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Coffee silverskin is a byproduct of the coffee industry, appearing in large quantities during the roasting step. In this work, a sober and simple water process is proposed, using extractions cycles, to produce valuable products including (a) an extract rich in caffeine, (b) possibly pure caffeine, and (c) insoluble fibers. The hypothetical number of necessary cycles was calculated and compared to the number of cycles used experimentally. Two types of cycles, with and without water compensation, were compared for their water consumption and the amount of caffeine extracted. The use of cycles, with the resulting product from a previous extraction as a solvent for fresh biomass, drove a significant rise in the content of caffeine determined by a UV-visible detector with a spectrophotometer and ultra-performance liquid chromatography (UPLC). After 11 extraction cycles with water compensation, we obtained an extract 4.5 times more concentrated in caffeine (4.25 mg/mL) than after a single extraction (1.03 mg/mL).
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With increasing environmental awareness and consumer demand for high-quality food products, industries are strongly required for technical innovations. The use of various emerging techniques in food processing indeed brings many economic and environmental benefits compared to conventional processes. However, lipid oxidation induced by some "innovative" processes is often "an inconvenient truth", which is scarcely mentioned in most studies but should not be ignored for the further improvement and optimization of existing processes. Lipid oxidation poses a risk to consumer health, as a result of the possible ingestion of secondary oxidation products. From this point of view, this review summarizes the advance of lipid oxidation mechanism studies and mainly discloses the shade of innovative food processing concerning lipid degradation. Sections involving a revisit of classic three-stage chain reaction, the advances of polar paradox and cut-off theories, and potential lipid oxidation factors from emerging techniques are described, which might help in developing more robust guidelines to ensure a good practice of these innovative food processing techniques in future.
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Manipulação de Alimentos , Lipólise , Manipulação de Alimentos/métodos , Oxirredução , LipídeosRESUMO
The present study aimed to investigate the qualitative and quantitative performance of five green solvents, namely 2-methyltetrahydrofuran (MeTHF), cyclopentyl methyl ether (CPME), p-cymene, d-limonene and ethanol to substitute n-hexane, for sesame seed oil extraction. In fact, both CPME and MeTHF gave higher crude yields than n-hexane (58.82, 54.91 and 50.84%, respectively). The fatty acid profile of the sesame seed oils remained constant across all the solvent systems, with a predominance of oleic acid (39.27-44.35%) and linoleic acid (38.88-43.99%). The total sterols gained the upmost amount with CPME (785 mg/100 g oil) and MeTHF (641 mg/100 g oil). CPME and MeTHF were also characterized by the optimum content of tocopherols (52.3 and 50.6 mg/100 g oil, respectively). The highest contents of total phenols in the sesame seed oils were extracted by CPME (23.51 mg GAE/g) and MeTHF (22.53 mg GAE/g) as compared to the other solvents, especially n-hexane (8 mg GAE/g). Additionally, sesame seed oils extracted by MeTHF and CPME also had the highest antioxidant and anti-inflammatory properties as compared to the other green solvents and n-hexane, encouraging their manufacturing use for sesame seed oil extraction.
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With the increase in the world's population and per capita wealth, oil producers must not only increase edible oil production but also meet the demand for a higher quality and variety of products. Recently, the focus has shifted from single processing steps to the entire vegetable oil production process, with an emphasis on introducing innovative technologies to improve quality and production efficiency. In this review, conventional methods of oilseed storage, processing and extraction are presented, as well as innovative processing and extraction techniques. Furthermore, the parameters most affecting the products' yields and quality at the industrial level are critically described. The extensive use of hexane for the extraction of most vegetable oils is undoubtedly the main concern of the whole production process in terms of health, safety and environmental issues. Therefore, special attention is paid to environmentally friendly solvents such as ethanol, supercritical CO2, 2-methyloxolane, water enzymatic extraction, etc. The state of the art in the use of green solvents is described and an objective assessment of their potential for more sustainable industrial processes is proposed.
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Etanol , Alimentos , Cabeça , Indústrias , Óleos de Plantas , SolventesRESUMO
Water is considered the greenest solvent. Nonetheless, the water solubility of natural products is still an incredibly challenging issue. Indeed, it is nearly impossible to solubilize or to extract many natural products properly using solely water due to their low solubility in this solvent. To address this issue, researchers have tried for decades to tune water properties to enhance its solvent potential in order to be able to solubilise or extract low-water solubility compounds. A few methods involving the use of solubilisers were described in the early 2000s. Since then, and particularly in recent years, additional methods have been described as useful to ensure the effective green extraction but also solubilisation of natural products using water as a solvent. Notably, combinations of these green methods unlock even higher extraction performances. This review aims to present, compare and analyse all promising methods and their relevant combinations to extract natural products from bioresources with water as solvent enhanced by green solubilisers and/or processes.
