Thermal degradation of 2-furoic acid and furfuryl alcohol as pathways in the formation of furan and 2-methylfuran in food

Delatour, Thierry; Huertas-Pérez, José F.; Dubois, Mathieu; Theurillat, Xanthippe; Desmarchelier, Aurélien; Ernest, Marion; Stadler, Richard H.

doi:10.1016/j.foodchem.2019.125406

Cited by 40 publications

(24 citation statements)

References 36 publications

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“…Furthermore, methylmalonic acid, 2-furoic acid, 3-phenyllactic acid, and 3-hydroxypropionic acid were clustered in HS Xiaoqu. The decarboxylation of 2furoic acid was confirmed as an alternative pathway in the formation of furan in heat-treated foods (Delatour et al, 2019), whereas 3-phenyllactic acid, which is widely present in fermented foods, has highly effective and broad-spectrum antimicrobial activity (Xu et al, 2020). However, we did not observe any dominant organic acids in AS Xiaoqu.…”

Section: Analyses Of Non-volatile Metabolitesmentioning

confidence: 55%

Integrative Metagenomics–Metabolomics for Analyzing the Relationship Between Microorganisms and Non-volatile Profiles of Traditional Xiaoqu

Zhao

et al. 2021

Front. Microbiol.

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Xiaoqu, one of three traditional jiuqu in China, is a saccharifying and fermenting agent used in Xiaoqu jiu brewing, with different ingredient compositions and preparation techniques used in various regions. The yield and quality of Xiaoqu jiu are significantly affected by the metabolites and microbiota of Xiaoqu; however, the associated relationship remains poorly understood. This study aimed to analyze this relationship in three typical traditional Xiaoqu from the Guizhou province in China. The non-volatile metabolites of Xiaoqu were detected using gas chromatography time-of-flight mass spectrometry, whereas the classification and metabolic potential of the microbiota were investigated using metagenomic sequencing. Results show that Firmicutes, Proteobacteria, and Actinobacteria represent the dominant bacterial phyla, with Lactobacillus, Bacillus, Acinetobacter, Leuconostoc, and Weissella found to be the dominant bacterial genera. Meanwhile, Ascomycota, Mucoromycota, and Basidiomycota are the dominant fungal phyla with Aspergillus, Saccharomyces, Pichia, Rhizopus, and Phycomyces being the predominant fungal genera. Functional annotation of the microbiota revealed a major association with metabolism of carbohydrates, cofactors, and vitamins, as well as amino acids. A total of 39 significantly different metabolites (SDMs) were identified that are involved in 47 metabolic pathways, primarily that of starch and sucrose; glycine, serine, and threonine; glyoxylate and dicarboxylate; pyruvate; as well as biosynthesis of pantothenate and CoA. Further, based on Spearman's correlation analysis, Aspergillus, Saccharomyces, Lactobacillus, Acetobacter, Weissella, Pantoea, Desmospora, and Bacillus are closely correlated with production of physicochemical indexes and SDMs. Moreover, the metabolic network generated for the breakdown of substrates and formation of SDMs in Xiaoqu was found to primarily center on the metabolism of carbohydrates and the tricarboxylic acid cycle. These results provide insights into the functional microorganisms and metabolic patterns present in traditional Guizhou Xiaoqu and might guide researchers in the production of stable and efficient Xiaoqu in the future.

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Section: Analyses Of Non-volatile Metabolitesmentioning

confidence: 55%

Integrative Metagenomics–Metabolomics for Analyzing the Relationship Between Microorganisms and Non-volatile Profiles of Traditional Xiaoqu

Zhao

et al. 2021

Front. Microbiol.

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“…UV light also resulted in the formation of furan (60 ng/mL) in apple cider (Hu et al., 2016). A recent study showed that furan can be formed from the decarboxylation of 2‐furoic acid (2‐FA) (Delatour et al., 2020).…”

Section: Mechanism Of Furan Formationmentioning

confidence: 99%

Formation of furan in baby food products: Identification and technical challenges

Javed

Shahbaz

Nawaz

et al. 2021

Comp Rev Food Sci Food Safe

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Furan is generally produced during thermal processing of various foods including baked, fried, and roasted food items such as cereal products, coffee, canned, and jarred prepared foods as well as in baby foods. Furan is a toxic and carcinogenic compound to humans and may be a vital hazard to infants and babies. Furan could be formed in foods through thermal degradation of carbohydrates, dissociation of amino acids, and oxidation of polyunsaturated fatty acids. The detection of furan in food products is difficult due to its high volatility and low molecular weight. Headspace solid‐phase microextraction coupled with gas chromatography/mass spectrometer (GC/MS) is generally used for analysis of furan in food samples. The risk assessment of furan can be characterized using margin of exposure approach (MOE). Conventional strategies including cooking in open vessels, reheating of commercially processed foods with stirring, and physical removal using vacuum treatment have remained unsuccessful for the removal of furan due to the complex production mechanisms and possible precursors of furan. The innovative food‐processing technologies such as high‐pressure processing (HPP), high‐pressure thermal sterilization (HPTS), and Ohmic heating have been adapted for the reduction of furan levels in baby foods. But in recent years, only HPP has gained interest due to successful reduction of furan because of its nonthermal mechanism. HPP‐treated baby food products are commercially available from different food companies. This review summarizes the mechanism involved in the formation of furan in foods, its toxicity, and identification in infant foods and presents a solution for limiting its formation, occurrence, and retention using novel strategies.

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“…Furan is a colorless toxic chemical produced in various food items during heat processing and in some industrial processes (Delatour et al, 2020;Rehman et al, 2019;Morehouse et al, 2018;Sirot et al, 2019). It has been reported that furan can induce oxidative stress, endocrine disruption and toxic effects on the reproductive system of male rats (Rehman et al, 2019).…”

Section: Chemical Contextmentioning

confidence: 99%

Crystal structure ofN′-[4-(dimethylamino)benzylidene]furan-2-carbohydrazide monohydrate

et al. 2020

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The condensation of 2-furoic hydrazide and 4-dimethyl aminobenzaldehyde in ethanol yielded a yellow solid formulated as the title compound, C14H15N3O2·H2O. The crystal packing is stabilized by intermolecular O(water)—H...O,N(carbohydrazide) and N—H...O(water) hydrogen bonds, which form a two-dimensional network along the bc plane. Additional C—H...O interactions link the molecules into a three-dimensional network. The dihedral angle between the mean planes of the benzene and the furan ring is 34.47 (6)°. The carbohydrazide moiety, i.e., the C=N—N—C=O fragment and the benzene ring are almost coplanar, with an angle of 6.75 (9)° between their mean planes.

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Thermal degradation of 2-furoic acid and furfuryl alcohol as pathways in the formation of furan and 2-methylfuran in food

Cited by 40 publications

References 36 publications

Integrative Metagenomics–Metabolomics for Analyzing the Relationship Between Microorganisms and Non-volatile Profiles of Traditional Xiaoqu

Integrative Metagenomics–Metabolomics for Analyzing the Relationship Between Microorganisms and Non-volatile Profiles of Traditional Xiaoqu

Formation of furan in baby food products: Identification and technical challenges

Crystal structure ofN′-[4-(dimethylamino)benzylidene]furan-2-carbohydrazide monohydrate

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