Search Results (155)

(1) Background: This study investigated changes in bioactive components and volatile compounds (VCs) during the production of red millet by comparing two varieties: Miao Xiang glutinous millet (waxy) and Jigu-42 (non-waxy). The samples were solid-state-fermented with “Red Ferment” and evaluated for bioactive components. (2) Methods: Multiple analytical methods—including principal component analysis (PCA), partial least squares-discriminant analysis (PLS-DA) and orthogonal PLS-DA (OPLS-DA), cluster analysis, and correlation analysis—were employed to systematically compare bioactive components and VCs. (3) Results: Significant varietal differences were observed: (1) Miao Xiang glutinous millet showed higher monacolin K (MK) and fatty acid contents; (2) Jigu-42 contained significantly more polyphenols; (3) linoleic acid dominated the fatty acid profiles of two varieties; and (4) a total of twenty-seven VCs were identified, including six alcohols, four aldehydes, seven ketones (corrected from duplicated count), two aromatic hydrocarbons, three heterocycles, one acid, three furans, and one ether. (4) Conclusions: The two varieties exhibited significant differences in MK, pigment profiles, fatty acid composition, polyphenol content, and volatile-compound profiles. These findings provide scientific guidance for the selection of the appropriate millet varieties in functional food production. Full article

N-heterocyclic carbenes (NHCs) have demonstrated their versatility as catalysts for new activations and synthetic transformations of aldehydes. NHCs were originally applied in benzoin condensation and the Stetter reaction, while the development of new protocols under oxidative conditions has further expanded the potential of this methodology for the formation of carbon−carbon and carbon−heteroatom bonds. Among these reactions, NHCs are recognized as promising organocatalysts for the aerobic oxidation of aldehydes to carboxylic acids. However, to our knowledge, a comparison with other metal-free protocols has never been conducted. This review is intended to provide a perspective on aldehyde oxidation into the corresponding carboxylic acid catalyzed by NHCs, from its first practical description in 2009 until the beginning of 2025, and to compare it with other metal-free methods. Full article

In the field of green chemistry, the development of more sustainable and cost-efficient methods for synthesizing primary amines is of paramount importance, with catalyst research being central to this effort. This work presents a facile, aqueous-phase synthesis of highly active cobalt catalysts (Co-Ph@SiO₂(x)) via pyrolysis of silica-supported cobalt–phenanthroline complexes. The optimized Co-Ph@SiO₂(900) catalyst achieved exceptional performance (>99% conversion, >98% selectivity) in the reductive amination of acetophenone to 1-phenylethanamine using NH₃/H₂. Systematic studies revealed that its exceptional performance originates from the in situ pyrolysis of the cobalt–phyllosilicate complex. This process promotes the uniform distribution of metal cobalt nanoparticles, simultaneously enhancing porosity and imparting bifunctional (acidic and basic) properties to the catalyst, resulting in outstanding catalytic activity and selectivity. The catalyst demonstrated broad applicability, efficiently converting diverse ketones (aryl-alkyl, dialkyl, bioactive) and aldehydes (halogenated, heterocyclic, biomass-derived) into primary amines with high yields (up to 99%) and chemoselectivity (>40 examples). This sustainable, non-noble metal-based catalyst system offers significant potential for industrial primary amine synthesis and provides a versatile tool for developing highly selective and active heterogeneous catalysts. Full article

Kujingcha (KJC) is a widely consumed substitute tea due to its unique flavor quality and health benefits. However, the biochemical basis for the formation of KJC’s unique flavor quality and health benefits remain unclear. In this study, using Camellia sinensis green tea and its processed fresh leaves as a control, we systematically analyzed the non-volatile and volatile components in KJC and its processed fresh leaves. The results indicate that high levels of flavonoids and water-soluble sugars, and low levels of amino acids and water-soluble proteins, are important biochemical foundations for the formation of taste quality in KJC. High aldehyde, alkene and heterocyclics contents contribute significantly to the aroma of KJC, among which heterocyclics are the key components for the formation of KJC’s rich pan-fried bean-like aroma. Flavonoids such as neohesperidin, hyperoside, rutin, astilbin and morin are important components for the formation of KJC’s health benefits. Full article