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Hexane is a solvent used extensively in the food industry for the extraction of various products such as vegetable oils, fats, flavours, fragrances, colour additives or other bioactive ingredients. As it is classified as a "processing aid", it does not have to be declared on the label under current legislation. Therefore, although traces of hexane may be found in final products, especially in processed products, its presence is not known to consumers. However, hexane, and in particular the n-hexane isomer, has been shown to be neurotoxic to humans and has even been listed as a cause of occupational diseases in several European countries since the 1970s. In order to support the European strategy for a toxic-free environment (and toxic-free food), it seemed important to collect scientific information on this substance by reviewing the available literature. This review contains valuable information on the nature and origin of the solvent hexane, its applications in the food industry, its toxicological evaluation and possible alternatives for the extraction of natural products. Numerous publications have investigated the toxicity of hexane, and several studies have demonstrated the presence of its toxic metabolite 2,5-hexanedione (2,5-HD) in the urine of the general, non-occupationally exposed population. Surprisingly, a tolerable daily intake (TDI) has apparently never been established by any food safety authority. Since hexane residues are undoubtedly found in various foods, it seems more than necessary to clearly assess the risks associated with this hidden exposure. A clear indication on food packaging and better information on the toxicity of hexane could encourage the industry to switch towards one of the numerous other alternative extraction methods already developed.
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Despite its severe toxicity and negative environmental impact, hexane remain the solvent of choice for the extraction of vegetable oils. This is in contrast with the constantly growing demand for sustainable and green extraction processes. In recent years a variety of alternatives to hexane have been reported, among them 2-methyloxolane (2-MeOx), which has emerged as a promising bio-based alternative. This study evaluates the possibility of replacing hexane, in the extraction of olive pomace (OP), with 2-MeOx, both dry and saturated with water (4.5%), the latter of which is called 2-MeOx 95.5%. The three solvents have been compared in terms of extraction yield and quality, as well as the lipid and polyphenol profiles of the extracts. The work concluded that both dry 2-MeOx and 2-MeOx 95.5% can replace hexane in OP extraction, resulting in higher yields and extracts richer in phenolic compounds. This study should open the road to further semi-industrial scale investigations toward more sustainable production processes.
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The water-based extraction of bioactive components from flavonoid-rich medicinal plants is a key step that should be better investigated. This is especially true when dealing with easy-to-use home-made conditions of extractions, which are known to be a bottleneck in the course for a better control and optimization of the daily uptake of active components from medicinal plants. In this work, the water-based extraction of Blackcurrant (Ribes nigrum) leaves (BC) and Chrysanthellum americanum (CA), known to have complementary pharmacological properties, was studied and compared with a previous work performed on the extraction of Hawthorn (Crataegus, HAW). Various extraction modes in water (infusion, percolation, maceration, ultrasounds, microwaves) were compared for the extraction of bioactive principles contained in BC and CA in terms of extraction yield, of amount of flavonoids, phenolic compounds, and proanthocyanidin oligomers, and of UHPLC profiles of the extracted compounds. The qualitative and quantitative aspects of the extraction, in addition to the kinetic of extraction, were studied. The optimized easy-to-use-at-home extraction protocol developed for HAW was found very efficient to easily extract bioactive components from BC and CA plants. UHPLC-ESI-MS and high-resolution Fourier transform ion cyclotron resonance mass spectrometry (FT-ICR MS) were also implemented to get more qualitative information on the specific and common chemical compositions of the three plants (including HAW). Their antihyaluronidase, antioxidant, and antihypertensive activities were also determined and compared, demonstrating similar activities as the reference compound for some of these plants.
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A valued marine oil rich in omega-3 lipids and natural astaxanthin is obtained with remarkably high yield (up to 5 wt %) extending to pink shrimp waste (head and carapace) using the approach to extract fish oil from fish processing byproducts using d-limonene. Biobased limonene is an excellent solvent for both unsaturated lipids and astaxanthin-based carotenoids preventing oxidative degradation during the extraction cycle including solvent separation at 85 °C. Explaining the deep red color of the shrimp oil obtained, computational simulation suggests that d-limonene is also a good solvent for natural astaxanthin abundant in shrimp.
