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Review

Extraction, Quantification and Characterization Techniques for Anthocyanin Compounds in Various Food Matrices—A Review

by
Oana Emilia Constantin
and
Daniela Ionela Istrati
*
Faculty of Food Science and Engineering, Dunărea de Jos University of Galati, 111 Domnească Street, 800201 Galati, Romania
*
Author to whom correspondence should be addressed.
Horticulturae 2022, 8(11), 1084; https://doi.org/10.3390/horticulturae8111084
Submission received: 12 October 2022 / Revised: 9 November 2022 / Accepted: 14 November 2022 / Published: 16 November 2022
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Abstract

:
Anthocyanins are water-soluble pigments characterized by various intense colors found in fruits and vegetables. Scientific studies have shown growing evidence to support their health benefits. Therefore, estimating the anthocyanin content in food is essential to identify the ideal analytical method. Moreover, due to the instability of plant anthocyanins, it is important to select and optimize their extraction, separation and qualitative and quantitative analysis, steps that are indispensable and important in their study. The present article reviews the latest procedures for extracting anthocyanins from various food matrices and analytical methods for their quantification. Therefore, various forms of preliminary treatments of samples for anthocyanin extraction, extraction procedures for various fruits, vegetables and cereals, purification of samples and quantification of anthocyanins are highlighted and evaluated. Using ultrasound-assisted extraction (UAE) might be effective for anthocyanin extraction and the Amberlite XAD-7HP method is the most effective for purifying anthocyanins. Combining the liquid chromatography (LC) method with electrospray ionization (ESI) and mass spectrometry (MS) or quadrupole time-of-flight (QTOF) with mass spectrometry (MS) better quantifies the anthocyanins in the food complex samples. Therefore, the extraction and separation of anthocyanins and their qualitative and quantitative analyses are essential steps in their research. As a result, the study concentrates on a detailed characterization of various qualitative and quantitative analytical methodologies, while briefly describing the main anthocyanin extraction processes.

1. Introduction

Anthocyanins are bioactive compounds found naturally in plants, with essential roles in higher plants’ propagation, protection and physiology [1,2]. Anthocyanins are water-soluble pigments that provide various fruits and vegetables their blue, purple and red hues [3] (Table 1), such as red cabbage, beans, onions, radishes, berries, grapes, pomegranates, etc. [4,5,6]. There is growing interest in the additional effects on the diet with anthocyanins, not only in terms of the effect on disease but also as a possible preventive intervention for a healthy life. In the scientific literature, anthocyanins are characterized as having an antioxidant and anti-inflammatory effect, but the most promising effect seems to be in relation to cardiovascular diseases [7].
Chemically, anthocyanins are polyphenols and belong to a large class of secondary metabolites known as flavonoids, with a central structure in cation 2-phenylbenzopyryllium (flavylium) [2]. They are polyhydroxy and polymethoxy derivatives of the flavylium cation and may have carbohydrate components or acylated fragments attached in different positions.
Although more than 700 compounds have been described in the literature, they are derived mainly from six anthocyanidins (aglycone form): pelargonidin, cyanidin, delphinidin, malvidin, peonidin and petunidin [4,8,9,10]. In general, anthocyanins have esterified carbohydrates (sugar) and the most common sugars related to anthocyanin are glucose, galactose, arabinose, rhamnose and xylose. Anthocyanins (anthocyanosides) can be classified according to the number of carbohydrate residues into monoglycosides and diglycosides. Both categories may have carbohydrates or acylated with one, less often two, remnants of p-coumaric acid, p-hydroxybenzoic acid, p-hydroxycinnamic acid or acetic acid. Acylation of carbohydrate residues, especially with hydroxycinnamic acids, increases the stability and coloring capacity of the anthocyanin molecule [8,10].
Anthocyanidins that are relatively unstable substances are stabilized by glycosylation, leading to a dynamic balance between the two resulting forms: glycosylated (anthocyanin) and non-glycosylated (anthocyanidin).
In an acidic environment, such as grapes and wine, anthocyanidins, found in the form of flavylic-type cations, can be isolated only as salts, usually chlorides. The heterocyclic nucleus of anthocyanin can be formed by oxidation from that of flavans by reducing flavones. This gives anthocyanin a junction and transition role between proanthocyanidins and flavonoid substances (kaempferol, quercetin and myricetin). These reactions are reversible; based on a biochemical mechanism, anthocyanidins pass into a discolored form via reduction [11,12].
Anthocyanins must be extracted, separated and subjected to both qualitative and quantitative analysis as part of the research process. In the last five years, 143 studies have focused on identifying and characterizing anthocyanin compounds from the food industry and related fields. Previous studies reviewed research progress in anthocyanin extraction [13,14,15], analyzed the effects of different extraction and purification methods on the extraction rate and purity of anthocyanins [16,17] or presented the methods of quantification and identification [15]. Considering that research registers continuous progress, the methods of analyzing anthocyanins must be systematically reviewed for a better understanding of them. As a result, this study focused on providing a detailed explanation of various techniques for the qualitative and quantitative evaluation of some of the key anthocyanin-extraction methodologies.

2. Procedures for the Extraction of Anthocyanins from Different Food Matrices

The extraction and separation of anthocyanins from plants is important, especially due to the instability of plant anthocyanins, selecting and optimizing. Anthocyanins are prone to degradation by several factors, including pH, temperature, oxygen, water activity, co-pigments and enzymes [18,19]. Unwanted compounds, such as sugars, proteins, lipids, acids and other flavonoids, can also be removed from plant material by appropriate extraction methods. The most used method for anthocyanin extraction is the conventional one, solid–liquid extraction, also known as solvent extraction, during which anthocyanins can be dissolved in polar solvents (methanol/glycolic acid and acetone) [9,10], followed by their quantification, achieved by using spectrophotometry, the differential pH method, which is a rapid and convenient quantitative assay [20]. Starting from this point, it has developed and there are many anthocyanin-extraction methods, such as conventional solvent extraction (CSE), enzyme-assisted extraction (EAE), fermentation extraction (FE), supercritical fluid extraction (SFE) (CO2) extraction [21], microwave-assisted extraction (MAE) [22], ultrasonic-assisted extraction (UAE), high-hydrostatic-pressure extraction (HHPE) and pressurized-liquid extraction (PLE) [23,24]. One of the most frequent techniques for obtaining anthocyanins from plants is conventional solvent extraction [13]. Furthermore, in order to meet the demands of safety and environmental sustainability, new extraction technologies with shorter extraction periods and higher yields have been developed (e.g., PLE, EFS, UAE, MAE, EAE, etc.).
Preparation of samples for the quantification and identification of anthocyanins involves applying three successive stages: extraction, purification and identification (Figure 1).

