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The development of selective extraction protocols for Cannabis-inflorescence constituents is still a significant challenge. The characteristic Cannabis fragrance can be mainly ascribed to monoterpenes, sesquiterpenes and oxygenated terpenoids. This work investigates the entrapment of Cannabis terpenes in olive oil from inflorescences via stripping under mild vacuum during the rapid microwave-assisted decarboxylation of cannabinoids (MW, 120 °C, 30 min) and after subsequent extraction of cannabinoids (60 and 100 °C). The profiles of the volatiles collected in the oil samples before and after the extraction step were evaluated using static headspace solid-phase microextraction (HS-SPME), followed by gas chromatography coupled to mass spectrometry (GC-MS). Between the three fractions obtained, the first shows the highest volatile content (~37,400 mg/kg oil), with α-pinene, ß-pinene, ß-myrcene, limonene and trans-ß-caryophyllene as the main components. The MW-assisted extraction at 60 and 100 °C of inflorescences using the collected oil fractions allowed an increase of 70% and 86% of total terpene content, respectively. Considering the initial terpene amount of 91,324.7 ± 2774.4 mg/kg dry inflorescences, the percentage of recovery after decarboxylation was close to 58% (mainly monoterpenes), while it reached nearly 100% (including sesquiterpenes) after extraction. The selective and efficient extraction of volatile compounds, while avoiding direct contact between the matrix and extraction solvents, paves the way for specific applications in various aromatic plants. In this context, aromatized extracts can be employed to create innovative Cannabis-based products within the hemp processing industry, as well as in perfumery, cosmetics, dietary supplements, food, and the pharmaceutical industry.
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Cannabinoides , Cannabis , Alucinógenos , Sesquiterpenos Policíclicos , Sesquiterpenos , Terpenos/química , Cannabinoides/química , Cannabis/química , Aceite de Oliva , Descarboxilación , Microondas , Monoterpenos/química , Sesquiterpenos/química , Agonistas de Receptores de CannabinoidesRESUMEN
The search for a wide spectrum of antimicrobial agents that can avoid resistance while maintaining reasonable side effects has led to ozonated oils experiencing an increase in scientific interest and clinical applications. The treatment of vegetable oils with ozone leads to the creation of a reservoir of ozone that slowly releases into the skin thanks to the fact that ozone can be held as ozonides of unsaturated fatty acids. Interest in the use of ozonated oils has meant that several ozonated-vegetable-oil-containing products have been commercialized as cosmetic and pharmaceutical agents, and in innovative textile products with antibacterial activity. New approaches to the delivery of ozonated oils have very recently appeared in an attempt to improve their characteristics and reduce drawbacks, such as an unpleasant odor, high viscosity and undesired effects on skin, including irritation and rashes. The present review focuses on the current status of delivery agents that use ozonated oils as antimicrobial agents in topical (dermal, skin, and soft tissues) treatments. Challenges and future opportunities for these delivery systems will also be discussed.
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Antibacterianos/administración & dosificación , Sistemas de Liberación de Medicamentos/métodos , Ozono/química , Aceites de Plantas/administración & dosificación , Enfermedades de la Piel/tratamiento farmacológico , Textiles , Administración Tópica , HumanosRESUMEN
High Brassicaceae consumption reduces the risk of developing several cancer types, probably due to high levels of glucosinolates. Extracts from Sinapis nigra L. (S. nigra) and Sinapis alba L. (S. alba) have been obtained from leaves and seeds under different conditions using ethanol/water mixtures because their glucosinolates are well accepted by the food industry. The EtOH/H2O 8:2 mixture gives better yields in glucosinolate amounts from ground seeds, mainly, sinalbin in S. alba and sinigrin in S. nigra. The highest antiproliferative activity in both non-tumor and tumor cell lines was induced by S. alba seeds extract. To evaluate whether the effect of Sinapis species (spp) was only due to glucosinolate content or whether it was influenced by the extracts' complexity, cells were treated with extracts or glucosinolates, in the presence of myrosinase. Pure sinigrin did not modify cell proliferation, while pure sinalbin was less effective than the extract. The addition of myrosinase increased the antiproliferative effects of the S. nigra extract and sinigrin. Antiproliferative activity was correlated to Mitogen-Activated Protein Kinases modulation, which was cell and extract-dependent. Cell-cycle analysis evidenced a proapoptotic effect of S. alba on both tumor cell lines and of S. nigra only on HCT 116. Both extracts showed good antimicrobial activity in disc diffusion tests and on ready-to-eat fresh salad. These results underline the potential effects of Sinapis spp in chemoprevention and food preservation.