Monoterpenes and their derivatives are important starting compounds in the design of new biologically active substances. In particular, cineole, isolated from eucalyptus essential oil, exhibits a wide range of biological activities. Here, the synthesis of new heterocyclic compounds containing a cineole fragment by the acid-catalyzed condensation of α-pinene-derived 8-hydroxy-6-hydroxymethyllimonene with monoterpene aldehydes was carried out for the first time. The reactions of 8-hydroxy-6-hydroxymethyllimonene with cuminaldehyde, perillylaldehyde, myrtenal, citral, and geranial were studied in the presence of heterogeneous K10 clay or Lewis acid BF₃·Et₂O. The main products of these reactions were compounds with the methanopyrano[4,3-b]pyran scaffold having a 1,8-cineole fragment. As a result of this work, five new compounds with the methanopyrano[4,3-b]pyran scaffold were synthesized. The use of BF₃·Et₂O led to an increase in the yields of target products, compared with the results obtained on K10 clay. Full article

Tetrasubstituted furans and their derivatives represent a versatile class of important heterocyclic frameworks widely distributed in natural products. These scaffolds also demonstrate significant potential in pharmaceutical chemistry, materials science, and organic synthesis methodologies. In this study, we successfully established a synergistic catalytic system utilizing benzoylacetonitriles, aldehydes, and benzoyl chlorides as substrates, facilitated by tributylphosphine and immobilized lipase (Novozym 435), to achieve efficient synthesis of cyano-containing tetrasubstituted furans. Under optimized conditions, we obtained a series of target products exhibiting exceptional substrate tolerance with good to excellent isolated yields ranging from 80% to 94%. Additionally, we proposed a reasonable reaction mechanism and verified it through controlled experiments. This methodology not only expands the synthetic utility of lipase in non-natural transformations but also establishes a paradigm of green chemistry for the construction of tetrasubstituted furans. Full article

Exercise is one of the main challenges to the body’s homeostasis since it needs an immediate, substantial rise in ATP re-synthesis, which leads to the prevention of response capacity and performance of players. Therefore, it is vital to monitor sweat metabolites in soccer players during vigorous exercise to comprehend their functional variations. This flagged the requirement metabonomic approaches for the determination of the distinct metabolic pathways and signature metabolites that are involved in soccer players pre- and post-exercise. In this study, metabolomics and chemometrics approaches were integrated to accelerate and unravel signature-altered metabolites involved pre- and post-exercise. Metabolites profiling revealed a total of 57 signatures and the identified signature altered metabolites belonging to carboxylic acids, ketone, alcohols, aldehydes, aromatics, alkenes, hexoses, hydroxy fatty acids, tetracyclic N-heterocycles, aldopentose, benzenes, alkanes, phenols, and heterocyclic. Niacin is the most downregulated and abundant pre-induced exercise, which can employ its effects through energy metabolism as a precursor for nicotinamide adenine dinucleotide (NAD) and nicotinamide adenine dinucleotide phosphate (NADP). Significant alterations were also specifically observed in the Alanine, aspartate and glutamate, Valine, leucine and isoleucine, Pantothenate and CoA biosynthesis, and Galactose metabolisms following exercise. Full article

Microalgae are among the most promising feedstocks for a wide range of applications due to their ease of cultivation, rapid growth rate, and ability to accumulate significant amounts of lipids and other valuable compounds. In the current study, two microalgae species, Chlorella sp. and Spirulina platensis, were studied regarding chemical composition, lipid extraction by ultrasound-assisted solvent extraction, and volatile compounds analysis. The optimization of the lipid extraction process was investigated with respect to the influence of different process parameters. The highest lipid content was found in Chlorella sp., which was more than twice as high compared to Spirulina platensis. Both microalgae contain saturated fatty acids (SFAs), monounsaturated fatty acids (MUFAs), and polyunsaturated fatty acids (PUFAs). Spirulina platensis contains high palmitic acid (42.9%) and linolenic acid (22.5%), and is low in MUFA content (8.5%), whereas Chlorella sp. contains high oleic (21.9%), linoleic (25.3%), and α-Linolenic acid (10.2%). Based on the fatty acids profile, nutritional lipid indices were calculated. Regarding the volatile content, Spirulina platensis contains amines, aldehydes, alcohols, ketones, and hydrocarbons, whereas Chlorella sp. contains hydrocarbons, heterocycle, aldehydes, thiocyanates, and esters which give the odor profile. Full article