2.1. Preliminary Treatments

Anthocyanins can be found inside the vacuoles of cells in several types of tissues, thus, influencing their accessibility, which depends on the integrity of plant tissues and the ability of solvents to penetrate tissues [16]. The preliminary treatments before the anthocyanin extraction increase the anthocyanin’s accessibility from the plant matrix to the extraction medium and the stability of the anthocyanins in the extract [27]. According to prior research, there are three main pretreatment methods for anthocyanins: chemical, biological and physical [28].
Acid treatment and alkaline immersion are chemical techniques used to increase extraction efficiency. The most popular method is applying acid pretreatments, since it can enhance the stability of anthocyanins due to a more favorable extraction environment and the inactivation of enzymes that degrade anthocyanins. Alkaline treatments improve solvent penetration during extraction by removing the waxy outer layer in the case of food matrices containing wax bloom [29].
Enzymatic treatments are one biological technique that increases the effectiveness of anthocyanin extraction by destroying the cell wall of plant materials. Anthocyanins are found inside plant cells called vacuoles. Using enzymes to dissolve the cell wall, anthocyanins can be extracted from plant cells more easily, especially those with thicker cell walls and pectin [28].
Other methods for improving anthocyanins extraction are the physical methods, a breakdown of cell walls [27]. Commonly used preliminary treatments include non-thermal treatments (grinding, pulsed electric field treatment, freezing and homogenization) and heat treatments (hot-air drying). Obtaining powders from mechanical pretreatment is a conventional approach to reduce plant tissue particle size and increase solvents’ permeability. The drawback of such treatments is that they make it easier for anthocyanins to be exposed to oxidizing chemicals, which leads to their destruction. Heat treatments can improve the efficiency of anthocyanin extraction by damaging the cells’ membranes and have the disadvantage that they can cause the degradation of specific types of anthocyanins. Thus, new methods of thermal pretreatment have been developed, such as microwave heating. Alternative heat treatments can be used before or during extraction and can have a reduced rate of thermal degradation compared to conventional thermal methods.

2.2. Extraction

Sample preparation for anthocyanin analysis varies depending on the type of sample. Juices, syrups and wines are examples of liquid products requiring minimal preparation before analysis, while solids must be fractionated and/or homogenized before extraction [15]. Qualitative research involves extraction with a weakly acidified alcoholic solvent, concentrated under vacuum, purification and pigment separation. The procedure must recover the anthocyanins while avoiding their modification. Thus, acylated anthocyanins, which degrade in solvents containing mineral acids, such as sulphuric acid (H2SO4) or hydrochloric acid (HCl), must be extracted with acidified solvents with organic acids, such as acetic acid or formic acid (FA) [30]. Further, anthocyanins are sensitive to heat and avoiding high temperatures during extraction and concentration is recommended. The solvents most often used to prepare plant extracts are water (H2O), methanol (MeOH), ethanol (EtOH), acetone, dichloromethane and hexane [31,32,33]. The extraction procedure also separates free sugars, organic acids, alcohols, proteins and amino acids from the plant in addition to anthocyanins [34,35]. Some of these, such as free sugars, cause the degradation of anthocyanins while being stored, becoming necessary for separating these compounds [34].
Table 2 summarizes the procedures and methods of extracting anthocyanins from different food matrices.

