Compositional Study of Phospholipids from the Dried Big Head and Opossum Shrimp, Mussel, and Sea Cucumber Using 31P NMR Spectroscopy: Content and Fatty Acid Composition of Plasmalogen.

Herein, we present a qualitative and quantitative analysis of the compositions of plasmalogens and phospholipids (PLs) in dried big head shrimp (Solenocera melantho), opossum shrimp (Neomysis awatschensis), mussel (Mytilus galloprovincialis), and sea cucumber (Apostichopus japonicus). We also analyze the fatty acid composition of the extracted lipids, phosphatidyl choline (PtdCho), and plasmalogen choline (PlsCho) from each sample. In big head shrimp, opossum shrimp, and mussel, phosphatidyl choline (PtdCho) was the most abundant PL at 1677.9, 1603, and 1661.6 mg/100 g of dried sample, respectively, whereas the most abundant PL in sea cucumber was PlsCho (206.9 mg/100 g of dried sample). In all four samples, plasmalogen ethanolamine (PlsEtn) was higher than phosphatidyl ethanolamine (PtdEtn). The content (mg/100 g of dried sample) of PlsCho was highest in mussel (379.0), and it was higher in big head shrimp (262.3) and opossum shrimp (245.6) than sea cucumber (206.9). The contents (mg/100 g of dried sample) of PlsEtn were in the order of mussel (675.4) > big head shrimp (629.5) > opossum shrimp (217.9) > sea cucumber (51.5). For analyzing the fatty acids at the sn-2 position of PlsCho, the consecutive treatment with phospholipase A1, solid phase extraction, thin-layer chromatography (TLC), and GC-FID were applied. The most abundant fatty acid was eicosapentaenoic acid (EPA, C20:5, n-3) in big head shrimp and sea cucumber, palmitoleic acid (C16:1, n-7) in opossum shrimp, and docosadienoic acid (C22:2, n-6) in mussel.

Development and Physicochemical Properties of Low Saturation Alternative Fat for Whipping Cream.

We developed an alternative whipping cream fat using shea butter but with low saturation. Enriched stearic-oleic-stearic (SOS) solid fat was obtained from shea butter via solvent fractionation. Acyl migration reactant, which mainly contains asymmetric SSO triacylglycerol (TAG), was prepared through enzymatic acyl migration to obtain the creaming quality derived from the ß'-crystal form. Through enzymatic acyl migration, we obtained a 3.4-fold higher content of saturated-saturated-unsaturated (SSU) TAG than saturated-unsaturated-saturated (SUS) TAG. The acyl migration reactant was refined to obtain refined acyl migration reactant (RAMR). An alternative fat product was prepared by blending RAMR and hydrogenated palm kernel oil (HPKO) at a ratio of 4:6 (w/w). The melting points, solid fat index (SFI), and melting curves of the alternative products were similar to those of commercial whipping cream fat. The alternative fat had a content of total unsaturated fatty acids 20% higher than that of HPKO. The atherogenic index (AI) of alternative fat was 3.61, much lower than those of whipping cream fat (14.59) and HPKO (1220.3), because of its low atherogenic fatty acid content and high total unsaturated fatty acids. The polymorphic crystal form determined by X-ray diffraction spectroscopy showed that the ß'-crystal form was predominant. Therefore, the alternative fat is comparable with whipping cream that requires creaming quality, and has a reduced saturated fat content.

Presence of Cholesterol in Non-Animal Organisms: Identification and Quantification of Cholesterol in Crude Seed Oil from Perilla frutescens and Dehydrated Pyropia tenera.

Studies have reported that cholesterol, a molecule found mainly in animals, is also present in some plants and algae. This study aimed to determine whether cholesterol exists in three dehydrated algae species, namely, Pyropia tenera, Saccharina japonica, and Undaria pinnatifida, and in one plant species, namely, Perilla frutescens (four perilla seed oil samples were analyzed). These species were chosen for investigation because they are common ingredients in East Asian cuisine. Gas chromatography-flame ionization detection (GC-FID) analysis found that cholesterol was present in P. tenera (14.6 mg/100 g) and in all four perilla seed oil samples (0.3-0.5 mg/100 g). High-performance liquid chromatography with evaporative light-scattering detection (HPLC-ELSD) also demonstrated that cholesterol was present in P. tenera (14.2 mg/100 g) and allowed the separation of cholesterol from its isomer lathosterol. However, cholesterol could not be detected by HPLC-ELSD in the perilla seed oil samples, most likely because it is only present in trace amounts. Moreover, liquid chromatography-tandem mass spectrometry (LC-MS/MS) confirmed the presence of cholesterol in both P. tenera and perilla seed oil. MRM results further suggested that lathosterol (a precursor of cholesterol) was present in P. tenera.