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Antibacterianos/farmacología , Antioxidantes/farmacología , Apoptosis , Bacterias/efectos de los fármacos , Proliferación Celular , Neoplasias Colorrectales/patología , Extractos Vegetales/farmacología , Sinapis/química , Neoplasias Colorrectales/tratamiento farmacológico , Humanos , Semillas/química , Sinapis/clasificación , Células Tumorales CultivadasRESUMEN
BACKGROUND: For the processing industry, it is crucial to know what effect the roasting process and conditions have on hazelnut quality. The present study investigates, for the first time, the effects of hot-air and infrared (IR) roasting at different time-temperature combinations on Tonda Gentile Trilobata hazelnut: whole kernels and derived processing products (paste and oil). RESULTS: The nutritional and physical characteristics of hazelnuts and processing products were investigated to determine the influence of the different roasting conditions as a function of intended use. The antioxidant profile (2.2-diphenyl-1-picrylhydrazyl radical, oxygen radical absorbance capacity and total phenolic content) were analyzed on roasted hazelnut and paste extracts. For a comprehensive understanding of the complex biochemical phenomena occurring during roasting, E-nose and near-IR spectroscopy were also applied. All analytical data were processed using univariate and multivariate data analyses. Hazelnuts derived from IR roasting at higher temperatures (195 °C) showed a richer antioxidant profile and a more intense flavour. On the other hand, the yield associated with the oil extraction under the same conditions was unsatisfactory, making this process completely inadequate for oil production. Oil obtained by hot-air roasting and IR roasting at lower temperature (135 °C) was found to be of good quality, showing rather similar acidity grade, peroxide number and acidic composition. In particular, a slightly but significantly lower acidity was related to lower roasting temperatures (0.21-0.22% versus 0.27% for higher temperatures). All roasting conditions tested allowed the quantitative homogeneous hazelnut paste to be obtained and, from a rheological point of view, a higher roasting temperatures resulted in pastes characterized by higher density and viscosity values. CONCLUSION: The use of IR was found to be a promising alternative method for hazelnut roasting, as a result of its capability with respect to preserving nutritional values and enhancing organoleptic quality. © 2018 Society of Chemical Industry.
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Culinaria/métodos , Corylus/química , Nueces/efectos de la radiación , Antioxidantes/química , Culinaria/instrumentación , Corylus/efectos de la radiación , Calor , Rayos Infrarrojos , Valor Nutritivo , Nueces/química , Fenoles/química , Extractos Vegetales/químicaRESUMEN
Citrus is a major processed crop that results in large quantities of wastes and by-products rich in various bioactive compounds such as pectins, water soluble and insoluble antioxidants and essential oils. While some of those wastes are currently valorised by various technologies (yet most are discarded or used for feed), effective, non-toxic and profitable extraction strategies could further significantly promote the valorisation and provide both increased profits and high quality bioactives. The present review will describe and summarize the latest works concerning novel and greener methods for valorisation of citrus by-products. The outcomes and effectiveness of those technologies such as microwaves, ultrasound, pulsed electric fields and high pressure is compared both to conventional valorisation technologies and between the novel technologies themselves in order to highlight the advantages and potential scalability of these so-called "enabling technologies". In many cases the reported novel technologies can enable a valorisation extraction process that is "greener" compared to the conventional technique due to a lower energy consumption and reduced utilization of toxic solvents.
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Citrus/química , Frutas/química , Extractos Vegetales/aislamiento & purificación , Residuos de Alimentos , Tecnología Química Verde , Residuos/análisisRESUMEN
ßN-alkanoyl-5-hydroxytryptamines (Cn-5HTs) are the main constituents of coffee wax and may be responsible for the increased severity of gastric disorders in sensitive consumers. Their removal from green coffee beans can result in a "stomach-friendly" brew. This work presents a green approach to Cn-5HTs extraction using the bio-based solvent 2-methyloxolane (2-MeOx). HPLC/DAD analyses on Arabica Brazil samples show that mild conditions (30 min at 50 °C) extract about 90% of the wax, without affecting the caffeine content of the beans, whereas almost complete removal is achieved in 60 min at reflux. 2-MeOx forms an azeotrope with water, its possible re-use has been demonstrated using aqueous 2-MeOx (95.5%) as the solvent. These preliminary results make 2-MeOx a possible candidate for the replacement of dichloromethane (DCM) in coffee dewaxing. The importance of fermentation in reducing Cn-5HTs by about 36% has been demonstrated in an analysis of green beans subjected to different post-harvest treatments.
