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PubMed2003

Multicomponent analysis of encapsulated marine oil supplements using high-resolution 1H and 13C NMR techniques.

Multicomponent high-resolution 1H and 13C NMR analysis has been employed for the purpose of detecting and quantifying a wide range of fatty acids (as triacylglycerols or otherwise) in encapsulated marine cod liver oil supplements. The 1H NMR technique provided quantitative data regarding the docosahexaenoic acid content of these products, which serves as a valuable index of fish oil quality, and a combination of both 1H and 13C spectroscopies permitted the analysis of many further components therein, including sn-1 monoacylglycerols, sn-1,2 and -1,3 diacylglycerol adducts, together with a range of minor components, such as trans-fatty acids, free glycerol and cholesterol, and added vitamins A and E. The identities of each of the above agents were confirmed by the application of two-dimensional 1H-1H spectroscopies. The NMR techniques employed also uniquely permitted determinations of the content of nonacylglycerol forms of highly unsaturated (or other) fatty acids in these products (i.e., ethyl esters), and therefore served as a means of distinguishing "natural" sources of cod liver oils from those subjected to chemical modification to and/or supplementation with synthetic derivatives such as ethyl docosahexaenoate or eicosopentaenoate. The analytical significance and putative health effects of the results acquired are discussed.

Cod Liver Oil↗
PubMed1990

Fatty acid content of marine oil capsules.

The use of dietary omega 3 fatty acid capsules has been associated with a decrease in plasma triglyceride levels. In addition, populations consuming diets rich in fish appear to have a decreased incidence of cardiovascular disease. Eicosapentaenoic acid (EPA, 20:5 omega 3) and docosahexaenoic acid (DHA, 22:6 omega 3) are major fatty acids in fish oils. It is believed that fish oils exert their biologic effect through these fatty acids. Many individuals are currently taking fish oil capsules to lower lipids, increase bleeding time, and possibly decrease cardiovascular risk. These capsules also have been classified as food additives with less stringent controls on content. We assessed the fatty acid, cholesterol, and vitamin A and E content of eight commercially available capsules along with cod liver oil. The content of EPA was found to range from 8.7-26.4% (wt %) with a mean of 17.3% (82.4% of labeled content), and that of DHA from 8.9-17.4% with a mean of 11.5% (90.0% of labeled content) as assessed by capillary column gas-liquid chromatography. The mean content of the polyunsaturated omega 3 fatty acids was 31.9%, and that of the omega 6 fatty acids was 1.4%. The content of saturated fatty acids was 32.0%, and that of monounsaturated fatty acids was 25.1%. Cholesterol content was low, with a range of 0.7-8.3 mg/g, the alpha-tocopherol range was 0.62-2.24 mg/g, and the range of retinyl esters was 0.4-298.4 micrograms/g. Cod liver oil had substantially more retinyl esters (2450.1 micrograms/g) than did fish oil capsules.(ABSTRACT TRUNCATED AT 250 WORDS)

Capsules↗
PubMed2005

Improved malonaldehyde assay using headspace solid-phase microextraction and its application to the measurement of the antioxidant activity of phytochemicals.

A modified malonaldehyde (MA) assay for antioxidant activity, which involves derivatization and headspace solid-phase microextraction (HS-SPME) was developed and validated. The recovery of MA as 1-methylpyrazole (product of MA and N-methylhydrazine) from a headspace of an aqueous solution containing MA, buffer, surfactant, and cod liver oil using HS-SPME with a PDMS/DVB fiber was 91.3 +/- 3.38%. MA was analyzed by a gas chromatograph with a nitrogen-phosphorus detector, and its detection limit was 0.0103 nmol/mL. The antioxidant activities of natural compounds were determined as the percentage inhibition of MA formed from cod liver oil oxidized by Fenton's reagents in the above aqueous solution. Sesamol inhibited MA formation most (86.1%), followed by eugenol (84.4%), capsaicin (80.7%), ethylvanillin (45.3%), and vanillin (31.6%) at a level of 50 microg/mL. This method did not require any organic solvents and is a simple, fast, and a highly sensitive method for MA determination.