Correlations of Fat Content in Human Milk with Fat Droplet Size and Phospholipid Species.

Fat globule size and phospholipid (PL) content in human milk (HM) were investigated. HM was classified into three groups depending on fat content (A < B < C). PL content (mg/100 g HM) was significantly higher in the C group (p < 0.05), indicating its positive relationship with HM fat content. When the PL content was normalized (mg/g fat), that of group A was significantly higher (p < 0.05) and fat droplet size in group C was slightly larger, suggesting that HM fat content is affected by fat droplet numbers to a larger extent than by fat droplet size. A correlation between PC and SM content in HM was observed regardless of fat content, while correlation between PE and either PC or SM increased in the order of C > B > A, hence the composition and content of PL species in HM varied according to its fat content.

Approach Study for Mass Balance of Pesticide Residues in Distillers' Stillage along with Distillate and Absence Verification of Pesticides in Distilled Spirits from Pilot-Scale of Distillation Column.

Herein, contaminants remaining in distillate and distillers' stillage were quantitatively measured after distillation. After rice bran powder was contaminated with 10 ppm of lead (Pb) and cadmium (Cd) or 0.02-1.27 ppm of five pesticides (terbufos, fenthion, iprobenfos, flutolanil, and ethoprophos) followed by fermentation, single-stage distillation was performed. In the obtained distillate, no Pb or Cd was found, as expected. However, when the pesticides were added as contaminants, trace-0.05 ppm of some pesticides were detected in the distillate, possibly due to the high vapor pressure (e.g., that of ethoprophos) and contamination amount (e.g., that of flutolanil, terbufos, and fenthion). In contrast, none of the contaminating pesticides were observed in the distilled spirits when a fermented liquefaction contaminated with 0.04-4 ppm of six pesticides (fenthion, terbufos, ethoprophos, iprobenfos, oxadiazon, and flutolanil) was distilled using a pilot-plant scale distillation column, indicating that the pesticides hardly migrate to the distilled spirits.

Quantitative Analysis of Nervonic and Erucic Acids in Human Milk: Comparison with Infant Formula with Different Fat Sources and Nutritional Stages.

This study aims to quantitatively analyze nervonic (C24:1 n-9) and erucic (C22:1 n-9) acids in human milk (HM) collected from Korean mothers, along with the infant formulas (IFs) with different fat sources and nutritional stages. The content of nervonic and erucic acids in HM from Korean mothers were 2.13 and 2.81 mg/100 g, accounting for 0.06 and 0.08% of the total fatty acids (FAs), respectively. These acids in IFs based on fat from plant-oil formula were higher than those in IFs based on cow milk formula. The composition of erucic acid in IFs based on cow milk formula and plant-oil formula increased with the nutritional stages, while nervonic acid only increased in IFs based on the plant-oil formula.

Comparison of the Fatty Acid Composition in Phospholipid Species from Korean Human Milk.

In this study, the phospholipid species [i.e., phosphatidylethanolamine (PE), phosphatidylcholine (PC), and sphingomyelin (SM)] in human milk (HM) were compared according to their fatty acid (FA) composition. 34 HM samples were collected and classified into three groups (A < B < C) according to their fat content. Stearic acid (C18:0) was the main FA in PE, PC, and SM. The highest concentrations of arachidonic acid (AA), eicosapentaenoic acid (EPA), and docosapentaenoic acid (DPA) were observed in PE, whereas docosahexaenoic acid (DHA) was predominant in SM. Although PC exhibited the highest total saturated FAs (SFAs) and PE contained the highest unsaturated FAs (UFAs), very long-chain SFAs and monounsaturated FAs (MUFAs) were preferentially distributed in SM. PC and SM had higher saturation compared to PE. Regarding the effect of the fat content of HM on the FA composition of the phospholipid species, a limited influence was observed on the composition of SFAs and MUFAs of PE, SM, and particularly PC. However, a more pronounced effect on the composition of polyunsaturated FAs (PUFAs) in phospholipids was observed, especially for linoleic acid (LA), α-linolenic acid (ALA), EPA, and DHA, indicating that the composition of FAs in the phospholipid species was probably affected by the maternal diet.

