References
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2.1. Bioactive Compounds Extraction
As stated before, the chemical composition of Citrus fruits and their by-products are directly dependent on the edaphoclimatic conditions to which the plant is exposed. Additionally, the chemical composition varies, varies mainly according to the species and cultivar. However, in terms of its essential oils (EOs) and extracts, the extraction protocol directly influences the content of the active compounds and the yield. The most common extraction method to obtain EOs and extracts are hydro and steam distillation, solvent extraction, and cold pressing [28,29,30]. &#;Greener&#; and recent extraction techniques, such as microwave extraction, ultrasound extraction, and supercritical fluid extraction, have emerged as a more sustainable alternative to more traditional techniques since they require less use of energy and solvent(s) [31,32]. The application of Citrus EOs is extensive and transversal to several industries, including the food, cosmetic, and pharmaceutical industries [33,34].
Steam distillation is the most used method to obtain EOs from plants. Generally, using this method for EOs extraction, around 93% yield is obtained. Briefly, the application of heat in the form of steam is responsible for the breakdown of the cell structure of the plant material and the consequent release of the essential oil [35,36,37,38]. Sikdar & Baruah [39] compared the extracted essential oils from orange, sweet lime, and lemon peels obtained with steam distillation varying the applied temperature and extraction time. For all the conditions, essential oil from orange peels presented the highest yield, followed by the sweet lime essential oil. The authors reach the optimal conditions of 96 °C for a period of 60 min [39]. Hydrodistillation is often used to extract essential oils from flowers and wood. This technique consists of the complete immersion of the plant material in water, followed by heating the mixture until boiling and the condensation of the steam and essential oil vapor to an aqueous phase. The water protects the oil from overheating, acting as a barrier [38]. Although a relatively economical and easy-to-apply technique, the extraction by distillation processes presents some disadvantages such as low efficiency, loss of volatile compounds, long extraction times, and degradation of unsaturated or ester compounds as a result of the use of high temperatures [38].
Solvent extraction is a conventional technique used mostly for extracting compounds from fragile parts of plants, such as flowers. Usually, contrary to distillation techniques, it does not resort to high temperatures, protecting the active compounds that are thermo-sensitive. Several solvents can be used in this extraction, such as hexane, ethanol, methanol, and acetone. However, the solvent choice is directly dependent on the final use of the extract or essential oil, since it is possible that the toxic solvent may be present in the extract or essential oil [38]. The solvents and the authorized additives to be directly or indirectly used are specified in the European Commission Regulation No 231/ and its amendments [40].
To overcome some limitations of the solvent extraction techniques, researchers started to apply supercritical fluids as solvents in this technique. A supercritical fluid is any substance at a pressure and temperature above its endpoint of a phase equilibrium curve (critical point), below the pressure required to compress it into a solid, where there is no distinction between the gas and liquid phase [41]. The extraction by supercritical fluids presents a higher efficiency and a lower loss of volatile compounds than the previous extraction methods. Supercritical carbon dioxide is one of the most used fluids in this type of extraction. Besides being eco-friendly, the use of carbon dioxide allows the extraction process to occur at relatively low temperatures since its critical temperature is 31 °C, as well as its easy application at high-pressure conditions, presents in a liquid form [38,42]. However, this extraction technique using carbon dioxide has disadvantages, due to its non-polar properties. Although, this can be compensated by adding other solvents such as ethanol, methanol, and water [42,43,44]. Menichini et al. [45] compared the essential oil extracted from Citrus medica L. cv. Diamante peels by three different methods: hydrodistillation, supercritical CO2, and cold pressing. Limonene was the major compound found in the essential oils extracted by hydrodistillation and cold pressing followed by γ-Terpinene, while in the essential oil obtained with the supercritical CO2 extraction, the major compound was citropen (84.5%), followed by 2,3-Dihydrobenzofuran (2.9%) [45]. Also, the authors found that the essential oil obtained by supercritical CO2 presented no anti-inflammatory activity, while the essential oils obtained by hydrodistillation and cold-pressing presented anti-inflammatory activity [45]. Sicari & Poiana [46] compared the EOs extracted through hydrodistillation, solvent extraction by Soxhlet with pentane, and supercritical CO2 extraction from kumquat (Fortunella margarita Swingle) peels. All three essential oils presented almost the same content in limonene (around 96%) and their chemical composition was not significantly different. However, the EO obtained with supercritical CO2 presented a slightly higher content in esters and sesquiterpenes, which improved the essential oil aroma [46].
