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    Cyclic Fatty Acids in Food: An Under-Investigated Class of Fatty Acids

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    Cyclic fatty acids are an unusual class of minor fatty acids generally produced by bacteria and less frequently by plants. Among plants, the most known cyclic fatty acid is sterculic acid (9, 10-methyleneoctadecenoic acid) produced by Sterculia foetida. Bacteria (e.g., lactic acid bacteria) synthetize cyclopropane fatty acids, such as dihydrosterculic acid (9, 10-methylene octadecanoic acid) and lactobacillic acid (11, 12 methylene octadecanoic acid), to strength their membrane, improving their resistance to environmental stress. Another class of cyclic fatty acids is omega-cyclohexyl fatty acids, present in milk and probably produced by rumen bacteria. Cyclopropane and omega-cyclohexyl fatty acids have been recently found in bovine meat and dairy products, representing important foodstuffs in human diet. In this chapter, a review of literature data concerning the presence of cyclic fatty acids in foods, their metabolism in humans, and their potential bioactivity will be provided. The role of some cyclic fatty acids as molecular markers for food authenticity will also be highlighted

    Novel foods/feeds and novel frauds: The case of edible insects

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    Background Novel foods demand in EU is increasing, and their consumption is expected to grow in the next years. This increased use enhances the risk of misidentification and counterfeiting. Scope and approach In this review, the vulnerability to frauds of the incoming edible insect value chain was analysed. The starting point was the regulatory framework in the EU scenario, which encompasses the authorized species for food and/or feed but also the authorized feeding substrates for insects. The market scenario in which insects have been/will be introduced was also analysed. The possible safety issue related to fraud in insect market have been analysed, especially focusing on allergenic risk related to species substitution. The analytical tools currently available to assure insect/rearing substrate authentication have been also evaluated. Key findings and conclusions The key factors making the insect market vulnerable to fraud are the evolving legislative framework, the possible importation of wild/non-authorized species, the use of insect meal/powder in which insects are non-recognizable, the lack of robust and high throughput analytical method. The safety issue, due to the allergenic risk, makes of outmost importance to make steps forward on analytical tools dedicated to insect species and rearing substrates authentication

    Development of a 1H qNMR method for the identification and quantification of monosaccharides in dietary fibre fractions

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    : Recent research has increasingly focused on the health benefits of dietary fibre (DF), including improved digestion, blood glucose and cholesterol regulation, satiety, and prebiotic effects, which depend on the specific DF type. Traditional gravimetric methods (e.g. Van Soest and AOAC) quantify DF fractions but lack molecular or monosaccharide detail. Advanced chromatographic methods offer more insights but require extensive sample preparation. To address this limitation, the study developed a method using proton Nuclear Magnetic Resonance (1H NMR) spectroscopy to directly analyse DF hydrolysed fractions (mainly pectin, hemicellulose, and cellulose) without the need for derivatisation or neutralisation. It provides detailed structural insights, including the monosaccharide composition, carbohydrate modifications (methylation and acetylation), and the degradation products. The method was validated and then applied to hydrolysed DF fractions obtained from the AOAC process. 1H NMR shows a comparable monosaccharide distribution to GC-MS, but yields higher recoveries, particularly for uronic acids. In addition, it offers faster sample preparation and acquisition, making it a powerful tool for comprehensive DF analysis

    An Overview on Cyclic Fatty Acids as Biomarkers of Quality and Authenticity in the Meat Sector

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    peer-reviewedA survey was conducted to determine the content of cyclopropane fatty acids (CPFAs) and ω-cyclohexyl fatty acids (CHFAs) by using gas chromatography- mass spectrometry (GC-MS) and proton nuclear magnetic resonance (1H NMR) techniques in various meat samples from different species, including commercial samples and complex and thermally processed products (i.e., Bolognese sauce). The CPFAs concentration (as the sum of two isomers, namely dihydrosterculic acid and lactobacillic acid) in bovine meat fat (ranging between 70 and 465 mg/kg fat) was positively related to a silage-based diet, and therefore, they are potential biomarkers for monitoring the feeding system of cattle. CHFAs, such as 11-cyclohexylundecanoic and 13-cyclohexyltridecanoic acids, were only found in lipid profiles from ruminant species, and a linear trend was observed in their content, together with iso-branched fatty acids (iso-BCFAs) deriving from ruminal fermentation, as a function of bovine meat percentage in both raw and cooked minced meat. Thus, CHFAs are potential biomarkers for the assurance of the meat species and, combined with iso-BCFAs, of the beef/pork ratio even in complex meat matrices. The proposed approaches are valuable novel tools for meat authentication, which is pivotal in the management of meat quality, safety, and traceability