Antioxidants↗
PubMed1986

Effects of dietary fish oil supplementation on polymorphonuclear leukocyte inflammatory potential.

Polymorphonuclear leukocytes (PMNLs) are an important contributor to inflammation and are thus a part of the pathophysiology of many human diseases. We assessed the effect of fish oil on PMNL inflammatory potential by measuring chemiluminescence and superoxide production before and after six weeks of daily cod liver oil ingestion by healthy volunteers. Phagocytosing PMNLs demonstrated a 27% decrease in chemiluminescence (P less than 0.05) and a 64% decrease in superoxide production (P less than 0.01), following the cod liver oil supplementation. Analysis of PMNL and platelet fatty acids revealed the appearance of eicosapentaenoic acid and a significant decrease in arachidonic acid in both types of cells.

Dietary Fats↗
PubMed1996

Simultaneous determination of acrolein, malonaldehyde and 4-hydroxy-2-nonenal produced from lipids oxidized with Fenton's reagent.

Ethyl linoleate, ethyl linolenate, ethyl arachidonate and cod liver oil were oxidized with Fenton's reagent. Acrolein, malonaldehyde and 4-hydroxynonenal formed were derivatized to N-methylpyrazoline, N-methylpyrazole and 5-(1'-hydroxyhexyl)-1-methyl-2-pyrazoline with N-methylhydrazine, respectively. The derivatives were simultaneously analysed by gas chromatograph equipped with a fused silica capillary column and a nitrogen-phosphorus detector. The maximum amounts of acrolein (9.7 +/- 2.11 nmol/ml) and malonaldehyde (61.18 +/- 6.51 nmol/ml) were formed from cod liver oil. The highest amount of 4-hydroxynonenal (6.83 +/- 0.53 nmol/ml) was produced from ethyl arathidonate.

Acrolein↗
PubMed2000

Determination of antioxidant properties of aroma extracts from various beans.

Aroma extracts from fresh soybeans, mung beans, kidney beans, and azuki beans were prepared using simultaneous steam distillation and solvent extraction (SDE) under mild conditions (55 degrees C and 95 mmHg). Extracts were examined for antioxidative activities in two different assays. The aroma extracts isolated from all beans inhibited the oxidation of hexanal for nearly one month at a level of 250 microL/mL. Mung bean and soybean extracts inhibited malonaldehyde (MA) formation from cod-liver oil by 86% and 88%, respectively, at the 250 microL/mL level. Azuki and kidney bean extracts inhibited MA formation from cod-liver oil by 76% and 53%, respectively, at the 250 microL/mL level. The antioxidative activities of mung bean and soybean extracts were comparable with that of the natural antioxidant, alpha-tocopherol (vitamin E).

Antioxidants↗
PubMed1997

Serum phospholipid fatty acid composition and habitual intake of marine foods registered by a semi-quantitative food frequency questionnaire.

OBJECTIVE: To examine the relation between consumption of fish and fish products registered by a comprehensive food frequency questionnaire and the composition of fatty acids in serum phospholipids. DESIGN: Cross-section study. SETTING: Cardiovascular screening centre in Trondheim, Mid-Norway. SUBJECTS: Of 256 eligible women 242 agreed to participate in the present study. Altogether 234 middle-aged women (91.4%) completed the questionnaire and gave a valid blood sample. RESULTS: Total frequency consumption of fish for dinner showed only weak association with serum phospholipid fatty acid composition. In separate analyses of lean and fatty fish, consumption of fatty fish was negatively associated with n-6 and positively associated with n-3 fatty acids in serum phospholipids, while no significant associations were found for lean fish consumption. Cod liver oil consumption was strongly related to the phospholipid fatty acid composition. The associations improved moderately when adding portion size information. Spearman's correlation coefficient between dietary intake of eicosapentaenoic acid (EPA) and serum phospholipid EPA was 0.58, and Spearman's correlation coefficient between intake of docosahexaenoic acid (DHA) and serum phospholipid DHA was 0.53. CONCLUSIONS: This study suggests that in populations with a high consumption of fish and cod liver oil, habitual intake can be reflected in serum phospholipids. However, as the fat content of fish is highly variable, separate registration of lean and fatty fish consumption is needed.

