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Skeletal muscle is essential for locomotion and plays a crucial role in energy homeostasis. It is regulated by nutrition, genetic factors, physical activity and hormones. Furan fatty acids (FuFAs) are minor fatty acids present in small quantities in food from plants and animals origin. Recently, we showed that a preventive nutritional supplementation with furan fatty acid in a DIO mouse model reduces metabolic disorders. The present study was designed to determine the influence of FuFA-F2 extracted from Hevea brasiliensis latex on skeletal muscle phenotype. In C2C12 myotubes we found that FuFA-F2 whatever the concentration used increased protein content. We revealed that in C2C12 myotubes FuFA-F2 (10 µM) increases protein synthesis as shown by the stimulation of mTOR phosphorylation. Next, to confirm in vivo our results C57Bl6 mice were supplemented by oral gavage with vehicle or FuFA-F2 (20 mg/kg) for 3 and a half weeks. We found that mice supplemented with FuFA-F2 had a greater lean mass than the control mice. In line with this observation, we revealed that FuFA-F2 increased muscle mass and promoted more oxidative muscle metabolism in mice as attested by cytochrome c oxidase activity. In conclusion, we demonstrated that FuFA-F2 stimulates muscle anabolism in mice in vitro and in vivo, mimicking in part physical activity. This study highlights that in vivo FuFA-F2 may have health benefits by increasing muscle mass and oxidative metabolism.

We have undertaken a detailed study of the reactivity of furan fatty acids (F‐acids) with singlet oxygen (1O2) produced by thermal decomposition of endoperoxide and photosensitizer reaction of rose bengal in ethanol. Accordingly, we measured the second order rate constant (kQ) for the reaction of F‐acids with 1O2. As a result, the reactivity of F‐acids against 1O2 exhibited a decrease in the order tetra‐alkyl F‐acid (F3) > tri‐alkyl F‐acid (F2) > di‐alkyl F‐acid (NMF). In addition, we also employed the density functional theory (DFT) and quantum chemical calculations to predict the chemical reactivity, stability, and thermodynamic properties of F‐acids with respect to the quenching 1O2. In consequence, it is clear that log kQ values of F‐acids correlate with the energy level of the highest occupied molecular orbital (EHOMO), and HOMO of F‐acids may react with the lowest unoccupied molecular orbitals (LUMO) of 1O2. Moreover, the reaction of F‐acids with 1O2 proceeds spontaneously in ethanol based on the calculation by thermodynamics method. These results suggest that the F‐acids may contribute to the protection of oxidative damage in animals by quenching 1O2. [ABSTRACT FROM AUTHOR]

The increase in obesity has become a major global health problem and is associated with numerous metabolic dysfunctions. Furan fatty acids (FuFAs) are minor lipids present in our diet. Recently we showed that FuFA-F2 extracted from Hevea brasiliensis latex stimulates muscle anabolism in mice in vitro and in vivo, mimicking in part physical activity. While skeletal muscle is essential for energy metabolism and is the predominant site of insulin-mediated glucose uptake in the post prandial state, our results suggested that FuFA-F2 could have favorable effects against obesity. The aim of this work was therefore to study whether a preventive nutritional supplementation with FuFA-F2 (40 mg or 110 mg/day/kg of body weight) in a diet-induced obesity (DIO) mouse model may have beneficial effects against obesity and liver and skeletal muscle metabolic dysfunction. We showed that 12 weeks of FuFA-F2 supplementation in DIO mice decreased fat mass, increased lean mass and restored normal energy expenditure. In addition, we found that FuFA-F2 improved insulin sensitivity. We revealed that FuFA-F2 increased muscle mass but had no effect on mitochondrial function and oxidative stress in skeletal muscle. Furthermore, we observed that FuFA-F2 supplementation reduced liver steatosis without impact on mitochondrial function and oxidative stress in liver. Our findings demonstrated for the first time that a preventive nutritional supplementation with a furan fatty acid in DIO mice reduced metabolic disorders and was able to mimic partly the positive effects of physical activity. This study highlights that nutritional FuFA-F2 supplementation could be an effective approach to treat obesity and metabolic syndrome.

Long-chain polyunsaturated fatty acids of n-3 family (n-3 LC PUFAs) are physiologically essential compounds required for normal growth and development of animals, including humans. The ability of fish species to synthesize n-3 LC PUFAs varies significantly across different trophic levels. We have studied fatty acid (FA) content (mg/g of wet weight) and level (% of total FAs) in the brain, liver, heart, intestine, female and male gonads, muscle, and adipose tissues of commercially important wild freshwater Baikal grayling. Additionally, FA content and level of Baikal grayling juveniles have been studied. In all tissues of Baikal grayling, some LC PUFAs, namely, 24:5n-3 and 24:6n-3 (C24 PUFAs), have been found. These FAs are the intermediate products in the synthesis of docosahexaenoic acid (DHA, 22:6n-3) by the Sprecher pathway. The levels of C24 PUFAs in tissues differed significantly: the highest levels of C24 PUFAs were found in adipose tissue and the lowest values in the gonads of females, liver, brain, and head of juveniles. According to the dynamics of DHA and C24 PUFAs, the maximum rate of DHA synthesis is achieved in brain of Baikal grayling, while the lowest rate of DHA synthesis probably occurs in adipose tissue. Although all studied tissues had differences in the number of FAs and their levels, 16:0, 18:1n-9, 16:1n-7, 20:5n-3, and DHA dominated. Male gonads contained an extremely high level of furan FAs — presumably beneficial substances for human health. Additionally, the nutritional value of the tissues of Baikal grayling as a source of n-3 LC PUFAs for humans has been estimated. [ABSTRACT FROM AUTHOR]

