Extraction Of Hesperidin Research Articles

Maximizing the Hesperidin Extraction Using Supercritical Carbon Dioxide and Ethanol: Theoretical Prediction and Experimental Results

Agroindustrial waste can be valorized towards the obtaining of several products such as pigments, proteins, fibers, and polyphenolic compounds with antioxidant capacity. Orange peel waste is a promising source of polyphenolic compounds such as hesperidin. However, conventional extraction techniques present some environmental limitations such as high solvent consumption and high wastewater generation. Supercritical fluid extraction (SFE) has emerged as a green extraction technique due to the low use of solvent. The aim of this study was to maximize the hesperidin extraction based on theoretical predictions of the operating conditions from empirical thermodynamic models using SFE with carbon dioxide (CO2) as a solvent. The theoretical conditions were validated experimentally on a semi-pilot scale. The extracts were evaluated in terms of hesperidin content, total polyphenol content, and antioxidant capacity. Thermodynamic prediction of the operating conditions showed that the ethanol used as a co-solvent promotes hesperidin extraction. The optimum operating conditions were 25 °C, 80 bar, and a volumetric co-solvent concentration of 10%. The validation of the operating conditions resulted in a final hesperidin concentration of 11.5 ± 0.03 g/kg of orange peel waste. The experimental results were 30.26-times higher using 10% vol of ethanol than the extraction of hesperidin with pure ethanol as a co-solvent. The total polyphenol content and antioxidant capacity resulted in 831.92 ± 40.01 mg Galic acid/100 g orange peel waste, 15.41± 0.91 EC50/mL, and 5.31 ± 0.67 µMolTrox/100 g orange peel. Finally, the prediction of operating conditions from empirical thermodynamic models such as the Peng–Robinson equation of state with some modifications (Stryjek Vera) for solid–gas equilibrium solubility calculations, allows for maximizing the content of the polyphenolic compounds using SFE.

Pulsed electric field-assisted extraction of hesperidin from tangerine peel and its technological optimization through response surface methodology.

Tangerine peel is rich in flavonoids, particularly hesperidin, which has anti-inflammatory, antioxidant and anticancer biological activities. However, it is often wasted during citrus processing. The current common extraction method for hesperidin is solvent extraction, which has the characteristics of low extraction rate and high contamination. The aim of this study was to investigate the effect of pulsed electric field-assisted alkali dissolution extraction, followed by an acidification precipitation method, on the extraction rate and structure of hesperidin from tangerine peel. The results showed that the selected factors (material/liquid ratio, electric field intensity and pulse number) had a significant effect on the extraction yield. An optimum condition of 66.00 mL g-1, 4.00 kV cm-1 and 35.00 pulses gave the maximum amount (669.38 μg mL-1), which was consistent with the theoretically predicted value by software (672.10 μg mL-1), indicating that the extraction process was feasible. In addition, the purified extract was further identified as hesperidin from UV and NMR spectra. An appropriate strength of pulsed electric field-assisted alkali dissolution extraction followed by an acidification precipitation method can effectively improve the extraction rate of orange peel, and the purity of the extracted orange peel is higher. Compared with the traditional extraction, the pulsed electric field-assisted extraction method may be a potential technology for hesperidin extraction, which is beneficial for the high-value utilization of citrus resources. © 2024 Society of Chemical Industry.

Sequential extraction of hesperidin, pectin, lignin, and cellulose from orange peels: towards valorization of agro‐waste

AbstractTo maximize the reuse of citrus fruit processing waste, which is generated in large amounts due to juice production, this work shows the results of a new renewable approach for the extraction of high‐added‐value compounds present in orange biomass, specifically in orange peels (OP). The method is based on the use of diluted Ca2+, acid, and base solutions for the extraction of hesperidin (HSD), pectin, lignin, and cellulose sequentially, without generating any organic solid waste at the end, and without the need for air drying the starting biomass. Good yields of hesperidin were recovered (~1.56%), with excellent purity (up to 95%), as well as lignin (yield ~2.2%) and cellulose (yield ~12%). Pectin obtained by this process showed a high amount of galacturonic acid (~88%) and a low degree of methylation (~16%). All products were thoroughly characterized by applying Fourier transform infrared (FTIR) spectroscopy and solid‐state cross‐polarization/magic angle spinning carbon‐13 nuclear magnetic resonance spectroscopy (CP/MAS 13C‐NMR). The products recovered from OP can be applied in a wide array of fields, such as food, medicine, and pharmaceuticals, among others.

