Analogous Products Research Articles

Alternative Protein-Based Meat and Fish Analogs by Conventional and Novel Processing Technologies: A Systematic Review and Bibliometric Analysis

This study aimed to explore the extent of research on developing meat and fish analogs using alternative proteins. It examined the novel and conventional technologies employed to produce these analogs and identified the primary alternative proteins that were used in their production through a systematic literature review (SLR) using Preferred Reporting Items for Systematic Reviews and Meta-Analyses (PRISMA) and bibliometric analysis. The SLR resulted in 46 and 13 meat and fish analog records, respectively, according to defined selection and exclusion criteria. Meat analogs are mainly produced using extrusion, followed by the novel 3D printing and mixing technology. Additionally, fish analogs are mainly produced by mixing and 3D printing. Meat analogs are mainly produced from pulses, followed by cereal, fungi, microalgae, other sources, and insects. Similarly, pulse proteins were the most used alternative protein source for the fish analogs, followed by macro- and microalgae, plant, cereal, and fungal proteins. According to keyword analysis, rheological and textural properties are essential for meat and fish analogs. This review provides up-to-date information to clarify the critical role of alternative proteins and the utilization of novel technologies in the production of meat and fish analogs. It also gives essential insights into the expected increase in studies to determine sustainability and overcome challenges related to textural, sensorial, and nutritional properties.

Development of a Highly Selective Synthesis of 4–Substituted Tetrahydroquinolines: Substrate Scope and Mechanistic Study

Herein, we describe a general and selective deprotonation functionalization reaction of tetrahydroquinolines at the 4–position using organolithiums and phosphoramide ligands. In addition to the development of a direct deprotonation alkylation reaction with primary and secondary alkyl halides, a Negishi cross–coupling protocol was realized to afford products with a range of aromatic halides. These methods were applied to the late‐stage installation of tetrahydroquinolines into a variety of substrates including pharmaceuticals as well as natural product analogues. The use of thorough mechanistic investigations revealed the aggregation state of the newly formed tetrahydroquinoline anion to be a separated ion pair, which proved critical to optimizing the reaction conditions.

Analysis of Volatile Profile of Polish Gouda-Type Cheese and Its Analogue

Gouda-type cheese originated in the Netherlands, but is now produced all over the world. Analogue cheeses are cheese-like products with a lower price level that are based on non-dairy fats and proteins. The market demand for analogue cheese is currently also growing due to customers’ preference for low-fat foods. In this report, samples of Gouda-type cheese and its analogues produced by a dairy cooperative (Warmian-Masurian Voivodeship, Poland) were used as the subject of analysis; their volatile profiles were analyzed by gas chromatography coupled with mass spectrometry (GC-MS). In addition, measurements were carried out using a low-cost electronic nose based on MOX sensors. The results showed a richer chemical composition of the cheese volatiles compared to the analogue product. The measurements with the electronic nose made it possible to differentiate between the sample categories but also revealed similarities between them. The research demonstrated that both methods could be used for the assessment of the volatile profiles of the products.

3-Halo-3-nitro-aza/thioflavanones: DNMT inhibitors with a two-site binding mode in the hDNMT3A catalytic pocket

Flavonoid derivatives are natural product analogues that have shown great interest for therapeutic applications as modulators of DNA methylation. In this article we report new synthesis pathways to access ten novel flavonoid derivatives (i.e. 3-halo-3-nitro-aza/thioflavanones) to be used as potential DNA methyltransferase inhibitors. These compounds have a micromolar inhibition against human DNA methyltransferase 3A in our in vitro fluorescence-based assay. Importantly, a docking study of representative compounds of this series in the enzyme pocket highlights a mode of interaction in the catalytic pocket of hDNMT3A that has never been described.

Biocatalytic diversification of abietic acid in Streptomyces.

Biocatalysis provides access to synthetically challenging molecules and commercially and pharmaceutically relevant natural product analogs while adhering to principles of green chemistry. Cytochromes P450 (P450s) are amongst the most superlative and versatile oxidative enzymes found in nature and are desired regio- and stereoselective biocatalysts, particularly for structurally complex hydrocarbon skeletons. We used 10 genome-sequenced Streptomyces strains, selected based on their preponderance of P450s, to biotransform the bioactive diterpenoid abietic acid. We isolated and structurally characterized seven oxidized abietic acid derivatives from three different strains, including four products that are new bacterial biotransformants or enzymatic products. Oxidations (hydroxylation, dehydrogenation, and aromatization) were seen on both the B and C rings of abietic acid and five products had multiple modifications. Notable conversions observed in the study was that of abietic acid to 15-hydroxy-7-oxo-8,11,13-abietatrien-18-oic acid, 7, which involves multiple hydroxylation reactions and dehydrogenation. The findings from this study will lead to identifying P450s or other enzymes that may act as general biocatalysts to modify abietanes and other labdane-type diterpenoid skeletons.