2.2.1. Procedures for the Extraction of Anthocyanins from Fruits

Several scientific papers report using various anthocyanin-extraction processes in food matrices, such as fruit extracts. For example, Chandra Singh et al. [23] proposed an extraction procedure for blueberry (Vaccinium coroymbosum L.) using a single-extraction method, ultrasound-assisted extraction (UAE) and combined-extraction methods (extraction method by grinding/UAE and grinding with a Dounce/UAE homogenizer). Therefore, twelve mixed solvents (MeOH/H2O, EtOH/H2O) were adjusted to pH 2.0 or pH 3.0 with concentrated HCl in different proportions (60:40, 70:30, 80:20, 70:30). The extraction methods included the following conditions: UAE extraction (30 min, at a temperature of 15 °C); extraction with sample grinding (using a system of 24 ceramic spheres (1,4 mm) to crush and shake the sample for 44 s) and for grinding with a Dounce homogenizer (sample was crushed to destroy cells and tissues by applying mechanical force in glass homogenizers). Further, Ultra-High-Performance Liquid Chromatography–Photodiode Array–Electrospray Ionization–Mass Spectrometry (UHPLC-PDA-ESI Chandra Singh -MS) was performed for anthocyanin quantification. The chromatographic profile of blueberry extract indicated the presence of three anthocyanin compounds by correlating them with the reference standards for anthocyanins: dpd-3-glu < ptd-3-glu < mvd-3-glu. The study suggests that using the UAE to quantify anthocyanins may be an effective method with acceptable performance, the reaction in which the mixture of MeOH solvents (80:20) produced the maximum extraction yield at pH 3.0. In another protocol, the anthocyanins from blueberry (Vaccinium spp.) were extracted using acidified glycerol coupled with the pulse ultrasound-assisted extraction (P-UAE) method and analyzed by UPLC-Triple-TOF/MS, which led to the identification of 10 anthocyanin compounds [55]. The study concluded that the glycerol extraction method was responsible for a better extraction and preservation of anthocyanins. Further, da Silva et al. [56] investigated the extraction of anthocyanins from blueberry with natural deep eutectic solvents (NADESs) based on choline chloride, glycerol and citric acid. Therefore, the extraction efficiency of NADES was compared with that of an organic solvent (methanol:water:formic acid 50:48.5:1.5 v/v.) and a 1% (v/w) citric acid aqueous solution. The blueberry extracts were analyzed using HPLC equipment coupled to a reverse phase Symmetry C-18 column and mass spectrometer (MS) detector. Natural deep eutectic solvent (NADES) based on choline chloride:glycerol:citric acid at a molar ratio of 0.5:2:0.5 was demonstrated to be equally efficient to the conventional organic solvent.
In the extraction procedure established by Wang et al. [57], the blueberry (Vaccinium spp.) fruit parts (pulp and peel samples) were finely chopped with liquid nitrogen. The ratio of the processed fruit powders to the solvents, as mixtures of various types and solvent concentrations, was 1:10. The samples were immersed in a water bath or an ultrasonic water bath of 30/40 kHz/185 W, using the following extraction parameters (temperature/time): CSE method (solvent type: MeOH, EtOH, acetone, solvent concentration: 60%, 70%, 80%, extraction temperature: 50 °C, 60 °C, 70 °C); UAE (solvent type: MeOH, EtOH, acetone; solvent concentration: 60%, 70%, 80%; extraction temperature: 20 °C, 40 °C, 60 °C). The optimized parameters were 60% MeOH, 50 °C, 1 h (CSE) or 70% MeOH, 30 °C, 20 min (UAE). The extracts’ anthocyanins were detected by using an HPLC-PDA system (High-Performance Liquid Chromatography–Photodiode Array), which revealed the presence of 14 compounds for blueberries (Table 3, Figure 2A).
The above-mentioned protocol of extraction was also applied to sweet cherries (Prunus avium) [57]. The results revealed the following optimized parameters: 60% EtOH, 70 °C, 1 h (CSE) or 80% EtOH, 30 °C, 20 min (UAE). The anthocyanins from the extracts were identified using an HPLC-PDA system and two compounds for red cherries were identified, dpd-3-gal and dpd-3-glu (Table 3, Figure 2A). Blackhall et al. [58] extracted the anthocyanins from sweet cherries (Prunus avium) in acidified methanol and acidified ethanol (0.1% v/v 12 N HCl) at different solvent/solid ratios (2.5, 5, 7.5, 10 or 12.5 mL/g cherries). The quantitation of total anthocyanins was accomplished by ultra-performance liquid chromatography (UPLC) using a diode array UV/Vis detector. This study identified the optimum variables for the extraction of anthocyanins from cherries’ extraction time of 90 min, temperature of 37 °C and a 10 mL/g solvent/solid ratio followed by 100% ethanol acidification.
In another protocol, the fresh sweet cherries in Early rivers (Prunus avium L.) [59] were subjected to four cycles of microwave irradiation at 1000 W for 45 s each. The extracts collected constituted the raw extract, centrifuged at 7000 rpm for 5 min at 10 °C. The anthocyanins were then purified via semipreparative liquid chromatography using an isocratic mobile phase consisting of a H2O/EtOH/FA mixture circulating in a “closed-loop” system. HPLC-MS determined the anthocyanin content and the following compounds were identified and quantified: cyd-3-O-glu and cyd-3-O-rutinosides.
Karaaslan et al. [38] applied a procedure of extraction at room temperature with acidified solvent (5:1 ratio) to extract anthocyanins from cranberries (Vaccinium oxycoccos). The extracts were centrifuged at 4000 rpm for 10 min and the supernatants were filtered (0.45 μm filter). The anthocyanins identified using an HPLC-ESI-MS system were: dpd-3-O-glu, cyd-3-O-glu, plg-3-O-glu and mvd-3-O-glu. The procedure developed by Alrugaibah et al. [60] involved the extraction of anthocyanins from cranberry pomace (Vaccinium macrocarpon) using different formulas of NADES and their efficiency was compared with that of 75% ethanol. The identification of anthocyanins was carried out using the HPLC system. The extraction with NADES had higher extraction efficiency and selectivity ethanol extraction. At NADES, an extraction mixture of glucose, lactic acid (1:5) and 20 mL/100 mL water produced the best yield, approximately 1.8-times higher than the yield with 75% ethanol. In the protocol developed by Saldana et al. [42], using a pressurized fluid reactor (40–160 °C and 50–200 bar) and water, 30–100% ethanol or 5% citric acid, anthocyanins were extracted from cranberry pomace (Vaccinium macrocarpon) and measured using an HPLC-UV system. According to this protocol, the optimal conditions for extracting anthocyanins from cranberries are: 70% ethanol at 120 °C and 50 bar and 5 mL/min flow rate.
The extraction procedures of grapes (Vitis amurensis) applied by Ji et al. [47] used lyophilized samples (Muscat Hamburg grape skin) extracted with 70% alcohol, for 24 h, in the dark. After 25 min of ultrasonication at 60 kHz, the samples were filtered and concentrated in a rotary evaporator at 35 °C in a vacuum. Before HPLC injection, the extracts were dissolved in MeOH and filtered with an 0.45 m filter. The HPLC-DAD-ESI-MS analysis identified 12 anthocyanin compounds (Table 3).
Cvjetko Bubalo et al. [42] used lyophilized and ground samples (grape skin Vitis vinifera L. of the Plavac mali variety) for the extraction procedure. Conventional solvents, DES or three different extraction techniques (shaker, MAE and UAE) were used. The samples were extracted and centrifuged at 5000 rpm for 15 min and the supernatant obtained was decanted and adjusted. The anthocyanin content was determined by HPLC-MS, with eight compounds identified and quantified (Table 3). Further, Loarce et al. [61] used, in their protocol, freeze-dried under vacuum samples (grape pomace from V. vinifera L. cv. ‘Tempranillo’), extracted by pressurized hot water with NADES. HPLC-DAD-ESI-MS/MS analysis of anthocyanins was applied, the best extraction results being recorded for 30% choline chloride and oxalic acid (ChOx) at 60 °C.
For the extraction procedure elaborated by Fang et al. [62], the plum (Prunus salicina Lindl.) peel was ground with liquid nitrogen obtaining a fine powder. The powders were extracted with 0.05% HCl in MeOH at 4 °C for 24 h and then centrifuged at 8000× g for 20 min.
Ambigaipalan et al. [51] used a lyophilized sample degreased with hexane (1:5.5 min) to extract pomegranates (Punica granatum L.). The anthocyanins were extracted with acetone 70% (1:40), using an ultrasonic water bath at 30 °C for 20 min. The extracts were centrifuged at 4000× g for 5 min; the supernatant was evaporated at 40 °C until the acetone was removed and the solid residue was dried at 40 °C for 48 h. The free phenols were extracted five times with diethyl ether and ethyl acetate after the aqueous phase had been evaporated and acidified with HCl 6 M (pH = 2) (1:1). Anhydrous sodium sulfate was used to filter the organic phase, which was then dried under vacuum at 40 °C. The anthocyanin content was determined by HPLC-DAD-ESI-MS/MS, with 12 compounds identified and quantified (Table 3). Recent studies suggest that β-cyclodextrin-assisted extraction represents a new strategy for anthocyanin extraction [63]. The advantages of this method derive from the high efficiency of the extract; it is not necessary to use organic solvents and the ability to stabilize the bioactive compound.
Karaaslan et al. [64] obtained a homogeneous mixture from shredded strawberries (Fragaria spp.) for the extraction procedure. The samples were extracted at room temperature with acidified solvents and the obtained extracts were centrifuged at 4000 rpm for 10 min and filtered. In order to optimize the extractive process, the following parameters were varied: solvent type, extraction time and liquid-to-solid ratio as follows: solvents (H2O, acetone, ACN, MeOH and EtOH acidified by 0.1% HCl); extraction time (0, 30, 60, 120 and 240 min); liquid/solid ratio (1:1, 2:1, 4:1, 6:1, 8:1 and 10:1). HPLC-ESI-MS determined the anthocyanin content and the following compounds were identified and quantified: dpd-3-O-glu, cyd-3-O-glu, plg-3-O-glu and mvd-3-O-glu. The optimized parameters were acidified MeOH (solvent), 30 min (extraction time) and 1:1 liquid ratio: solid. Further, a recent study used microwave hydrodiffusion and gravity (MHG) to extract anthocyanins from strawberries [65]. The anthocyanins extracted using this method were characterized using the UHPLC-DAD-MS/MS. Using this extraction method, five anthocyanin compounds were identified in strawberry extracts, pelargonidin-3-glucoside being the major compound.