Hesperidin from Orange Peel as a Promising Skincare Bioactive: An Overview.

The pursuit for better skin health, driven by collective and individual perceptions, has led to the demand for sustainable skincare products. Environmental factors and lifestyle choices can accelerate skin aging, causing issues like inflammation, wrinkles, elasticity loss, hyperpigmentation, and dryness. The skincare industry is innovating to meet consumers' requests for cleaner and natural options. Simultaneously, environmental issues concerning waste generation have been leading to sustainable strategies based on the circular economy. A noteworthy solution consists of citrus by-product valorization, as such by-products can be used as a source of bioactive molecules. Citrus processing, particularly, generates substantial waste amounts (around 50% of the whole fruit), causing unprecedented environmental burdens. Hesperidin, a flavonoid abundant in orange peels, is considered to hold immense potential for clean skin health product applications due to its antioxidant, anti-inflammatory, and anticarcinogenic properties. This review explores hesperidin extraction and purification methodologies as well as key skincare application areas: (i) antiaging and skin barrier enhancement, (ii) UV radiation-induced damage, (iii) hyperpigmentation and depigmentation conditions, (iv) wound healing, and (v) skin cancer and other cutaneous diseases. This work's novelty lies in the comprehensive coverage of hesperidin's promising skincare applications while also demonstrating its potential as a sustainable ingredient from a circular economy approach.

A Two-Step Approach to Orange Peel Waste Valorization: Consecutive Extraction of Pectin and Hesperidin.

Citrus consumption translates into large amounts of residue, the disposal of which is associated with environmental issues and high costs. Current trends in citrus waste focus on the extraction of highly valued bioactive compounds via single-compound extraction. There is a lack of knowledge on how these methodologies can be introduced into extraction schemes of bioactive compounds, maximizing the residue potential and reducing its amount. The present work aimed to address this issue by designing a consecutive extraction of pectin and hesperidin from orange peel waste. A novel method for extraction and precipitation of hesperidin with an eco-friendly approach is also presented. After neutral pretreatment, pectin extraction was conducted under acidic conditions, followed by hesperidin extraction with a drastic pH change. Pectin had a high AUA content (66.20 ± 1.25%), meeting the criteria for use in the food industry. The best-tested conditions for hesperidin extraction (30 min, 70 °C, 1:10 (w/v)) provided a yield of 1% and a purity of 84%. The designed extraction scheme shows the potential of citrus waste as a source of bioactive compounds of good quality and high interest in the food industry while following the principles of green chemistry and circular economy.

CO2-responsive deep eutectic solvents for the enhanced extraction of hesperidin from Fertile orange peel

Hesperidin, also known as vitamin P, is widely studied for its distinctive potential in food and pharmaceutical industries. This work focuses on the research of CO2-responsive deep eutectic solvents (DESs) used as recyclable extractants for efficient extraction of hesperidin from Fertile orange peel. Reversible phase transformation of DES solution was achieved by bubbling CO2/N2. The maximum extraction yield of 22.39 mg/g was obtained for hesperidin under the following conditions: DES-6 (triethanolamine: 4-methoxyphenol = 1:1) used as extractant, water content of 35 wt%, solid–liquid ratio of 1:60 g/mL, extraction temperature of 25 °C, and ultrasonic time of 25 min, which was much higher than that extracted by methanol. Hesperidin of 74.38% was recovered in top phase after CO2 triggering. Density function theory (DFT) results indicated that hydrogen and π-π bonds were the main factors affecting hesperidin extraction. This study provides a new idea for extracting natural bioactive compounds using recyclable extractants.