To investigate the formation of flavor compounds in sheep bone soup, E-nose, gas chromatograph (GC), and gas chromatography-mass spectrometry (GC-MS) were used to determine the changes in lipid oxidation, Maillard reaction, and volatile flavor compounds during the slow cooking process of 4 h. The thiobarbituric acid reactive substances (TBARS) value began to increase significantly (p < 0.05) after 2 h of cooking, reaching its peak in the third hour before significantly decreasing. The intensity of the Maillard reaction significantly increased after 2 h of cooking and subsequently stabilized. Thirty-nine flavor compounds were identified, primarily comprising aldehydes, ketones, alcohols, esters, aromatic compounds, and heterocyclic compounds. The formation of volatile flavor compounds in sheep bone soup was associated with lipid oxidation, particularly the oxidation of unsaturated fatty acids, and the Maillard reaction. Lipid oxidation produced a large number of volatile flavor compounds, such as aldehydes and ketones. The Maillard reaction gave sheep bone soup a certain flavor. Aldehydes were mostly influenced by cooking time, becoming the main flavor compounds in the bone soup after 2.5 h of cooking, accounting for more than half of the total volatile flavor compounds. The highest content and richest profile of volatile flavor compounds were obtained in the soup cooked for 2.5 h and 3 h. This study provides a theoretical basis for the flavor regulation of sheep bone soup. Full article

American ginseng (AG) has long been used as an ingredient in the food and pharmaceutical industries because of its nutritional and economic value. AG is rich in nutrients, and its quality is greatly affected by how it is processed. However, there is a relative paucity of research on the comprehensive evaluation of different processing techniques of AG. This study evaluated the differences in quality formation and properties of low-temperature softened, blanched, steamed followed by hot air drying, and vacuum freeze-dried AG (LTS-HAD, BL-HAD, ST-HAD, and VFD, respectively). The results demonstrated that AGs treated with VFD had the fastest drying time (85 h) and succeeded in preserving the color and microstructure of fresh ginseng. The contents of ginsenoside Rg1 and Rb1 in LTS-HAD samples were 2.81 ± 0.01 mg/g and 10.68 ± 0.66 mg/g, respectively, which were significantly higher than those in VFD samples (p < 0.05). Moreover, ST-HAD samples had an attractive reddish-brown appearance and higher antioxidant activity. Simultaneously, the formation of the ginsenosides Rg6, (S) Rg3, (R) Rg3, Rk1, and Rg5 was discovered. BL-HAD samples had an intermediate quality among the above samples. A total of 58 volatile compounds were identified, including aldehydes (14), alcohols (13), ketones (10), esters (6), terpenes (6), acids (5), and heterocyclic compounds (4). PCA of ginsenosides and volatile components, as well as correlation analysis with color and antioxidant activity, resulted in the identification of different processed products and potential bioactive components. Full article

To compare the impact of different post-harvest handling methods on volatile and non-volatile compounds, a total of 54 live large yellow croakers were subjected to commercial slaughter (CS), spinal cord cutting (SCC), or spinal cord cutting and bleeding (SCCB). The fish samples were ice-stored for 72 h, followed by the analysis of volatile compounds using gas chromatography–ion mobility spectrometry and non-volatile compounds using LC-MS-based untargeted metabolomics. The results revealed the detection of a total of 28 volatile organic compounds, with 23 being successfully identified, predominantly including alcohols, aldehydes, esters, ketones, and heterocyclic compounds. Substances such as (E)-2-nonenal and 2-butanone are highly sensitive to post-harvest handling methods during ice storage. Furthermore, 943 non-volatile metabolites were identified, showing significant differences in 180, 100, 117, and 186 metabolites across comparisons of SCC 0 h/CS 0 h, SCCB 0 h/CS 0 h, SCC 72 h/CS 72 h, and SCCB 72 h/CS 72 h, respectively. Notably, the altered metabolic pathways mainly involved fatty acid and amino acid metabolism, including pathways like glycerophospholipid metabolism and arginine biosynthesis. This study revealed the potential mechanisms underlying the enhancement of fish quality through spinal cord cutting and bleeding. Full article

Background: Black tea processing conditions significantly affect the final taste and flavor profiles, so researchers are now focusing on developing equipment and improving the appropriate processing conditions of major black tea varieties. Methods: Here, we tested the effect of four different initial drying temperatures, i.e., R65 (65 °C), R85 (85 °C), R105 (105 °C), and R125 (125 °C), on the sensory and biochemical profiles and volatilome of the black tea variety “Lishui wild” (LWV). Results: Our results indicate that both 85 and 105 °C are better than 65 and 125 °C for initial drying for 20 min. R105 had the highest sensory evaluation scores due to better shape, aroma, taste, leaf base, thearubigins, theanine, caffeine, and ratio of theaflavins + thearubigins to theaflavins. Both R85 and R105 had higher catechins than R65 and R125. The LWV volatilome consisted of esters (19.89%), terpenoids (18.95%), ketones (11.3%), heterocyclic compounds (9.99%), and alcohols (8.59%). In general, acids, aldehydes, amines, aromatics, ethers, hydrocarbons, phenols, sulfur compounds, and terpenoids accumulated in higher amounts in R85 and R105. The highly accumulated compounds in R105 were associated with green, fruity, sweet, woody, floral, hawthorn, mild, nutty, powdery, rose, and rosy flavors. The main pathways affected are secondary metabolites, sesquiterpenoid and triterpenoid biosynthesis, glycerolipid metabolism, zeatin biosynthesis, phenylpropanoid biosynthesis, ABC transport, glutathione metabolism, etc. Therefore, R105 can be used to achieve the optimal taste, flavor, and aroma of LWV. Conclusions: Overall, the presented data can be used by the tea industry for processing black tea with the most optimum volatile substances, catechins, theanine, amino acids, and other compounds. Full article