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Coffea , Semillas , Coffea/química , Semillas/química , Solventes/química , Extractos Vegetales/química , Extractos Vegetales/aislamiento & purificación , BrasilRESUMEN
o-Phenylphenol (OPP) is not a commonly used pesticide in the coffee production chain. Although it has only been detected in roasted coffee, it is unlikely that OPP can be formed during roasting. Its acidic nature may lead to the formation of conjugates with natural matrix components. The objective of this study is to optimize an analytical method to discover how these conjugates may mask the presence of OPP in coffee. Sample extraction with hexane followed by basic hydrolysis and then a QuEChERS method allows the presence of OPP to be quantitatively detected via UPLC-MS/MS. The optimized method was applied to the same Arabica coffee (Brazil), and the quantification of comparable amounts of OPP was observed in both green and roasted samples (34.8 vs 32.2 µg/kg). The optimized procedure detected twice the amount of OPP in roasted samples, compared to the QuEChERS method, suggesting that roasting causes the partial hydrolysis of OPP conjugates.
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Coffea , Café , Cromatografía Liquida , Espectrometría de Masas en Tándem/métodosRESUMEN
BACKGROUND: Hydrodistillation (HD) has been used since ancient times for the extraction of essential oils (EO). Despite the intrinsic limitations of this technique, it remains the most common method both in the laboratory and on an industrial scale. The main drawbacks are the long extraction time involved and the risk of thermal degradation. Over the last decade, microwave-assisted extraction (MAE) and in situ microwave-generated hydrodistillation (MGH) have been shown to be the most promising techniques in improving plant extraction and hydrodistillation. RESULTS: In this study we compare HD with MGH in the extraction of several mint species cultivated in Piedmont: Mentha spicata L. var. rubra, Mentha spicata L. var. viridis and Mentha piperita L. MGH requires either fresh plant or rehydrated material, it is extremely fast and allows a reduction in energy consumption and overall cost. All the EO have been analyzed by gas chromatography-mass spectrometry. A mechanism of microwave-generated essential oil extraction has been proposed to explain the differences in the composition of the oil obtained from this environmentally friendly technique. CONCLUSIONS: The yields and composition percentages of the EO obtained by HD and in situ MGH of fresh and dried mint leaves lie in a relatively narrow range, although MGH is faster. MW polarization effects and the water solubility of the components influence extract composition.
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Destilación/métodos , Manipulación de Alimentos/métodos , Mentha/química , Microondas , Extractos Vegetales/química , Hojas de la Planta/química , Desecación , Aceites Volátiles/aislamiento & purificaciónRESUMEN
C6O4 is a water soluble perfluoroether carboxylic acid ammonium salt used as surfactant in the synthesis of fluoropolymers. Available experimental data in rats exposed by the oral route indicate it is eliminated in urine. Previous studies with various linear perfluorocarboxylic acids have suggested that these compounds are substrates of renal membrane transporters in rats and humans, and that the interaction with basal and apical membrane transporters can influence the elimination kinetic by these organisms and explain, in part, the observed differences in the respective half-lives. In particular, apical transporters may contribute to the reuptake of these exogenous compounds from the tubule lumen. The present study was designed to investigate the uptake of C6O4 in two renal cell lines transiently transfected with the human apical membrane transporters, organic anion transporter 4 (OAT4), and urate transporter 1 (URAT1). The uptake of the linear perfluorohexanoic acid (PFC6) was evaluated in parallel. While the uptake of the conjugated steroid estrone-3-sulfate (E3S), a known substrate for renal transporters, and of PFC6 was clearly observed in both cell types transfected with either OAT4 or URAT1, no significant uptake of C6O4 was measured under the same test conditions. The results of the transporter's functionality measured in vitro were consistent with molecular docking simulations. Both outward and inward models of the transporters showed a reduced interaction between C6O4 and URAT1 or OAT4. In contrast, more stable interactions were predicted for PFC6 and PFOA, as well as for the E3S substrate, as shown by the respective docking scores reflecting the binding strength and by the poses assumed in the transporter channels. Altogether, the in vitro and in silico modeling results showed a low reuptake potential and limited interactions of C6O4 molecule with two human apical membrane transporters, contrasting with the more efficient reuptake of PFC6 from the tubule lumen. These results suggest reabsorption from the proximal tubule by apical renal transporters is not likely to interfere with the elimination pathway of C6O4 in humans.