Optimization of hesperidin extraction using hot methanol method assisted with ultrasound waves from the peel wastes of bitter orange (Citrus aurantium) and Persian orange (Citrus reticulata)

Optimization of hesperidin extraction using hot methanol method assisted with ultrasound waves from the peel wastes of bitter orange (Citrus aurantium) and Persian orange (Citrus reticulata)

Improving Solubility and Permeability of Hesperidin through Electrospun Orange-Peel-Extract-Loaded Nanofibers.

Orange peel, which is a rich source of polyphenolic compounds, including hesperidin, is produced as waste in production. Therefore, optimization of the extraction of hesperidin was performed to obtain its highest content. The influence of process parameters such as the kind of extraction mixture, its temperature and the number of repetitions of the cycles on hesperidin content, the total content of phenolic compounds and antioxidant (DPPH scavenging assay) as well as anti-inflammation activities (inhibition of hyaluronidase activity) was checked. Methanol and temperature were key parameters determining the efficiency of extraction in terms of the possibility of extracting compounds with the highest biological activity. The optimal parameters of the orange peel extraction process were 70% of methanol in the extraction mixture, a temperature of 70 °C and 4 cycles per 20 min. The second part of the work focuses on developing electrospinning technology to synthesize nanofibers of polyvinylpyrrolidone (PVP) and hydroxypropyl-β-cyclodextrin (HPβCD) loaded with hesperidin-rich orange peel extract. This is a response to the circumvention of restrictions in the use of hesperidin due to its poor bioavailability resulting from low solubility and permeability. Dissolution studies showed improved hesperidin solubility (over eight-fold), while the PAMPA-GIT assay confirmed significantly better transmucosal penetration (over nine-fold). A DPPH scavenging assay of antioxidant activity as well as inhibition of hyaluronidase to express anti-inflammation activity was established for hesperidin in prepared electrospun nanofibers, especially those based on HPβCD and PVP. Thus, hesperidin-rich orange peel nanofibers may have potential buccal applications to induce improved systemic effects with pro-health biological activity.

Intensifying Effect of Instant Controlled Pressure Drop (DIC) Pre-Treatment on Hesperidin Recovery from Orange Byproducts: In Vitro Antioxidant and Antidiabetic Activities of the Extracts.

The orange byproduct is a widely accessible and valuable source of functional phenolic compounds, particularly hesperidin. Hesperidin extraction remains a challenging phase in its valorization chain due to its low solubility and limited extractability in solvents. This work aims to examine the effect of conventional solvent extraction (CSE) compared to emerging and innovative extraction methods: accelerated solvent extraction (ASE) and ultrasound-assisted extraction (UAE) when applied with or without a pretreatment process of instant controlled pressure drop (DIC) to intensify extraction, antioxidant, and antidiabetic activities. The total phenols, flavonoids, hesperidin contents, radical scavenging activities, iron chelating activity, and in vitro α-amylase inhibition of the extracts were determined for CSE (80%, 70 °C), UAE (ethanol 80%, 70 °C, 200 W), and ASE (ethanol 60%, 100 °C, 100 bars) with or without DIC pretreatment (pressure = 0.4 MPa, total thermal time = 30 s). The hesperidin amounts obtained were 0.771 ± 0.008 g/100 g DM, 0.823 ± 0.054 g/100 g DM, and 1.368 ± 0.058 g/100 g DM, for CSE, UAE, and ASE, respectively. DIC pretreatment of orange byproducts increased hesperidin recovery by 67%, 25.6%, and 141% for DIC-CSE, DIC-UAE, and DIC-ASE, respectively. The DPPH and ABTS radical scavenging and iron chelating activities of extracts were also significantly enhanced, and the in vitro antidiabetic activity of extracts was preserved.