Having emerged in the 20th century, microwave extraction, or microwave-assisted extraction (MAE), is one of the most applied extraction techniques. Microwaves, located between the higher infrared frequencies and the lower radio frequencies, are non-ionizing electromagnetic waves [47]. In the MAE, microwaves act as energy vectors which, when applied to a certain material will absorb the electromagnetic energy and transforms it into heat [48,49]. The transformation of electromagnetic energy into heat relies on two mechanisms, that can occur simultaneously in both the sample and the solvent: ionic conduction and dipole rotation [48,50]. This guarantees that the system heating takes place at the same time, meaning, that the heating of both the solvent and the solid matrix occurs at the same time, unlike other extraction techniques where the heating occurs from the outside to the inside of the matrix and the mass transference occurs from the inside to the outside [50]. When compared with the more conventional/traditional extraction techniques, MAE presents several advantages, such as the use of lower quantities of solvent and lower human exposure to the used solvent, significant reduction in the extraction time, higher selectivity of the extracted compounds and the possibility of a solvent-free extraction [48,50,51,52]. However, not all are advantages regarding MAE. Method optimization is one of them. Several parameters must be considered when implementing/developing an MAE method, such as applied power, extraction time, solvent: matrix ratio, and matrix composition [48]. The choice of solvent is particularly important. Although both polar and non-polar solvents can be used, the choice must consider the solvent&#;s dielectric properties: a low dissipation factor translates into less dissipated heat, originating from the absorption of the microwave energy [48,50]. For instance, the water has a very low dissipation factor, which can lead to superheating and the extraction of some thermo-sensitive compounds is not advised [48]. Ferhat et al. [53] compared the extraction of EOs from fresh lemon (Citrus limon L.) peels by microwave accelerated distillation (or microwave &#;dry&#; distillation) with the conventional techniques of cold pressing and hydrodistillation. The microwave extraction resulted in a higher yield with a lower extraction time period. Also, the oxygenated fraction in the OE extracted with microwaves was 10% higher than the essential oil extracted with hydrodistillation and 40% higher than the OE extracted by cold pressing [53]. Bustamante et al. [54] also compared MAE of EOs from orange peels with hydrodistillation extraction, stating that MAE EO possessed slightly higher quantities of monoterpenes (0.78% higher), including D-Limonene, α-pinene, β-pinene and γ-Terpinene [54].
Usually applied to liquid and semi-solid foods, Pulsed Electric Field (PEF) extraction is one of the most recent extraction techniques applied in the food industry. Usually applied to liquid and semi-solid foods, consists of applying short pulses, micro- or milliseconds, of high voltage between 10 to 80 kV/cm, to the food placed between two electrodes [55,56]. The application of short high-voltage pulses increases the cell membrane conductivity and permeability due to the incensement of the transmembrane potential [56,57]. PEF is largely applied in the food industry to assure food microbiological safety since it has the advantage of inactivating pathogenic microorganisms without having to apply high temperatures, maintaining the original sensorial (texture, flavor, color) and nutritional value of unprocessed foods [55]. Coupled with other extraction techniques, such as solvent extraction, PEF can be used as a tool to improve the extraction or recovery of valuable compounds, such as phytochemicals. For instance, Hwang et al. [58] applied PEF to subcritical water extraction in Citrus unshiu peels improving the hesperidin content from 38.45 mg/g to 46.96 mg/g. Also, Kantar et al. [59] applied PEF in the extraction of polyphenols with ethanol extraction from orange pomelo and lemon. The authors found that the application of the PEF treatment increased the polyphenol content of ethanolic extracts by 50%. In addition, it can also increase the efficiency of juice extraction and increase the yield, from fruits by-products and plants, of bioactive compounds, extracts, and essential oils [55,57]. Luengo et al. [18] used PEF by applying 1, 3, 5 and 7 kV/cm to sweet orange (C. sinensis) peels, increasing the orange peels&#; antioxidant capacity extract by 51%, 94%, 148%, and 192%, respectively. The authors also concluded that the total polyphenol extraction yield increased by 20%, 129%, 153%, and 159% for the respective applied high voltages and, for the extract obtained with the 5 kV/cm, the content of naringin from 1 to 3.1 mg/100 g of fresh weight (FW) of peel and hesperidin from 1.3 to 4.6 mg/100 g FW of peel [18]. In another study led by El Kantar et al. [59]), PEF was applied to orange, pomelo, and lemon fruits in aqueous media at 3 kV/cm. The authors found that the applied current increased the juice yield by 25% for oranges, 37% for pomelo, and 59% for lemons [59]. In a more recent study, led by Peiró et al. [21], an electric field of 7 kV/cm was applied to lemon peels, which increased the polyphenol extraction by 300%, with astonishing contents of hesperidin (84 mg/100 g FW) and eriocitrin (176 mg/100 FW).
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