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This report demonstrates the first asymmetric synthesis of enantiopure structured triacylglycerols (TAGs) of the ABC type presenting three non-identical fatty acids, two of which are unsaturated. The unsaturated fatty acids included monounsaturated oleic acid (C18:1 n-9) and polyunsaturated linoleic acid (C18:2 n-6). This was accomplished by a six-step chemoenzymatic approach starting from (R)- and (S)-solketals. The highly regioselective immobilized Candida antarctica lipase (CAL-B) played a crucial role in the regiocontrol of the synthesis. The synthesis also benefited from the use of the p-methoxybenzyl (PMB) ether protective group, which enabled the incorporation of two different unsaturated fatty acids into the glycerol skeleton. The total of six such TAGs were prepared, four constituting the unsaturated fatty acids in the sn-1 and sn-2 positions, with a saturated fatty acid in the remaining sn-3 position of the glycerol backbone. In the two remaining TAGs, the different unsaturated fatty acids accommodated the sn-1 and sn-3 end positions, with the saturated fatty acid present in the sn-2 position. Enantiopure TAGs are urgently demanded as standards for the enantiospecific analysis of intact TAGs in fats and oils. [ABSTRACT FROM AUTHOR]

Pulses are healthy and sustainable but induce gut symptoms in people with a sensitive gut. Oats, on the contrary, have no fermentable oligo- di-, monosaccharides and polyols compounds and are known for the health effects of their fibres. This 4-day cross-over trial investigated the effects of oat and rice flour ingested with pulses on gut symptoms and exhaled gases (4th day only) in subjects with a sensitive gut or IBS (n 21) and controls (n 21). The sensitive group perceived more symptoms after both meals than controls (P = 0·001, P = 0·001). Frequency, intensity or quality of the symptoms did not differ between meals during the first 3 d in either group. More breath hydrogen was produced after an oat than rice containing meal in both groups (AUC, P = 0·001, P = 0·001). No between-group difference was seen in breath gases. During day 4, both sensitive and control groups perceived more symptoms after the oat flour meal (P = 0·001, P = 0·0104, respectively) as mainly mild flatulence. No difference in moderate or severe symptoms was detected. Increased hydrogen production correlated to a higher amount of perceived flatulence after the oat flour meal in both the sensitive and the control groups (P = 0·042, P = 0·003, respectively). In summary, ingestion of oat flour with pulses increases breath hydrogen levels compared with rice flour, but gastrointestinal symptoms of subjects sensitive to pulses were not explained by breath hydrogen levels. Additionally, consumer mindsets towards pulse consumption and pulse-related gut symptoms were assessed by an online survey, which implied that perceived gut symptoms hinder the use of pulses in sensitive subjects. [ABSTRACT FROM AUTHOR]

Fortification of foods with fish oil rich in n–3 fatty acids improves the nutritional value, but creates challenges with flavor and oxidative stability, especially during storage. Pea, soy, and sunflower proteins were used in combination with whey protein or maltodextrin to encapsulate fish oil by spray-drying. The use of whey protein compared with maltodextrin as wall material improved oxidative stability of spray-dried emulsions, although the use of whey protein increased the number of observed cracks in outer shell of the particles. Non- and encapsulated oil were used in cookies and chocolates to examine flavor characteristics by generic descriptive analysis and volatile products by solid-phase microextraction with gas chromatography-mass spectrometry. A long-term storage test at room temperature was conducted to evaluate the oxidative stability of the food models. Fortification changed the texture, odor, and flavor of the food models with fishy flavor being the most impactful attribute. For both food models, use of pea protein with maltodextrin resembled attributes of control the best. Fortification and encapsulation material also affected volatile profiles of food models. Both non-encapsulated oil and whey protein formulations performed well in regard to oxidative stability for both food models. Generally, the cookie model showed more potential for fortification than the chocolate one. [ABSTRACT FROM AUTHOR]

Anthocyanins, the natural red and purple colorants of berries, fruits, vegetables, and tubers, improve carbohydrate metabolism and decrease the risk factors of metabolic disorders, but their industrial use is limited by their chemical instability. Acylation of the glycosyl moieties of anthocyanins, however, changes the chemical properties of anthocyanins and provides enhanced stability. Thus, acylated anthocyanins are more usable as natural colorants and bioactive components of innovative functional foods. Acylated anthocyanins are common in pigmented vegetables and tubers, the consumption of which has the potential to increase the intake of health‐promoting anthocyanins as part of the daily diet. For the first time, this review presents the current findings on bioavailability, absorption, metabolism, and health effects of acylated anthocyanins with comparison to more extensively investigated nonacylated anthocyanins. The structural differences between nonacylated and acylated anthocyanins lead to enhanced color stability, altered absorption, bioavailability, in vivo stability, and colonic degradation. The impact of phenolic metabolites and their potential health effects regardless of the low bioavailability of the parent anthocyanins as such is discussed. Here, purple‐fleshed potatoes are presented as a globally available, eco‐friendly model food rich in acylated anthocyanins, which further highlights the industrial possibilities and nutritional relevance of acylated anthocyanins. This work supports the academic community and industry in food research and development by reviewing the current literature and highlighting gaps of knowledge. [ABSTRACT FROM AUTHOR]