The present study aims to perform a comparative analysis of the chemical composition and thermal behavior of two distinct milk types, namely animal and plant-based. The thermal analysis revealed the presence of the following classes of compounds: hydrocarbons, heterocycles, aldehydes, ketones, amines and alcohols. All types of milk contain saturated fatty acids (SFAs), monounsaturated fatty acids (MUFAs) and polyunsaturated fatty acids (PUFAs), though the relative proportions of these vary depending on the specific milk type. Animal milk powders contain SFAs, including palmitic, stearic, and myristic acids, as well as moderate amounts of MUFAs, such as oleic and palmitoleic acids. They also contain lower PUFAs, including linoleic and alpha-linolenic acids. In contrast, plant-based milk powders, particularly soy milk powder, are rich in both linoleic and alpha-linolenic acids. Plant-based milk typically exhibits lower levels of SFAs and higher levels of MUFAs and PUFAs when compared to milk of animal origin. In conclusion, the fatty acid profiles of animal and plant-based milk powders reflect the different nutritional attributes and health implications associated with each. Thermal behavior analysis offers insights into the stability and potential flavor changes that may occur during processing and storage. The comparative analysis highlights significant differences in the chemical composition and thermal behavior of animal and plant-based milk powders. Full article

A new approach to 1,2,5-trisubstituted 1H-indole-3-carboxylic esters has been developed and studied. The method begins with the preparation of imines from aldehyde and primary amine derivatives. Treatment of these imines with the K₂CO₃-derived anion from methyl 2-(2-fluoro-5-nitrophenyl)acetate or methyl 2-(5-cyano-2-fluorophenyl)acetate in DMF initiates a [3+2] cyclization by addition of the anion to the imine followed by ring closure of the adduct nitrogen to the activated aromatic moiety via an S_NAr process. Twenty-one examples are reported. Temperatures required for the conversion range from 90 to 95 °C for the nitro-activated substrates to 125 to 130 °C for the cyano-activated precursors. Though efficient and atom economical, limitations arise from steric hindrance in the reacting partners. The initial indoline formed is not observed but instead undergoes spontaneous air oxidation to the give the aromatic heterocycle. Imines from nonaromatic aldehydes and amines are also possible, but these give slightly lower yields of 1H-indoles and only react with the nitro-activated substrates. The results are presented with a discussion of the mechanism and the factors important to the success of the reaction. Full article

To investigate the source of the bitter almond taste in whole corn silage (WPCS), headspace solid-phase microextraction combined with gas chromatography–mass spectrometry (HS-SPME-GC-MS), headspace gas chromatography–ion migration spectrometry (HS-GC-IMS), and electronic nose (E-nose) technology were employed. The study analyzed the differences in volatile compounds between two WPCS samples with distinct odors from the same cellar. GC-IMS and GC-MS identified 32 and 101 volatile organic compounds (VOCs), respectively, including aldehydes, alcohols, esters, ketones, and other compounds. Three characteristic volatile organic compounds associated with the bitter almond taste were detected: benzaldehyde, cyanide, and isocyanate. The electronic nose demonstrated varying sensitivities across its sensors, and principal component analysis (PCA) combined with variable importance projection (VIP) analysis revealed that W5S (nitrogen oxides) could differentiate between the two distinct silage odors. This finding was consistent with the GC-MS results, which identified 34 nitrogen-containing heterocyclic compounds in the abnormal silage sample, accounting for 77% of the total nitrogen-containing compounds. In summary, significant differences in aroma composition were observed between the bitter almond-flavored silage and the other silage in the same cellar. These differences were primarily attributed to changes in volatile organic compounds, which could serve as indicators for identifying bitter almond-flavored silage. Full article