2.2.2. Procedures for the Extraction of Anthocyanins from Vegetables

Wiczkowski et al. [66] used powder from red cabbage (Brassica oleracea) for the extraction procedure. The sample was extracted by sonication for 30 s with a mixture of MeOH/H2O/TFA (0.58/0.38/0.04). Subsequently, the mixture was stirred for 30 s, sonicated and centrifuged for 10 min (13,200× g at 4 °C). HPLC-MS determined the anthocyanin content and twenty compounds were identified. Therefore, 2 identified cyd derivatives were non-oscillated, 11 monoacylated and 7 diacylates.
Strauch et al. [67] used 70% MeOH with 0.1% acetic acid in another extraction procedure for red cabbage (Brassica oleracea) anthocyanins. The mixture was stirred and sonicated for 10 min at room temperature, then centrifuged at 4000 rpm for 20 min. Before HPLC analysis of anthocyanins, the supernatant was filtered (0.2 μm polytetrafluoroethylene filters) and stored at −20 °C. UPLC-DAD-MSE determined the anthocyanin content and 29 anthocyanin compounds were identified. Among them, 27 were derivatives of glycosylate cyanidin in varying degrees and acylated with p-cumaryl, feruloyl or synapyl groups. Moreover, Yiğit et al. [68] used microwave-assisted extraction of red cabbage (Brassica oleracea) anthocyanins. For the extraction procedure, the authors used lyophilized red cabbage extracted via conventional extraction (maceration at 40 and 70 °C for 4 and 6 h) and microwave-assisted extraction MAE (solvents: water and 50/50 (v/v) ethanol–water mixture; microwave irradiation power: 200, 400 and 600 W) and for anthocyanin identification, HPLC-DAD-MS. The maximum extraction yield of MAE (220.0 mg cyanidin-3-glycoside/L) was recorded at 10 min using only part of the solvent compared to the amount used in the conventional extraction method.
For the extraction procedure [69,70], purple pulp sweet potato (Ipomoea batatas) powder was used, in which an internal standard, cyd-3,5-diglu, was introduced. The compounds were extracted with 5% FA using an orbital stirrer at a temperature of 40 °C for 12 h and centrifugated for 20 min (4000× g at 4 °C). The supernatant obtained by combining the two steps was purified using a C18 solid-phase extraction cartridge. The resulting eluent was evaporated dry and reconstituted in 5% FA. HPLC ESI/MS/MS was used in this study to identify anthocyanin compounds. Thus, fourteen anthocyanins were eluted and found in the roots of three varieties of sweet potatoes (Table 3, Figure 2B). A recent study [71] demonstrated the superiority of applying the high-pressure carbon dioxide method (HPCD) on the purple sweet potato anthocyanin extraction compared to conventional aqueous- and ethanol-extraction methods (the extraction yield was over 25% higher compared to conventional methods).
The peels of mature green and ripe red tomatoes (Solanum lycopersicum L.) were used for the extraction procedure [72]. The lyophilized peel was extracted with a mixture of MeOH:H2O: TFA (70:29.5:0.5), with a ratio of 1/20 at room temperature. After centrifugation at 3500× g for 10 min, the extraction was repeated for 1 h under the same condition. The supernatant was evaporated at 32 °C to 1/3 of the original volume, then freeze-dried. The extracts were analyzed using an HPLC-PDA system and two compounds were identified: petanin and negretein. The procedure described by Wang et al. [73] used Indigo Rose tomato powder (Solanum lycopersicum) for anthocyanin extraction. The extraction was conducted utilizing methanol/formic acid (9:1, v/v) and, for the quantification of anthocyanin content, was added to the samples peonidin-3-glucoside chloride as an internal standard. UPLC-QTOF-MS was used to analyze tomato extracts and 12 anthocyanins were identified.
Table
Table 3. Anthocyanin compounds identified in different food matrices.
Table 3. Anthocyanin compounds identified in different food matrices.
Matrix
Genus, Species, Variety		LocationCompoundsDetection MethodRef.
Anthocyanins from fruits
Blackberries
Rubus fruticosus		Iaşi, Romaniacyd-3-O-glu; dpd-3-xilozid; cyd-3-O-arab; cyd-3-malonil-glu; cyd-3-rutHPLC-ESI-MS[74]
Blackberries
Rubus spp.		Samsun, Turkeycyd-3-glu; cyd-3-rut; plg-3-glu; cyd cloridHPLC[75]
Blueberries
Vaccinium coroymbosum L.		Wollongong, Australiadpd-3-glu; ptd-3-glu; mvd-3-gluUHPLC-PDA-ESI-MS[23]
Blueberries
Vaccinium cyanococcus		Corvallis, USAdpd-3-gal; dpd-3-glu; cyd-3-gal; dpd-3-arab; cyd-3-glu; ptd-3-gal; cyd-3-arab; ptd-3-glu; ptd-3-arab; pnd-3-glu; mvd-3-gal; pnd-3-arab; mvd-3-glu; mvd-3-arabHPLC[57]
Blueberries
Vaccinium corymbosum		Huelva, Spainmvd-gal; pnd-gal; ptd-gal; cyd-gal; dpd-gal; mvd-glu; pnd-glu; cyd-glu; mvd-arb; ptd-arb; cyd-arb; dpd-arb; cyd; mvdHPLC-DAD[76]
Cherries
Prunus cerasus L.
Cranberries
Vaccinium oxycoccos		Lazig, Turkeydpd-3-O-glu; cyd-3-O-glu; plg-3-O-glu; mvd-3-O-gluHPLC-ESI-MS[38]
Grapes