Highlights • DHA was efficiently absorbed in Sprague-Dawley rats with mild n-3 deficiency. • No significant differences in the absorption between DHA in sn -1 and sn -3 positions. • Less fecal DHA from the sn -2 position compared with the sn -1 and sn -3 positions. • 5-Day intervention enough to modify the fatty acid profile of plasma phospholipids. Abstract Lack of synthetic enantiospecific triacylglycerols (TAGs) has hindered our understanding of the impact of TAG structure on the absorption and metabolic fate of fatty acids (FAs). In a five-day feeding trial with mildly (n-3) deficient rats, the bioavailability of docosahexaenoic acid [22:6(n-3), DHA] and stearic acid (18:0) from the two different enantiomers of TAG: sn -22:6(n-3)-18:0-18:0 and sn -18:0-18:0-22:6(n-3), and their regioisomeric TAG: sn -18:0-22:6(n-3)-18:0 was compared. Less secretion of fecal DHA was detected from the sn -2 position compared with the sn -1 and sn -3 positions, but no difference was found in DHA content of the fasting plasma or in the weight of the body or organs. 18:0 was lost to feces mainly as cleaved from the primary positions but also as glycerol-bound. The 5-day intervention in rats was long enough to modify the fatty acid profile of plasma phospholipids. [ABSTRACT FROM AUTHOR]

Breast feeding results in long term health benefits in the prevention of communicable and non-communicable diseases at both individual and population levels. Geographical location directly impacts the composition of breast milk including microbiota and lipids. The aim of this study was to investigate the influence of geographical location, i.e., Europe (Spain and Finland), Africa (South Africa), and Asia (China), on breast milk microbiota and lipid composition in samples obtained from healthy mothers after the 1 month of lactation. Altogether, 80 women (20 from each country) participated in the study, with equal number of women who delivered by vaginal or cesarean section from each country. Lipid composition particularly that of polyunsaturated fatty acids differed between the countries, with the highest amount of n-6 PUFA (25.6%) observed in the milk of Chinese women. Milk microbiota composition also differed significantly between the countries (p = 0.002). Among vaginally delivered women, Spanish women had highest amount of Bacteroidetes (mean relative abundance of 3.75) whereas Chinese women had highest amount of Actinobacteria (mean relative abundance 5.7). Women who had had a cesarean section had higher amount of Proteobacteria as observed in the milk of the Spanish and South African women. Interestingly, the Spanish and South African women had significantly higher bacterial genes mapped to lipid, amino acid and carbohydrate metabolism (p < 0.05). Association of the lipid profile with the microbiota revealed that monounsaturated fatty acids (MUFA) were negatively associated with Proteobacteria (r = -0.43, p < 0.05), while Lactobacillus genus was associated with MUFA (r = -0.23, p = 0.04). These findings reveal that the milk microbiota and lipid composition exhibit differences based on geographical locations in addition to the differences observed due to the mode of delivery. [ABSTRACT FROM AUTHOR]

The aim of the current study was to characterize the anthocyanin content and composition of a purple potato landrace cultivar (Solanum tuberosum‘Synkeä Sakari’) and to compare the postprandial effects of purple-fleshed potatoes, yellow-fleshed potatoes and bilberries in potato starch on postprandial glycemia and insulinemia in healthy males. The purple potato meal caused smaller insulinemia than the yellow potato meal (iAUC 120 min 1347 and 2226, respectively,p = 0.012 and iAUC 240 min 1448 and 2403,p = 0.007) or the bilberry meal (iAUC 120 min 1920,p = 0.027). The purple potato meal caused a smaller plasma glucose at 40 min postprandially compared with the yellow potato meal (p = 0.044). The results of this study suggest that anthocyanin-containing purple-fleshed potatoes influence the postprandial insulinemia positively. Since potatoes are the world’s largest non-grain commodity, replacing yellow-fleshed potatoes with purple-fleshed potatoes as staple food could have large potential in maintaining public health. [ABSTRACT FROM AUTHOR]