Adult↗
PubMed2006

Human metabolism of arsenolipids present in cod liver.

We report results from the first investigation of the human metabolism of arsenic-containing lipids (arsenolipids), significant arsenic constituents of some seafood products. Two male volunteers ingested canned cod liver and the arsenic metabolites in their urine were monitored by high-performance liquid chromatography inductively coupled plasma mass spectrometry over a 66-h period. Volunteer A consumed 85 g (wet mass) of cod liver containing a total of approximately 120 microg arsenic, 77% of which was present as arsenolipids, and volunteer B consumed 85 g (wet mass) of cod liver, 25% of which was present as arsenolipids, together with 20 g of cod liver oil, containing a total of about 180 microg arsenic. The structures of the arsenolipids are currently unknown, whereas the majority of the non-lipid arsenic in the cod liver was identified as arsenobetaine, which was excreted unchanged. The arsenolipids were rapidly metabolised to water-soluble compounds and excreted in the urine; peak arsenic concentrations were recorded between 7 and 15 h (volunteer A) and between 6.5 and 15 h (volunteer B), and by the end of the experiment about 90% of the ingested arsenic had been accounted for in the urine for both volunteers. The major arsenolipid metabolite was dimethylarsinate (DMA), constituting 73% (volunteer A) or 41% (volunteer B) of the total urinary arsenic, and most of the remaining arsenolipid-derived arsenic, constituting about 10% (volunteer A) and 5% (volunteer B), comprised four novel arsenic-containing fatty acids, namely oxo-dimethylarsenopropanoic acid, thio-dimethylarsenopropanoic acid, oxo-dimethylarsenobutanoic acid, and thio-dimethylarsenobutanoic acid. Unchanged arsenobetaine (15% for volunteer A and 51% for volunteer B) made up the remaining urinary arsenic together with trace quantities of other, mostly unknown, arsenicals. In a second experiment (volunteer A only), performed with pure cod liver oil, which contains only arsenolipids, DMA and the same four arsenic fatty acids were excreted in the urine. The study shows that arsenolipids in cod liver are bioavailable, and that they are quickly biotransformed to several water-soluble arsenicals, the structures of which suggest that the native arsenolipids contain a dimethylarsine oxide moiety.

Animals↗
PubMed2003

Behavioral attraction of Leach's storm-petrels (Oceanodroma leucorhoa) to dimethyl sulfide.

A recent model for olfactory foraging by procellariiform seabirds suggests that these birds use biogenic sulfur compounds to locate productive areas for foraging in the southern oceans. The present study refines a simple approach to test birds' responses to odors on land and extends our knowledge to a northern species, the Leach's storm-petrel (Oceanodroma leucorhoa). Rather than working at sea, we tested the behavioral response to dimethyl sulfide (DMS) at night in breeding colonies on Kent Island, New Brunswick, Canada. Birds were presented with either 5 ml DMS (100 micro mol l(-1) concentration) or control (water) solutions from a platform 1.5 m in height positioned in a flyway 10 m from a breeding colony. We also tested birds' responses to cod liver oil, a well-established olfactory attractant of procellariiforms foraging at sea. Leach's storm-petrels approached DMS presentations nearly twice as frequently as they approached controls. We next compared the distribution of approaches against a Poisson process to test for evidence of social cueing. We found that approaches to DMS were significantly clustered. By contrast, the distribution of approaches did not depart significantly from a Poisson distribution for either cod liver oil or control presentations. Taken together, these results suggest that Leach's storm-petrels can smell DMS and potentially use it as a foraging cue. The results are consistent with the hypothesis that the detection of biogenic sulfur compounds in combination with other cues assists birds in locating foraging hotspots.

Animals↗
PubMed2002

Lipid metabolism and FA composition in tissues of Eurasian perch Perca fluviatilis as influenced by dietary fats.