Vitis spp. Othello		Iași, Romaniacyd-3-glu-etil-coum; cyd-3-glu-etil-coum; cyd-3-O-gal; cyd-3-O-glu; dpd-3-(6-O-acetilgluc); dpd- 3-O-glu; dpd-3-O-glu; mvd-3-(6-O-acetilgluc) piruvat; mvd-3-glu-8-vinil(epi)catechina; mvd-3-O-gluHPLC-ESI-MS[74]
Grapes
Vitis amurensis		Daze, Chinapnd 3,5-β-do-diglu; pnd 3-O-β-d-(6″-acetil) glu 5-β-d-glu; pnd 3- (6″-op-coum)-β-d-glu; cyd 3-O-β-d-glu-5-O-β-d-glu; cyd 5-O-β-d-glu; cyd; dpd 3,5-β-do-diglu; ptd 3,5-β-do-diglu; mvd 3,5-β-do-diglu; ptd 3-(6″-O-trans-p-coum)-β-d-glu; mvd 3-(6″-O-cis-p-coum)-β-d-gluLC-MS-MS[47]
Grapes
Vitis vinifera cv. Plavac mali		Dalmatia, Croatiadpd-3-O-monoglu; cyd-3-O-monoglu; ptd-3-O-monoglu; pnd-3-O-monoglu; mvd-3-O-monoglu; mvd-3-O-acetilmonoglu; pnd- 3-(6-op coum)monoglu; mvd-3-(6-op-coum)monogluHPLC[48]
Pomegranate
Punica granatum L.		California, USAcyd-3-O-pentozid; plg-3-O-glu; cyd-3-O-glu; dpd-3-O-glu; cyd-pentozid-hexozid; cyd-3-O-rut; cyd 3,5 -O-diglu; dpd 3,5-diglu; (epi) afzelchin-dpd-3-O-hexozid; (epi) galocatechin-plg 3-O-hexozid; (epi) afzelchin-dpd-3-O-hexozid; (epi) galocatechin-cyd-3-O-hexozidHPLC-DAD-ESI-MS[51]
Red pears
Red D’Anjou
Pyrus communis		Corvallis
USA		cyd-3-gal; cyd-3-gluHPLC[57]
Strawberries
Fragaria spp.		Lazig, Turkeydpd-3-O-glu; cyd-3-O-glu; plg-3-O-glu; mvd-3-O-gluHPLC-ESI-MS[64]
Strawberries
Fragaria × ananassa		Gwangju, Koreacyd-3-O-glu; plg-3-O-glu; plg-3-O-rutHPLC[77]
Sweet cherries
Prunus avium		Corvallis, USAcyd-3-glu; cyd-3-rutHPLC[57]
Anthocyanins from vegetables
Black carrot
Daucus carota L. ssp. sativus var. atrorubens Alef.		Eregli, Turkeycyd-3-xyl-glu-gal; cyd-3-xyl-gal; cyd 3-xyl-(caf-glu)-gal; cyd 3-xyl-(p-hydbenz-glu)-gal; cyd 3-xyl-sin-glu-gal; cyd 3-xyl-fer-glu-gal; cyd 3-xyl-p-coum-glu-gal; plg 3-xyl-fer-glu-gal; pnd 3-xyl-fer-glu-gal; cyd 3-xyl-gal + vinylphen; cyd 3-xyl-gal + vinylcatecLC-DAD-ESI-MS/MS[78]
Corn
Zea mays L.		Commercial sourcescyd 3-glu; plg 3-glu; pnd 3-glu; cyd malonyl-glu; plg malonyl-glu; cyd dimalonyl-glu; pnd-malonylglu; plg dimalonyl-glu; pnd dimalonyl-gluHPLC[79]
Purple carrot
Purple 68
Daucus carota ssp. sativus		Cottage Grove, Oregon, USAcyd-3-(2″-xylose-gal); cyd-3-(2″-xylose-6-glucose-gal); cyd-3-(2″-xylose-6″-fer-glu-gal); cyd-3-(2″-xylose-6″-sin-glu-gal); cyd-3-(2″-xylose-6″-(4-coum)glu-gal)UHPLC[80]
Red cabbage
Brassica oleracea L. var.
capitata L. f. rubra		Olszty, Polandcyd-3-diglu-5-glu; cyd-3-(p-coumaroyl)-diglu-5-glu; cyd -3-(feruloyl)-digluc-5-gluc; cyd-3-(sin)-di-glu-5-glu; cyd-3-(fer)(fer)-di-glu-5-glu; cyd-3-(fer)(sin)-di-glu-5-glu; cyd-3-(sin)(sin)-di-glu-5-gluHPLC–DAD–MS/MS[80]
Kannapolis, United Statescyd-3-diglu -5glu; cyd -3g-5glu; cyd -3diglu (sin)-5glu; cyd -3triglu(sin)-5glu; cyd -3triglu (pcoum)-5glu; cyd -3triglu(fer)-5glu; cyd -3tri glu(sin)-5glu; cyd -3triglu(pcoum)(sin)-5glu; cyd -2diglu(caf)-5 glu; cyd -3triglu(fer)(sin)-5glu; cyd -3tri glu (sin)(sin)-5 glu; cyd -3 glu (sin)-5 glu; cyd -3di glu (fer)-5 glu; cyd -3diglu (pcoum)-5glu; cyd -3glu(pcoum)-5glu; cyd -3diglu(fer)-5 glu; cyd -3diglu(sin)-5glu; cyd -3glu(fer)-5glu; cyd -3glu(sin)-5glu; peo-3diglu(pcoum)-5glu; cyd -3diglu(pcoum)(sin)-5glu; cyd -3diglu(caf)(fer)-5glu; cyd -3diglu(sin)(fer)-5glu; cyd -3diglu(sin)(caf)-5glu; cyd -3diglu(sin)(sin)-5glu; cyd -3diglu(fer)(fer)-5glu; cyd -3diglu(fer)(sin)-5glu; cyd -3glu(fer)(sin)-5glu; peo-3diglu(pcoum)(sin)-5gluUPLC-DAD-MS[56]
Sweet potatoes with purple pulp
Ipomoea batatas		Haysville, USAcyd-3-soph-5-glu; pnd 3-soph-5-glu; cyd 3-soph-5-glu; cyd-3-soph-5-glu; pnd 3-soph-5-glu; pnd 3-soph-5-glu- 5-gluc; cyd 3-soph-5-glu; cyd 3-(6,6′-di-caf--soph)-5-glu; cyd 3-(6,6′-caf-pidroxibenzoil soph)-5-glu; cyd 3-(6, 6′-caf-fer-soph)-5-glu; pnd 3-(6,6′-di-caf-soph)-5-glu; pnd 3-(6,6′--caf-pidroxibenzoil-soph)-5-glu; pnd 3-(6,6′--caf-fer-soph)-5-glu; pnd 3-caf-p-cum-soph-5-gluHPLC-MS/MS[69]
Tomato
Solanum lycopersicum L.		Viterbo, Italypetanin; negreteinHPLC/NMR[72]
Anthocyanins from cereals
Black rice
Oryza sativa L. ‘Violet Nori’		Collobiano, Italycyd-3,5-diglu; cyd-3-glu; cyd-3-rut; pnd-3-gluHPLC [81,82]
Purple barley
Hordeum vulgare L.		Tibetcyd; cyd acetyl gal; cyd malonyl glu; cyd succinyl glu; cyd 3-O-glu; plg succinyl glu; pnd acetyl galUPLC[83]
Sweet corn
Zea mays L.		Guangzhou, Chinacyd, plg, pndHPLC[84]
Sweet purple/reddish-purple corn; purple/purple blue/blue corn
Zea mays L.		Gatton, Australiacyd-3-O-glu; cyd-3- malonylglu; plg-3 -O-glu, plg-3- (dimalonylglu); pnd-3 -O-glucUHPLC-DAD-MS[85]
Note: cyanidin—cyd; delphinidin—dpd; petunidin—ptd; peonidin—pnd; pelargonidin—plg; malvidin—mvd; glu—glucoside; gal—galactoside; arab—arabinoside; rut—rutinoside; caffeoyl—caf; xylosyl—xyl; sinapoyl—sin; feruloyl—fer; coumaroyl—coum; phenol—phen; p-hydroxybenzoyl—hydbenz; sophoroside—soph; catechol—catec; Nuclear Magnetic Resonance—NMR; Ultra High-Performance Liquid Chromatography—UHPLC; Liquid Chromatography—LC; High-Performance Liquid Chromatography—HPLC; Diode-Array Detector—DAD; Pulsed Amperometric Detector -PDA; Electrospray Ionization—ESI; Mass Spectrometry—MS.