Mass transfer mechanism of the multivariate consecutive extraction process of pectin and hesperidin from Citrus aurantium L.: Kinetics, thermodynamics, diffusion and mass transfer coefficients

In the previous research, the multivariate consecutive extraction process of pectin and hesperidin from FAI was completed, and it was found that the extraction efficiency of hesperidin could be significantly improved because of the priority extraction of pectin. The main objective ofthis paper is to further elucidate the mass transfer mechanism of the extraction process. The kinetics, thermodynamics, activation energy, diffusion coefficients, mass transfer coefficients and Biot number of the multivariate consecutive extraction process as well as the single extraction process of hesperidin in FAI were estimated and compared. It was confirmed that the mass transfer of the process was effectively strengthened because of the priority extraction of pectin from FAI. Its kinetic data was demonstrated to the pseudo-second-order kinetic model, and the activation energy of hesperidin extraction was as low as 2.27 kJ/mol, far lower than that of the single extraction process (16.67 kJ/mol). In particular, the diffusion coefficien and mass transfer coefficient were larger while the Biot number was lower compared with the single extraction process. These results further proved that the priority extraction of pectin from FAI led to the destruction of cell structure and the exposure of hesperidin crystals, which can effectively reduce the internal resistance of the mass transfer and the activation energy of extraction process, therefore accelerating the penetration and wetting of the extractant into the raw material internally, improving the transfer of hesperidin from the inside to the surface of the raw material as well. In addition, the extraction thermodynamics illustrated that the extraction process of hesperidin was endothermic, irreversible and spontaneous.

RECOVERY OF HESPERIDIN FROM LEMON BY-PRODUCTS USING GREEN TECHNIQUES

The food industry is the main producer of food waste. Therefore, the development of methodologies to reuse and make the most of it is of great interest. Food industry waste can contain compounds with added value that, if properly extracted and used, can be applied to the development of healthy foods (clean label), nutraceuticals, senior food, cosmetics, etc. The revaluation of by-products from the citrus industry will make it possible to reduce the large volume of lemon waste, reducing the cost of waste management and obtaining compounds of interest from them. In this work, different alternative methodologies to the use of organic solvents have been used for the extraction of Hesperidin in lemon by-products, including thermal, enzymatic and ultrasound treatment and purification adsorption processes with resins, granular activated carbon and zeolite were optimized. The optimum Hesperidin extraction (86371 ± 422 mg GAE/g dry extract) was achieved using an enzymatic pre-treatment, cellulase enzyme (Validase TRL®-Sigma) at 0.01% of weight of the lemon peel by-product, treatment time of 60 min, and water/citrus by-product ratio of 3:1 w/w, followed by a purification adsorption/desorption process through Purolite PAD610 resin.

Statistical optimization of cellulase production and its efficacy in hesperidin extraction from orange peel and bioethanol production from rice straw by simultaneous saccharification and fermentation

Cellulolytic enzymes are of great interest for the hydrolysis of cellulosic biomass and their demand is increasing intensely due to their potential applications in second generation bioethanol production. In this study, cellulase production from Bacillus cereus KG10 was explored and the production media and cultural conditions were optimized through Box-Behnken design. Under optimized conditions, the cellulase activity was improved to 0.51 U/mL. The purity and the molecular mass of the enzyme (55.1 kDa) were confirmed by HPLC and MOLDI-TOF MS respectively. Additionally, cellulase mediated extraction of hesperidin was performed to prove extraction efficiency by ESI-MS. Likewise, the cellulase efficiency in bioconversion of lignocellulosic biomass was also confirmed towards improving the ethanol yield. The results showed that higher amounts of reducing sugar 73.2 and 89.3 % were explored from cellulase mediated hydrolysis of rice straw than that from acidalkali mediated hydrolysis. A high ethanol yield was also achieved in media added with cellulase treated rice straw (38.1 g/L) than that of acid-alkali treated rice straw (27.4 g/L) through simultaneous saccharification and fermentation (SSF) process using cellulase from B. subtilis KG10 and Saccharomyces cerevisiae. Thus, the cellulase from B. cereus KG10 could be a potential candidate in various industrial sectors.