Eurasian perch, Perca fluviatilis, were fed a semipurified fat-free diet for 4 wk, followed by a 16% feeding supplementation of either olive oil (OO), safflower oil (SO), linseed oil (LO), or cod liver oil (CLO) as the only lipid source in each diet for 10 wk. Significant reductions in total lipid of tissues were observed (31.4% in viscera, 66.7% in muscle, and 74.1% in liver) after feeding the fat-free diet. The SO-, LO-, and CLO-fed fish significantly increased lipid deposition in liver and viscera compared to fish fed the OO diet; however, muscle lipid levels were not significantly affected. Large amounts of dietary 18:1 n-9 were incorporated directly into tissue lipids when fish were fed the OO diet. The LO diet significantly elevated 18:4n-3, 20:5n-3, 22:5n-3, and 22:6n-3 in the liver compared to fish fed OO or SO diets, and the n-3/n-6 ratio was 16 times that of the SO group, with significantly high desaturation and elongation products of 18:3n-3. These results suggest that delta6 and delta5 desaturases are highly active in Eurasian perch, and that the enzymes at this dietary n-3/n-6 ratio favor 18:3n-3 over 18:2n-6 as substrate. The SO diet significantly increased 18:3n-6, 20:3n-6, and 22:5n-6 in the liver and significantly decreased EPA and DHA. This indicates that desaturation enzymes were not specifically favoring n-3 over n-6 acids in perch lipid metabolism, and that these elongation and desaturation enzymes were influenced by n-3 and n-6 FA content in the diet. The present study indicates that high tissue content of DHA in the muscle of Eurasian perch was attributable to the greater ability for n-3 acid bioconversion.

Animal Feed↗
PubMed1990

Effect of dietary lipid on collagen- and adenosine diphosphate-induced platelet aggregation and thromboxane A2 synthesis in the rat.

Dietary lipids containing different proportions of long-chain polyunsaturated fatty acids can affect platelet thromboxane A(2) formation and aggregation. In the present work, the effects of dietary lipid, from animal and vegetable sources, on collagen- and adenosine diphosphate (ADP)-induced thromboxane A(2) (measured as thromboxane B(2)) production and aggregation in washed rat platelets were studied. In addition, plasma thromboxane B(2) levels in rats fed different dietary lipids were measured. Animals were fed 10% fat by weight as lard (LRD), corn oil, soy bean oil, canola oil (CAN), or cod liver oil (CLO) for a period of 7 weeks. Circulating thromboxane B(2) levels detected in platelet-poor plasma of the CLO-fed animals were significantly lower than those of rats fed all other dietary lipids. The platelets of CLO-fed animals synthesized significantly less thromboxane A(2) compared with those from other dietary groups following ex vivo stimulation of platelets with agonists such as collagen and ADP, with the exception of platelets from the LRD-fed animals. Ex vivo stimulation of platelets obtained from this group with collagen resulted in the synthesis of significantly greater levels of thromboxane A(2) compared with all other groups. However, aggregation responses to collagen and ADP were not significantly affected by dietary treatment, although relatively the lowest responses to these agonists were apparent in the CLO-fed and CAN-fed groups, respectively.

Journal Article↗
PubMed1998

Morphological and biological characterization of two mesenchymal murine tumors and the modulation of their growth parameters by n-3 and n-6 polyunsaturated fatty acids.

Certain tumor growth parameters (GP) of two mesenchymal transplantable tumors maintained on C57BL/6J mice were characterized. Considering that many experimental, clinical and epidemiologic data have indicated that n-3 and n-6 essential fatty acids are nutrients which may delay the development as well as improve the course of cancer, GPs were evaluated on hosts fed on a semisynthetic formula containing 5% of corn oil (CO) or cod liver oil (CLO) and stock diet (C group). Although survival and latency time of tumor-bearing mice were shortened, other GP as percentage of successful implants were improved by both oils in sarcoma-bearing hosts, suggesting that n-3 and n-6 fatty acids might play a modulating role for the development of these tumors.

Animals↗
PubMed2005

A gas chromatography/electron ionization-mass spectrometry-selected ion monitoring method for determining the fatty acid pattern in food after formation of fatty acid methyl esters.