2.2.3. Procedures for the Extraction of Anthocyanins from Cereals

Zhang et al. [83] used a barley powder (Hordeum vulgare L.) and 90% EtOH for the extraction procedure. Subsequently, the mixture extracted for 30 min at 50 °C in an ultrasonic water bath was centrifuged for 20 min (10,200× g). The extracts were filtered (0.45 μm filter) and concentrated at 40 °C in a rotary evaporator. They were then loaded onto a balanced AB-8 resin column and eluted with 1% FA in 80% MeOH. The effluent of the MeOH solution was concentrated at 40 °C, purified and freeze-dried. B UPLC-MS analysis identified anthocyanin compounds as cyd, plg and pnd (Table 3).
For the extraction procedure [81,82], a black rice (Oryza sativa L. ‘Violet Nori’) powder and 40 mL EtOH/H2O mixture (60:40) were used. The mixture was homogenized in two steps: 0.5 min at 8000 rpm and 1.5 min at 24,000 rpm. Direct sonication was used to achieve the final extraction for 5 min at an amplitude and pulse rate of 30% and 80%, respectively. The extracts were analyzed using an HPLC DAD system and the following compounds were identified: cyd-3,5-diglu, cyd-3-glu, cyd-3-rut and pnd-3-glu. Yi et al. [86] used their protocol, the nanobiocatalyst, to extract anthocyanins from black rice (Oryza sativa L.). The magnetic nanobiocatalyst was prepared by immobilizing cellulase and α-amylase on amino-functionalized magnetic nanoparticles. This procedure had a maximum yield at 30 °C compared to the anthocyanin extraction procedure using free enzymes, which recorded a maximum yield at 40 °C. Therefore, using the nanobiocatalyst can be advantageous because it could reduce energy costs during processing. Further, the enzymes immobilized on the nanobiocatalyst will be recovered at the end of the extraction process and reused in other extraction cycles.

2.3. Purification

Currently, the methods used to extract anthocyanins result in solutions containing amounts of unwanted elements, such as sugars, acids, amino acids and proteins, that require removal. In order to remove sugars, acids and other water-soluble substances, the crude extracts were purified using C18 cartridges that had been activated with MeOH, H2O and HCl with 0.01% or 3% FA [87,88,89].
Purification of anthocyanins by adsorption is an effective and straightforward method. Chandrasekhar et al. [90] used silicone gel (Amberlite IRC 80, Amberlite IR 120, DOWEX 50WX8, Amberlite XAD-4 and Amberlite XAD-7HP) to purify anthocyanins from red cabbage extract. The Amberlite XAD-7HP proved to be the most effective. Desorption of anthocyanins was successfully carried out with EtOH, with a concentration of more than 60% vol.
The use of the same adsorbents was also investigated by Jampani et al. [35] to purify anthocyanins from Malabar plum extract (Syzygium cumini). In this case, the Amberlite XAD-7HP also proved to be the most effective.

