antioxidants Review Effect of HHP and UHPH High-Pressure Techniques on the Extraction and Stability of Grape and Other Fruit Anthocyanins Antonio Morata 1, * , Juan Manuel del Fresno 1 , Mohsen Gavahian 2 , Buenaventura Guamis 3 , Felipe Palomero 1 and Carmen López 1 1 enotecUPM, Department of Chemistry and Food Technology, ETSIAAB, Universidad Politécnica de Madrid, 28040 Madrid, Spain; juanmanuel.delfresno@upm.es (J.M.d.F.); felipe.palomero@upm.es (F.P.); carmen.lopez@upm.es (C.L.) 2 Department of Food Science, National Pingtung University of Science and Technology, Pingtung 91201, Taiwan; mg@mail.npust.edu.tw 3 Centre d’Innovació, Recerca I Transferència en Tecnologia Dels Aliments (CIRTTA), TECNIO, XaRTA, Departament de Ciència Animal I Dels Aliments, Facultat de Veterinària, Universitat Autònoma de Barcelona, 08193 Bellaterra, Spain; buenaventura.guamis@uab.cat * Correspondence: antonio.morata@upm.es Abstract: The use of high-pressure technologies is a hot topic in food science because of the potential for a gentle process in which spoilage and pathogenic microorganisms can be eliminated; these technologies also have effects on the extraction, preservation, and modification of some constituents. Whole grapes or bunches can be processed by High Hydrostatic Pressure (HHP), which causes poration of the skin cell walls and rapid diffusion of the anthocyanins into the pulp and seeds in a short treatment time (2–10 min), improving maceration. Grape juice with colloidal skin particles of less than 500 µm processed by Ultra-High Pressure Homogenization (UHPH) is nano-fragmented with high anthocyanin release. Anthocyanins can be rapidly extracted from skins using HHP and cell fragments using UHPH, releasing them and facilitating their diffusion into the liquid quickly. HHP and UHPH techniques are gentle and protective of sensitive molecules such as phenols, terpenes, and vitamins. Both techniques are non-thermal technologies with mild temperatures and residence times. Citation: Morata, A.; del Fresno, J.M.; Moreover, UHPH produces an intense inactivation of oxidative enzymes (PPOs), thus preserving Gavahian, M.; Guamis, B.; Palomero, the antioxidant activity of grape juices. Both technologies can be applied to juices or concentrates; in F.; López, C. Effect of HHP and addition, HHP can be applied to grapes or bunches. This review provides detailed information on UHPH High-Pressure Techniques on the main features of these novel techniques, their current status in anthocyanin extraction, and their the Extraction and Stability of Grape effects on stability and process sustainability. and Other Fruit Anthocyanins. Antioxidants 2023, 12, 1746. https:// doi.org/10.3390/antiox12091746 Keywords: anthocyanins; HHP; UHPH; grape; wine; clean labels Academic Editors: Agustín G. Asuero and Noelia Tena Received: 7 August 2023 1. Introduction Revised: 3 September 2023 Anthocyanins are flavonoid pigments with variable colors from yellow-orange (490 nm) Accepted: 8 September 2023 to red-blue (540 nm), with healthy nutritional properties widely distributed in fruits and Published: 10 September 2023 flowers and with useful properties as food pigments [1–5]. Anthocyanins can act as antioxi- dants, phytoalexins, or antimicrobial compounds [6,7]. Anthocyanins behave as weak acids, hard and soft electrophiles, nucleophiles, and metal ion binders [8]. The main degradation effects that can affect anthocyanins are oxidative yield processes, which can be accelerated Copyright: © 2023 by the authors. by temperature [9]. Anthocyanins can also be affected by light (photooxidation) [10] and oxi- Licensee MDPI, Basel, Switzerland. This article is an open access article dized by oxygen directly or via enzymes such as polyphenol oxidases and peroxidases [9,10]. distributed under the terms and Stability and color are also affected by pH, SO2 bleaching, copigmentation, or the forma- conditions of the Creative Commons tion of polymers with other flavonoids, such as catechins or proanthocyanidins (Figure 1). Attribution (CC BY) license (https:// Non-thermal emerging technologies such as high-pressure processing by High Hydrostatic creativecommons.org/licenses/by/ Pressure (HHP) or Ultra-High Pressure Homogenization (UHPH) can be used to gently 4.0/). extract and preserve juice anthocyanins, increasing extraction rates and stability [11,12]. Antioxidants 2023, 12, 1746. https://doi.org/10.3390/antiox12091746 https://www.mdpi.com/journal/antioxidants Antioxidants 2023, 12, x FOR PEER REVIEW 2 of 15 Antioxidants 2023, 12, x FOR PEER REVIEW 2 of 15 