Lipid peroxidation-derived cytotoxic aldehyde, 4-hydroxy-2-nonenal in smoked pork

Munasinghe, D.M.S.; Ichimaru, Ken-Ichiro; Matsui, Takanao; Sugamoto, Kazuhiro; Sakai, Tadashi

doi:10.1016/s0309-1740(02)00096-7

Cited by 28 publications

(16 citation statements)

References 15 publications

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“…On the contrary, both the HNE and MA contents increased in pork stored at À20 C 13) and in pork containing sugi wood vinegar stored at 0 C. 14) These results strongly suggested that the mechanism for HHE formation in fish meat might differ from that for HNE formation in pork. However, the reason for this difference has not previously been clarified.…”

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confidence: 89%

Effects of NaCl on 4-Hydroxy-2-hexenal Formation in Yellowtail Meat Stored at 0 °C

Munasinghe

Kawahara

Sakai

2006

Bioscience, Biotechnology, and Biochemistry

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Changes in the 4-hydroxy-2-hexenal (HHE) and malonaldehyde (MA) contents were investigated in the meat of the yellowtail Seriola quinqueradiate containing 0, 0.3, 0.6, and 0.9 M NaCl stored at 0 C for 7 days. After 7 days of storage, the HHE content was significantly lower and the MA content significantly higher in the meat containing NaCl than in the control without NaCl.Key words: yellowtail; NaCl; 4-hydroxy-2-hexenal; malonaldehydeLipid peroxidation is one of the major causes of quality deterioration in meat and meat products. 1)During the lipid peroxidation process, various secondary reactions occur and various aldehydes are consequently formed. Among these aldehydes, 4-hydroxy-2-alkenals are particularly interesting because they have been reported to elicit various powerful biological activities such as the inhibition of enzymes, chemotactic activity toward neutrophils, and the inhibition of protein synthesis. [2][3][4][5][6][7][8] Among the 4-hydroxy-2-alkenals, 4-hydroxy-2-hexenal (HHE) and 4-hydroxy-2-nonenal (HNE) are the major aldehydes that are respectively formed during the peroxidation of n-3 polyunsaturated fatty acid (PUFA) and n-6 PUFA; 4) however, the mechanism for their formation has not been fully understood. We have reported that HHE was present in some fish meat 9) and HNE in pork.10) The HHE content increased in yellowtail meat stored at À20 C 11) and also in yellowtail meat containing sugi wood vinegar stored at 0 C; 12) however, the malonaldehyde (MA) content barely increased in this meat. On the contrary, both the HNE and MA contents increased in pork stored at À20 C 13) and in pork containing sugi wood vinegar stored at 0 C. 14) These results strongly suggested that the mechanism for HHE formation in fish meat might differ from that for HNE formation in pork. However, the reason for this difference has not previously been clarified. We have observed that both the HNE and MA contents in pork containing 1% or 2% NaCl were significantly higher than those in the control sample after 7 days of storage at 0 C. 15) We investigated in this study the effects of NaCl on the formation of HHE in yellowtail meat stored at 0 C. Yellowtails were obtained from commercial market sources. The ordinary muscle was minced, mixed with an appropriate amount of NaCl, and stored at 0 C. In all experiments, 3 samples from each group were analyzed. 2,4-Dinitrophenylhydrazine (DNPH) was obtained from Wako Pure Chemicals (Tokyo, Japan). The chemical reaction between DNPH and HHE was carried out according to the procedure reported by Goldring et al. 16)The HHE-DNPH derivative was analyzed by highperformance liquid chromatography (HPLC), as reported by Sakai et al.,9) under the following conditions: column, Ultrasphere C18 (25 cm Â 4:6 mm i.d., Beckman, California, USA); mobile phase, 30 mM sodium citrate/27.7 mM acetate buffer (pH ¼ 4:75):methanol = 35:65; flow rate, 1 ml/min; column temperature, 40 C; and detection wavelength, 365 nm. 1,3-Diethyl-2-thiobarbituric acid (DETBA) was obtained from Aldrich Chemicals (Mi...