Migration Degree of Selected Mycotoxins in the Distillation Process and Their Determination in Distilled Spirits from Pilot-Scale Continuous Distillation.

Mycotoxins (ochratoxin A (20 ppb), aflatoxin B1 (40 ppb), deoxynivalenol (4 ppm), and zearalenone (800 ppb)) were intentionally added to rice bran raw materials. After fermentation, their contents were determined in the distillate and distillery stillage obtained using single-stage and continuous pilot plant-scale columns. After single-stage distillation, aflatoxin B1, deoxynivalenol, and zearalenone were not detected in the distillate, indicating that even if a certain amount (four times the maximum residue limit (MRL)) was present in the raw material, it would not remain in the distillate after fermentation and distillation. Most mycotoxins remained in the distillery stillage, and their residual rates ranged from 54.0-96.2%. For ochratoxin A, 0.19 ppb was found in the distillate and this migration occurred in three consecutive distillations (0.11-0.22 ppb). Ochratoxin A and aflatoxin B1 were not detected in the distillate (alcohol content 93.9% and 95.4%, respectively) obtained from the contaminated fermented liquid (approximately three times the MRL based on the raw material) using the pilot-plant scale continuous distillation column. Therefore, the migration of mycotoxins is difficult when the distilled spirit is produced using a continuous distillation column, even if the raw material is contaminated with certain amounts of the investigated mycotoxins.

Oxidation stability of oil-in-water emulsion prepared from perilla seed oil and soy sauce with high salt concentration using OSA-starch.

The O/W emulsions were prepared using perilla seed oil (PSO) dispersed in soy sauce (PSE) and in distilled water (PWE), respectively. Octenyl succinic anhydride-modified starch (OSA starch, 3 wt%) showed the most efficient emulsifying ability and its stabilities of emulsion and oxidation in PSE and PWE were studied at different storage periods (0, 4, and 8 weeks) and temperatures (4, 25, and 40 °C). Negligible change in droplet diameter of PSE was observed without coalescence or flocculation during storing for 8 weeks at 4 °C. The stabilizing ability of OSA-starch despite the high ionic strength of soy sauce is attributed to the starch backbone, which promotes steric repulsions between droplets. A lower oxidation degree was observed for PSE prepared than PWE and PSO under all storage conditions. Thus, the O/W emulsion prepared from PSO and soy sauce can be applied to the production of ω-3 fatty acid-enriched Asian-style emulsified products.

A genome-wide association study for the fatty acid composition of breast meat in an F2 crossbred chicken population.

The composition of fatty acids determines the flavor and quality of meat. Flavor compounds are generated during the cooking process by the decomposition of volatile fatty acids via lipid oxidation. A number of research on candidate genes related to fatty acid content in livestock species have been published. The majority of these studies focused on pigs and cattle; the association between fatty acid composition and meat quality in chickens has rarely been reported. Therefore, this study investigated candidate genes associated with fatty acid composition in chickens. A genome-wide association study (GWAS) was performed on 767 individuals from an F2 crossbred population of Yeonsan Ogye and White Leghorn chickens. The Illumina chicken 60K significant single-nucleotide polymorphism (SNP) genotype data and 30 fatty acids (%) in the breast meat of animals slaughtered at 10 weeks of age were analyzed. SNPs were shown to be significant in 15 traits: C10:0, C14:0, C18:0, C18:1n-7, C18:1n-9, C18:2n-6, C20:0, C20:2, C20:3n-6, C20:4n-6, C20:5n-3, C24:0, C24:1n-9, monounsaturated fatty acids (MUFA) and polyunsaturated fatty acids (PUFA). These SNPs were mostly located on chromosome 10 and around the following genes: ACSS3, BTG1, MCEE, PPARGC1A, ACSL4, ELOVL4, CYB5R4, ME1, and TRPM1. Both oleic acid and arachidonic acid contained the candidate genes: MCEE and TRPM1. These two fatty acids are antagonistic to each other and have been identified as traits that contribute to the production of volatile fatty acids. The results of this study improve our understanding of the genetic mechanisms through which fatty acids in chicken affect the meat flavor.