Furan fatty acids (FuFAs) are valuable minor compounds in our food with excellent antioxidant properties. Naturally occurring FuFAs are characterised by a central furan moiety with one or two methyl groups in β-/β'-position of the heterocycle (monomethyl- or M-FuFAs and dimethyl- or D-FuFAs). Comparably high concentrations of D-/M-FuFAs were reported in soybeans, but soy is often consumed as a processed product, such as full-fat soy flour and flakes, soy drink, tofu and texturised soy protein (TSP). Due to the chemical lability of D-/M-FuFAs, e.g. in the presence of light or oxygen, a degradation during the processing is possible. For this purpose, freshly harvested soybeans (n = 4) and differently processed soybean products (n = 22) were analysed on FuFAs. Three FuFAs, i.e. 11-(3,4-dimethyl-5-pentylfuran-2-yl)-undecanoic acid (11D5), 9-(3,4-dimethyl-5-pentylfuran-2-yl)-nonanoic acid (9D5), and 9-(3-methyl-5-pentylfuran-2-yl)-nonanoic acid (9M5), were identified and quantified in all fresh soybeans and most of the processed soy products (n = 20). A trend towards lower D-/M-FuFA contents in higher processed products was observable. Lower FuFA concentrations were usually accompanied with a decrease of the share of the less stable D-FuFAs (9D5, 11D5) in favour of the M-FuFA 9M5. Furthermore, one or two 3,4-nonmethylated furan fatty acids (N-FuFAs), i.e. 8-(5-hexylfuran-2-yl)-octanoic acid (8F6) and partly 7-(5-heptylfuran-2-yl)-heptanoic acid (7F7), were detected in all processed products, but not in the freshly harvested soybeans. Our results indicate that D-/M-/N-FuFAs may serve as suitable markers for both, careful manufacturing processes and adequate storage conditions of soy products. [ABSTRACT FROM AUTHOR]

A food that has been praised for its beneficial effects on overall health is fish, particularly its polyunsaturated n‐3 fatty acids, including docosahexaenoic acid (DHA) and eicosapentaenoic acid (EPA). However, it has recently been suggested that minor fatty acids such as furan fatty acids are needed in combination with DHA and EPA to exert these positive effects of fish and fish oils. Only recently have furan fatty acids become available in quantities that allow the investigation of their biofunctional properties. In this study, the uptake and effect of the furan fatty acid 9‐(3‐methyl‐5‐pentylfuran‐2‐yl)‐nonanoic acid (9M5) as a sole component and in combination with DHA and EPA on adipogenesis were analyzed using the 3T3‐L1 cell model. 9M5 is taken up and metabolized into 7M5, 5M5, and 3M5 in 3T3‐L1 adipocytes during a 24‐h period as shown with gas chromatography with mass spectrometry (GC/MS). Furthermore, 9M5 significantly increased lipid accumulation during the differentiation process of 3T3‐L1 preadipocytes into adipocytes. In addition, the combinations of DHA + 9M5 and EPA + DHA + 9M5 also exerted a significant increase compared to control adipocytes. 3T3‐L1 cells incubated with 9M5 resulted in an increased protein expression of PPARγ, C/EBPα, FABP4, and adiponectin, although not to the extent that DHA as a sole component or DHA + 9M5 did. Earlier studies have shown that DHA is a natural ligand for PPARγ, thus being a potential alternative to the antidiabetic thiazolidinediones. We show that 9M5 activates a PPARγ‐responsive reporter gene and could therefore be a natural ligand for PPARγ. [ABSTRACT FROM AUTHOR]

The furan fatty acid (F-fatty acid) content was determined in different marine sources as well as in commercially available marine oil products that claim to be health promoting. The five F-fatty acids typically representing the majority of F-fatty acids in fish, 9M5 (9-(3-methyl-5-pentylfuran-2-yl)-nonanoic acid), 9D5 (9-(3-dimethyl-5-pentylfuran-2-yl)-nonanoic acid), 11D3 (11-(3,4-Dimethyl-5-propylfuran-2-yl)-undecanoic acid), 11D5 (11-(3,4-Dimethyl-5-pentylfuran-2-yl)-undecanoic acid), and 11M5 (11-(3-Methyl-5-pentylfuran-2-yl)-undecanoic acid) were measured as methyl esters using a gas chromatograph linked with a tandem mass spectrometer (GC/MS-MS). The results showed a significant difference in F-fatty acid levels between the different marine oil products analyzed, depending on the source of raw material. Of the 11 different Icelandic marine catches analyzed, the highest total amount of F-fatty acids was found in the farmed fish. [ABSTRACT FROM AUTHOR]

Skeletal muscle is essential for locomotion and plays a crucial role in energy homeostasis. It is regulated by nutrition, genetic factors, physical activity and hormones. Furan fatty acids (FuFAs) are minor fatty acids present in small quantities in food from plants and animals origin. Recently, we showed that a preventive nutritional supplementation with furan fatty acid in a DIO mouse model reduces metabolic disorders. The present study was designed to determine the influence of FuFA-F2 extracted from Hevea brasiliensis latex on skeletal muscle phenotype. In C2C12 myotubes we found that FuFA-F2 whatever the concentration used increased protein content. We revealed that in C2C12 myotubes FuFA-F2 (10 µM) increases protein synthesis as shown by the stimulation of mTOR phosphorylation. Next, to confirm in vivo our results C57Bl6 mice were supplemented by oral gavage with vehicle or FuFA-F2 (20 mg/kg) for 3 and a half weeks. We found that mice supplemented with FuFA-F2 had a greater lean mass than the control mice. In line with this observation, we revealed that FuFA-F2 increased muscle mass and promoted more oxidative muscle metabolism in mice as attested by cytochrome c oxidase activity. In conclusion, we demonstrated that FuFA-F2 stimulates muscle anabolism in mice in vitro and in vivo , mimicking in part physical activity. This study highlights that in vivo FuFA-F2 may have health benefits by increasing muscle mass and oxidative metabolism. [Display omitted] • FuFA-F2 increased muscle anabolism in C2C12 myotubes. • FuFA-F2 supplementation in C57Bl6 mice increased muscle mass and oxidative metabolism. • FuFA-F2 supplementation in C57Bl6 mice partly mimicked the effect of physical activity. • FuFA-F2 supplementation might have health benefits by increasing muscle mass. [ABSTRACT FROM AUTHOR]