    Identification of Cyclopropane Fatty Acids in Human Plasma after Controlled Dietary Intake of Specific Foods

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    Cyclopropane fatty acids (CPFAs) are an investigated class of secondary fatty acids of microbial origin recently identified in foods. Even though the dietary daily intake of this class of compounds it has been recently estimated as not negligible, to date, no studies specifically have investigated their presence in human plasma after consumption of CPFA-rich sources. Therefore, the aims of this study were (i) to test CPFAs concentration in human plasma, thus demonstrating their in vivo bioaccessibility and potential bioavailability, (ii) to investigate a dose-response relationship between medium term chronic intake of CPFAs-rich foods and both CPFAs and plasma total fatty acid profiles in healthy subjects. Ten healthy normal weight adults were enrolled for conducting an in vivo study. Participants were asked to follow a CPFA-controlled diet for 3 weeks, consuming 50 g of Grana Padano cheese (GP) and 250 mL of whole cow milk, which correspond to a total of 22.1 mg of CPFAs. Fasting CPFAs concentration were monitored for eight timepoints during the whole study and plasma total fatty acids composition was determined by GC-MS. CPFAs, mainly dihydrosterculic acid (DHSA), were identified in plasma total fatty acids profile at the beginning of the study and after dietary treatment. A significant (p < 0.05) increase of CPFAs mean plasma concentration (n = 10) were observed at the end of the dietary intervention. Contrarily, the total fatty acids composition of the general plasma fatty acids profile did not significantly change (p ≥ 0.05) during the dietary intervention period. This is the first investigation demonstrating that CPFAs are bioaccessible in vivo and, as expected, their plasmatic concentration may be affected by consumption of CPFAs-rich foods. This research will open the door to further detailed research, which may better elucidate the role of these compounds in human health

    Development of a Quantitative GC-MS Method for the Detection of Cyclopropane Fatty Acids in Cheese as New Molecular Markers for Parmigiano Reggiano Authentication

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    Cyclopropane fatty acids (CPFA), as lactobacillic acid and dihydrosterculic acid, are components of bacterial membranes and have been recently detected in milk and in dairy products from cows fed with corn silage. In this paper, a specific quantitative gas chromatography-mass spectrometry (GC-MS) method for the detection of CPFA in cheeses was developed, and the quality parameters of the method (limit of detection, limit of quantitation, and intralaboratory precision) were assessed. Limit of detection and quantitation of CPFA were, respectively, 60 and 200 mg/kg of cheese fat, and the intralaboratory precision, determined on three concentration levels, satisfied the Horwitz equation. This method was applied to 304 samples of PDO cheeses of certified origin, including Parmigiano Reggiano (Italy), Grana Padano (Italy), Fontina (Italy), Comté (France), and Gruyère (Switzerland). Results showed that CPFA were absent in all of the cheeses whose Production Specification Rules expressly forbid the use of silages (Parmigiano Reggiano, Fontina, Comté, and Gruyère). CPFA were instead present in variable concentrations (300-830 mg/kg of fat) in all of the samples of Grana Padano cheese (silages admitted). A mix of grated Parmigiano Reggiano and Grana Padano was also prepared, showing that the method is able to detect the counterfeiting of Parmigiano Reggiano with other cheeses up to 10-20% Grana Padano content. These results support the hypothesis that CPFA can be used as a marker of silage feedings for cheeses, and the data reported can be considered a first attempt to create a database for CPFA presence in PDO cheeses
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