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confidence: 89%

Effects of NaCl on 4-Hydroxy-2-hexenal Formation in Yellowtail Meat Stored at 0 °C

Munasinghe

Kawahara

Sakai

2006

Bioscience, Biotechnology, and Biochemistry

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“…The results of the present study indicated a low level of 4-HNE production in mackerel, in agreement with previously published data, 41 owing to the lower content of ω-6 PUFAs in fish than in other meats. 18,41,42 Nevertheless, a low concentration of 4-HNE can still contribute to many diseases, including cardiovascular disease. Moreover, other aldehydes such as malonaldehyde, glutaraldehyde and hexanal are also produced from lipid peroxidation in stored frozen mackerel.…”

Section: Mechanism and Significance Of 4-hne Formation In Stored Mackmentioning

confidence: 99%

Formation of 4‐hydroxynonenal (4‐HNE) in frozen mackerel (Scomber scombrus) in the presence and absence of green tea

Alghazeer

Howell

2008

J Sci Food Agric

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BACKGROUND: Aldehydes are secondary lipid oxidation products formed during processing and storage of food. 4-Hydroxynonenal (4-HNE) is a major toxic lipid peroxidation product which has been extensively investigated in the clinical field but less so in food products. The aim of the present study was to investigate the formation of aldehydes in stored frozen fish (Atlantic mackerel, Scomber scombrus) with and without antioxidant (green tea).

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“…The compounds are highly reactive toward nucleophiles to form Schiff base adducts or Michael addition adducts and they modify structurally and irreversibly one or more functionally important sites on the nucleophiles through adducts formation, by which 4-hydroxy-2-alkenals have induced various biological effects depending on their concentrations or tissues and pathological conditions Bruenner et al 1995;Fukuda et al 1996;Xu and Sayre 1998). Therefore, it has been of interest to determine their levels, but mostly HNE, in relevant foods (Lang et al 1985;Sakai et al , 1998Surh and Kwon 2002, 2005Zanardi et al 2002;Munasinghe et al 2003) and biological samples (Benedetti et al 1980;Esterbauer et al 1990;Zollner et al 1991).…”

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confidence: 99%

4-Hydroxy-2-alkenals in polyunsaturated fatty acids-fortified infant formulas and other commercial food products

Surh

Lee

Kwon

2007

Food Additives & Contaminants

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4-Hydroxy-2-hexenal (HHE) and 4-hydroxy-2-nonenal (HNE) were determined using selected ion-monitoring gas chromatography-mass spectrometry (GC-MS) in 56 kinds of commercially available PUFA-fortified foods including infant formulas and baby foods. HHE and HNE, each specifically coming from the oxidation of n-3 and n-6 polyunsaturated fatty acids (PUFA), were observed at <10-77 and 41-132 microg kg(-1) in the infant formulas (n = 12) and at <10-52 and 36-116 microg kg(-1) in the baby foods (n = 7), respectively. 4-Hydroxy-2-alkenals in infant formulas and baby foods were further determined at 10 and 30 days after opening in an attempt to examine the time dependence of the levels of 4-hydroxy-2-alkenals. The values of HHE and HNE had increased appreciably to <10-220 and 79-792 microg kg(-1) in infant formulas and to <10-112 and 135-572 microg kg(-1) in baby foods, respectively, at 10 days and decreased, although statistically not significant, in most of the tested samples after 30 days, which suggested that the reactive compounds might interact with other constituents like proteins in the samples to form adducts or be decomposed with time. Based on the current study, it was calculated that 3-month to 1-year-old babies maintained exclusively on these commercially available PUFA-fortified infant formulas or baby foods could be exposed to a maximum of 20.2 microg kg(-1) body weight day(-1) of 4-hydroxy-2-alkenals, which is two orders of magnitude higher than the exposure of Korean adults estimated in a previous study of the authors' (2005). The present study may trigger future studies investigating the physiological influence of 4-hydroxy-2-alkenals originating from the diet on man at an early stage of development.

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Lipid peroxidation-derived cytotoxic aldehyde, 4-hydroxy-2-nonenal in smoked pork

Cited by 28 publications

References 15 publications

Effects of NaCl on 4-Hydroxy-2-hexenal Formation in Yellowtail Meat Stored at 0 °C

Effects of NaCl on 4-Hydroxy-2-hexenal Formation in Yellowtail Meat Stored at 0 °C

Formation of 4‐hydroxynonenal (4‐HNE) in frozen mackerel (Scomber scombrus) in the presence and absence of green tea

4-Hydroxy-2-alkenals in polyunsaturated fatty acids-fortified infant formulas and other commercial food products

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