Ageing is associated with a prolonged and exaggerated postprandial lipaemia. This study aimed to examine the contribution of alterations in chylomicron synthesis, size and lipid composition to increased lipaemia. Healthy older (60-75 years; n 15) and younger (20-25 years; n 15) subjects consumed a high-fat breakfast. Chylomicron dynamics and fatty acid composition were analysed for 5 h in the postprandial state. Plasma TAG levels were elevated following the meal in the older subjects, relative to younger subjects (P <0·01). For older subjects compared with younger subjects, circulating chylomicron particle size was smaller (P<0·05), with greater apoB content (P<0·05) at all postprandial time points. However, total chylomicron TAG concentration between the groups was unaltered post-meal. Compared with younger subjects, the older subjects exhibited a greater proportion of oleic acid in the TAG and phospholipid (PL) fraction (P<0·05), plus lower proportions of linoleic acid in the TAG fraction of the chylomicrons (P <0·01). Thus, following the ingestion of a high-fat meal, older individuals demonstrate both smaller, more numerous chylomicrons, with a greater total MUFA and lower PUFA contents. These data suggest that the increased postprandial lipaemia of ageing cannot be attributed to increased chylomicron TAG. Rather, ageing is associated with changes in chylomicron particle size, apoB content and fatty acid composition of the chylomicron TAG and PL fractions. [ABSTRACT FROM AUTHOR]

The aim of the current study was to characterize the anthocyanin content and composition of a purple potato landrace cultivar (Solanum tuberosum 'Synkeä Sakari') and to compare the postprandial effects of purple-fleshed potatoes, yellow-fleshed potatoes and bilberries in potato starch on postprandial glycemia and insulinemia in healthy males. The purple potato meal caused smaller insulinemia than the yellow potato meal (iAUC 120 min 1347 and 2226, respectively, p = 0.012 and iAUC 240 min 1448 and 2403, p = 0.007) or the bilberry meal (iAUC 120 min 1920, p = 0.027). The purple potato meal caused a smaller plasma glucose at 40 min postprandially compared with the yellow potato meal (p = 0.044). The results of this study suggest that anthocyanin-containing purple-fleshed potatoes influence the postprandial insulinemia positively. Since potatoes are the world's largest non-grain commodity, replacing yellow-fleshed potatoes with purple-fleshed potatoes as staple food could have large potential in maintaining public health. [ABSTRACT FROM AUTHOR]

Abstract: Based on the results from a human study which showed significantly reduced incorporation of DPA compared with EPA into chylomicrons, this study was designed to test if dietary DPA was significantly less absorbed than EPA. Male Sprague Dawley rats were randomly assigned to three groups of six, and were fed a semi-synthetic high fat diet (23.5% fat) for 9 days. The test omega 3 fatty acids (EPA and DPA, 250mg/animal/day, free fatty acid form) or olive oil (250mg/animal/day) were added to the high fat diet on days 5, 6 and 7. Dietary EPA and DPA appeared in the faeces on days 6, 7 and 8, with the total amount of DPA excreted being 4.6-fold greater than that of EPA. The total amount of faecal fat did not differ significantly between the groups. At the conclusion of the study (day 9), it was found that liver DPA, EPA and total n-3 LC-PUFA levels were significantly increased by both DPA and EPA feeding compared with the olive oil fed control group. In the heart, DPA feeding increased the DPA content and both DPA and EPA feeding increased the total n-3 LC-PUFA levels. This study showed that DPA and EPA, both provided in free form, are metabolised differently, despite being chemically similar. [Copyright &y& Elsevier]

Abstract: The study of the metabolism of docosapentaenoic acid (DPA, 22:5n−3) in humans has been limited by the unavailability of pure DPA and the fact that DPA is found in combination with eicosapentaenoic acid (EPA, 20:5n−3) and docosahexaenoic acid (DHA, 22:6n−3) in natural products. In this double blind cross over study, pure DPA and EPA were incorporated in meals served to healthy female volunteers. Mass spectrometric methods were used to study the chylomicron lipidomics. Plasma chylomicronemia was significantly reduced after the meal containing DPA compared with the meal containing EPA or olive oil only. Both EPA and DPA were incorporated into chylomicron TAGs, while there was less incorporation into chylomicron phospholipids. Lipidomic analysis of the chylomicron TAGs revealed the dynamic nature of chylomicron TAGs. The main TAG species that EPA and DPA were incorporated into were EPA/18:1/18:1, DPA/18:1/16:0 and DPA/18:1/18:1. There was very limited conversion of DPA and EPA to DHA and there were no increases in EPA levels during the 5h postprandial period after the DPA meal. In conclusion, EPA and DPA showed different metabolic fates, and DPA hindered the digestion, ingestion or incorporation into chylomicrons of the olive oil present in the meal. [Copyright &y& Elsevier]