Countercurrent chromatography (CCC) is an all liquid based separation technique typically used for the isolation and purification of natural compounds. The simplicity of the method makes it easy to scale up CCC separations from analytical to preparative and even industrial scale. However, scale-up of CCC separations requires two different instruments with varying coil dimensions. Here we developed two variants of the CCC multiple injection mode as an alternative to increase the throughput and enhance productivity of a CCC separation when using only one instrument. The concept is based on the parallel injection of samples at different points in the CCC column system and the simultaneous separation using one pump only. The wiring of the CCC setup was modified by the insertion of a 6-port selection valve, multiple T-pieces and sample loops. Furthermore, the introduction of storage sample loops enabled the CCC system to be used with repeated injection cycles. Setup and advantages of both multiple injection modes were shown by the isolation of the furan fatty acid 11-(3,4-dimethyl-5-pentylfuran-2-yl)-undecanoic acid (11D5-EE) from an ethyl ester oil rich in 4,7,10,13,16,19-docosahexaenoic acid (DHA-EE). 11D5-EE was enriched in one step from 1.9% to 99% purity. The solvent consumption per isolated amount of analyte could be reduced by ∼40% compared to increased throughput CCC and by ∼5% in the repeated multiple injection mode which also facilitated the isolation of the major compound (DHA-EE) in the sample. [ABSTRACT FROM AUTHOR]

Using high-performance liquid chromatography coupled to high-resolution electrospray ionization quadrupole time-of-flight mass spectrometry (HPLC/ESI-Q-TOF-MS), we have developed a new method for detection and identification of furan fatty acids (F-acids), which are widely distributed in living organisms and foods as minor lipid components and are known to have antioxidant and anti-inflammatory effects. For this purpose, total fatty acids prepared from the testis lipids of Japanese chum salmon ( Oncorhynchus keta ) were examined without any concentration or isolation of F-acids. In negative ESI mode, F-acids gave a prominent [M−H] − ion, by which individual F-acids could be detected and identified. High-resolution extracted ion chromatograms clearly showed the occurrence of five major F-acid homologs as already reported by GC/MS. The method was successfully applied to several fish samples and revealed the occurrence of F-acids for the first time in the two New Zealand fish, hoki ( Macruronus novaezelandiae ) and school shark ( Galeorhinus galeus ). [ABSTRACT FROM AUTHOR]

Abstract: 3‐carboxy‐4‐methyl‐5‐propyl‐2‐furanpropanoic acid (CMPF) is a known metabolite of furan fatty acids and was first referred to as a urofuran fatty acid, as it was found in urine of humans and other species after consumption of furan fatty acids or foods containing furan fatty acids. More recently, CMPF has been identified as a highly prominent metabolite following the consumption of fish oil, fish oil fractions and diets rich in fish, and can be regarded as biomarker of oil‐rich fish or fish oil intakes. As furan fatty acids are known to occur in fish and fish oil (at a low level), it is possible that the CMPF in plasma arises from these furan fatty acids. On a structural basis, this is a likely explanation rather than the CMPF being an actual metabolite of long‐chain marine omega‐3 fatty acids. Recent studies in high fat‐fed mice given purified CMPF suggest that CMPF might contribute to the improved metabolic effects observed following consumption of long‐chain marine omega‐3 fatty acids but much is still to be known about the relationships between CMPF and health. [ABSTRACT FROM AUTHOR]

Furan fatty acids (furan-FAs) are valuable antioxidants which are supposed to play an important role in the protection of polyunsaturated fatty acids from getting oxidised. Scattered literature reports indicated that these fatty acids are widely present at low concentrations in various biological and food samples. Here, we determined the furan-FA composition in 35 samples including seven fresh herb matrices, as well as in spinach and grass. Samples were transesterified and furan-FAs were enriched from the fatty acid methyl ester fraction by means of silver ion chromatography followed by analysis with gas chromatography with mass spectrometry operated in selected ion monitoring mode (GC/MS-SIM). The samples featured between one (rosemary) and eight different furan-FAs (curly-leaf parsley). Six saturated and four unsaturated furan-FAs were identified with clear dominance of β,β’-dimethyl-substituted representatives. The total amount of furan-FAs ranged from 15 to 2650 μg/100 g fresh weight with dill, grass and curly-leaf parsley being the richest sources among the sample matrices. The rarely described unsaturated furan-FAs were detected in eight of the nine matrices and were predominant in flat-leaf parsley. Curly-leaf and flat-leaf parsley as well as fresh and deep-frozen spinach samples showed remarkable differences in the furan-FA pattern. [ABSTRACT FROM AUTHOR]

The emergence of methicillin-resistant Staphylococcus aureus (MRSA) infections with multi-drug resistance needs effective and alternative control strategies. In this study we investigated the adjuvant effect of a novel furan fatty acid, 7,10-epoxyoctadeca-7,9-dienoic acid (7,10-EODA) against multidrug-resistant S. aureus (MDRSA) strain 01ST001 by disc diffusion, checker board and time kill assays. Further the membrane targeting action of 7,10-EODA was investigated by spectroscopic and confocal microscopic studies. 7,10-EODA exerted synergistic activity along with β-lactam antibiotics against all clinical MRSA strains, with a mean fractional inhibitory concentration index below 0.5. In time-kill kinetic study, combination of 7,10-EODA with oxacillin, ampicillin, and penicillin resulted in 3.8-4.2 log reduction in the viable counts of MDRSA 01ST001. Further, 7,10-EODA dose dependently altered the membrane integrity ( p < 0.001) and increased the binding of fluorescent analog of penicillin, Bocillin-FL to the MDRSA cells. The membrane action of 7,10-EODA further facilitated the uptake of several other antibiotics in MDRSA. The results of the present study suggested that 7,10-EODA could be a novel antibiotic adjuvant, especially useful in repurposing β-lactam antibiotics against multidrug-resistant MRSA. [ABSTRACT FROM AUTHOR]