Pressurised hot water extraction of phenolic compounds with a focus on eriocitrin and hesperidin from lemon peel

SummaryIn this study, the extraction of bioactive compounds from lemon peel, a by‐product of the food industry, was investigated using pressurised hot water extraction (PHWE) at different extraction temperatures (40–200 °C) and times (5–30 min) under 10.34 MPa pressure. The selectivity of the PHWE process on eriocitrin and hesperidin extraction was also tested. The highest total phenolic content (TPC) (59.57 mg gallic acid equivalents g−1), total flavonoid content (TFC) (8.22 mg catechin equivalents g−1) and antioxidant capacity by DPPH (42.59 mg Trolox equivalents (TE) g−1) were obtained at 160 °C for 30 min. The maximum eriocitrin (30.41 mg g−1) and hesperidin (25.90 mg g−1) contents were achieved at 160 °C for 5 min with a 5‐hydroxymethyl furfural content of 0.07 mg g−1. PHWE provided better results for individual compounds and antioxidant capacities than conventional extraction. The results indicated the potentiality of PHWE in the selective extraction of eriocitrin and hesperidin from lemon peel by controlling the extraction temperature and time.

Sustainable Single-Stage Solid–Liquid Extraction of Hesperidin and Rutin from Agro-Products Using Cyrene

Hesperidin and rutin are two sought-after natural flavonoids, traditionally extracted from abundant natural citrus fruits and tea leaves using large amounts of ethanol or methanol solvents. Recent ...

A High-Yield Process for Production of Biosugars and Hesperidin from Mandarin Peel Wastes.

In this research, novel biorefinery processes for obtaining value-added chemicals such as biosugar and hesperidin from mandarin peel waste (MPW) are described. Herein, three different treatment methods were comparatively evaluated to obtain high yields of biosugar and hesperidin from MPW. Each method was determined by changes in the order of three processing steps, i.e., oil removal, hesperidin extraction, and enzymatic hydrolysis. The order of the three steps was found to have a significant influence on the production yields. Biosugar and hesperidin production yields were highest with method II, where the processing steps were performed in the following order: oil removal, enzymatic hydrolysis, and hesperidin extraction. The maximum yields obtained with method II were 34.46 g of biosugar and 6.48 g of hesperidin per initial 100 g of dry MPW. Therefore, the methods shown herein are useful for the production of hesperidin and biosugar from MPW. Furthermore, the utilization of MPWs as sources of valuable materials may be of considerable economic benefits and has become increasingly attractive.

A High-Yield Process for Extraction of Hesperidin from Orange (Citrus sinensis L. osbeck) Peels Waste, and Its Transformation to Diosmetin, A Valuable and Bioactive Flavonoid

An alternative and high-yield method to obtain hesperidin, a bitter flavored flavanone glucoside, from orange (Citrus sinensis L. osbeck) peels waste is described. The proposed process, which add high-value to this kind of residue from orange juice processing industry, was based on a successful modification applied to extraction of naringin from grapefruit. This method involves extraction with methanol and crystallization in water with addition of dichloromethane, requiring shorter times and reducing of volume of solvent employed. Changing to hot extraction with methanol of fresh orange albedo led to higher yields of extraction in half the time required due to the direct method, avoiding air-dried albedo step. Application of described method led to 2.8% yield (w/w dry albedo) of hesperidin extracted in 89.4% purity determined by HPLC analysis. To add high-value to the flavanone obtained, it was subject to chemical transformation (oxidation and hydrolysis, 83% and 88% yield, respectively) into the flavone diosmetin (73% yield for 2 steps), an expensive and naturally-occurring flavonoid in low yields which exhibits a wide range of pharmacological properties. This paper describes high-yield process for extraction of hesperidin from orange peels waste, and their use as feedstock in the production of diosmetin.

Optimization of chemical extraction of phenolic compounds from fruits and vegetable residue by UPLC-MSE

ABSTRACT Phenolic compounds (PC) extraction can be affected by many intrinsic characteristics of food matrix, as well as the analytical method employed to separate and identify these compounds. In this study, 30 conditions were analyzed considering as variables: time, temperature, and ethanol:water proportions as solvent. All extracts were analyzed into a UPLC ESI-Q-TOF-MS/MS in negative ion mode. All data were processed by QI Progenesis software by using a customized database based on phenolic compounds. The antioxidant activity (AA) was assessed by DPPH method. Globally, 43 PC were tentatively identified, and flavonoids were the most abundant. The increase in temperature was the main interfering with the extraction process. However, the temperature of 40°C for 24 h with ethanol:water ratio (75:25; v/v) promoted the most abundant extraction of hesperidin, and the highest AA (28.23 ± 0.01 µmol Trolox.g−1). All extraction conditions lead to extracts with similar qualitative profiles, but different AA.