3. Methods for the Quantification of Anthocyanins

The official anthocyanin analysis method is reported by AOAC International, the quantitative spectrophotometric method, which is fast and easy to apply, especially for liquid products [20]. Other validated methods for identifying and quantifying anthocyanins include chromatographic methods, in which identification depends either on comparison with high-purity standards or previously reported procedures (Table S1).
Anthocyanin molecules consist of an anthocyanin aglycon and several sugar fragments. Common plant anthocyanins include cyd, pnd, plg, mvd, dpd, ptd, etc. More than 600 anthocyanins were identified based on the number of sugar molecules and the type of acylation groups. In addition to applying anthocyanins as natural colors or creating functional foods, it is crucial to precisely identify the many anthocyanins and gain a greater knowledge of their structure and diverse structural features [91].
Presently, the most common techniques for identifying types of anthocyanins include high-performance liquid chromatography coupled with mass spectrometry (HPLC-MS), high-performance liquid chromatography (HPLC), UV-VIS spectroscopy and nuclear magnetic resonance (NMR). Among them, the most important and used qualitative and quantitative methods for anthocyanin quantification are:
  • High-performance liquid chromatography (HPLC), which requires a short analysis time and a small sample, but the results must be compared with a standard.
  • Liquid chromatography–mass spectrometry (HPLC-MS), which is widely used for the qualitative analysis of anthocyanins with the identification of molecular weight and the structure of anthocyanins, with effective results in the identification of anthocyanins. Therefore, due to its ability to ionize and vaporize labile and complex molecules, mass spectrometry (MS) is a significant step in analyzing anthocyanins [92].
MS has become a powerful tool used to identify anthocyanin compounds due to its use in combination with other separation and identification techniques, such as liquid chromatography (LC) and gas chromatography (GC). However, LC remains the most commonly used analytical method to identify and characterize anthocyanins in plant extracts (fruit and vegetables) [38]. Combining the LC method with electrospray ionization (ESI)-MS or Quadrupole time-of-flight (QTOF)-MS better quantifies anthocyanins in complex samples. Many studies are also investigating the negative effect of ESIF on identifying anthocyanins [4].

4. Conclusions

Many studies have been focused on anthocyanins as biologically active chemicals and on their processing, extraction, separation and purification in odor to obtain high-purity samples. The advanced and practical analysis of the type and purity of the samples obtained from a processing series is a necessary step for thorough research into anthocyanins. The primary variables that influence anthocyanin extraction from various food matrices are the properties of the analyzed matrix (water activity, the cell wall of the plant, etc.) and the extraction process parameters (pH, solvent, temperature, time). Different extraction methods have developed over time, from traditional methods with solvents to emerging technologies (UAE, MFA, CSC, etc.). Currently, research on anthocyanin extraction is mainly aimed at selecting an optimized extraction process or method by comparing the different extraction processes. Data for simulating industrial production and the purification of anthocyanins must consider factors, such as productivity, costs of production and simple operation.

Supplementary Materials

The following supporting information can be downloaded at: https://www.mdpi.com/article/10.3390/horticulturae8111084/s1. Table S1. Qualitative and quantitative methods for the quantification of anthocyanins.

Author Contributions

Conceptualization, O.E.C. and D.I.I.; data curation, D.I.I.; writing—original draft preparation, O.E.C.; writing—review and editing. O.E.C. and D.I.I. All authors have read and agreed to the published version of the manuscript.

Funding

This research received no external funding.

Institutional Review Board Statement

Not applicable.

Informed Consent Statement

Not applicable.

Data Availability Statement

Not applicable.

Acknowledgments

This paper was supported by a grant offered by the Romanian Ministry of Research as Intermediate Body for the Competitiveness Operational Program 2014–2020, call POC/78/1/2/, project number SMIS2014 + 136213, acronym METROFOOD-RO.

Conflicts of Interest

The authors declare no conflict of interest.

