteriocins. The best known sakacins are sakacin A, G, K, P, and Q. In particular, sakacin A and P have been well characterized.

<span class="mw-page-title-main">Microbial symbiosis and immunity</span>

Long-term close-knit interactions between symbiotic microbes and their host can alter host immune system responses to other microorganisms, including pathogens, and are required to maintain proper homeostasis. The immune system is a host defense system consisting of anatomical physical barriers as well as physiological and cellular responses, which protect the host against harmful microorganisms while limiting host responses to harmless symbionts. Humans are home to 1013 to 1014 bacteria, roughly equivalent to the number of human cells, and while these bacteria can be pathogenic to their host most of them are mutually beneficial to both the host and bacteria.

<span class="mw-page-title-main">Actin assembly-inducing protein</span>

The Actin assembly-inducing protein (ActA) is a protein encoded and used by Listeria monocytogenes to propel itself through a mammalian host cell. ActA is a bacterial surface protein comprising a membrane-spanning region. In a mammalian cell, the bacterial ActA interacts with the Arp2/3 complex and actin monomers to induce actin polymerization on the bacterial surface generating an actin comet tail. The gene encoding ActA is named actA or prtB.

<i>Pediococcus acidilactici</i> Species of bacterium

Pediococcus acidilactici is a species of Gram-positive cocci that is often found in pairs or tetrads. P. acidilactici is a homofermentative bacterium that can grow in a wide range of pH, temperature, and osmotic pressure, therefore being able to colonize the digestive tract. It has emerged as a potential probiotic that has shown promising results in animal and human experiments, though some of the results are limited. They are commonly found in fermented vegetables, fermented dairy products, and meat.

<span class="mw-page-title-main">Biopreservation</span>

Biopreservation is the use of natural or controlled microbiota or antimicrobials as a way of preserving food and extending its shelf life. The biopreservation of food, especially utilizing lactic acid bacteria (LAB) that are inhibitory to food spoilage microbes, has been practiced since early ages, at first unconsciously but eventually with an increasingly robust scientific foundation. Beneficial bacteria or the fermentation products produced by these bacteria are used in biopreservation to control spoilage and render pathogens inactive in food. There are a various modes of action through which microorganisms can interfere with the growth of others such as organic acid production, resulting in a reduction of pH and the antimicrobial activity of the un-dissociated acid molecules, a wide variety of small inhibitory molecules including hydrogen peroxide, etc. It is a benign ecological approach which is gaining increasing attention.

Hurdle technology is a method of ensuring that pathogens in food products can be eliminated or controlled. This means the food products will be safe for consumption, and their shelf life will be extended. Hurdle technology usually works by combining more than one approach. These approaches can be thought of as "hurdles" the pathogen has to overcome if it is to remain active in the food. The right combination of hurdles can ensure all pathogens are eliminated or rendered harmless in the final product.

<i>Latilactobacillus sakei</i> Species of bacterium

Latilactobacillus sakei is the type species of the genus Latilactobacillus that was previously classified in the genus Lactobacillus. It is homofermentative; hexoses are metabolized via glycolysis to lactic acid as main metabolite; pentoses are fermented via the Phosphoketolase pathway to lactic and acetic acids.

Listeria virus P100 is a virus of the family Herelleviridae, genus Pecentumvirus.

Listeria ivanovii is a species of bacteria in the genus Listeria. The listeria are rod-shaped bacteria, do not produce spores, and become positively stained when subjected to Gram staining. Of the six bacteria species within the genus, L. ivanovii is one of the two pathogenic species. In 1955 Bulgaria, the first known isolation of this species was found from sheep. It behaves like L. monocytogenes, but is found almost exclusively in ruminants. The species is named in honor of Bulgarian microbiologist Ivan Ivanov. This species is facultatively anaerobic, which makes it possible for it to go through fermentation when there is oxygen depletion.

<span class="mw-page-title-main">Lipid II</span> Chemical compound

Lipid II is a precursor molecule in the synthesis of the cell wall of bacteria. It is a peptidoglycan, which is amphipathic and named for its bactoprenol hydrocarbon chain, which acts as a lipid anchor, embedding itself in the bacterial cell membrane. Lipid II must translocate across the cell membrane to deliver and incorporate its disaccharide-pentapeptide "building block" into the peptidoglycan mesh. Lipid II is the target of several antibiotics.

Proteobiotics are natural metabolites which are produced by fermentation process of specific probiotic strains. These small oligopeptides were originally discovered in and isolated from culture media used to grow probiotic bacteria and may account for some of the health benefits of probiotics.

<span class="mw-page-title-main">Ethyl lauroyl arginate</span> Chemical compound

Ethyl lauroyl arginate (LAE) is a food preservative, antimicrobial compound, and drug more commonly known as E243. It is used to treat dermatological disorders and is often provided in the form of its hydrochloride salt. LAE is an amino acid-based surfactant with broad-spectrum antimicrobial activity, high biodegradability and low toxicity. Due to these features, LAE is a preservative used in food and cosmetic formulations.

References

  1. ↑ https://pubmed.ncbi.nlm.nih.gov/2493449/
  2. ↑ ageconsearch.umn.edu/bitstream/90779/2/CP%2001%2005%20Nisin%20Report.pdf
  3. 1 2 3 4 And, H. Chen; Hoover, D. G. (2003). "Bacteriocins and their Food Applications". Comprehensive Reviews in Food Science and Food Safety. 2 (3): 82–100. doi:10.1111/j.1541-4337.2003.tb00016.x. ISSN   1541-4337. PMID   33451234.
  4. ↑ Chandrasekar, Vaishnavi (2015). "Modeling development of inhibition zones in an agar diffusion bioassay". Food Science & Nutrition. 3 (5): 394–403. doi:10.1002/fsn3.232. PMC   4576963 . PMID   26405525.
  5. ↑ Chandrasekar, Vaishnavi (2017). "Release Kinetics of Nisin from Chitosan–Alginate Complex Films". Journal of Food Science. 81 (10): E2503–E2510. doi:10.1111/1750-3841.13443. PMID   27635864.
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