Nutritional Quality of Plant-Based Fish and Seafood Analogs: A Study of the Italian Market

Among plant-based analogs, fish and seafood analogs (PBFSAs) represent a growing sector. This study analyzed the nutritional quality of PBFSAs in Italy and compared it to their animal-based counterparts. Nutritional declarations, ingredient lists, and claims were collected from PBFSA food labeling. Nutri-Scores of PBSFAs and animal-based counterparts were also determined as nutritional quality indicators. Fifty-one products were collected, with most attributed to tuna, salmon, and cod categories (n = 18, 12, and 14, respectively). Results showed large heterogeneity in nutritional quality, with cod products having higher energy (217 (201–257) kcal/100 g), protein (10.5 (7.9–13.0) g/100 g), and carbohydrate (19.4 (14.2–26.0) g/100 g) levels, while tuna and salmon products had a higher fat content (15.0 (10.0–19.7) and 13.5 (5.0–17.0) g/100 g, respectively). Products with fiber or fat nutrition claims did not necessarily indicate higher fiber or lower fat content, while products with a protein claim had a higher protein content. Most animal-based counterparts, except cod and sturgeon caviar, received an “A” Nutri-Score, and often scored better than the PBSFA due to lower salt content. In conclusion, PBFSAs on the market should not be considered animal product analogs regarding nutritional quality, but drawing definitive conclusions is challenging due to the limited number and high variability of the products. However, these findings provide insights that may improve PBFSA nutritional quality, such as decreasing salt and sugar content, for people trying to incorporate such foods into their diet.

Multiple Enzymes Expressed by the Gut Microbiota Can Transform Typhaneoside and Are Associated with Improving Hyperlipidemia.

The mechanism of multiple enzymes mediated drug metabolism in gut microbiota is still unclear. This study explores multiple enzyme interaction process of typhactyloside (TYP) with gut microbiota and its lipid-lowering pharmacological activity. TYP, with bioavailability of only 2.78%, is an active component of Typha angustifolia L. and Pushen capsules which is clinically treated for hyperlipidemia. The metabolic process of TYP is identified, and key enzymes involved in TYP metabolism are validated through gene knockout and overexpression techniques. Through overexpressing α-rhamnosidase (Rha) in Escherichia coli, TYP is verified to metabolize into isorhamnetin-3-O-neohesperidin (M1) and isorhamnetin-3-O-glucoside (M2) after removing rhamnose through Rha. Besides, knockout of β-glucosidase (Glu) confirms that TYP generates M3 through Glu after removing glucose. Combined with molecular docking, M3 is transformed to generate 3,4-dihydroxyphenylacetic acid (M4), protocatechuic acid (M5), and 3-hydroxyphenylacetic acid (M6) through flavonoid reductase (Flr) and chalcone isomerase (Chi). In conclusion, multiple enzymes involved in TYP metabolism (Rha/Glu→Flr→Chi) are identified. Through in vivo experiments, combined use of M3 and M5 also shows excellent anti-hyperlipidemia efficacy. This is the first study on complex metabolism mechanism and pharmacological activity of natural flavonoids mediated by multiple enzymes, which provide insight to investigate analogous natural products.

Production of prototype lab-scale oak barrel analogues using additive manufacturing

Production of prototype lab-scale oak barrel analogues using additive manufacturing

Selective separation of tanshinone homologs by biocomposite membranes based on poly(ionic liquids) and natural fibers.

Membranes have been used as versatile tools for the separation of various natural products; however, the selective separation of structural analogs of natural products using membranes remains challenging. In this study, biocomposite membranes based on poly(ionic liquids) and different natural fibers (jute, cotton, or wool) were successfully prepared. Natural fibers can regulate the microstructure and improve the mechanical properties of membranes. Fourier transform infrared spectroscopy, nuclear magnetic resonance spectroscopy, scanning electron microscopy, X-ray photoelectron spectroscopy, atomic force microscopy, Brunauer-Emmett-Teller analysis, and thermo gravimetric analysis were used to characterize the membranes. The membranes were used to separate tanshinone homologs (tanshinone I, tanshinone IIA, cryptotanshinone, and dihydrotanshinone I), allowing cryptotanshinone to penetrate the membrane while rejecting tanshinone I. A maximal selectivity of 44.57% was obtained for the tanshinone homologs using a one-step separation protocol. These poly(ionic liquids)/natural fiber membranes possess high water flux, good self-cleaning, and good antibacterial properties. The membranes were effective in separating tanshinone homologs and have the potential to separate other natural homologs.