The increase in obesity has become a major global health problem and is associated with numerous metabolic dysfunctions. Furan fatty acids (FuFAs) are minor lipids present in our diet. Recently we showed that FuFA-F2 extracted from Hevea brasiliensis latex stimulates muscle anabolism in mice in vitro and in vivo, mimicking in part physical activity. While skeletal muscle is essential for energy metabolism and is the predominant site of insulin-mediated glucose uptake in the post prandial state, our results suggested that FuFA-F2 could have favorable effects against obesity. The aim of this work was therefore to study whether a preventive nutritional supplementation with FuFA-F2 (40 mg or 110 mg/day/kg of body weight) in a diet-induced obesity (DIO) mouse model may have beneficial effects against obesity and liver and skeletal muscle metabolic dysfunction. We showed that 12 weeks of FuFA-F2 supplementation in DIO mice decreased fat mass, increased lean mass and restored normal energy expenditure. In addition, we found that FuFA-F2 improved insulin sensitivity. We revealed that FuFA-F2 increased muscle mass but had no effect on mitochondrial function and oxidative stress in skeletal muscle. Furthermore, we observed that FuFA-F2 supplementation reduced liver steatosis without impact on mitochondrial function and oxidative stress in liver. Our findings demonstrated for the first time that a preventive nutritional supplementation with a furan fatty acid in DIO mice reduced metabolic disorders and was able to mimic partly the positive effects of physical activity. This study highlights that nutritional FuFA-F2 supplementation could be an effective approach to treat obesity and metabolic syndrome. [Display omitted] • FuFA-F2 supplementation in DIO mice decreased fat mass, increased lean mass and restored normal energy expenditure. • FuFA-F2 supplementation in DIO mice increased insulin sensitivity and reduced liver steatosis. • FuFA-F2 supplementation in DIO mice partly mimicked the effect of physical activity. • FuFA-F2 supplementation might be an effective approach to treat obesity and metabolic syndrome. [ABSTRACT FROM AUTHOR]

Furan fatty acids are found in plants, algae, and fish, and reported to have some positive health benefits, including anti-oxidant and anti-inflammatory activities, and inhibition of non-enzymatic lipid peroxidation. A major metabolite of furan fatty acids, 3-carboxy-4-methyl-5-propyl-2-furanpropanoic acid (CMPF), has been reported to be increased in patients who progress from prediabetes to type 2 diabetes, although CMPF is not necessarily associated with impaired glucose metabolism. Other studies report that CMPF levels are lower in subjects with diabetes than control subjects. Plasma CMPF levels increase in subjects who consume fish or fish oil, and in patients with renal failure. It is not known where furan fatty acids are converted to CMPF and it is speculated that this might be a result of microbiome activity. The plasma levels reported for CMPF in healthy, diabetic and patients with renal disease vary by factors of more than 100-fold within each of these three groups, so measurement error appears to be limiting the ability to interpret studies. This review explores these controversies and raises questions about whether CMPF is a marker for healthy diets or indeed associated with diabetes and renal health. The review concludes that, on balance, furan fatty acids are beneficial for health. [ABSTRACT FROM AUTHOR]

The profile and distribution of fatty acids in neutral lipids, phosphatidylethanolamine and phosphatidylcholine of appreciated crustaceans species caught in the Adriatic Sea during the autumn months, namely caramote prawn ( Penaeus kerathurus ), mantis shrimp ( Squilla mantis ) and crab ( Liocarcinus vernalis ), were investigated. The crab’s total fatty acid profile significantly differed from that of caramote prawn and mantis shrimp. Crab was the most valuable dietary source of omega-3 polyunsaturated fatty acids ( n –3 PUFA), with approximately 2-fold higher eicosapentaenoic acid content (131.6 ± 31.6 mg/100 g of edible part) than caramote prawn and mantis shrimp. The caramote prawn presented the highest furan fatty acids (F-acids) level (2.5 ± 0.5 mg/100 g). All crustaceans preferentially accumulated the n –3 PUFA in phosphatidylethanolamine fraction. The F-acid distribution among the lipid classes changed according to the crustacean species. Crab presented F-acids mainly in the neutral lipid whereas caramote prawn contained them predominantly in the phospholipids. On the contrary, F-acids were not detected in the phosphatidylcholine of mantis shrimp. These differences in the distribution suggest different nutritional and health properties given by the consumption of the crustaceans investigated. Moreover, the F-acid profile of the different lipid classes could be used to discriminate these crustaceans. [ABSTRACT FROM AUTHOR]

Introduction: The mink exhibit an obligatory diapause. The metabolic changes during the transition from diapause to implantation and established pregnancy are currently unknown. Objectives: The study aimed to characterize changes in the urinary metabolome in mink during the period from mating to early gestation and to identify the metabolites involved. Methods: Urine samples were collected from 56 female mink on March 24, April 8, and April 15, covering the period from mating to early pregnancy. The urine samples were subjected to non-targeted LC-MS metabolomics. Processed data were evaluated by principal component analysis (PCA) and the peak area of identified metabolites were subjected to ANOVA. Results: The samples showed clear clustering according to sampling date in a PCA scores plot, and 35 metabolites differing significantly between sampling days were identified. The excretion of dicarboxylic acids and acylcarnitines of dicarboxylic acids exhibited a decline on April 8, and the same trend was observed for four unidentified metabolites, two of which were putatively identified as acids of the furan fatty acid type. The decreased excretion of lipid components was suggested to be a result of increased oxidation of these compounds. In contrast, the excretion of amino acid-related metabolites showed an increase on April 8 which was attributed to increased metabolism of amino acids at this time point. Conclusion: The urinary metabolic profile of mink showed distinct changes during the period studied. The major changes were observed at the time of implantation where increases in the lipid and protein metabolism were evident. [ABSTRACT FROM AUTHOR]