Cloning, sequencing, and characterization of lipase genes from a polyhydroxyalkanoate (PHA)-synthesizing Pseudomonas resinovorans.

Lipase (lip) and lipase-specific foldase (lif) genes of a biodegradable polyhydroxyalkanoate (PHA)-synthesizing Pseudomonas resinovorans NRRL B-2649 were cloned using primers based on consensus sequences, followed by polymerase chain reaction-based genome walking. Sequence analyses showed a putative Lip gene product (314 amino acids, a.a.) with its catalytic active site (Ser(111), Asp(258), and His(280)) identified. The foldase lif gene that is located 55 bp downstream of lip codes for a putative Lif (345 a.a.). To verify the biological function of the cloned lip gene for lipase expression in P. resinovorans, we constructed a lip knock-out mutant (lip::Tn5) by transposon insertion. Complementation of the lip knock-out P. resinovorans mutant with a lipase expression plasmid (pBS29-P2-lip) was performed, and its effect on lipase expression was investigated. The wild-type P. resinovorans and the lip::Tn5[pBS29-P2-lip] recombinant (but not the lip::Tn5 mutant) showed fluorescence on rhodamine B plates indicative of lipase activity. The wild type exhibited extracellular lipase activity when grown on medium containing triacylglycerol substrates (tallow, olive oil, and tributyrin) as sole carbon sources, but the lip::Tn5 mutant did not show such activity. Lipase activity of various strains was also confirmed by TLC analysis of the composition of acylglycerols and free fatty acid in the extracts of the spent culture medium. We further found that tributyrin was more effective than olive oil in inducing lipase expression in P. resinovorans.

Differential effect of corn oil-based low trans structured fat on the plasma and hepatic lipid profile in an atherogenic mouse model: comparison to hydrogenated trans fat.

BACKGROUND: Trans fat are not desirable in many aspects on health maintenance. Low trans structured fats have been reported to be relatively more safe than trans fats. METHODS: We examined the effects of low trans structured fat from corn oil (LC), compared with high trans fat shortening, on cholesterol and fatty acid metabolism in apo E deficient mice which is an atherogenic animal model. The animals were fed a high trans fat (10% fat: commercial shortening (CS)) or a low trans fat (LC) diet for 12 weeks. RESULTS: LC decreased apo B and hepatic cholesterol and triglyceride concentration compared to the CS group but significantly increased plasma total cholesterol and triglyceride concentration and fecal lipids with a simultaneous increase in HDL-cholesterol level, apo A-I, and the ratio of HDL-cholesterol to total cholesterol (HTR). Reduction of hepatic lipid levels by inclusion of LC intake was observed alongside modulation of hepatic enzyme activities related to cholesterol esterification, fatty acid metabolism and fecal lipids level compared to the CS group. The differential effects of LC intake on the plasma and hepatic lipid profile seemed to be partly due to the fatty acid composition of LC which contains higher MUFA, PUFA and SFA content as well as lower content of trans fatty acids compared to CS. CONCLUSIONS: We suggest that LC may exert a dual effect on plasma and hepatic lipid metabolism in an atherogenic animal model. Accordingly, LC, supplemented at 10% in diet, had an anti-atherogenic effect on these apo E-/- mice, and increased fecal lipids, decreased hepatic steatosis, but elevated plasma lipids. Further studies are needed to verify the exact mode of action regarding the complex physiological changes and alteration in lipid metabolism caused by LC.

Effect of Fermentation on Cyanide and Ethyl Carbamate Contents in Cassava Flour and Evaluation of Their Mass Balance during Lab-Scale Continuous Distillation.