Engineering terpene synthases and their substrates for the biocatalytic production of terpene natural products and analogues.

Terpene synthases produce a wide number of hydrocarbon skeletons by controlling intramolecular rearrangements of allylic pyrophosphate subtrates via reactive carbocation intermediates. Here we review recent research focused on engineering terpene synthases and modifying their substrates to rationally manipulate terpene catalyisis. Molecular dynamic simulations and solid state X-ray crystallography are powerful techniques to identify substrate binding modes, key active site residues for substrate folding, and the location of active site water. Variants in specific 'hotspots' of terpene synthases including the G1/2, K/H and Hα-1 helices have been targeted to modify active site water management and yield new products. We discuss the potential of exploiting substrate analogues to synthesise novel compounds and briefly outline biphasic flow systems for biocatalysis of terpenes. We forsee greater applications for terpenes as the field converges on effective methods for engineering of terpene synthases by new computational and high throughput experimental methods and for high-yield production. It is crucial when engineering terpene synthases that both product distribution and enzyme activity are simultaneously optimised.

Key epigenetic enzymes modulated by natural compounds contributes to tumorigenicity.

Dysregulation of epigenetic regulation is observed in numerous tumor cells. The therapeutic effects of natural products on tumors were investigated through a comprehensive analysis of active ingredients derived from various structured natural products. The analysis focuses on regulating key enzymes involved in epigenetic control. To study the modulation of these enzymes for tumor treatment, the structural characteristics of natural products that impact tumorigenesis were identified. The presence of specific patterns suggests that compounds sharing structural similarities can potentially induce therapeutic effects on identical tumors through modulation of distinct modifying enzymes. Structurally analogous natural products can likewise achieve therapeutic effects across diverse tumor types via their interaction with a common epigenetic enzyme. There exist numerous flavonoids with the capability to modulate METTL3, thereby influencing the development of various tumors. The normalization process was implemented to account for a common phenomenon, wherein structurally distinct compounds effectively target the same tumor by modulating a shared key enzyme. By summarizing, valuable insights into the role of compound-epigenetic enzymes in tumor development have been obtained. This discovery establishes a crucial scientific foundation for the prevention and treatment of tumor development through the utilization of structurally similar natural active ingredients.

Mechanochemistry Metal-Free Synthesis and Molecular Modeling Study of 4-Arylamino-1,2-naphthoquinones by Csp2-Csp2 Bond Formation

The present work explores the mechanochemical synthesis and computational study of C–C bond formation at the C-4 position of sodium 1,2-naphthoquinone-4-sulfonate (1, β-NQSNa) with dialkylanilines (2a-2f). This is the first example of using mechanochemistry without transition metal catalysts and solvents to produce 4-(4-(dialkylamino)phenyl)naphthalene-1,2-dione (3a-3f) from symmetric and non-symmetric N,N’-dialkylanilines in good to moderate yields. Preliminary, computational studies were conducted to explain the use of sterically hindered and less hindered anilines, which caused variations in the yields of the analogous products, suggesting the formation of π-π interactions between the anilines and the B ring of the naphthoquinone. Molecular modeling was performed using density functional theory (DFT), employing the hybrid functional M06-2X and the polarized valence triple-zeta basis set augmented for improved correlation (aug-cc-pVTZ).

S‐Nucleophilic Imidazoline Ring Expansion: a Novel Approach to the Formation of Medium‐Sized Thiolactames

AbstractA novel method has been successfully developed for the synthesis of medium‐sized heterocycles containing thioamide groups. This approach facilitates the expansion of the imidazoline moiety within the condensed ring system through the action of S‐nucleophiles, enabling access to a broader and more diverse chemical space for natural product analogs and bioactive compounds. A series of [1,4,7]thia‐(oxa−)diazecin‐9‐thiones were efficiently synthesized from diarene‐fused [1.4]heteroazepines using this transformation, achieving yields ranging from 28–58 %.

Modulation of adzuki (Vigna angularis) bean milk analog substrates and metabolites through singular and/or combined treatment of germination and lactic acid fermentation.