A method using gas chromatography/electron ionization-mass spectrometry (GC/EI-MS) in the selected ion monitoring (SIM) mode was developed for the analysis of fatty acids as methyl esters (FAMEs) in order to determine their percentage contribution to the fatty acid profile in food. In the GC/EI-MS-SIM mode, saturated fatty acids were determined with m/z 87, monoenoic fatty acids were determined with m/z 74, and polyenoic fatty acids were determined via the sum of m/z 79 and m/z 81. The ratios of these fragment ions and the GC retention data provided additional information for tentative structural assignments. The 28 FAME standards tested provided similar results for the novel GC/EI-MS-SIM method and GC/EI-MS in the full scan mode, both of which were slightly worse than GC/flame ionization detection (FID). Analysis of sunflower oil, suet, and cod liver oil verified that both major and minor fatty acids (20-60% and down to 0.001% contribution to the fatty acid pattern) were determined with sufficient quality that justifies application of the GC/EI-MS-SIM method for the analysis of food samples. Furthermore, the method was approximately 20- or approximately 10-fold more sensitive than GC/EI-MS in the full scan mode or GC/FID, respectively. The method is suited for both quantitative purposes and fatty acid identification in samples where only low amounts of lipids are available.

Chromatography, Gas↗
PubMed1986

The oxidation of benzo[a]pyrene mediated by lipid peroxidation in irradiated synthetic diets.

The effect of gamma-irradiation (1000-4000 Gy) on the formation of lipid peroxides and on the oxidation of the environmental carcinogen benzo[a]pyrene (BP) has been studied in mixtures of starch/fat and BP which were used as models for natural foods. When mixtures containing polyunsaturated fats (mackerel oil and cod-liver oil which contain relatively large proportions of C20:5 and C22:6) were exposed to gamma-irradiation, large concentrations of lipid peroxide were formed and a concomitant oxidation of BP to mutagenic and toxic BP quinones took place. The rate of BP oxidation was closely related to the extent of peroxidation of the lipids in the starch mixtures and was dependent on the dose of gamma-irradiation and the presence of air. Mackerel oil also underwent peroxidation during the storage of both irradiated and unirradiated starch/mackerel oil/BP mixtures and this resulted in a significant oxidation of the BP present in these samples. Antioxidants such as vitamin E and BHA inhibited both lipid peroxidation and BP oxidation resulting from gamma-irradiation. These results demonstrate that the species generated during the peroxidation of unsaturated fats in foodstuffs can react with polycyclic aromatic hydrocarbons such as BP and convert them into active mutagenic and toxic products. This has important toxicological implications, particularly as the consumption of polyunsaturated fat in the Western world is increasing and gamma-irradiation may soon be widely used for food sterilization.

Benzo(a)pyrene↗
PubMed1997

Fish oil source differentially affects rat immune cell alpha-tocopherol concentration.

We have previously reported that both the source of dietary fish oil and the chemical form of vitamin E supplied in the diet affect the vitamin E status of immune cells in rats. The purpose of this study was to investigate further the effect of fish oil source on immune cell vitamin E status using free alpha-tocopherol (alpha-T) at the AIN recommended level as the sole source of vitamin E. Sixty weanling female rats were fed semipurified, high fat (20 g/100 g) diets containing either tocopherol-stripped lard (LRD), menhaden fish oil (MFO), sardine fish oil (SRD) or cod liver oil (CLO) as the primary lipid source. Endogenous alpha-T concentration was measured and equalized to 150 mg/kg oil by addition of free RRR-alpha-T to each lipid source, allowing for a final concentration of alpha-T in the mixed diet of 30 mg/kg. An additional group of rats was fed LRD without supplemental vitamin E (LRD-) as a negative control. After feeding experimental diets for 5 or 10 wk, tissues were collected for alpha-T analysis by HPLC. After 5 wk, plasma and liver alpha-T (micromol alpha-T/g lipid) were significantly lower in SRD- and CLO-fed rats compared with LRD-fed rats. At 10 wk, only plasma alpha-T in CLO-fed rats remained significantly depressed. Plasma and liver alpha-T concentrations (micromol alpha-T/g lipid) were not significantly lower in MFO-fed rats than LRD-fed rats at either time point. Compared with LRD, feeding MFO to rats for 5 or 10 wk resulted in significantly greater alpha-T content of immune cells. In similar fashion, SRD-fed rats, compared with LRD-fed rats, also had significantly greater alpha-T content in splenocytes at both time points and greater thymocyte alpha-T at 10 wk. In all instances, the alpha-T status of rats fed CLO was indistinguishable from that of rats fed the vitamin E-free diet (LRD-). These data further demonstrate the complexity of the relationship between vitamin E status and dietary (n-3) polyunsaturated fatty acids (PUFA).