• A highly sensitive method for analysis of FuFAs based on GC-TQ/MS was developed. • The quantitative protocol for detection of FuFAs showed an LOQ of 0.6 pg. • The concentration of FuFAs in common edible oils was analyzed. Furan fatty acids (FuFAs) have been recognized as beneficial food ingredients to human health. Herein, a targeted quantitation approach by gas chromatography coupled to triple quadrupole tandem mass spectrometry (GC-TQ/MS) was developed for the identification of FuFAs in common marine and other edible oils in multiple reaction monitoring (MRM) mode without any isolation and enrichment. The limit-of-quantitation (LOQ, 0.6 pg) was determined under the optimized parameters in MRM mode. Identification of FuFAs in common edible oils demonstrated that marine fish oils were concentrated sources of 9-(3-methyl-5-pentylfuran-2-yl)nonanoic acid (9M5), 11-(3,4-dimethyl-5-propylfuran-2-yl)undecanoic acid (11D3) and 11-(3,4-dimethyl-5-pentylfuran-2-yl)undecanoic acid (11D5). However, FuFAs were not identified in common plant oils. Additionally, 11D5 was identified in the lipids of Schizochytrium limacinum at a comparable level with that in marine fish oil. We believe that this protocol could facilitate the qualitative and quantitative analysis of FuFAs in food and biological samples. [ABSTRACT FROM AUTHOR]

We analyzed the antimicrobial potential of a novel furan fatty acid, 7,10-epoxyoctadeca-7,9-dienoic acid (7,10-EODA) against methicillin-resistant and -sensitive S. aureus (MRSA and MSSA). The anti-staphylococcal activity of 7,10-EODA and its consequences on cell physiology was determined by disc diffusion, broth microdilution, and flow cytometry. Anti-virulence activity of 7,10-EODA was evaluated by bioassays. 7,10-EODA was anti-staphylococcal with minimum inhibitory concentration (MIC) range of 125-250 mg/L. 7,10-EODA exhibited a dose response and inhibited MRSA 01ST001 by 90.5% and ATCC 29213 (MSSA) by 85.3% at 125 mg/L. MIC of 7,10-EODA permeabilized >95 % of MRSA 01ST001 cells to small molecules. Sublethal dose of 7,10-EODA was non-toxic but markedly reduced the hemolytic, coagulase, and autolytic activities of MRSA and MSSA at 15.6 mg/L. The results provide a lead for the utilization of natural furan fatty acids as novel anti-MRSA agents. [ABSTRACT FROM AUTHOR]

Cardiovascular disease (CVD) is a major cause of mortality. The effects of several unsaturated fatty acids on cardiometabolic health, such as eicosapentaenoic acid (EPA) docosahexaenoic acid (DHA), α linolenic acid (ALA), linoleic acid (LA), and oleic acid (OA) have received much attention in past years. In addition, results from recent studies revealed that several other uncommon fatty acids (fatty acids present at a low content or else not contained in usual foods), such as furan fatty acids, n-3 docosapentaenoic acid (DPA), and conjugated fatty acids, also have favorable effects on cardiometabolic health. In the present report, we searched the literature in PubMed, Embase, and the Cochrane Library to review the research progress on anti-CVD effect of these uncommon fatty acids. DPA has a favorable effect on cardiometabolic health in a different way to other long-chain n-3 polyunsaturated fatty acids (LC n-3 PUFAs), such as EPA and DHA. Furan fatty acids and conjugated linolenic acid (CLNA) may be potential bioactive fatty acids beneficial for cardiometabolic health, but evidence from intervention studies in humans is still limited, and well-designed clinical trials are required. The favorable effects of conjugated linoleic acid (CLA) on cardiometabolic health observed in animal or in vitro cannot be replicated in humans. However, most intervention studies in humans concerning CLA have only evaluated its effect on cardiometabolic risk factors but not its direct effect on risk of CVD, and randomized controlled trials (RCTs) will be required to clarify this point. However, several difficulties and limitations exist for conducting RCTs to evaluate the effect of these fatty acids on cardiometabolic health, especially the high costs for purifying the fatty acids from natural sources. This review provides a basis for better nutritional prevention and therapy of CVD.

Fatty acid (FA) composition was analyzed in muscle and gonad tissues of marketed common carp ( Cyprinus carpio ). The extracted lipids were separated into four fractions: polar lipids (PL), diacylglycerols, free fatty acids and triacylglycerols (TAG) using thin layer chromatography. FA content within the lipid fractions was determined by gas chromatography with flame ionization detector (GC/FID). The muscle lipids consisted primarily of TAG (96.9% of total FA), while PL were the major component of both male (67.6%) and female gonad (58.6%) lipids. Polyunsaturated fatty acids predominated in PL of all tissues (52.2–55.8% of total FA); monounsaturated fatty acids were the most abundant FA group in TAG of muscle (51.8%) and female gonads (47.8%) whereas high proportion of furan fatty acids (F-acids) (38.2%) was detected in TAG of male gonads. Eight F-acids were identified by gas chromatography–mass spectrometry (GC/MS) in male gonad samples, including less common 12,15-epoxy-13,14-dimethylnonadeca-12,14-dienoic acid with even-numbered alkyl moiety. [ABSTRACT FROM AUTHOR]