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Nowadays, "green analytical chemistry" challenges are to develop techniques which reduce the environmental impact not only in term of analysis but also in the sample preparation step. Within this objective, pressurized liquid extraction (PLE) was investigated to determine the initial composition of key antioxidants contained in rosemary leaves: Rosmarinic acid (RA), carnosic acid (CA), and carnosol (CO). An experimental design was applied to identify an optimized PLE set of extraction parameters: A temperature of 183 °C, a pressure of 130 bar, and an extraction duration of 3 min enabled recovering rosemary antioxidants. PLE was further compared to conventional Soxhlet extraction (CSE) in term of global processing time, energy used, solvent recovery, raw material used, accuracy, reproducibility, and robustness to extract quantitatively RA, CA, and CO from rosemary leaves. A statistical comparison of the two extraction procedure (PLE and CSE) was achieved and showed no significant difference between the two procedures in terms of RA, CA, and CO extraction. To complete the study showing that the use of PLE is an advantageous alternative to CSE, the eco-footprint of the PLE process was evaluated. Results demonstrate that it is a rapid, clean, and environmentally friendly extraction technique.
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The potential of using the bio-based solvent 2-methyloxolane, also known as 2-methyltetrahydrofuran or 2-MeTHF, as an alternative to petroleum solvents such as hexane, was investigated for the extraction of volatile compounds from hop cones (Humulus lupulus L.). Lab scale extractions were coupled with in silico prediction of solutes solubility to assess the technical potential of this bio-based solvent. The predictive approach was performed using the simulation software COSMO-RS (conductor like screening model for real solvants) and showed that the 2-methyloxolane is as good as or better than hexane to solubilize the majority of aromas from hop cones. The experimental results indicated that the highest aroma yield was obtained with 2-methyloxolane with 20.2% while n-hexane was only able to extract 17.9%. The characterization of aromas extracted by the two solvents showed a similar composition, where lupulone was the main component followed by humulone. No selectivity of the solvents was observed for any of the major analytes. Finally, a sensory analysis was performed on the extracts, showing that both concretes using 2-methyloxolane and hexane have similar olfactory profiles. The results indicate that 2-methyloxolane could be a promising bio-based extraction solvent for hexane substitution.
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Química Verde , Humulus/química , Odorantes/análise , Extratos Vegetais/química , Extratos Vegetais/isolamento & purificação , Solventes/química , Extração Líquido-Líquido , Modelos Moleculares , Compostos Fitoquímicos , Extração em Fase Sólida , SolubilidadeRESUMO
Hawthorn (Crataegus) is used for its cardiotonic, hypotensive, vasodilative, sedative, antiatherosclerotic, and antihyperlipidemic properties. One of the main goals of this work was to find a well-defined optimized extraction protocol usable by each of us that would lead to repeatable, controlled, and quantified daily uptake of active components from hawthorn at a drinkable temperature (below 60 °C). A thorough investigation of the extraction mode in water (infusion, maceration, percolation, ultrasounds, microwaves) on the yield of extraction and the amount of phenolic compounds, flavonoids, and proanthocyanidin oligomers as well as on the Ultra High Performance Liquid Chromatography (UHPLC) profiles of the extracted compounds was carried out. High-resolution Fourier transform ion cyclotron resonance mass spectrometry was also implemented to discriminate the different samples and conditions of extraction. The quantitative and qualitative aspects of the extraction as well as the kinetics of extraction were studied, not only according to the part (flowers or leaves), the state (fresh or dried), and the granulometry of the dry plant, but also the stirring speed, the temperature, the extraction time, the volume of the container (cup, mug or bowl) and the use of infusion bags.
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Crataegus/química , Flavonoides/isolamento & purificação , Proantocianidinas/isolamento & purificação , Cromatografia Líquida de Alta Pressão , Flores/química , Extratos Vegetais/química , Folhas de Planta/química , Espectroscopia de Infravermelho com Transformada de Fourier , Água/análiseRESUMO
We investigate selected chemical, technical, and economic aspects of the production of fish oil rich in polyunsaturated omega-3 fatty acids from anchovy filleting leftovers using d-limonene as the extraction solvent at ambient temperature and pressure. Entirely derived from the orange peel prior to orange squeezing for juice production, the bio-based solvent is easily recovered, affording a circular economy process with significant potential for practical applications.