When cassava is used for the production of distilled spirits through fermentation and distillation, toxic hydrogen cyanide (HCN) is released from linamarin and carcinogenic ethyl carbamate is produced. Herein, cyanide and ethyl carbamate contents were monitored during the fermentation and lab-scale continuous distillation processes. Thereafter, mass balance and the influence of copper chips were evaluated. Results showed that 81.5% of cyanide was removed after fermentation. Use of copper chips completely prevented the migration of cyanide into the distilled spirits, while 88.3% of cyanide migrated from the fermented liquid in the absence of copper chips. Formation of ethyl carbamate was significantly promoted during distillation. Most of the produced ethyl carbamate (73.2%) was transferred into the distilled spirits in the absence of copper chips, only 9.6% of the ethyl carbamate was transferred when copper chips were used. Thus, copper chips effectively prevented the migration of cyanide and ethyl carbamate into the distilled spirts during continuous distillation.

Enrichment of pinolenic acid at the sn-2 position of triacylglycerol molecules through lipase-catalyzed reaction.

Reports have shown that Delta-5 polyunsaturated fatty acids (-5 PUFA) are enriched at sn-1,3 positions of triacylglycerols (TAG) in pine (Pinus koraiensis) nut oil (Pn). As a major Delta-5 PUFA, pinolenic acid (Pi) is about 14.2% in the oil, while the percentage of Pi at the sn-1 and/or sn-3 positions in TAG was found more than 20%. In this current study, the enhancement of Pi at the sn-2 position has been achieved by acyl migration during the lipase-catalyzed inter-esterification between Pn and palm stearin (Ps). After reaction, the proportion of Pi increased at sn-2 positional fatty acid even is similar to that in total fatty acid; for example, in the inter-esterified product of 50:50 (Pn:Ps), the same amount of Pi (7.1%) present was detected both at the sn-2 and sn-1,3 positions. However, the reduction of phytosterols and tocopherols are observed in the inter-esterified products.

Optimisation of tripalmitin-rich fractionation from palm stearin by response surface methodology.

BACKGROUND: Solvent fractionation is effective in improving separation at low temperature, resulting in higher yield and purity of the final product. Tripalmitin (PPP) is an important substrate for the synthesis of human milk fat substitute (HMFS). In this study a fraction rich in PPP was separated from palm stearin by solvent fractionation. RESULTS: The PPP-rich fraction was concentrated from palm stearin by acetone fractionation. Response surface methodology (RSM) was employed to optimise PPP purity (Y(1), %) and PPP content (Y(2), g kg(-1) palm stearin) with the independent variables fractionation temperature (X(1), 25, 30 and 35 degrees C) and weight ratio of palm stearin to acetone (X(2), 1:3, 1:6 and 1:9). The predictive models for PPP purity and PPP content of the solid fraction were adequate and reproducible, with no significant lack of fit and satisfactory levels of R(2). PPP purity showed a positive correlation with temperature and acetone ratio, whereas PPP content exhibited a negative correlation. The optimised fractionation condition for a targeted PPP-rich fraction with > 92% PPP purity and > 225 g kg(-1) PPP content from palm stearin was predicted. CONCLUSION: The RSM model for optimising PPP purity and PPP content in the PPP-rich fraction from palm stearin by acetone fractionation was valid. The scaled-up PPP-rich fraction obtained can be used as a substrate for the synthesis of 1,3-dioleoyl-2-palmitoylglycerol, which is a main component of HMFS in infant formulas.

Production of trans-free margarine stock by enzymatic interesterification of rice bran oil, palm stearin and coconut oil.

BACKGROUND: Trans-free interesterified fat was produced for possible usage as a spreadable margarine stock. Rice bran oil, palm stearin and coconut oil were used as substrates for lipase-catalyzed reaction. RESULTS: After interesterification, 137-150 g kg(-1) medium-chain fatty acid was incorporated into the triacylglycerol (TAG) of the interesterified fats. Solid fat contents at 25 degrees C were 15.5-34.2%, and slip melting point ranged from 27.5 to 34.3 degrees C. POP and PPP (beta-tending TAG) in palm stearin decreased after interesterification. X-ray diffraction analysis demonstrated that the interesterified fats contained mostly beta' polymorphic forms, which is a desirable property for margarines. CONCLUSIONS: The interesterified fats showed desirable physical properties and suitable crystal form (beta' polymorph) for possible use as a spreadable margarine stock. Therefore, our result suggested that the interesterified fat without trans fatty acid could be used as an alternative to partially hydrogenated fat.

Determination of acetaldehyde, methanol and fusel oils in distilled liquors and sakès by headspace gas chromatography.