Antioxidants 2023, 12, 1746 (UHPH) can be used to gently extract and preserve juice anthocyanins, increasing extrac- 2 of 14 (UHPH) can tion rates bestability and used to [11,12]. gently extract and preserve juice anthocyanins, increasing extrac- tion rates and stability [11,12]. OH OH R1 O OH OMe R1 OH O OH OH HO OMe HO O OH OH + OH R2 HO HO O OMe HO O [CH3CHO] / pH<1 + R2 R1 OH HO O O-Gl OMe H [CH3CHO] / pH<1 3' OH O-Gl OH SO O-Gl 2' R1 3H 4' OH H [SO2] 8 1 + B 3' OH O-Gl OH SO 3H HO 7 O 2' Polymeric pigments 2 B 4' 5' R2 OH [SO2] HO 8 A 1 O + SO2 bleaching Polymeric resistant pigments 7 HO 6 23 O 5' R2 A5 4 SO2 bleaching resistant 6 HO OH OH 3 O OH Hydratation 5 4 O Flavylium cation OH + OH Hydratation -H pH<1 Flavylium cation O OH + OH pH<1 -H R1 pH<1 R1 OH pH<1 OH R1 R1 -H+ R1 OH OH OH OH R1 OH O HO O -H+ OH R2 OH HO OH O O OH O R2 HO O R2 HO O-Gl R2 R2 uncoloured O O O-Gl O-Gl R2 Chalcone OH Carbinol O-Gl Pseudo−Base blue−violet OH uncoloured light yellow O-Gl OH Quinoidal−Base O-Gl Chalcone OH Carbinol Pseudo−Base blue−violet OH light yellow OH Tautomeric ring−chain equilibrium Quinoidal−Base Tautomeric ring−chain equilibrium Figure 1. Reactions that can affect anthocyanins as a function of pH, hydration, SO2 concentration, Figure 1. Reactions and flavonoid that can affect content. affect anthocyanins as a function of pH, pH, hydration, hydration, SO SO22 concentration, and flavonoid content. and flavonoid content. High Hydrostatic Pressure (HHP) is the application of pressure to food by a pressur- izingHigh fluid, Hydrostatic Hydrostatic usually water, Pressure Pressure (HHP) inside(HHP) isisthe a highly theapplication application resistant ofof pressure pressure steel vessel (Figure to to2). foodfoodby by a pres- a pressur- Initially, the ves- surizing izing fluid, sel isfluid, filledusually usually with waterwater,water, inside inside using a highly a highly resistant a high-flow, resistant low-pressure steel steel vessel vessel pump,(Figure (Figure and later, 2). Initially, 2). Initially, the waterthe the ves- is pres- vessel sel surized is filled is filledto with with a typical water water using range using a high-flow, ofa500–600 high-flow,MPa low-pressure low-pressure using a specialpump, pump, pump and later, andcalled later, athe the water water pressure is isintensi- pres- pressurized surized fier (Figure to 2).aUnder to a typical typical range range these of 500–600 of 500–600 pressure MPa MPa ausing using conditions, speciala special the water pump pump andcalled the food acalled pressurea pressure inside intensi- are com- intensifier pressed by about 4%. The pressurization is produced with some temperature increase are fier (Figure (Figure 2). Under2). Under these these pressurepressure conditions, conditions, the the water water and and the foodthe food inside inside are com- due compressed pressed to adiabatic by by about about heat 4%. 4%. pressurization The compression,The pressurization which is typically is produced is produced lowerwith with some than 4some temperature temperature °C/100 MPa increase increase (<3.4 °C due water, due to°Cadiabatic ◦ ◦C to adiabatic <3.8 heat heat orange juice, compression, compression, which [13]), producing which is typically is typically a global lower heating lower than 4than of up to424C/100 °C/100 MPa °C MPa at(<3.4 600 °C(<3.4 MPa. water, The water, ◦ ◦ <3.8 °C<3.8 orange temperature C increase orange juice, juice, also[13]), [13]), producing producing depends ona the a composition, global global heating heating of upup ofwhich toto2424 is °CCatat600 higher 600oil for MPa. MPa. The The compo- temperature temperature increase nents. HHP increase also depends also depends is a technique on that canon the be thecomposition, composition, considered which is higher which is higher a non-thermal for technology oil components. for oil compo- because of HHP nents. isHHP a technique is a that canthat technique be considered can be a non-thermal considered a technology non-thermal because of technology this soft because of this soft heating, without any degradative effect on thermally sensitive molecules such as heating, this soft without heating, any degradative without effect on thermally any degradative sensitive molecules such as pigments pigments or aromatic compounds [14,15].effect on thermally Low adiabatic sensitive heating can bemolecules additionally suchcon-as or aromatic pigments compounds [14,15]. Low adiabatic heating can be additionally controlled by trolled byorcooling aromaticthecompounds vessel with [14,15]. Low adiabatic heating can be