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In recent years, almost all extraction processes in the perfume, cosmetic, pharmaceutical, food ingredients, nutraceuticals, biofuel and fine chemical industries rely massively on solvents, the majority of which have petroleum origins. The intricate processing steps involved in the industrial extraction cycle makes it increasingly difficult to predict the overall environmental impact; despite the tremendous energy consumption and the substantial usage of solvents, often the yields are indicated in decimals. The ideal alternative solvents suitable for green extraction should have high solvency, high flash points with low toxicity and low environmental impacts, be easily biodegradable, obtained from renewable (non-petrochemical) resources at a reasonable price and should be easy to recycle without any deleterious effect to the environment. Finding the perfect solvent that meets all the aforementioned requirements is a challenging task, thus the decision for the optimum solvent will always be a compromise depending on the process, the plant and the target molecules. The objective of this comprehensive review is to furnish a vivid picture of current knowledge on alternative, green solvents used in laboratories and industries alike for the extraction of natural products focusing on original methods, innovation, protocols, and development of safe products.
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Produtos Biológicos/química , Extratos Vegetais/química , Solventes/química , Animais , Alimentos , HumanosRESUMO
This study aims at investigating p-menthane, a novel bio-based solvent resulting from the hydrogenation of d-limonene, as a green alternative to n-hexane or toluene for the extraction and solubilization of natural substances. First, conductor-like combination of quantum chemistry (COSMO) coupled with statistical thermodynamics (RS) calculations show a comparable solubilization profile of p-menthane and n-hexane for carotene, volatile monoterpenes such as carvone and limonene, and model triglycerides. Other data obtained experimentally in solid/liquid extraction conditions further indicate that p-menthane showed similar performances to n-hexane for extracting carotenes from carrots, aromas from caraway seeds, and oils from rapeseeds, as these products showed a comparable composition. p-Menthane was also tested using common analytical extraction procedures such as Soxhlet for determination of oil content via multiple extraction stages, and Dean-Stark for determination of water content via azeotropic distillation. For both systems, yields were comparable, but for Dean-Stark, the distillation curve slope was higher when using p-menthane, and the time needed to attain 100% water recovery was 55% shorter than for toluene. Taken together, these results reveal the potential of p-menthane as a green replacer for petroleum-based solvents such as n-hexane or toluene.
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Produtos Biológicos/química , Citrus sinensis/química , Química Verde/métodos , Mentol/química , Solventes/química , Carotenoides/isolamento & purificação , Carum/química , Daucus carota/química , Destilação , Ácidos Graxos/análise , Cinética , Odorantes/análise , Óleo de Brassica napus , Sementes/química , Solubilidade , Tolueno/química , Água/químicaRESUMO
The zero-waste biorefinery concept inspired a green oleo-extraction of both natural volatile (e.g., borneol, camphor, o-cymene, eucalyptol, limonene, α-pinene, and terpinen-4-ol) and non-volatile (e.g., carnosol, carnosic, and rosmarinic acid) bioactive compounds from rosemary leaves with vegetable oils and their amphiphilic derivatives as simple food-grade solvents. It is noteworthy that soybean oil could obtain the highest total phenolic compounds (TPCs) among 12 refined oils including grapeseed, rapeseed, peanut, sunflower, olive, avocado, almond, apricot, corn, wheat germ, and hazelnut oils. Furthermore, the addition of oil derivatives to soybean oils, such as glyceryl monooleate (GMO), glyceryl monostearate (GMS), diglycerides, and soy lecithin in particular, could not only significantly enhance the oleo-extraction of non-volatile antioxidants by 66.7% approximately, but also help to remarkably improve the solvation of volatile aroma compounds (VACs) by 16% in refined soybean oils. These experimental results were in good consistency with their relative solubilities predicted by the more sophisticated COSMO-RS (COnductor like Screening MOdel for Real Solvents) simulation. This simple procedure of using vegetable oils and their derivatives as bio-based solvents for simultaneously improving the extraction yield of natural antioxidants and flavors from rosemary showed its great potential in up-scaling with the integration of green techniques (ultrasound, microwave, etc.) for zero-waste biorefinery from biomass waste to high value-added extracts in future functional food and cosmetic applications.