Furan fatty acids are valuable and bioactive minor fatty acids that usually contribute <0.1% to the fatty acid content of food samples. Their biological role still remains unclear as authentic furan fatty acid standards are not readily available and thorough experimental studies verifying the relevance of furan fatty acids are thus virtually impossible. An efficient protocol for the isolation of the furan fatty acid 9-(3-methyl-5-pentylfuran-2-yl)-nonanoic acid from hydrolyzed and centrifuged latex of Hevea brasiliensis was developed using countercurrent chromatography. A first run using pH-zone-refining countercurrent chromatography provided 48.4 mg of 9-(3-methyl-5-pentylfuran-2-yl)-nonanoic acid from 210 mg latex extract in a purity of 95%. The purity was increased to 99% by means of one second run in conventional countercurrent chromatography mode. The Structure and purity of 9-(3-methyl-5-pentylfuran-2-yl)-nonanoic acid were determined by gas chromatography coupled to mass spectrometry and 1H and 13C NMR spectroscopy. [ABSTRACT FROM AUTHOR]

Furan fatty acids (F-acids) are heterocyclic fatty acids having a furan ring in their structure. Most existing studies on F-acids are related to either fish or other marine animals. Even though F-acids have been detected in many plant species, not much work has been done exclusively in plants of economic importance, especially oilseed crops. This review focuses mainly on the functions and roles of F-acids in plants. In plants, they are bound to phospholipids by substituting PUFA and function as free radical scavengers suggesting their role in defense against oxidative stress. Owing to their antioxidative property F-acids are highly unstable and their photooxidative products can contribute to the flavor of edible oils. [ABSTRACT FROM AUTHOR]

Furan fatty acids (F-acids) are valuable, bioactive minor components in lipids which are characterized by a furan moiety in the acyl chain. Here, we present a gas chromatography/mass spectrometry method operated in the selected ion monitoring mode (GC/MS-SIM) for the thorough determination of F-acid as methyl esters in fish. The method takes advantage of the molecular ion and two characteristic fragment ions and enables the unequivocal detection of >350 saturated, mono- and dienoic F-acids in four GC/MS-SIM runs. This method was applied to the analysis of the methyl esters obtained from the triacylglyceride (TG) and the cholesteryl ester (CE) fraction of ten individual fish liver samples. Up to 23 F-acids, including several new or scarcely detected homologues, were detected in the samples. The concentrations of total F-acids ranged from 25 to 280 mg/100 g lipids in the TG fractions and <0.11 to 115 mg/100 g lipids in the CE fractions. [ABSTRACT FROM AUTHOR]

Optimised syntheses of F 5 - and F 6 -furan fatty acids 2 and 3 are described in full. Key steps include furan formation from a single 3-alkyne-1,2-diol 6 using 5- endo -dig cyclisations triggered by silver(I) nitrate or iodine. Introduction of the final carboxylic acid function and one-carbon homologation were achieved by cross metathesis with benzyl acrylate and hydrogenation. Iodine-methyl exchange of intermediate iodofurans was achieved by direct treatment with methyl lithium, which gave trideuterated derivatives 16 of the F 6 acid by using CD 3 Li. The two acids 2 and 3 proved very unstable; thus, if samples are to be stored for extended periods, this should be as an ester and not as the free acids. This instability does raise questions regarding previously determined levels of these free acids (and perhaps some of their structurally close relatives) in various natural sources. [ABSTRACT FROM AUTHOR]

Furan fatty acids (F-acids) are a class of natural antioxidants with a furan moiety in the acyl chain. These minor fatty acids have been reported to occur with high proportions in the cholesteryl ester fraction of fish livers. Here we present a method for the direct analysis of intact cholesteryl esters with F-acids and other fatty acids in cod liver lipids. For this purpose, the cholesteryl ester fraction was isolated by solid phase extraction (SPE) and subsequently analyzed by gas chromatography with mass spectrometry (GC/MS) using a cool-on-column inlet. Pentadecanoic acid esterified with cholesterol was used as an internal standard. GC/MS spectra of F-acid cholesteryl esters featured the molecular ion along with characteristic fragment ions for both the cholesterol and the F-acid moiety. All investigated cod liver samples ( n = 8) showed cholesteryl esters of F-acids and, to a lower degree, of conventional fatty acids. By means of GC/MS-SIM up to ten F-acid cholesteryl esters could be determined in the samples. The concentrations of cholesteryl esters with conventional fatty acids amounted to 78-140 mg/100 g lipids (mean 97 mg/100 g lipids), while F-acid cholesteryl esters were present at 47-270 mg/100 g lipids (mean 130 mg/100 g lipids). [ABSTRACT FROM AUTHOR]

Furan fatty acids (F-acids) are valuable bioactive compounds found at low concentrations in food. A method for the quantitative determination of saturated F-acids in food is reported. The sample preparation is based on accelerated solvent extraction, transesterification into methyl esters and silver ion chromatography (20% AgNO in silica, 1% deactivated) of the resulting methyl esters. There then follows determination of the enriched F-acid methyl (or ethyl) esters by GC/EI-MS in the selected ion monitoring (SIM) mode. The 9-(3-methyl-5-pentylfuran-2-yl)-nonanoic acid ethyl ester (9M5-EE) was used as an internal standard for recovery checks. The limit of detection was 11 pg, and the recovery rate of the silver ion chromatography was 85% ( n = 5). Further F-acid standards were used for evaluation of individual SIM-responses. Application of the method to various biological samples gave the following results: champignons ( n = 2) contained 1.7 or 2.5 mg/100 g dry weight F-acids, while fish oil capsules ( n = 5) contained between 18 and 234 mg/100 g oil F-acids distributed over up to seven F-acids. The concentrations and patterns were different to fresh fish. Accordingly, fish oil supplements seem to be a minor source for F-acids compared to (fresh) fish. Organic butter samples ( n = 4) contained about twice the amount of F-acids when compared with conventional butter ( n = 5). [ABSTRACT FROM AUTHOR]