additionally con- heat exchangers. cooling trolled by thecooling vessel with heat exchangers. the vessel with heat exchangers. Figure2.2.HHP Figure HHPsystem systemscheme schemewith withsteel steelvessel, vessel,low-pressure low-pressurepump, pump,and andhigh-pressure high-pressureintensifier. intensifier. Arrows Figure Arrows2.around aroundthe thegrape HHP system grapecluster scheme simulate with cluster the thehydrostatic steel vessel, simulate effect low-pressure hydrostatic ofofthe pump, effect pressure. and the high-pressure intensifier. pressure. Arrows around the grape cluster simulate the hydrostatic effect of the pressure. HHP, HHP,unlike unlikethermal thermaltreatments, treatments,does doesnot nothave haveenough enoughenergy energytotoaffect affectcovalent covalent bonds; bonds; therefore, HHP, therefore,small unlike thermalmolecules with treatments, small molecules sensory withdoes impact not have sensory are enough impact protected, and energy toand are protected, HHP affect HHP can canbe covalentbe considered bonds; a gentle therefore, technology. small molecules The withformation of unexpected sensoryofimpact molecules are protected, has not been considered a gentle technology. The formation unexpected moleculesand hasHHP can not been be ob- observed consideredduring HHP processingThe a gentle [16]. Furthermore, HHP is a molecules pressure process produced served during HHPtechnology. processing [16].formation of unexpected Furthermore, HHP is a pressure has not process been ob-in produced in a closed vessel where aeration and oxidative processes are minimized, thus served during HHP processing [16]. Furthermore, HHP is a pressure process produced reducingin damage to anthocyanins. Many studies have shown that using HHP at room temperature preserves nutritional value and has a very low effect on the levels of anthocyanins in fruits and vegetables [17]. Antioxidants 2023, 12, x FOR PEER REVIEW 3 of 15 a closed vessel where aeration and oxidative processes are minimized, thus reducing dam- Antioxidants 2023, 12, 1746 age to anthocyanins. 3 of 14 Many studies have shown that using HHP at room temperature preserves nutritional value and has a very low effect on the levels of anthocyanins in fruits and vegetables [17]. The HHP-treated The HHP-treated juices show showgoodgoodcolor colorstability, stability,better better phenolic phenolic content, andand content, higher an- higher tioxidant activity antioxidant activity [18]. [18]. Ultra-HighPressure Ultra-High Pressure Homogenization Homogenization (UHPH) (UHPH) is a high-pressure is a high-pressure technology technology in which in a which fluid a fluid isatpumped is pumped more than at 200 more MPathan 200 MPa (typically 300(typically MPa) through300 MPa) a thin,through a thin, high- high-resistance steel resistance pipeline andsteel laterpipeline and later depressurized via a depressurized special valve made via of a aspecial valve made high-resistance alloyof[19,20]. a high-re- The valve is often sistance alloymade of tungsten [19,20]. The valve carbide and is often is usually made coatedcarbide of tungsten with nanolayers of extremely and is usually coated resistant carbon polymers. with nanolayers of extremely Inside the valve, resistant carbon fluids are subjected polymers. to extreme Inside the shearare valve, fluids forces sub- and impacts, jected causing to extreme nanofragmentation shear forces and impacts,of microorganisms, colloids, and biopolymers causing nanofragmentation of microorgan- to 100–500 nm [20,21] isms, colloids, and(Figure 3). biopolymers to 100–500 nm [20,21] (Figure 3). Figure3.3.Effect Figure Effectofof impact impact andand shear shear forces forces on colloid on colloid nanofragmentation nanofragmentation and temperature and temperature in a in a UHPH UHPH valve (adapted from http://www.ypsicon.com/ (accessed on valve (adapted from http://www.ypsicon.com/ (accessed on 15 July 2023)).15 July 2023)). Some interesting Some interesting effects effects of of submicron submicron nanofragmentation nanofragmentation are are the the elimination elimination of of mi- mi- croorganisms, inactivation of enzymes (including oxidative polyphenol oxidases, croorganisms, inactivation of enzymes (including oxidative polyphenol oxidases, PPOs), PPOs), increasein increase inantioxidant antioxidantactivity, activity,and andbetter bettercolloidal colloidalstability stability[20–23]. [20–23]. Additionally, Additionally,UHPH UHPH isisvery verygentle gentlewith withsensory sensoryquality. quality.NoNodegradation degradationof ofterpenes terpenes[21], [21],anthocyanins anthocyanins[22], [22],or or thermalmarkers thermal markers such suchas ashydroxymethyl hydroxymethylfurfural furfuralwas was observed observed during during the theprocessing processingof of grapejuices grape juices[21]. [21]. 