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Transportadores de Anión Orgánico , Animales , Transporte Biológico , Humanos , Riñón/metabolismo , Proteínas de Transporte de Membrana/metabolismo , Simulación del Acoplamiento Molecular , Transportadores de Anión Orgánico/genética , Transportadores de Anión Orgánico/metabolismo , RatasRESUMEN
The aim of the present study is to develop a new industrial process for the continuous-flow extraction of virgin olive oil (VOO) using the non-thermal ultrasound (US) and pulsed electric field (PEF) treatments. These technologies have been tested both separately and in combination, with the aim of making the malaxation step unnecessary. The ultrasound-assisted extraction (UAE) and PEF treatments are both effective technologies for VOO production and have been well documented in the literature. The present study combines a new continuous-flow set-up, with four US units and PEF treatment. The industrial-plant prototype is able to improve VOO yields, thanks to powerful non-thermal physical effects (acoustic cavitation and electroporation), from 16.3% up to 18.1%. Moreover, these technologies increased the content of nutritionally relevant minor components, which, in turn, improves VOO quality and its commercial value (overall tocopherols and tocotrienols improved from 271 mg/kg under the conventional process to 314 mg/kg under the US process). The combined UAE and US-PEF process also increased the extraction yield, while overcoming the need for kneading in the malaxation step and saving process water (up to 1512 L per working day). Continuous-flow US and PEF technologies may be a significant innovation for the VOO industry, with benefits both for oil millers and consumers. The VOO obtained via non-thermal continuous-flow production can satisfy the current trend towards healthier nutrient-enriched products.
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Chestnut peels are a poorly characterized, underexploited by-product of the agri-food industry. This raw material is rich in bioactive compounds, primarily polyphenols and tannins, that can be extracted using different green technologies. Scaling up the process for industrial production is a fundamental step for the valorization of the extract. In this study, subcritical water extraction was investigated to maximize the extraction yield and polyphenol content. Lab-scale procedures have been scaled up to the semi-industrial level as well as the downstream processes, namely, concentration and spray drying. The extract antioxidant capacity was tested using in vitro and cellular assays as well as a preliminary evaluation of its antiadipogenic activity. The temperature, extraction time, and water/solid ratio were optimized, and the extract obtained under these conditions displayed a strong antioxidant capacity both in in vitro and cellular tests. Encouraging data on the adipocyte model showed the influence of chestnut extracts on adipocyte maturation and the consequent potential antiadipogenic activity. Chestnut peel extracts characterized by strong antioxidant power and potential antiadipogenic activity were efficiently obtained by removing organic solvents. These results prompted further studies on fraction enrichment by ultra- and nanofiltration. The semi-industrial eco-friendly extraction process and downstream benefits reported here may open the door to production and commercialization.
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Polycyclic aromatic hydrocarbons (PAHs) are considered to be potentially genotoxic and carcinogenic in humans. These ubiquitous environmental pollutants may derive from the incomplete combustion and pyrolysis of organic matter. Coffee is an extensively consumed drink, and its PAHs contamination is not only ascribed to environmental pollution, but mainly to the roasting processes. Although no fixed limits have yet been set for residual PAHs in coffee, the present review intends to summarise and discuss the knowledge and recent advances in PAHs formation during roasting. Because coffee origin and brewing operations may affect PAHs content, we thoroughly analysed the literature on extraction and purification procedures, as well as the main analytical chromatographic methods for both coffee powders and brews. With regards to the safety of this appreciated commodity, the control on the entire production chain is desirable, because of coffee beverage could contribute to the daily human intake of PAHs.