Abstract: Glycolipids of fresh latex from three clones of Hevea brasiliensis were characterized and quantified by HPLC/ESI-MS. Their fatty acyl and sterol components were further confirmed by GC/MS after saponification. The four detected glycolipid classes were steryl glucosides (SG), esterified steryl glucosides (ESG), monogalactosyl diacylglycerols (MGDG) and digalactosyl diacylglycerols (DGDG). Sterols in SG, ESG and total latex unsaponifiable were stigmasterol, β-sitosterol and Δ5-avenasterol. The latter was found instead of fucosterol formerly described. Galactolipids were mainly DGDG and had a fatty acid composition different from that of plant leaves as they contained less than 5% C18:3. Glycolipids, which represented 27–37% of total lipids, displayed important clonal variations in the proportions of the different fatty acids. ESG, MGDG and DGDG from clone PB235 differed notably by their higher content in furan fatty acid, which accounted for more than 40% of total fatty acids. Clonal variation was also observed in the relative proportions of glycolipid classes except MGDG (8%), with 43–51% DGDG, 30–34% SG and 7–19% ESG. When compared with other plant cell content, the unusual glycolipid composition of H. brasiliensis latex may be linked to the peculiar nature of this specialized cytoplasm expelled from laticiferous system, especially in terms of functional and structural properties. [Copyright &y& Elsevier]

Abstract: Furan fatty acids (F-acids) were characterised in the fillet of European hake (Merluccius merluccius), horse mackerel (Trachurus trachurus), common sole (Solea solea), European anchovy (Engralius encrasicolus), Atlantic mackerel (Scomber scombrus), European pilchard (Sardina pilchardus) was harvested in Adriatic Sea during the spring and the summer. The main F-acids were of the saturated series: 12,15-epoxy-13-methyleicosa-12,14-dienoic acid [MonoMe(11,5)] in European hake and 12,15-epoxy-13,14-dimethyleicosa-12,14-dienoic acid [DiMe(11,5)] in all the other fish species; 12,15-epoxy-13,14-dimethyloctadeca-12,14-dienoic acid, 10,13-epoxy-11-methyloctadeca-10,12-dienoic acid and 14,17-epoxy-15,16-dimethyldocosa-14,16-dienoic acid were present in all fish species in trace amounts. Other identified F-acids were the olefinic congeners 12,15-epoxy-13,14-dimethyleicosa-12,15,16-trienoic acid and 12,15-epoxy-13,14-dimethyleicosa-10,12,14-trienoic acid. European pilchard had the highest F-acids content (30mg/100g fillet), whereas horse mackerel showed the lowest content (less than 0.1mg/100g fillet). Eicosapentaenoic acid (EPA) was positively correlated with MonoMe(11,5) and DiMe(11,5), showing that the biosynthesis of docosapentaenoic acid (DPA) and docosahexaenoic acid (DHA) is presumably competitive with that of F-acids. [Copyright &y& Elsevier]

Any change in the cell membrane structure activates lipoxygenases (LOX). LOX transform polyunsaturated fatty acids (PUFAs) to lipidhydroperoxide molecules (LOOHs). When cells are severely wounded, this physiological process switches to a non-enzymatic lipid peroxidation (LPO) process producing LOO· radicals. These oxidize nearly all-biological molecules such as lipids, sugars, and proteins. The LOO· induced degradations proceed by transfer of the radicals from cell to cell like an infection. The chemical reactions induced by LO· and LOO· radicals seem to be responsible for aging and induction of age dependent diseases. Alternatively, LO· and LOO· radicals are generated by frying of fats and involve cholesterol-PUFA esters and thus induce atherogenesis. Plants and algae are exposed to LOO· radicals generating radiation. In order to remove LOO· radicals, plants and algae transform PUFAs to furan fatty acids, which are incorporated after consumption of vegetables into mammalian tissues where they act as excellent scavengers of LOO· and LO· radicals. [ABSTRACT FROM AUTHOR]

The influence of light exposure of dried herbs and vegetables on the formation of dimethyl furan fatty acid (DiMeFFA) photooxidative degradation products such as 2,3-butanedione, 2,3-octanedione, 3-methyl-2,4-nonanedione (MND), 3,4-dimethyl-5-pentyliden-2(5H)-furanone (bovolide) and 3,4-dimethyl-5pentyl-2(5H)-furanone (dihydrobovolide) was investigated. To our knowledge, the occurrence of these compounds in tarragon, dill, basil, chervil, chive, leek, savory and onion has hitherto not been reported. The flavour fraction was isolated by simultaneous distillation extraction and analysed by GC-MS. The flavour compounds were determined in relation to the exposure time as peak area ratio to an internal standard.

Three new furan fatty acids, (9 Z, 19 Z)-3, 6-epoxyhexacosa-3,5,19-tetraenoic acid ( 1a), (8 Z, 11 Z, 14 Z, 17 Z)-3, 6-epoxyeicosa-3,5,8,11,14,17-hexaenoic acid ( 2a), and (8 Z, 11 Z, 14 Z, 17 E)-3, 6-epoxyeicosa-3,5,8,11,14,17-hexaenoic acid ( 3a), and a new polyunsaturated fatty acid (5 Z, 8 Z, 11 Z, 14 Z, 17 E)-eicosa-5,8,11,14,17-pentaenoic acid ( 6a), present in the sponge Dictyonella incisa as the respective steryl esters, have been isolated as methyl esters and their structures have been determined by spectral and chemical analysis. The furan fatty acid esters have shown a high inflammatory activity, which suggests their potential role as feeding deterrents. [ABSTRACT FROM AUTHOR]