2. 2. Main Main Features Featuresof ofHHP HHPand andUHPH UHPH High-pressure High-pressure techniques techniques can can bebeconsidered consideredgentle, gentle,non-thermal non-thermaltechnologies technologieswith with specific specificfeatures featurestotopreserve preservethe nutritional the nutritionalandandsensory quality sensory of food quality products. of food However, products. How- they ever,have theyseveral specifications have several regarding specifications the processing regarding conditions the processing (pressure, conditions residence (pressure, resi- time, dence time, and temperature), the requirements of the products to be processed size and temperature), the requirements of the products to be processed (particle and (particle liquid/solid), the antimicrobial capacity (pasteurization or sterilization), the inactivation size and liquid/solid), the antimicrobial capacity (pasteurization or sterilization), the inac- of enzymes, and the effects on molecules with sensory impact (Table 1). Microbial tivation of enzymes, and the effects on molecules with sensory impact (Table 1). Microbial inactivation in HHP depends inactivation on the in HHP pressure depends onand theresidence pressure time, with maximum and residence efficacy time, with being achieved maximum efficacy at 500–600 MPa for 1–10 min [16]. In UHPH, it is also dependent on being achieved at 500–600 MPa for 1–10 min [16]. In UHPH, it is also dependent on pressure, valve design, pres- and in-valve temperature, with better sure, valve design, and in-valve temperature, results obtained with better at 300 results MPa and obtained sterilization at 300 MPa at and in-valve temperatures of 140–150 ◦ C [19,20]. sterilization at in-valve temperatures of 140–150 °C [19,20]. UHPH has the advantage of being continuous [20] with high antimicrobial [19] and antioxidant effects [21,23,24] due to the efficient control of oxidative enzymes (PPOs). However, it can only be used for liquids (grape juice) with a particle size of less than 500 µm. Although high temperatures can be generated in the valve by mechanical effects, often higher than 75 ◦ C, UHPH can be considered a non-thermal technology because, at 300 MPa, the fluid flows in the valve at Mach 3 for less than 0.2 s, which is insufficient Antioxidants 2023, 12, 1746 4 of 14 for thermal degradation of small molecules with sensory impact. After the valve, the intense nanofragmentation reduces the average size of the colloidal particles as a function of pressure and temperature. The dimensions have been measured in grape juice by laser diffraction and atomic force microscopy, giving values in the range of 100–400 nm [21] and 235–744 nm (average 457 ± 140 nm), respectively [22]. HHP is a discontinuous or batch process but can be applied to whole grapes, bunches, or grape pomace [25,26]. The effect of HHP on enzymes is variable. In the case of PPOs, which can strongly affect the stability of anthocyanins, inactivation depends on the condi- tions (pressure, time, and temperature) [27]. For example, in raspberry and strawberry food products, at least 400–600 MPa and 5–10 min at room temperature are required [28–30]. Industrial scale-up of high-efficiency UHPH systems is now possible with existing UHPH pumps capable of continuous operation at 300 MPa or higher with a pressure imbalance of 1 MPa (<1%). UHPH pumps are available from 60 L/h to 10,000 L/h, covering the range from pilot systems to industrial devices (https://www.ypsicon.com/ (accessed on 24 August 2023)). The special high-strength tungsten carbide valves with ceramic or carbon nano coverings can be scaled up to several of these flow ranges. The electric motor of UHPH pumps, which is the most important consumption range, is 11–18 kW for pumps of 60–150 L/h (personal communication, Ypsicon, Barcelona, Spain). There are currently several companies (Hiperbaric (Burgos, Spain), Avure (Chicago, IL, USA), Uhde (Hagen, Germany), Kobelco (Livonia, MI, USA) and others [16]) working on industrial HHP systems capable of operating at up to 600 MPa with vessels ranging from 55 to 525 L suitable for processing 270–3210 kg/h of food products (https://www. hiperbaric.com/en/hpp-technology/ (accessed on 24 August 2023)). There are also semi- continuous bulk HHP systems for liquids able to work at over 4000 L/h ([16], https: //www.hiperbaric.com/en/hpp-technology/equipment/hpp-in-bulk/ (accessed on 24 August 2023)). Table 1. Main features of UHPH and HHP. Characteristics HHP References UHPH References Mode Batch or semi-continuous Continuous Temperature −20–60 ◦ C 70–160 ◦ C Pressure range 200–600 MPa 200–600 MPa Optimal pressure 500–600 MPa 300 MPa [13,14,16] [19,20,31] Residence time 2–10 min <0.2 s Increment of temperature <4 ◦ C/100 MPa 70–90 ◦ C during processing Size requirements Smaller than the vessel diameter Particle size < 500 µm Pasteurization Antimicrobial [32] Sterilizing if T > 140 ◦ C [20] Sterilizing variable if T > 100 ◦ C Variable Sometimes activation at low pressure Inactivation, highly effective Enzymes (200 MPa) and inactivation at 400–600 MPa [16,27,32,33] [21,23,24,34] of PPOs 1 In some conditions, suitable inactivation of PPOs 1 Terpenes unaffected unaffected Thiols unaffected [14,15,17,25] unaffected [21–23] Anthocyanins Protected Protected Similar formation during Pyranoanthocyanins Higher formation of Vitisin A [35,36] fermentation of grape juice [22] processed by UHPH Formation in some conditions in model Polymeric anthocyanins [35] Unknown solutions 1 PPOs: Polyphenol oxidases. Similar formation dur- ing fermentation of Pyranoanthocyanins Higher formation of Vitisin A [35,36] [22] grape juice processed by UHPH Formation in some conditions in Polymeric anthocyanins [35] Unknown Antioxidants 2023, 12, 1746 model solutions 5 of 14 1 PPOs: Polyphenol oxidases. Both Bothtechnologies technologieshave havebeen beenproposed proposedto toreplace replaceor orreduce reduce the theSOSO22content contentin ingrapes grapes and and wines due to their antimicrobial and antioxidant properties [21,23,25]. In thecase wines due to their antimicrobial and antioxidant properties [21,23,25]. In the caseofof grapes grapesororwhole wholebunches, bunches,they theycan canbe be processed processed directly directly without without packaging packagingand, and,after after depressurization, depressurization, destemmed, crushed, and destemmed, crushed, and pressed pressedtotoobtain obtaina ajuice juicewith witha higher a higher con- concen- centration of anthocyanins and other compounds such as phenols or aroma. Alternatively, tration of anthocyanins and other compounds such as phenols or aroma. Alternatively, the the crushed crushed grape grape cancan be pumped be pumped intointo a tank a tank for for redred winemaking winemaking to ferment to ferment the the juice. juice. 3.3.Extraction Extractionof ofAnthocyanins Anthocyaninsby byHHP HHP The Theextraction extractionof ofanthocyanins anthocyaninsby byHHP HHPisisinfluenced influencedby bythetheintensity intensityofofpressure, pressure, temperature, temperature,and andpolarity polarity(ethanol (ethanolcontent) content)[26]. [26].In In addition, addition, thethe substitution substitutionpattern in pattern the anthocyanin in the anthocyaninring ring also affects the extraction, also affects depending the extraction, on the -OCH depending on the3 and -OCH -OH3 substit- and -OH uents [26]. We[26]. substituents haveWeobserved that after have observed thatHHP after treatment HHP treatment of grapes, even even of grapes, if theifexternal ap- the external pearance remains unaffected, perhaps just a little more brilliant, the surface looks as if itif appearance remains unaffected, perhaps just a little more brilliant, the surface looks as it has has been been pored; pored; thethe migration migration of anthocyanins of anthocyanins intointo thethe pulp pulp cancan be observed be observed because because of of the the redred color color (Figure (Figure 4) [25]. 4) [25]. TheThe permeability permeability of the of the cellscells increases, increases, andand the the diffusion diffusion of of anthocyanins anthocyanins is improved is improved [37]. [37]. TheThe anthocyanins anthocyanins areare releasedfrom released fromthethevacuoles vacuolesininthethe skinsand skins andlater latermigrate migrateto tothe thepulp, pulp,butbutalso alsototothe theseeds seedsduring duringthe theHHP HHPtreatment, treatment,and and the effect is pressure-dependent. The higher the pressure, the more the effect is pressure-dependent. The higher the pressure, the more intense the extraction, intense the extraction, reachinghigher reaching higherconcentrations concentrationsofof anthocyanins anthocyanins in the in the juicejuice of grapes of the the grapes processed processed at 550at 550 MPa/10 min compared to the 200 and 400 MPa treatments MPa/10 min compared to the 200 and 400 MPa treatments [25]. A similar effect