Given the growing interest in dairy-free milk analog products, new and diversified alternatives are pivotal to push the market forward. Germination and fermentation are traditional processing technologies used in plant-based milk production. However, the combination of both has not been extensively investigated. The aim of this study was to investigate the potential combined beneficial effects of coupling germination and fermentation on selected substrates and metabolites in adzuki bean milk analog. It was found that germination increased essential amino acids to 1193.44 from 421.46mg/L in control while raising simple sugar and "green" (green odor) volatile compounds. Fermentation with probiotic Limosilactobacillus fermentum enriched the adzuki bean milk analog with probiotics and organic acids, whereby it also reduced some free amino acids (especially arginine) and "green" volatiles. Germination coupled with fermentation was able to overcome the deficiencies of the respective single treatment by elevating essential amino acid content (with a 4.8-fold increase in lysine and a 3.8-fold increase in histidine) and removing "green" odor volatiles while biofortifying the bean milk with probiotics, organic acids, and vitamin (nicotinic acid). Overall, a combination of germination and fermentation merits further research for substrate and metabolite modulation to develop novel and nutritious plant-based milk analogs with desirable flavor.

Comparison of Physical, Sensorial, and Microstructural Properties to Assess the Similarity Between Plant- and Animal-Based Meat Products

The aim of this study was to compare the physical, sensorial, and microstructural properties of selected meat products with their plant-based alternatives to assess how closely the alternatives mimic the original products. Six meat analogue products, including Frankfurter sausage (SuA), steak (StA), Hungarian sausage (KA), minced meat (MA), salami (SaA), and burger (BA), were compared with their corresponding meat products (SuM, StM, KM, MM, SaM, and BM, respectively). The study measured colour indicators, texture parameters, sensory attributes, and microstructural properties. The redness values (a*) of the external surfaces of SuM and KM, as well as the hardness of MM, were similar to those of their alternative products, with no statistically significant differences (p > 0.05). Sensory evaluation revealed similar ratings for two attributes: product similarity and overall appearance. However, significant differences were found in the descriptors for animal character and meat taste.

Methodologies of meat analogue production and nutritional perspectives: a review

With increasing global population and environmental concerns, the development of meat analogues, including plant-based proteins and cultivated meat, has become a solution for elevating global protein production and addressing sustainability issues. North America and Europe lead the meat analogue market, driven by elevated consumer awareness of health and environmental concerns. Under the influence of western diet, the Asian market is also poised for growth. While cultivated meat industry remains immature, advancements in production and cost reductions are expected to boost its market share over time. Although research on meat analogue methodology has increased in recent years, reviews that combine production methodologies and nutritional perspectives remain uncommon. This review comprehensively analyses the production methods, nutritional values, and market prospects of meat analogues. Meat analogue production has great potential in reducing water consumption, promoting sustainability, and improving animal welfare. Meat analogue provides high protein content and balanced amino acid profile, though certain micronutrient deficiencies due to production processes. This review outlines directions for further research in meat analogue production, emphasizing the importance of enhancing production efficiency and nutritional fortification to address food insecurity and environmental damage.

Bacterial microbiota associated with raw plant-based meat analogue products and their influences on selective enrichment for Escherichia coli O157:H7

Towards fostering a more sustainable food production system in face of the climate change challenge, alternative protein meat-substitute products that are plant-based and free of animal by-products have been gaining attractions from both food manufacturers and consumers. With these so-called plant-based meat analogues (PBMAs) becoming increasingly available at supermarkets, there is very little known about their microbial properties. In this short report, we characterized the bacterial composition of raw plant-based ground meat imitation retail products using 16S rRNA gene amplicon sequencing. Despite the observed bacterial community dissimilarity between sample brands, a total of 18 shared genera (dominated by Bacilli and Gammaproteobacteria classes) were identified as the core constituents of the bacterial microbiota of these PBMA products. Within the scope of food safety testing, to gain insights on the dynamics of the enrichment process for E. coli O157:H7 in accordance with the Health Canada reference method MFHPB-10, bacterial taxonomic analyses were conducted at different stages of the prescribed cultural procedures. Using both control and E. coli O157:H7-inoculated PBMA samples it was revealed that, independent of the presence of E. coli O157:H7, off-target bacteria of the Clostridium sensu stricto 1 genus were significantly enriched from the uncultured samples. Additionally, the abundance of Hafnia-Obesumbacterium bacteria in the PBMA samples was also increased in the enrichment products, but only when E. coli O157:H7 was absent. Consistent with the spread-plating results indicating that the inoculated E. coli O157:H7 cells were capable of reaching a high density (>108 CFU/ml) in the resultant enrichment cultures, the significant enrichment of bacterial 16S rRNA gene sequences belonging to the targeted genus of Escherichia, but not Hafnia-Obesumbacterium. This further highlights the competitive nature of the selective enrichment for E. coli O157:H7 against specific background bacteria associated with the PBMA products.