The triacylglycerol (TAG) response to fatty meals containing dried and crushed berries or berry extraction residues was studied in a postprandial cross-over study with healthy normal-weight male volunteers. The berry material included sea buckthorn berries, sea buckthorn CO2 extraction residue (CO2-sea buckthorn) and sea buckthorn or black currant CO2 and ethanol extraction residue (CO2-EtOH-sea buckthorn, CO2-EtOH-black currant). Extraction residues were used in order to advance the potential use of valuable side stream components containing polyphenols and fibre as human food. Compared to the berry-depleted control, all berry meals delayed lipemia, whereas there were no differences in the total area under the TAG response curve. The lipemic delay largely derived from the fibre rather than from the polyphenols. Even so, the effect of polyphenols may be complementary since sea buckthorn and CO2-sea buckthorn showed significant differences in relation to control in a wider range of TAG areas than polyphenol-depleted CO2-EtOH-sea buckthorn. [ABSTRACT FROM AUTHOR]

The dietary intake of fatty acids (FAs) affects the composition and distribution of FAs in the body. Here, a first-generation (n-3)-deficiency study was conducted by keeping young (age 21 ± 2 days) Sprague–Dawley male rats on a peanut-oil-based diet for 33 days after weaning in order to compare the effect of mild (n-3)-deficiency on the lipid composition of different organs and feces. Soybean-oil-based diet was used as a control. The plasma FA levels corresponded to FAs levels in the organs. Lower docosahexaenoic acid (DHA) content was detected in the plasma, brain, testis, visceral fat, heart, and lungs of the (n-3)-deficient group, whereas the DHA content of the eye and feces did not differ between the experimental groups. The DHA content of the brains of the (n-3)-deficient group was 86% of the DHA content of the brains of the (n-3)-adequate group. The DHA level of the organs was affected in the order of visceral fat > liver triacylglycerols > lung > heart > liver phospholipids > testis > eye > brain, with brain being least affected. The low levels of (n-3) FAs in the liver, brain, eye, heart, and lung were offset by an increase in the (n-6) FAs, mainly arachidonic acid. These results indicate that, in rats, adequate maternal nutrition during pregnancy and weaning does not provide enough (n-3) FAs for 33 days of an (n-3)-deficient diet. Results of this study can be used also to evaluate the conditions needed to reach mild (n-3) deficiency in the first generation of rats and to evaluate the feasibility to collect data from a variety of organs or only selected ones. [ABSTRACT FROM AUTHOR]

The aim of this study was to determine whether the properties of the native oat grain or non-heat-treated groats (laboratory-scale dehulling) can be used to predict the quality of the industrially produced oat flour produced from heat-treated groats. Quality properties such as the color, hectoliter weight, thousand seed weight and hull content of Finnish native grains (n = 30) were determined. Furthermore, the relationship between the properties of the native grains and the chemical composition of the raw oat materials before and after the milling process were studied. A significant relationship (p < 0.01) was observed between the thousand seed weight of the native oat groats and the chemical composition of the industrially produced oat flour. Furthermore, the protein content of the native grains measured by NIT correlated with the chemical composition of the oat flours. These results suggest that the properties of oat flour produced on an industrial scale, including heat treatment, could be predicted based on the properties of native oat grains. [ABSTRACT FROM AUTHOR]

• A direct inlet MS/MS method was developed to analyze triacylglycerol regioisomers. • Method was used to analyze human milk, bovine milk, and commercial infant formulas. • The study revealed differences between human milk, bovine milk and infant formulas. • Vegetable oil based formulas showed larger differences compared with human milk. A previously developed direct inlet tandem mass spectrometric method for analysis of triacylglycerol (TAG) regioisomers was updated and validated for operation with current instrumentation with improved sensitivity and throughput. TAG regioisomers in pooled Chinese and Finnish human milk samples, two bovine milk samples and 11 infant formulas were identified and quantified. A total of 241 TAG regioisomers were identified and quantified, consisting of over 60 mol% of all TAGs in the human milk samples. The infant formulas deviated largely from human milk in regioisomeric composition of TAGs. In the Finnish and Chinese human milks, the most abundant ones were 1,3-dioleoyl-2-palmitoylglycerol (OPO; 7.4 and 8.8 mol% of all TAGs) and 1(3)-linoleoyl-2-palmitoyl-3(1)-oleoylglycerol (LPO; 4.7 and 8.3 mol% of all TAGs). In the infant formulas 1,2(2,3)-dioleoyl-3(1)-palmitoylglycerol (OOP) and 1(3)-linoleoyl-2-oleoyl-3(1)-palmitoylglycerol/1(3)-palmitoyl-2-linoleoyl-3(1)-oleoylglycerol (LOP/PLO) were more abundant than OPO and LPO. The differences between human milk and infant formula prompt for further development of current formulas. [ABSTRACT FROM AUTHOR]