was ob- [25]. A similar effect was observed served in total polyphenols in total polyphenols but withbut with a less a less pressure-dependent pressure-dependent behaviorbehavior when a when a compa- comparable rable extraction extraction was observed was observed at pressures at pressures in theinrange the range of 200–550 of 200–550 MPa. MPa. The The increase increase in in the extraction of total polyphenols was in the range of 20–25% the extraction of total polyphenols was in the range of 20–25% [25]. The extraction of an- [25]. The extraction of anthocyanins can range from 20 to 80%, depending on the processing thocyanins can range from 20 to 80%, depending on the processing parameters (pressure, parameters (pressure, time,temperature, time, temperature,and andpolarity) polarity)and andthetheconditions conditionsof ofthe thegrape grape(ripeness, (ripeness,skin skinthickness thickness and resistance, and previous processes) or grape by-products and resistance, and previous processes) or grape by-products [25,26,34]. [25,26,34]. EffectofofHHP Figure4.4.Effect Figure HHPononthe thesurface surfaceand andpulp Vitisvinifera pulpofofVitis viniferacv cvTempranillo Tempranillogrape grapeberries berriesand andon on color extraction with a treatment of 550 MPa for 10 color extraction with a treatment of 550 MPa for 10 min.min. HHPhas HHP hasshown shownaa protective protective effect effect on on several several anthocyanins anthocyaninswith withlow low degradation degradation after treatment (Table 2) and protection of antioxidant capacity [33,38,39]. The protective after treatment (Table 2) and protection of antioxidant capacity [33,38,39]. The protective effect on anthocyanins is better when pre-processing is carried out at low effect on anthocyanins is better when pre-processing is carried out at low oxygen oxygen levels [40]. levels Inertization by a nitrogen atmosphere in the pre-processing of berries probably [40]. Inertization by a nitrogen atmosphere in the pre-processing of berries probably reduces the effect of residual PPO activity on anthocyanin oxidation. Color retention is usually better in HHP treatments than in conventional thermal processing (80–90 ◦ C) [41], probably due to the intensification of oxidation. The protective effect on anthocyanins in preserving the antioxidant capacity and the partial inactivation of PPOs make HHP a gentle technique for extracting anthocyanins from fruits or vegetable tissues. The subsequent stability of the extracted anthocyanins under refrigeration favors the stability and valorization of these pigments to be used in the food industry, obtain wines with faster macerations, or even fermentations in the absence of skins, facilitating winemaking. Antioxidants 2023, 12, 1746 6 of 14 Table 2. Effect of different HHP treatments on the extraction and stability of anthocyanins in various fruits, juices, or by-products. Fruit Anthocyanins HHP Parameters Effects References Delphinidin, Petunidin, Anthocyanin loss of 70% Muscadine grape juice Peonidin and Malvidin 400–550 1 MPa, 15 min (400 MPa) and 46% at [42] (Vitis rotundifolia) 3,5-diglucosides (D35G, Pt35G, (550 MPa) Pn35G, M35G) Higher anthocyanin content in Merlot grape juice C3G, Pt3G, Pn3G & M3G, acetyl 600 MPa, 10 ◦ C, 3 min HHP treatments compared to [43] (Vitis vinifera L.) C3G, acetyl Pn3G, acetyl M3G controls Higher extraction at 600 MPa, 50 ◦ C, 100% ethanol (+23%) Grape pomace from 200–600 MPa, ethanol and related to the higher Dornfelder variety D3G, C3G, Pt3G, Pn3G & M3G (20–100%), 30–90 min, and number of -OCH3 and -OH [32] (Vitis vinifera L.) temperature 20–70 ◦ C groups in the flavylium nucleus, extraction of M3G > Pn3G > Pt3G > D3G > C3G Migration of anthocyanins D3G, C3G, Pt3G, Pn3G and M3G ◦ C, from skins to pulp and seeds. Tempranillo grapes 200–550 MPa, 20 and acylated derivatives (acetyl, Increased extraction +80%. [29] (Vitis vinifera L.) 10 min caffeoyl and p-coumaroyl) Higher concentration after fermentation. Higher contents that the Concord grape puree Total monomers 600 MPa, 5 ◦ C, 3 min, control and enough stability [39] (Vitis labrusca) for 4 months 200–800 MPa, 18–22 ◦ C, Cyanidin-3-glucoside (C3G) Higher stability for 800 MPa Raspberry (Rubus idaeus) 15 min. Stored at: 4, 20, 30 [44] Cyanidin-3-sophoroside (C3S) ◦ C for 9 days stored at 4 ◦ C Strawberry 200–800 MPa, 18–22 ◦ C, Pelargonidin-3-glucoside (P3G) Higher stability for 800 MPa (Fragaria × ananassa, cv. 15 min. Stored at: 4, 20, [45] Pelargonidin-3-rutinoside (P3R) stored at 4 ◦ C Elsanta) 30 ◦ C for 9 days 200–800 MPa, 18–22 ◦ C, Blackcurrant Delphinidin-3-rutinoside (D3R) Higher stability for 15 min. Stored at: 5, 20, [46] (Ribes nigrum) Cyanidin-3-rutinoside (C3R) 600–800 MPa stored at 5 ◦ C 30 ◦ C for 7 days C3G, p-coumaroyl D3G, and 200–600 MPa, 20 ◦ C, Anthocyanins protected, Lonicera caerulea [33] D3R 10 min higher antioxidant activity Delphinidin3-galactoside (D3Gal), D3G, Cyanidin-3-galactopyranoside (Cy3Gal), Delphinidin-3-arabinoside (D3A), C3G, HHP with low oxygen shows Blueberry pulp Petunidin-3-galactoside (Pt3Gal); 500 MPa, 5 min higher anthocyanin content [40] (Vaccinium spp.) Peonidin-3-galactoside (Pn3Gal), and protective effect on color Cyanidin-3-arabinoside (C3A), Pt3G, Pn3G, Malvidin-3-galactoside (M3Gal), Peonidin-3-arabinoside (Pn3A), Malvidin-3-arabinoside (M3A). Protective effect on color. D3Gal, D3G, Cy3Gal, C3G, C3A, Blueberry (Vaccinium spp.) 200–600 MPa, 20 ◦ C, At 300MPa was obtained the Petunidin-3-arabinoside (Pt3A), [41] puree 20 min higher concentration of M3Gal, M3G, M3A anthocyanins Preservation of anthocyanins, Aronia (Aronia 200–600 MPa, 21–33 ◦ C, Total anthocyanins phenols and color. Antioxidant [38] melanocarpa) berry purée 2.5–5 min capacity unaffected Strawberry (Fragaria × ananassa 400–600 MPa, 20 ◦ C, Good stability of anthocyanins Total monomeric anthocyanins [47] Duch.) cv. Senga Sengana 1.5–3 min specially in juices purée and juice 1 MPa: Mega Pascal. Antioxidants 2023, 12, 1746 7 of 14 4. Extraction of Anthocyanins by UHPH Anthocyanins are essential for the color, antioxidant properties, and sensory quality of berry juices and their fermentative products, such as wine. After juice extraction, anthocyanins can remain entrapped or adsorbed in colloidal particles of the pulp and are also more exposed to the action of PPOs than in the whole berry. Mechanical action and nanofragmentation in the UHPH valve are powerful tools to release the anthocyanins from the colloidal fragments and to avoid the effects of PPOs by inactivating them. In the application of UHPH, the juice is pressurized by pumping with a special pump that works at >200 MPa (usually at 300 MPa); the capillary pipeline section is smaller than 1 mm so that any fluid with a colloid size higher than 500 µm cannot be processed [20]. Grapes or raw grape skins cannot be processed directly because of the previous size limitation, but UHPH can be applied to the unsettled must obtained by pressing after cold soaking or enzyme treatments of the crushed grape [22]. It would also be possible to mechanically process the skins with the pomace using a milling system and later apply UHPH to the puree. A high efficiency of UHPH to disaggregate and destroy biofilms by mechanical effects has been observed [48]. The processing of plant matrices by UHPH produces a better and more stable colloidal structure [49], which can be measured by particle settling produced by centrifugation [50]. In addition, higher viscosity and turbidity can be observed due to the formation of stable colloidal nanoparticles [51]. What can be observed after the UHPH processing at pressures higher than 200 MPa is the nano-fragmentation of all the microorganisms and colloidal fragments from the plant tissues (Figure 5). In the raw juice of unsettled Tempranillo grape (Vitis vinifera L.), yeast cells and large colloidal fragments can be observed (Figure 5A), which are nano-fragmented during UHPH by the impact and shear forces generated in the valve and a thinner and more regular colloidal structure can be observed (Figure 5B–D). In addition, the colloids are slightly colored red by the anthocyanins (Figure 5A (Tempranillo), Figure 5E (Cabernet sauvignon)), which disappear from them in the UHPH-treated juice (Figure 5B–D,F) [22]. Using Atomic Force Microscopy (AFM), the average colloid size in Cabernet sauvignon juice before and after UHPH treatment was measured to be 1.32 ± 0.46 µm (predominantly super-micron scale) and 0.46 + 0.14 µm (nanometric scale), respectively [22]. Previously, and in agreement with this value, a similar size range of 100–400 nm was measured in grape juice treated with UHPH using laser light scattering [21]. Nanofragmentation at a size greater than 100 nm is relevant because lower values may have nanosafety implications due to the possibility of crossing plasmatic barriers. Applying UHPH produces a highly effective nano-fragmentation of the plant tissues and cells, releasing the anthocyanins from them and facilitating high and rapid extraction (Figure 5) [22]. Therefore, the application of UHPH is a powerful, gentle technology not only to eliminate