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Café/química , Industria de Procesamiento de Alimentos/métodos , Hidrocarburos Policíclicos Aromáticos/análisis , Carcinógenos/análisis , Carcinógenos/toxicidad , Coffea/química , Contaminantes Ambientales/análisis , Contaminantes Ambientales/toxicidad , Contaminación de Alimentos/análisis , Humanos , Hidrocarburos Policíclicos Aromáticos/toxicidad , Semillas/químicaRESUMEN
Folpet, a fungicide used on several crops, easily degrades into phthalimide (PAI) at high temperatures and basic pH. The maximum admitted limit for Folpet in foodstuffs as coffee is defined by the sum of its amount and that of PAI. Noteworthy, PAI can also arise from the reaction between ubiquitous phthalate derivatives and NH3. This work aims to demonstrate that the detection of PAI in roasted coffee is not necessarily diagnostic for Folpet as it can also originate from the reaction between phthalic anhydride (PAA), derived from phthalates, and amino acids (AAs), as a NH3 source. Thermal treatment of AAs with PAA confirmed that PAI generation follows a temperature-dependent path. Experiments with diethyl phthalate (DEP) and AAs have shown that maximum PAI generation via heating occurs at 200 °C for 60 min. PAI generation has also been proven for Folpet-free green coffee beans that were heated under laboratory and industrial roasting conditions.
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Coffea , Café , Calor , FtalimidasRESUMEN
Combinations of different technologies are at the heart of the development and implementation of new, innovative processes and approaches for Industry 4.0 in the field of medicinal chemistry and drug discovery. Process intensification and advances in high-throughput synthetic techniques can dramatically improve reaction rates in processes for which slow kinetics represents a bottleneck. Easier access to target-based chemical library collections offers wider access to new leads for drug development. Green enabling technologies are a reliable ally for the design of environmentally friendly synthetic processes and more highly competitive pharmaceutical production. Mechanochemistry, microwaves, ultrasound and flow chemistry are mature techniques that can boast drug synthesis when properly integrated into the production chain. In this review, we selected examples from the literature of the last five years related to medicinal chemistry.
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Plomo , Preparaciones Farmacéuticas , Química Farmacéutica , Descubrimiento de Drogas , Humanos , Bibliotecas de Moléculas PequeñasRESUMEN
Rhizomes of Curcuma longa L. are well known for their content of curcuminoids, which are compounds with interesting biological activity against various inflammatory states and diseases. Curcuminoids can degrade during processing. This piece of work investigates fast, efficient and cost-effective metabolite recovery from turmeric under ultrasound-assisted extraction (UAE). An analytical evaluation of curcuminoid stability under sonication in different solvents is reported for the first time. HPLC and quantitative 1H-NMR were used. Under the applied conditions, EtOAc was found to be the optimal extraction medium, rather than EtOH, due to its lower radical generation, which facilitates better curcuminoid stability. Kinetic characterization, by means of the Peleg equation, was applied for single-step UAE on two different rhizome granulometries. Over a time of 90 min, maximum extraction yields were 25.63% and 47.56% for 6 and 2 mm matrix powders, respectively. However, it was observed that the largest portion of curcuminoid recovery was achieved in the first 30 min. Model outcomes were used as the basis for the design of a suitable multi-step cross-flow approach that supports and emphasizes the disruptive role of cavitation. The maximum curcuminoid yield was achieved over three steps (92.10%) and four steps (80.04%), for lower and higher granulometries, respectively. Finally, the central role of the solvent was further confirmed by turmeric oleoresin purification. The EtOAc extract was purified via crystallization, and a 95% pure curcuminoid product was isolated without any chromatographic procedure. No suitable crystallization was observed for the EtOH extract.
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Nowadays, approximately 1 billion kg/y of grape stalks, with a remarkable polyphenols content, are produced worldwide. In this paper, the extraction process intensification of polyphenols in water was achieved under ultrasound-assisted recovery, focusing on kinetics and scaling-up factors. Immersion and cup-horn systems were exploited as acoustic cavitation sources, and the total phenolic content (TPC) was chosen to assess the process efficiency. The kinetics were evaluated by Peleg's hyperbolic model, and the effect of both the initial feedstock granulometry and ultrasound size-reduction were determined. The results were compared with conventional extraction methods (data analysis by ANOVA). The best polyphenols yield was obtained after 45 min of sonication, giving between 29.71 and 31.89 mg/g (gallic acid equivalents over the dry matter). The extracts were characterized using HPLC-DAD, UPLC-ESI-MS/MS, DPPH⢠assay (2,2-diphenyl-1-picrylhydrazyl), TEAC assay (Trolox equivalent antioxidant capacity), and proanthocyanidin content determination. The flow-mode extraction procedure of grape stalks (2 kg) was carried out in a 15 L reactor. A semi-industrial decanter unit and a bag-filter were the keys units of the downstream operations. The resulting particle-free solution underwent nanofiltration on a membrane pilot skid, providing a final polyphenols-enriched stream concentrated up to 355.91%, as shown by the antioxidant activity and TPC.