The objective of this study was to identify autoxidation products of methyl 9,12-epoxyoctadeca-9,11-dienoate (F9,12). Previous work has shown that F9,12 is a product both of autoxidation and singlet oxygen oxidation of the methyl ester derivative of conjugated linoleic acid (CLA). F9,12, 95% pure, was synthesized from methyl ricinoleate. The synthetic F9,12 was heated at 50°C in sealed tubes containing air. Each tube contained 6 mg F9,12 and 1 mg methyl stearate as an internal standard. Samples were taken at 4.5, 7, 23, 46.5, 69.5, and 93 h. The oxidized F9,12 was dissolved in isooctane and analyzed by gas chromatography (GC), GC-direct deposition-Fourier transform infrared spectroscopy, and GC-electron ionization mass spectrometry. CLA methyl ester was oxidized in a similar manner. Under these conditions, the half-lives of CLA and F9,12 were 40 and 35 h, respectively. Oxidation products of F9,12 that were identified included: 5-hexyl-2-furaldehyde ( I), methyl 8-oxooctanoate ( II), methyl 13-oxo-9,12-epoxytrideca-9,11-dienoate ( III), methyl 8-oxo-9,12-epoxy-9,11-octadecadienoate ( IV), and methyl 13-oxo-9,12-epoxy-9,11-octadecadienoate ( V). [ABSTRACT FROM AUTHOR]

• ω-3 Fish oil had a high concentration (1.3 g/100 g lipids) of furan fatty acids. • Dimethyl furan fatty acids degraded faster than monomethyl ones in the fish oil. • Addition of 9M5 to fish oil inhibited oxidation reactions. • Antioxidant effect of 9M5 occurred after degradation of dimethyl furan fatty acids. • Dimethyl furan fatty acids degraded faster than tocopherols. This study investigated the lipid oxidation reactions of furan fatty acids, long-chain ω-3 polyunsaturated fatty acids, and tocopherols in an enriched ω-3 fish oil to better understand their degradation kinetics. Furthermore, the influence of an added monomethyl furan fatty acid 9-(3-methyl-5-pentylfuran-2-yl) nonanoic acid (9M5) at 50–250 µM on the oxidation reactions was evaluated. The results showed that the fish oil was rich in monomethyl and dimethyl furan fatty acids (c = 1.3 g/100 g lipids). Upon oxidation of the fish oil, the dimethyl furan fatty acids degraded faster than the monomethyl ones, but also faster than tocopherols. The addition of 9M5 revealed antioxidant activity: It inhibited the degradation of the ω-3 polyunsaturated fatty acids and the formation of primary and secondary lipid oxidation products, and slowed down the degradation of the furan fatty acids and tocopherols. This research offers new insights into the importance of furan fatty acids in lipid oxidation reactions. [ABSTRACT FROM AUTHOR]

Cardiovascular disease (CVD) is a major cause of mortality. The effects of several unsaturated fatty acids on cardiometabolic health, such as eicosapentaenoic acid (EPA) docosahexaenoic acid (DHA), α linolenic acid (ALA), linoleic acid (LA), and oleic acid (OA) have received much attention in past years. In addition, results from recent studies revealed that several other uncommon fatty acids (fatty acids present at a low content or else not contained in usual foods), such as furan fatty acids, n -3 docosapentaenoic acid (DPA), and conjugated fatty acids, also have favorable effects on cardiometabolic health. In the present report, we searched the literature in PubMed, Embase, and the Cochrane Library to review the research progress on anti-CVD effect of these uncommon fatty acids. DPA has a favorable effect on cardiometabolic health in a different way to other long-chain n -3 polyunsaturated fatty acids (LC n -3 PUFAs), such as EPA and DHA. Furan fatty acids and conjugated linolenic acid (CLNA) may be potential bioactive fatty acids beneficial for cardiometabolic health, but evidence from intervention studies in humans is still limited, and well-designed clinical trials are required. The favorable effects of conjugated linoleic acid (CLA) on cardiometabolic health observed in animal or in vitro cannot be replicated in humans. However, most intervention studies in humans concerning CLA have only evaluated its effect on cardiometabolic risk factors but not its direct effect on risk of CVD, and randomized controlled trials (RCTs) will be required to clarify this point. However, several difficulties and limitations exist for conducting RCTs to evaluate the effect of these fatty acids on cardiometabolic health, especially the high costs for purifying the fatty acids from natural sources. This review provides a basis for better nutritional prevention and therapy of CVD., Competing Interests: The authors declare no conflict of interest

Because of their antioxidant properties, furan fatty acids (furan-FAs) are valuable minor compounds with a widespread occurrence in all living matter. Unfortunately, pure standards are not readily available, because they usually contribute only 1% to the lipid fraction. A known exception of this is the milky fluid of Hevea brasiliensis, commonly known as latex, in which the furan-FA 9-(3-methyl-5-pentylfuran-2-yl)-nonanoic acid (9M5) contributes about 90% to the triacylglycerides. In this study, we investigated the content of 9M5 in 30 different disposable latex gloves, which ranged from 0.7 to 8.2 mg/g of glove. The light degradability of 9M5 in latex gloves was investigated, and different amounts of 9M5 in disposable latex gloves were attributed to varying exposure time to light. Additionally, over 100 mg of the methyl or ethyl ester of 9M5 (purity of >98%) could be extracted from disposable latex gloves, employing cold extraction and silver ion chromatography. With this method, standards for the quantitation of furan-FAs are obtained easily and rapidly in all laboratories.

Soybean oil is one of the most widely consumed vegetable oils. However, under photooxidative conditions, this oil develops a beany and green off-odor through a mechanism that has not yet been elucidated. Upon photooxidation, 3-methyl-2,4-nonanedione (3-MND) produces a strong aroma. In this study, the effect of furan fatty acids and 3-MND on odor reversion in soybean oil was investigated. Our findings suggest that the observed light-induced off-odor was likely attributable to the furan fatty acids present in the oil through the generation of 3-MND. While 3-MND may not be directly responsible for the development of light-induced off-odor, this compound appears to be involved because off-odor was detected in canola oil samples containing added 3-MND. In addition, in the present work, 3-hydroxy-3-methyl-2,4-nonanedione, which is derived from 3-MND, was identified for the first time in light-exposed soybean oil and shown to be one of the compounds responsible for odor reversion.