Animals↗
PubMed1991

Combined effects of age and dietary fat on beta 1-receptors and Ca2+ channels in rat hearts.

Male Wistar rats were fed a standard diet or diets supplemented with 10% butter, 10% corn oil, or 10% cod liver oil from the age of 2 mo. At 7 and 24 mo of age, the fatty acid composition of total phospholipids was determined in ventricular crude sarcolemma preparations; binding capacity and affinity (1/Kd) of [3H]dihydroalprenolol and [3H]nitrendipine binding were also determined. The arachidonic acid level was significantly higher at 24 mo than at 7 mo of age in the membrane phospholipids in rats fed no extra fat, but in rats fed fat-supplemented diets, age had no effect. Affinity of Ca2+ channels for [3H]nitrendipine decreased significantly in all dietary groups between 7 and 24 mo of age, whereas the affinity of beta 1-receptors for [3H]dihydroalprenolol increased in corn oil-fed rats. Density of beta 1-receptors decreased significantly in corn oil- and butter-fed rats and rats fed no extra fat between 7 and 24 mo of age, whereas the density of Ca2+ channels decreased significantly in corn oil-fed rats. We conclude that the antagonist binding properties of Ca2+ channels and beta 1-adrenergic receptors in rat hearts may change with age depending on the dietary fat.

Aging↗
PubMed1999

Multidimensional gas chromatographic enantiomer quantification of some chlorinated xenobiotics in cod liver and fish oils.

Four chiral HRGC column systems for the separation of selected organochlor pesticides and photoconversion products (heptachlor, cis- and trans-chlordane, o,p'-DDT, o,p'-DDD, and alpha-HCH) were tested. Cod hver oil and fish oil samples from different countries were comparatively analyzed. Of all these columns, the fourth was the most suitable one for the analysis of the selected compounds. The enantiomer ratios [ER] of cis-chlordane, trans-chlordane, photodieldrin, alpha-HCH, and o,p'-DDD in fish oils are nearly 1.0, while the ERs of the same substances are significantly different from 1.0 in cod liver oils. Contrary to that, the ER values of o,p'-DDT are remarkable different from 1 in the cod liver oils as well as in the fish oils.

Animals↗
PubMed1990

Modification of rat platelet fatty acid composition by dietary lipids of animal and vegetable origin.

There were no statistically significant differences in final body weight or in food intake among groups of rats fed for 7 wk various fats of animal origin (lard fat and cod liver oil) or vegetable origin (corn, soybean and canola oils); the fats were fed as 10% of the diet (by wt) and were of varied fatty acid composition. Nevertheless, the mean weights of the kidneys from cod liver oil-fed animals were significantly higher than those of all other dietary groups. Platelets of rats from the groups receiving the animal fat contained significantly lower levels of linoleic acid, 18:2(n-6) [a precursor of arachidonic acid, 20:4(n-6)], than did platelets from rats receiving the fat of vegetable origin. Although the soybean-, canola- and cod liver oil-fed animals received substantial quantities of (n-3) fatty acids [alpha-linolenic acid, 18:3(n-3); eicosapentaenoic acid, 20:5(n-3); and docosahexaenoic acid, 22:6(n-3)], only the platelets of the latter two groups contained detectable levels of these fatty acids along with their products of elongation/desaturation/retroconversion. Platelets of the cod liver oil-fed group contained significantly less arachidonic acid, a major precursor of eicosanoids, than did those from all other dietary groups. However, platelet arachidonic levels also varied markedly among the other dietary groups. Diet-induced fatty acid changes observed in platelets of various dietary groups may influence platelet responses, including secretion, aggregation and biosynthesis of eicosanoids.

Animals↗