Extrusion‐Based 3D Printing Technology in Soy Protein‐Based Meat Analogs: A Review

ABSTRACTExtrusion‐based 3D printing technology has emerged as a promising method for developing soy protein‐based meat analogs, addressing the urgent demand for sustainable and nutritious alternatives to traditional meat sources. There is a growing global interest in soy protein‐based diets, driven by environmental sustainability, health, and animal welfare concerns. Extrusion‐based 3D printing involves pushing soy protein pastes through a nozzle to develop layers that build up into three‐dimensional objects and enable the production of structures closely mimicking the texture and appearance of real meat. Soy proteins, characterized by their high protein content and balanced amino acid profile, are ideal for producing meat‐like textures and flavors. This review explores the application of extrusion and 3D printing technologies in soy protein‐based meat analog production, emphasizing their potential to replicate the sensory qualities of animal meat. It discusses the advantages and challenges associated with these technologies, including the optimization of printing parameters for consistency and quality. Rheological studies are conducted to achieve smooth extrusion and proper layer formation whereas integrating fats, fibers, and natural flavors to enhance texture and taste. The review provides an overview of extrusion processes, highlighting rheological studies optimizing the flow behavior of soy protein pastes for effective 3D printing. Additionally, it examines textural studies aimed at mimicking the mouthfeel and bite of real meat, as well as printing performance evaluated through shape retention, layer resolution, structural strength, and printing accuracy. Consumer acceptance of soy protein‐based meat analogs is also discussed, highlighting the familiarity with soy products and the increasing demand for plant‐based alternatives. The review concludes by considering prospects for these technologies, focusing on innovations in extrusion and 3D printing, market trends, and evolving consumer preferences.

Sustainable and Scalable Enzymatic Production, Structural Elucidation, And Biological Evaluation of Novel Phlorizin Analogues.

It is not unusual for naturally occurring compounds to be limited for their use in cosmetics due to their low water solubility. Recently, aiming at accessing novel phlorizin (a glycosylated bioactive recovered from apple tree wood and already used in cosmetics as antioxidant ingredient) analogues, we reported the synthesis of very promising - but low water-soluble - biomass-derived chalcones (CHs) and dihydrochalcones (DHCs) exhibiting antioxidant and anti-tyrosinase activities. Glycosylating bioactive compounds being one of the most common strategies to increase their water solubility, herein we report the enzymatic glycosylation of the CHs mentioned above, as well as DHC using cyclodextrin glycosyltransferases (CGTase), enzymes well-known for catalyzing the selective α(1→4) transglycosylation. Indeed, while most natural glycosides are β-glycosides (such as phlorizin), the selected enzyme produces selectively new α-glycosides, thus expanding their structural diversity. A first step of separation using Centrifugal Partition Chromatography (CPC) led to mono-, di- or triglycosides-enriched fractions, which were then submitted to a comprehensive purification strategy for an in-depth chemical profiling of the synthesized α-glycosides, revealing that the major compounds were glycosylpyranosides. Surprisingly, among the diglycosides characterized, besides the expected maltoside compounds, nigeroside derivatives were also identified in significant amounts, depending on the starting compound structure. Finally, evaluating the antiradical, anti-tyrosinase and antimicrobial activities of the major glycosides revealed them as potential sustainable alternatives to current petro-sourced cosmetic ingredients.

Creating glycoside diversity through stereoselective carboboration of glycals

Site-specific modification of glycosides to enhance or alter the physiological properties of the parent molecule has become a highly attractive strategy in drug development. However, creating glycoside building blocks with multiple diversifiable positions from readily available sugar precursors remains a challenging task. Herein, we present a highly regio- and stereoselective nickel-catalyzed carboboration of glycals, which offers a platform for generating glycoside diversity with diverse C1 and C2 modification potential. Specially, the integration of a readily modifiable boronate group at the C2 position markedly amplifies the versatility of this approach, furnishing a universal method for swiftly generating diverse rare sugars with C2-site modifications through expedited downstream transformations. This method demonstrates a broad substrate scope and tolerates various functional groups and complex natural or drug molecular architectures. Moreover, we illustrate the synthetic potential of this method through the synthesis of a diverse array of analogs of both natural products and pharmaceuticals.