Formation of γ and δ lactones in irradiated beef

Vajdi, M.; Nawar, W. W.; Merritt, Charles D.

doi:10.1007/bf02676366

Cited by 9 publications

(3 citation statements)

References 8 publications

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“…Hamilton et al (22) observed the formation of γ-palmitolactone [5-dodecyldihydro-2(3H)-furanone] when 2-DCB was stored as a hexane solution stored for several months, a result that has been confirmed in our laboratory. Vajdi et al (23) reported the formation of longchain γ and δ lactones in beef irradiated at very high doses. An oxidative process was proposed to explain the formation of lactones from fatty acids and triglycerides.…”

Section: Introductionmentioning

confidence: 99%

Metabolism by Rats of 2-Dodecylcyclobutanone, a Radiolytic Compound Present in Irradiated Beef

Gadgil

Smith

2006

J. Agric. Food Chem.

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Alkylcyclobutanones (2-ACBs) are suspected cancer promoters and clastogens, which have raised concerns about the safety of irradiated foods. Currently there are few data on the metabolism of 2-ACBs, which makes it very important to study this aspect of 2-ACBs to evaluate their safety. The objectives of this experiment were to quantify 2-dodecylcyclobutanone (2-DCB; formed from palmitic acid) in the feces and adipose tissue of rats and to check for metabolites of 2-DCB in the urine. Six female Sprague-Dawley rats were administered 2-DCB (5 mg/day) in corn oil for 5 days via gavage. Six control rats did not receive 2-DCB. Feces and urine were collected daily, whereas adipose tissue was collected upon euthanasia. Hexane extracts of feces and adipose tissue were analyzed by gas chromatography-mass spectroscopy (GC-MS). Urine with and without added beta-glucuronidase was monitored for glucuronide complexes by hexane extraction and GC-MS. The total amount of 2-DCB recovered in feces was 1.78 +/- 0.63 mg at the end of 5 days, which represents between 3 and 11% of the total 2-DCB administered. The total amount recovered in the adipose tissue was 0.08 +/- 0.01 mg, which was approximately 0.33% of the total 2-DCB administered. No metabolites were recovered in any of the urine extracts. The results show that at most 11% of the 2-DCB was recovered unchanged in the feces and adipose tissue. This indicates that either most of 2-DCB is metabolized and rapidly eliminated from the body or stored at sites other than adipose tissue.

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Section: Introductionmentioning

confidence: 99%

Metabolism by Rats of 2-Dodecylcyclobutanone, a Radiolytic Compound Present in Irradiated Beef

Gadgil

Smith

2006

J. Agric. Food Chem.

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“…These compounds are rarely detected in archaeological contexts (Buckley and Evershed 2001;Charrié-Duhaut et al 2009). A reasonable explanation for their occurrence in the present lipid extracts would be their formation from saturated fatty acids by free radical hydroxylation at carbon atom C 4 or C 5 and subsequent intramolecular esterification (Vajdi et al 1979;Nawar et al 1988). More diagnostic is the presence of a mixture of octedecenoic acid (C 18:1 ) isomers in samples BJ9 and BJ11 and a mixture of hydroxystearic acid (C 18:0 ) isomers in samples BJ9, BJ11 and BJ13 (Table 2 and Figs 2 and 3).…”

Section: Fatty Acid Degradation Productsmentioning

confidence: 79%

Molecular evidence for the mixing of Meat, Fish and Vegetables in Anglo‐Saxon coarseware from Hamwic, UK

Baeten

Jervis²,

Vos

et al. 2012

Archaeometry

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Absorbed lipid residues from 24 seventh-to ninth-century coarseware potsherds from the major Anglo-Saxon trading centre of Hamwic (Southampton, UK) were analysed by gas chromatography -mass spectrometry (GC-MS) in order to reconstruct the dietary habits of its population. The results show that the vessels were used for preparing ruminant fats and leafy vegetables. In addition, evidence was found for a minor contribution of aquatic foods. Beeswax was found once and most probably relates to a sealing function or to honey. Remarkable features were: (i) the isomeric mixture of octadecenoic acid (C 18:1 D 7,8,9,10,11,12,13,14,15,16 ) and 8-to 16-hydroxyoctadecanoic acid, and (ii) the co-occurrence of C 17:1 , C 19:1 and isoprenoid fatty acids. These features were proposed as biomarkers for ruminant and aquatic food sources, respectively. Furthermore, the carbonyl position distribution in midchain ketones was used to identify mixtures of animal-and plant-derived ketones. The paper highlights the difficulty in interpreting complex lipid signatures that show a mixture of various foods, as observed in the majority of the samples. This was linked to the preparation of stews or the recycling of vessels. The results are considered alongside ceramic usewear data and existing data relating to environmental remains recovered from the Hamwic excavations.

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“…Recently, Hartwig and others (2007) reported that γ‐palmitolactone formed when 2‐DCB standard was kept at room temperature for a few weeks. Vajdi and others (1979) detected long‐chain gamma‐ and delta‐lactones in beef irradiated at a very high dose (50 Mrad = 500 kGy). Horvatovich and others (2002) suggested that 2‐ACBs oxidize to form lactones in animal tissues.…”

Section: Introductionmentioning

confidence: 97%

In Vitro and In Vivo Metabolism of the Radiolytic Compound 2‐Dodecylcyclobutanone

Hijaz¹,

Shrestha²,

Bossman³

et al. 2010

Journal of Food Science

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Our knowledge about the metabolism of alkylcyclobutanones (2-ACBs) is limited, and the lack of literature on the metabolism of 2-ACBs causes consumers to doubt the safety of irradiated foods. The objectives of this study were to evaluate the metabolism of 2-dodecylcyclobutanone (2-DCB) and identify any possible metabolite. The 2-DCB was mixed with rat S9 (postmitochondrial supernatant fraction) and beta-nicotinamide adenine dinucleotide phosphate (NADPH) in phosphate buffer (pH 7.4) and incubated for 2 h at 37 degrees C. Then, the incubation mixture was mixed with sodium sulfate and extracted with n-hexane by using a Soxhlet apparatus. The hexane extract was concentrated under nitrogen and injected into the gas chromatography-mass spectrometry (GC-MS) machine running in selective ion monitoring mode (SIM) to measure 2-DCB concentration. The hexane extract from the in vitro and in vivo studies was also derivatized with a silylation reagent and injected into a GC-MS running in full scan mode. The average percentage of 2-DCB recovered from the test incubations was 23%, compared with 50% from the controls. The GC-MS chromatograms of the derivatized samples showed a unique peak in the in vitro test incubations and in the hexane extract of the rat feces that were given 2-DCB. This peak was later identified as 2-doecylcyclobutanol.

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Formation of γ and δ lactones in irradiated beef

Abstract: Beef ABSTRACT Formation of 7 and 6 lactones by irradiation in beef has been recently reported. This paper provides evidence for their presence and postulates a mechanism for their formation.

Cited by 9 publications

References 8 publications

Metabolism by Rats of 2-Dodecylcyclobutanone, a Radiolytic Compound Present in Irradiated Beef

Metabolism by Rats of 2-Dodecylcyclobutanone, a Radiolytic Compound Present in Irradiated Beef

Molecular evidence for the mixing of Meat, Fish and Vegetables in Anglo‐Saxon coarseware from Hamwic, UK

In Vitro and In Vivo Metabolism of the Radiolytic Compound 2‐Dodecylcyclobutanone

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