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Horticulturae 08 01084 g001 550
Figure 1. Techniques used in the characterization of anthocyanin compounds [25,26].
Figure 1. Techniques used in the characterization of anthocyanin compounds [25,26].
Horticulturae 08 01084 g001
Horticulturae 08 01084 g002 550
Figure 2. Majority of anthocyanin compounds in various fruits (A) and vegetables (B) [2] Note: cyanidin—cyd; delphinidin—dpd; petunidin—ptd; peonidin—pnd; pelargonidin—plg; malvidin—mvd; glu—glucoside; gal—galactoside; arabinoside—arab; rutinoside—rut; caffeoyl—caf; xylosyl—xyl; sinapoil—sin; feruloyl—fer; coumaroyl—coum; phenol—phen; p-hydroxybenzoyl—hydbenz; sophoroside—soph; rhamnosyl—rham.
Figure 2. Majority of anthocyanin compounds in various fruits (A) and vegetables (B) [2] Note: cyanidin—cyd; delphinidin—dpd; petunidin—ptd; peonidin—pnd; pelargonidin—plg; malvidin—mvd; glu—glucoside; gal—galactoside; arabinoside—arab; rutinoside—rut; caffeoyl—caf; xylosyl—xyl; sinapoil—sin; feruloyl—fer; coumaroyl—coum; phenol—phen; p-hydroxybenzoyl—hydbenz; sophoroside—soph; rhamnosyl—rham.
Horticulturae 08 01084 g002
Table
Table 1. Common anthocyanidins found in food matrices [4].
Table 1. Common anthocyanidins found in food matrices [4].
AnthocyanidinAbbreviationChemical StructureBasic Color
CyanidincydHorticulturae 08 01084 i001orange red
DelphinidindpdHorticulturae 08 01084 i002red, blue
PetunidinptdHorticulturae 08 01084 i003red, blue
PeonidinpndHorticulturae 08 01084 i004orange red
PelargonidinplgHorticulturae 08 01084 i005orange
MalvidinmvdHorticulturae 08 01084 i006red, blue
Table
Table 2. Extraction procedures applied for the recovery of anthocyanins from different food matrices.
Table 2. Extraction procedures applied for the recovery of anthocyanins from different food matrices.
MatrixExtraction MethodsExtraction ConditionsSolventsRef.
Aronia
Aronia melanocarpa		 UAE sonication 216W, T = 70 °C, τ = 45.6 min 50% EtOH [36]
Beans black
Phaseolus vulgaris L. 		PLE T = 40, 50 and 60 °C, P = 100, 200 and 250 bar acidified distilled H2O, 50% EtOH, 70% EtOH [21]
EFS T = 40, 50 and 60 °C, P = 160, 200 and 300 barco-solvents: acidified distilled H2O, 10% EtOH, 50% EtOH
Blueberries
Vaccinium coroymbosum L. 		UAE T = 15 °C, τ = 30 min solvent mixtures (MeOH:H2O, EtOH:H2O) at pH 2.0 or 3.0 corrected with concentrated HCl. [23]
UAE + shredding τ = 44 sec
UAE + shredding/maceration NR
Blueberry marc
Vaccinium ashei		 CSE T = 61 °C, τ = 35 min EtOH (70%), HCl (0.01%) [37]
UAE f = 24 kHz, T = 61 °C, τ = 24 min
Cherrie Prunus cerasus L. and cranberries Vaccinium oxycoccos CSE room temperature acidified ACN [38]
Corn
Zea mays L. 		CS shaking for 1 min, refrigeration for 60 min acidified MeOH [39]
CS shaking T = 4 °C, τ = 24 h in the dark H2O [40]
T = 4 °C, τ = 20–24 h in the dark 2% FA
extraction in water τ = 5 min, P = 1500 psi H2O [41]
Cranberry marc
Vaccinium macrocarpon 		CSE room temperature/τ = 15 min 98% MeOH with 2% HCl [42]
PLE T = 120, 140, or 160 °C, P = 50 or 200 bar100% EtOH; ultrapure H2O:EtOH (30 or 70%); EtOH, milli-Q H2O/5% citric acid
Grape marc
Vitis vinifera		 EAE T = 40 °C, τ = 0–48 h Acetate buffer 0.2 M (pH 3.5) [43]
maceration T = 4 °C, τ = 60 min MeOH (0.1% HCl), solvent/solid ratio 50:1 [44]
expeller extraction water flow (20–65 mL/min), water bath temperature (25–140 °C), expeller shaft temperature (50–100 °C), screw rotational speed, controlled by a frequency dimmer attached to the expulsor (20–60 Hz) H2O at 100 °C [45]
CSE T = 23.5 °C MeOH:H2O:FA (60:37:3)
sonication τ = 30 min/18 min in an ice bath H2O:MeOH:acetone 3.5:1.5:5 acidified with HCl (0.01 M) [46]
Grapes (skin)
Vitis vinifera		 CSE/UAE CSE—τ = 24 h in the dark, room temperature
UAE—f = 60 kHz, τ = 25 min		 EtOH (70%) [47]
CSE(DES)/UAE/MAE CSE(DES)—τ = 12 h, room temperature
MAE—T = 50–90 °C, τ = 15–90 min, microwave output power = 100 W
UAE—T = 30–90 °C, τ = 15–90 min, f—35 kHz		 H2O:MeOH (70:30) and acidified MeOH solution (MeOH:H2O:12 M HCl, 70:29:1, pH = 1.25) [48]
CSE(DES)/UAE CSE (DES)—room temperature, τ = 45 min
UAE—80% MeOH for 45 min using stirring, heating, stirring methods in the vortex and stirring + heating. 600 rpm without heating (stirring) or with heating T = 60 °C (shaking + heating).		 H2O:MeOH (100%, 80%), EtOH (100%, 70%) [49]
Onions red, yellow and white
Allium cepa L. 		UAE ultrasonic power = 700 W, room temperature, τ = 30 min.80% EtOH (EtOH:H2O/80:20) with 0.1% HCl[50]
Pomegranate (seeds)
Punica granatum L.		 UAE T = 30 °C, τ = 20 min 70% acetone [51]
Potatoes
Solanum tuberosum L.		 sonication sonication for τ = 5 min, drying in forced air furnace at T = 90 °C, τ = 3 hHCl 2.7 M in MeOH[52]
Red cabbage
Brassica oleracea		 shaking in an orbital agitator T = 24 ± 2 °C, 90 rpm, τ = 12 h H2O:H3PO4 0.05 M (1:10) [53]
Strawberries
Fragaria spp. 		UAE T = 20 °C, τ = 10min 0.2% HCl in MeOH [54]
Note: Conventional Solvent Extraction—CSE; Enzyme-Assisted Extraction—EAE; Microwave-Assisted Extraction—MAE; Extraction with Supercritical Fluid Extraction—EFS; Ultrasound-Assisted Extraction—UAE; High Hydrostatic Pressure Extraction—Pressurized Liquid Extraction—PLE; Deep Eutectic Solvents—DES; Not Reported—NR; Acetonitrile—CAN; Ethanol—EtOH; Methanol—MeOH; Formic acid—FA; Temperature—T; Pressure—P; Time—τ; Frequency—f; marc is the solid waste left from pressing the fruit to obtain the juice.
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Constantin, O.E.; Istrati, D.I. Extraction, Quantification and Characterization Techniques for Anthocyanin Compounds in Various Food Matrices—A Review. Horticulturae 2022, 8, 1084. https://doi.org/10.3390/horticulturae8111084

AMA Style

Constantin OE, Istrati DI. Extraction, Quantification and Characterization Techniques for Anthocyanin Compounds in Various Food Matrices—A Review. Horticulturae. 2022; 8(11):1084. https://doi.org/10.3390/horticulturae8111084

Chicago/Turabian Style

Constantin, Oana Emilia, and Daniela Ionela Istrati. 2022. "Extraction, Quantification and Characterization Techniques for Anthocyanin Compounds in Various Food Matrices—A Review" Horticulturae 8, no. 11: 1084. https://doi.org/10.3390/horticulturae8111084

APA Style

Constantin, O. E., & Istrati, D. I. (2022). Extraction, Quantification and Characterization Techniques for Anthocyanin Compounds in Various Food Matrices—A Review. Horticulturae, 8(11), 1084. https://doi.org/10.3390/horticulturae8111084

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