Isolation of decomposition products of tylosin using liquid chromatography

Paesen, J; Cypers, W; Busson, Roger; Roets, Eugène; Hoogmartens, Jos

doi:10.1016/0021-9673(94)01269-k

Cited by 34 publications

(19 citation statements)

References 7 publications

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“…Both are likely degradation products of TA-aldol and can be expected to elute before TA-aldol [14,[32][33][34]. For TA extraction from Toronto soil, a chromatographic peak at a later retention time was noted and confirmed through LC/MS to have a mass 46 units higher than that of TA.…”

Section: Sorption Isothermsmentioning

confidence: 92%

“…Tylosin A-aldol was synthesized from tylosin tartrate using a modification of a previously published method [14]. Tylosin tartrate (0.6 g) was dissolved in 5 ml of 50:50 (v:v) water/ ethanol and pH adjusted to 10 with aqueous sodium hydroxide.…”

Section: Preparation Of Tylosin Degradatesmentioning

confidence: 99%

“…1) of the various components of tylosin are characterized by a substituted, 16-membered lactone ring with an amino sugar (mycaminose) attached to the lactone ring at position 5 via a ␤-glycosidic linkage. Above pH 9, loss of the sugars can occur as well as condensation at the R 1 aldehyde group of TA, TB, and TC, forming the corresponding aldols [14]. The remaining related substances contain either one or neither of these two sugars.…”

Section: Introductionmentioning

confidence: 99%

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Sorption of tylosin A, D, and A-aldol and degradation of tylosin a in soils

Sassman

Sarmah

Lee

2007

Environmental Toxicology and Chemistry

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Heightened concerns regarding the potential impact on soil and water quality of veterinary antibiotics warrant a better understanding of the environmental fate of antibiotics in soil. Sorption of the macrolides tylosin A (TA), tylosin D, and TA-aldol was measured in several soils and evaluated with respect to soil pH, organic matter content, percentage clay, and cation-exchange capacity (CEC). Tylosin and related compounds exhibit similar sorption characteristics and generally are strongly sorbed, with sorption being well and positively correlated to surface area, clay content, and CEC. Sorption coefficients normalized by CEC were within a narrow range (10(4.1+/-0.21 L/molc) for all but one soil; however, good extraction recoveries with only methanol for most soils suggested that hydrophobic processes also contribute to sorption. Aerobic degradation of TA over a three-month period in two freshly collected agricultural soils and 60Co-irradiated soils indicated that both abiotic and microbial processes contribute to TA transformation. The abiotic process was much slower and dominated in the first two weeks, followed by rapid microbial degradation within 3 d. Three primary degradation products were identified using liquid chromatography with full-scan mass spectrometry, with unconfirmed identifications of TA having the aldehyde group oxidized to an acid (m/z = 932) in both soils and tyslosin B (m/z = 772) as well as tylosin B having the aldehyde group oxidized to an acid (m/z = 788) in the sandy soil.

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Section: Sorption Isothermsmentioning

confidence: 92%

Section: Preparation Of Tylosin Degradatesmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Sorption of tylosin A, D, and A-aldol and degradation of tylosin a in soils

Sassman

Sarmah

Lee

2007

Environmental Toxicology and Chemistry

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“…Hu and Coats (11) observed two different isomers as products during tylosin loss associated with light exposure in environmental microcosms. One isomer appeared quickly and they proposed it to be the γ/δ-cis-tylosin isomer identified by Paesen et al (10) and characterized in this study. Appearance of a second, unidentified isomer, occurred after a significant time delay (11).…”

Section: Discussionmentioning

confidence: 85%

“…Although Hu and Coats (11) noted that the experimental conditions filtered out a majority of the UVA and UVB wavelengths which tylosin absorbs, they observed two photoisomerization products at low concentrations. One of these products they suggested to be an photoisomer previously observed by Paesen et al (10), which was proposed to result from rotation about the distal alkene on the ketodiene functionality. Tylosin is known to be unstable upon exposure to sunlight.…”

Section: Introductionmentioning

confidence: 93%

Environmental Photochemistry of Tylosin: Efficient, Reversible Photoisomerization to a Less-Active Isomer, Followed by Photolysis

Werner

Chintapalli

Lundeen

et al. 2007

J. Agric. Food Chem.

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The environmental photochemical kinetics of tylosin, a common veterinary macrolide antibiotic and growth promoter, were investigated under simulated sunlight. An efficient, reversible photoisomerization was characterized using kinetic, mass spectrometry, and proton nuclear magnetic resonance data. The photoisomerization was confirmed to occur by a rotation about the distal alkene of the ketodiene functionality. Concurrent forward (quantum yield = 0.39 +/- 0.09) and back (quantum yield = 0.32 +/- 0.08) reactions lead to a photochemical equilibrium near a tylosin/photoisomer ratio of 50:50, completed in less than 2 min under a spectrum equivalent to noontime, summer sunlight. The activity of the isomer for the inhibition of Escherichia coli DH5alpha growth was observed to be less than that of tylosin. On a longer time scale than that of isomerization, the isomer mixture undergoes photolysis with a quantum yield of (1.4 +/- 0.3) x 10(-3). The observed quantum yields and UV-vis absorbance data allow for the prediction of the photochemical behavior of tylosin in most environmental systems. Indirect photosensitization was not a significant loss process in solutions of Suwannee River fulvic acid with concentrations from 1 to 20 mg L(-1).

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Antibiotics, Pharmaceutical Analysis of

Gilpin

Pachla³

2000

Encyclopedia of Analytical Chemistry

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An antibiotic is a chemical substance, produced by microorganisms (or recently, synthetic routes) which has the capacity to inhibit the growth of other microorganisms/bacterial agents. The terminology for antibiotics stems from the Latin term of antibiosis and the noun antibiotic was coined by Professor Waksman in 1942. Considered as a single therapeutic class, antibiotics are one of the most diverse groups of medicinal agents. They can be grouped into several subclasses depending on their source, structure and activity. These are the cephalosporins, penicillins, quinolones, streptomyces and tetracycline. In addition to these agents, the sulfonamides and other miscellaneous compounds are also included owing to their antibacterial activity.

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Isolation of decomposition products of tylosin using liquid chromatography

Cited by 34 publications

References 7 publications

Sorption of tylosin A, D, and A-aldol and degradation of tylosin a in soils

Sorption of tylosin A, D, and A-aldol and degradation of tylosin a in soils

Environmental Photochemistry of Tylosin: Efficient, Reversible Photoisomerization to a Less-Active Isomer, Followed by Photolysis

Antibiotics, Pharmaceutical Analysis of

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