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Three triterpene glycosides were isolated from the roots of Weigela florida "rumba" (Bunge) A. DC.: two previously undescribed 3-O-ß-d-xylopyranosyl-(1â2)-[ß-d-xylopyranosyl-(1â4)]-ß-d-xylopyranosyl-(1â4)-ß-d-xylopyranosyl-(1â3)-α-L-rhamnopyranosyl-(1â2)-α-l-arabinopyranosyloleanolic acid (1) and 3-O-ß-d-xylopyranosyl-(1â2)-[ß-d-glucopyranosyl-(1â4)]-ß-d-xylopyranosyl-(1â4)-ß-d-xylopyranosyl-(1â3)-α-l-rhamnopyranosyl-(1â2)-α-L-arabinopyranosyloleanolic acid (2), and one isolated for the first time from a natural source 3-O-ß-d-xylopyranosyl-(1â3)-α-l-rhamnopyranosyl-(1â2)-α-l-arabinopyranosyloleanolic acid (3). Their structures were elucidated mainly by 2D NMR spectroscopic analysis (COSY, TOCSY, NOESY, HSQC, HMBC) and mass spectrometry. Compounds 2 and 3 were further evaluated as antigens in enzyme-linked immunosorbent assay (ELISA) to recognize IgM antibodies in multiple sclerosis (MS) patients' sera.
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Caprifoliaceae/química , Glicosídeos/isolamento & purificação , Ácido Oleanólico/análogos & derivados , Raízes de Plantas/química , Ensaio de Imunoadsorção Enzimática , Humanos , Imunoglobulina M/química , Estrutura Molecular , Esclerose Múltipla/sangue , Ácido Oleanólico/isolamento & purificaçãoRESUMO
Extracts rich in antioxidants, such as rosemary extracts, are currently obtained by extraction of the plant material using hydro-alcoholic mixtures with high ethanol content. As this ratio is generally chosen by default and scarcely optimized, we intended to investigate the impact of the hydro-alcoholic composition on extract characteristics such as extraction yield, composition profile in selected compounds, and antioxidant/reducing activity such as Folin-Ciocalteu, DPPH, and ORAC. A theoretical determination of rosmarinic (RA) and carnosic (CA) acid solubilities in ethanol:water mixtures was also performed using COSMO-RS and was confronted to experiments. While the best solubilizing solvent (100% ethanol) was also the best extracting solvent for CA, it was not the case with RA since pure ethanol appeared as a poor solvent compared to 30% ethanol which was optimal. Finally, the best antioxidant activities were obtained with 30% ethanol.
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Near-infrared (NIR) spectroscopy was evaluated as a rapid method for the determination of oleic, palmitic, linoleic and linolenic acids as well as omega-3, omega-6, and to predict polyunsaturated, monounsaturated and saturated fatty acids, together with triacylglycerides, diglycerides, free fatty acids and ergosterol in salmon oil. To do it, Partial Least Squares (PLS) regression models were applied to correlate NIR spectra with aforementioned fatty acids and lipid classes. Results obtained were validated in front of reference procedures based on high performance thin layer and gas chromatography. PLS-NIR has a good predictive capability with relative root mean square error of prediction (RRMSEP) values below or equal to 1.8% and provides rapid analysis without the use of any chemicals making it an environmentally friendly methodology.
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Óleos de Peixe/química , Ácidos Graxos , Análise dos Mínimos Quadrados , Espectroscopia de Luz Próxima ao InfravermelhoRESUMO
Since solvents of petroleum origin are now strictly regulated worldwide, there is a growing demand for using greener, bio-based and renewable solvents for extraction, purification and formulation of natural and food products. The ideal alternative solvents are non-volatile organic compounds (VOCs) that have high dissolving power and flash point, together with low toxicity and less environmental impact. They should be obtained from renewable resources at a reasonable price and be easy to recycle. Based on the principles of Green Chemistry and Green Engineering, vegetable oils could become an ideal alternative solvent to extract compounds for purification, enrichment, or even pollution remediation. This review presents an overview of vegetable oils as solvents enriched with various bioactive compounds from natural resources, as well as the relationship between dissolving power of non-polar and polar bioactive components with the function of fatty acids and/or lipid classes in vegetable oils, and other minor components. A focus on simulation of solvent-solute interactions and a discussion of polar paradox theory propose a mechanism explaining the phenomena of dissolving polar and non-polar bioactive components in vegetable oils as green solvents with variable polarity.