Sustainable Green Procedure for Extraction of Hesperidin from Selected Croatian Mandarin Peels

The peels of Citrus reticulata Blanco mandarin cultivars of different Croatian varieties (Zorica rana, Chahara, Okitsu, Kuno) were extracted using 15 different choline chloride-based deep eutectic solvents (DESs) at 50 °C for 30 min and with 20% water addition. The extracts were analyzed by high performance liquid chromatography with diode array detection (HPLC-DAD) to determine the most suitable DES for the extraction of hesperidin in the samples. The screening results indicated that choline chloride: acetamide (1:2) provided the most efficient hesperidin extraction (112.14 mg/g of plant), while choline chloride:citric acid (1:1) solvent showed the lowest hesperidin yield (1.44 mg/g of plant). The Box–Behnken design was employed to optimize extraction parameters for each variety of mandarin peel, including extraction time, temperature and water content on hesperidin extraction. The results indicated that hesperidin content in mandarin peels was completely variety-dependent. Being a novel and efficient green media for hesperidin extraction, deep eutectic solvents could also serve as promising solvent systems for the production of extracts rich in bioactive compounds.

A Green Process for the Extraction and Purification of Hesperidin from Mexican Lime Peel (Citrus aurantifolia Swingle) that is Extendible to the Citrus Genus

The processing of Mexican limes generates great amounts of peel as a by-product. Lime peel is mainly rich in the flavonoid hesperidin, whose bioactivity is oriented mainly to cardiovascular diseases and cancer. The purpose of this work was to develop a green process for the extraction and purification of hesperidin from Mexican lime peel. The extraction of hesperidin was investigated on a laboratory scale by varying the solvent composition and the solid-to-solvent ratio, and then scaling this process (volume: 20 L). Next, a purification process using adsorption resins was assessed: first through static tests to determine the adsorption efficiency with two resins (FPX66, EXA118), and then on a packed column with 80 mL of resin at 25 °C. Lab-scale extraction showed that the best conditions were a solid-to-solvent ratio of 0.33 g/mL and 60% ethanol. After using these conditions at pilot scale and concentrating the solution, the hesperidin content of the extract was 0.303 mg/mL. Through static tests, higher adsorption efficiencies were achieved with the EXA-118 resin and diluted extract (4:6 ratio with 10% dimethylsulfoxide, (DMSO)). Finally, the purification process on a packed column from the diluted extract (hesperidin concentration of 0.109 mg/mL) had a mean recovery efficiency of almost 90%.

By-product of honeybush (Cyclopia maculata) tea processing as source of hesperidin-enriched nutraceutical extract

Cyclopia maculata (honeybush) plant material was evaluated to determine its potential as renewable source material for hesperidin-enriched extract preparation. Stems contained significantly higher hesperidin levels than leaves, while “fermentation” (high-temperature oxidation process), an essential processing step of the herbal tea product, honeybush, had no effect (P>0.05) on hesperidin content. Extraction of hesperidin from the by-product of honeybush tea processing, containing mostly stems, was optimised using response surface methodology (RSM). Four extraction parameters, namely ethanol concentration (% v/v), time (min), temperature (°C), and solvent:solid ratio (mL/g), were evaluated. Second order polynomial mathematical models for hesperidin yield and hesperidin content of the extract were constructed from RSM results and verification experiments indicated good accuracy and predictive ability. Practical process restrictions limited global optimisation and only an optimum for ethanol concentration could be predicted. The choice of process parameter values, feasible for industrial application, will depend on the product application and a cost-benefit analysis of the unit operations of the process.