Studies of the degradation products of nisin, a peptide antibiotic, using capillary electrophoresis with off-line mass spectrometry

Cruz, Lou Ann; Garden, Rebecca W.; Kaiser, Herbert J.; Sweedler, Jonathan V.

doi:10.1016/0021-9673(95)01144-7

Cited by 19 publications

(12 citation statements)

References 21 publications

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“…In particular, the Dha residues are susceptible to the acid catalysed addition of a water molecule at the double bond. Actually, all degradations reported in literature involve one or both Dha residues (Barber, Elliot, Bordoli, Green, & Bycroft, 1988;Chan, Bycroft, Lian, & Roberts, 1989;Cruz, Garden, Kaiser, & Sweedler, 1996;ISO, 2009). The addition of a water molecule to Dha33 at the b-C position due to Michael addition leads to the formation of serine (nisin + H 2 O) ( Fig.…”

Section: Introductionmentioning

confidence: 96%

“…1). However, following an imine-enamine tautomerism, the water molecule can also be added at the a-C position, leading to the cleavage of the polypeptide strain between the amino acids Val32 and Dha33 (Barber et al, 1988;Chan et al, 1989;Cruz et al, 1996;Rollema, Metzger, Both, Kuipers, & Siezen, 1996). It can be expected that nisin will also degrade during the production and storage of cheese.…”

Section: Introductionmentioning

confidence: 97%

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Analysis of nisin A, nisin Z and their degradation products by LCMS/MS

Schneider

Werkmeister²,

Pischetsrieder

2011

Food Chemistry

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Section: Introductionmentioning

confidence: 96%

Section: Introductionmentioning

confidence: 97%

Analysis of nisin A, nisin Z and their degradation products by LCMS/MS

Schneider

Werkmeister²,

Pischetsrieder

2011

Food Chemistry

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“…Nisin is synthesized within the ribosomes of microorganisms; therefore, it can be produced using genetic techniques (Dodd et al 1990). It is destroyed by pancreatic enzymes and is known to be naturally degraded during storage by Michael addition to the unsaturated amino acids dehydroalanine (Dha) and dehydrobutyrine (Dhb) (Barber et al 1988;Chan et al 1989;Cruz et al 1996).…”

Section: Introductionmentioning

confidence: 99%

Improved Pretreatment Method for Determination of Nisins A and Z and Monitoring in Cheese Using Liquid Chromatrography-Tandem Mass Spectrometry

Ko¹,

Park²,

Lim³

et al. 2015

Food Anal. Methods

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The peptide nisin produced by Lactococcus lactis subsp. lactis is known to be one of the natural preservatives that are used in various foods including cheese products. This study optimized and validated a liquid chromatographytandem mass spectrometry method for determining nisin A and nisin Z in cheese. Processed and natural cheeses were used for method validation. In addition, this study investigated the content of nisin A and nisin Z in 140 cheese samples comprised of imported and domestic cheese. The nisin A and nisin Z contents of 140 cheese samples were determined. An extraction solution consisting of 0.1 M acetate buffer containing 1 M NaCl (pH 2.0) and methanol (NaCl/MeOH, 1:1v/ v) was the optimal solution for nisin extraction from cheese. The limits of quantification of nisin A and nisin Z were approximately 10.2 and 12.6 μg/kg, respectively. For processed cheese and natural cheese, the recoveries were 80.1-107.3 % for nisin A and 74.4-113.9 % for nisin Z and low coefficients of variation. In monitoring study, nisins A and Z were detected in only three soft processed cheese out of 140 samples. The proposed analysis procedure can be used as an efficient tool for determination of nisin A and nisin Z in cheese using liquid chromatography-tandem mass spectrometry (LC-MS/MS).

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“…After approval of the pending New Animal Drug Application, a nisincontaining product would allow treatment of bovine mastitis with a zero milk discard time and zero meat withdrawal period (i.e., milk and/or meat from treated cattle would not have to be discarded). One drawback that has been noted for nisin is its limited stability at pH 7 (14)(15)(16)(17)(18). Hence, more stable analogs may prove more effective.…”

mentioning

confidence: 99%

Lantibiotics from Geobacillus thermodenitrificans

Garg¹,

Tang²,

Goto³

et al. 2012

Proc. Natl. Acad. Sci. U.S.A.

128

126

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The lantibiotic nisin has been used as an effective food preservative to combat food-borne pathogens for over 40 y. Despite this successful use, nisin’s stability at pH 7 is limited. Herein, we describe a nisin analog encoded on the genome of the thermophilic bacterium Geobacillus thermodenitrificans NG80-2. This analog termed geobacillin I was obtained by heterologous expression in Escherichia coli and subsequent purification. Extensive NMR characterization demonstrated that geobacillin I contains seven thioether cross-links, two more than the five cross-links found in nisin and the most cross-links found in any lantibiotic to date. The antimicrobial spectrum of geobacillin I was generally similar to that of nisin A, with increased activity against Streptococcus dysgalactiae , one of the causative agents of bovine mastitis. Geobacillin I demonstrated increased stability compared to nisin A. In addition to geobacillin I, the genome of G. thermodenitrificans NG80-2 also contains a class II lantibiotic biosynthetic gene cluster. The corresponding compound was produced in E. coli , and has a ring topology different than that of any known lantibiotic as determined by tandem mass spectrometry. Interestingly, geobacillin II only demonstrated antimicrobial activity against Bacillus strains. Seven Geobacillus strains were screened for production of the geobacillins using whole-cell MALDI-MS and five were shown to produce geobacillin I, but none produced geobacillin II.

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Studies of the degradation products of nisin, a peptide antibiotic, using capillary electrophoresis with off-line mass spectrometry

Cited by 19 publications

References 21 publications

Analysis of nisin A, nisin Z and their degradation products by LCMS/MS

Analysis of nisin A, nisin Z and their degradation products by LCMS/MS

Improved Pretreatment Method for Determination of Nisins A and Z and Monitoring in Cheese Using Liquid Chromatrography-Tandem Mass Spectrometry

Lantibiotics from Geobacillus thermodenitrificans

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