In this study, a headspace gas chromatography (HS-GC) method was carried out to determine the contents of acetaldehyde, methanol and fusel oils in distilled liquors and sakès from different countries. A DB-Wax column was adopted in HS-GC, which showed good linearity, high precision and accuracy and low LOQ and LOD on all the compounds. Results showed that distilled liquors contained higher levels of acetaldehyde with the values of 12.88-35.53 mg/L than sakès (0.83-29.13 mg/L). Methanol was only detected in a few distilled liquors with small amounts. Amyl alcohols, including isoamyl alcohol (2-methyl-1-butanol) and active amyl alcohol (3-methyl-1-butanol), isobutanol (2-methyl-1-propanol) and 1-propanol were the main fusel oils among the distilled liquors and sakès analyzed. Amyl alcohols contents were 2 to 4 times higher in Korean distilled liquors (203.01-428.66 mg/L) than that in Chinese distilled liquors (28.52-42.77 mg/L) and all the sakès (61.90-166.59 mg/L).

Evaluation of Oxidation Parameters of Caffeic Acid Phenethyl Ester Comparing with Caffeic Acid, Ascorbyl Palmitate, and α-Tocopherol on the Thermal Oxidation Model.

In this study, the antioxidative capacity of caffeic acid (CA), ascorbyl palmitate (AP), α-tocopherol (α-TO), and caffeic acid phenethyl ester (CAPE) was evaluated under the thermal oxidation model, in which 200 ppm of each compound was added to soybean oil, followed by thermal oxidation at 180°C for 32 h. Change of viscosity, acid value (AV), conjugated dienoic acid value (CDAV), p-anisidine value (p-AV), total polar materials (TPM), and the ratio of C18:2 to C16:0 (LA/PA) were evaluated during the reaction. All antioxidants showed significantly lower viscosity, TPM, and p-AV, and higher LA/PA, than the control (without antioxidant, CON), indicating that thermal oxidation was delayed. Among them, CAPE showed significantly lower viscosity, TPM, and p-AV, and higher LA/PA, than the other antioxidants (p < 0.05). In the correlation between the oxidation parameters measured from CON and CAPE, the correlation coefficient between p-AV and viscosity was rather low at r = 0.7603 (in CON) and r = 0.7338 (in CAPE), respectively.

Evaluation model for cocoa butter equivalents based on fatty acid compositions and triacylglycerol patterns.

An effective evaluation model was established to digitize the quality of cocoa butter equivalents (CBEs) based on determinations of total and sn-2 fatty acid compositions and triacylglycerol (TAG) profiles and the "deducting score" principle. Similarity scores for selected fats and oils calculated from the model revealed differences between them and parallel cocoa butter compositions. For CBE1 and CBE2, total similarity scores were 90.6 and 90.0, whereas those of mango (76.3), dhupa (84.1), sal fat (84.7), kokum (78.3), palm mid fractions (PMF, 77.9), shea butter (64.0), illipe butter (89.7) and Pentadesma butyracea butter (67.2), respectively. Similarity scores were found to agree with physical properties, including polymorphism, crystal morphology, crystallization or melting behaviors, and solid fat content. The present study provides an accurate means of assessing CBE quality and hopefully will contribute to the development of commercial CBEs.

Physicochemical characteristics of fat blend from hydrogenated coconut oil and acyl migrated palm mid-fraction.

Palm mid-fraction (PMF), which has a high content of symmetric POP, was converted to asymmetric PPO (APMF) via acyl migration. After solvent fractionation, the liquid phase of acyl migrated PMF (APMF-L) was obtained and blended with hydrogenated coconut oil (HCO, 50:50, w/w) to produce a fat blend (namely, an alternative fat blend) which had reduced saturated fatty acid content while having similar melting behavior to HCO. In an alternative fat blend, the major fatty acids were lauric (27.94), palmitic (26.93) and oleic (15.75 mol%) acid. The solid fat index was quite similar to that of HCO, especially at 28-44 °C. Nevertheless, an alternative fat blend had lower saturated fatty acid content, by 18%, compared to HCO. The content of highly atherogenic myristic acid was reduced by approximately 40%. The alternative fat blend in this study could be used as a raw material for non-dairy cream with low saturated fat content.