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Full analytical data of Ecuadorian cocoa wastes (raw shells) and beans (as benchmark), are herein reported. A detailed characterization of production residues may pave the road to a zero-waste strategy for the cocoa industry. Multiple analytical techniques have been exploited to define the composition of the matrices, among them: elemental analyses, FTIR, Py-GC/MS/FID and UHPLC-ESI-MS/MS. Quali-quantitative data of carbohydrates, lipids, lignin, polyphenols, alkaloids and proteins have been obtained by Py-GC/MS/FID and UHPLC-ESI-MS/MS. Assignations are fully supported by literature references. The FAMEs composition of lipophilic UAE extract is also reported for sake of comparison with cocoa butter. This data collection completes a wider valorization work, "Cocoa bean shell waste valorisation; extraction from lab to pilot-scale cavitational reactors" (Grillo et al., 2018).
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The use of zero-waste processes to integrate food-waste valorisation into the circular economy equation is currently one of the hottest topics in sustainability research. This goal is still far from being fully achieved despite the release of a number of patents and papers that deal with the topic. The present work aims to valorise cocoa shells, one of the main by-product of the roasting process, in order to enhance the effective extraction of high added value compounds by means of green protocols. The high potential added value of the residual waste has been demonstrated via a direct analytical comparison of extracts and bean composition. A range of raw matrix extraction procedures have been investigated in order to define the best solvent and technology; ultrasound (US) and hydrodynamic cavitation (HC) were compared with conventional methods. The high-energy microenvironments generated by cavitation substantially promote fast biomass deconstruction with low energy consumption. The optimized protocol couples a HC reactor with a ternary water/ethanol/hexane mixture, simultaneously providing a hydrophilic product, which is rich in methylxanthines and polyphenols, and a lipid layer. Sequential milling and sieving pretreatment provided an enriched shell fraction via the partial removal of husk fibres (54.45 vs. 81.36 w/w % total fibres). The disposal of the latter reduces mass balance, but is rerouted into animal feedstock components and crop mulching. The protocols herein reported produce valuable extracts, which are rich in antioxidant flavanols (catechins and epicatechins), theobromine (32.7⯱â¯0.12â¯mg/g shells), caffeine (1.76⯱â¯0.08â¯mg/g shells) and cocoa butter, in a simple and easy manner. This new valorisation process afforded 20.5 w/w % and 15.8 w/w % hydrophilic and lipophilic fractions, respectively, when scaled up to function in a pilot flow reactor. The fatty acids, obtained in remarkable yield (forming the 96.4 w/w % of the total light part) well match the commercial cocoa butter profile. The antioxidant extract shows an impressive total phenolic content of 197.4â¯mg/g extract (gallic acid eq.), with a radical scavenging activity of 62.0⯱â¯3.1⯵g/mL (expressed in DPPH EC50). This work should facilitate industrial design for the convenient recovery of cocoa by-products as part of a zero-waste strategy.
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Cacao/química , Extractos Vegetales/química , Residuos , Alimentación Animal , Antioxidantes/análisis , Biomasa , Carbohidratos/análisis , Catequina/análisis , Flavanonas/análisis , Industria de Alimentos , Fenoles/análisis , Polifenoles/análisis , Solventes , Teobromina/análisis , XantinasRESUMEN
Dehydrocholic acid (DHCA), an unnatural bile acid, is manufactured by oxidation of cholic acid. Its biotransformation by two basidiomycetes (Trametes hirsuta and Collybia velutipes) is reported. These mycelia showed different affinities for the substrate and selectivities of attack: T. hirsuta in particular regio- and stereoselectively reduced the 3-keto group to yield 3 alpha-hydroxy-7,12-diketo-5 beta-cholan-24-oic acid (7,12-diketolithocolic acid) as the main product. A number of different chemical reductions were carried out on DHCA; among them hydrogenation with Raney Nickel in water under high-intensity ultrasound proved highly regio- and stereoselective, yielding 7,12-diketolithocolic acid exclusively. (1)H and (13)C resonances were assigned in details thanks to a series of 1D and 2D NMR runs including DEPT, NOESY, H-H COSY, gHSQC and gHMBC.