microorganisms but also to release pigments [22], thus protecting the color [51,52] and other nutrients, antioxidants, and nutraceutical compounds [51–55]. Several significant works have been carried out on the use of High-Pressure Homogenization (HPH) or UHPH for the processing of juices or plant-based bever- ages [21,23,34,49–51,56–58], but not too much in the processing of red grape juice or berries rich in anthocyanins. However, there are some recent works at 150–300 MPa with important results, including the release of anthocyanins from plant cells or fragments, the protection of color and the control of browning, the specific effect on acylated anthocyanins, the inactivation of PPOs and the preservation of antioxidant activity (Table 3) [22,59,60], together with effective control of microbial loads. Conversely, a 33–38% reduction in anthocyanins was observed in mulberry juice processed at 200 MPa with a pilot UHPH system at a flow rate of 10 L/h, which the authors associate with uncontrolled peroxidase or polyphenol oxidase, but which can be avoided with ascorbic acid [61]. Most of the studies reporting a reduction in anthocyanin content work at lower pressures (50–200 MPa) and in multi-cycle mode (2–5 passes) [60,62,63], which increases the possibilities of oxidation and damage by mechanical effects during several Antioxidants 2023, 12, 1746 8 of 14 passes through the UHPH valve. Furthermore, at a pressure of 200 MPa or less, we are at the limit of UHPH and work more in the HPH range. In these conditions, the inactivation of PPOs is lower [20]. An intense inactivation of PPOs (>90%, [21]) has been observed at 300 MPa, and therefore, the oxidative damage to anthocyanins will be more intense, especially in a longer multipass process. The design shape and nanocoating of the valve and seat valve is another key aspect to enhance the mechanical effects and inactivation [20,31]. From our experience, working at 300 MPa in a single pass, the inactivation of PPOs, the antimicrobial effect, and the stability of anthocyanins are opti- mal, with strong protection of the color and better antioxidant activity [22]. In general, several works have observed a clear effect on particle size and viscosity after (U)HPH, which affects the extraction of molecules such as anthocyanins, phenolic aroma, and other nutrients, as well as the colloidal stability of the juice [62]. The effect on size is pressure-dependent, as observed by optical microscopy and light scattering [62] and AFM microscopy [22]. Table 3. Effect of different (U)HPH treatments on the extraction and stability of anthocyanins in various fruits, juices, or by-products. Fruit Anthocyanins UHPH Parameters Effects References D3G, C3G, Pt3G, Pn3G and Higher contents of M3G, acylated derivatives 1 anthocyanins in UHPH must 60 L/h, 300 ± 3 MPa, (acetyl, caffeoyl and with a selective protection of Cabernet sauvignon inlet temperature 4 ◦ C, p-coumaroyl), Vitisin B and the acylated derivatives red must in-valve 78 ± 2 ◦ C [22] Malvidin 3-glucoside +9.3% with more red-bluish (Vitis vinifera L.) (0.2 s) outlet vinylphenol (M3GvPh) and color temperature of 15 ◦ C Malvidin 3-glucoside Absence of anthocyanins in vinylguaiacol (M3GvG) colloids. Not differences in color. 100–150 MPa, inlet Pomegranate In certain conditions higher C3G, D3G, just optically temperature 10 ◦ C, (Punica granatum L.) polyphenol content and [59] evaluated OD520nm 1–10 cycles, outlet max juice antioxidant activity than in 42–46 ◦ C the fresh juice. Slight reduction of Blackcurrant 50–220 MPa, inlet anthocyanins. Preserve the (Ribes nigrum) fruit D3G, D3R, C3G and C3R temperature 4–20 ◦ C, [60] bioactive and juice 1–5 passes physicochemical quality. Anthocyanins and color 50–200 MPa, inlet slightly affected depending temperature 25 ◦ C, Strawberry nectar P3G on number of cycles. [62] 1–5 passes, Higher polyphenol content ∆T ≈ 19 ◦ C/100 MPa with multi passes at 200 MPa Color, anthocyanins and 60–100 MPa, inlet antioxidant activity increases Strawberry Color evaluation CieLab temperature 4–20 ◦ C, until 2 passes. Later [63] (F. Ananassa) juice 1–5 passes degradation probably by thermal effect. 1 MPa: Mega Pascal. Antioxidants 2023,12, Antioxidants2023, 12,1746 x FOR PEER REVIEW 89 of of 14 15 Figure5. Figure 5. Optical Optical microscopy microscopyofofred redjuices from juices two from varieties two treated varieties withwith treated UHPH, Tempranillo UHPH, (Vitis Tempranillo vinifera L.) (A) Control 0.1 Mpa; (B) UHPH 240 Mpa; (C) UHPH 270 Mpa; (D) UHPH 300 MPa.; (Vitis vinifera L.) (A) Control 0.1 Mpa; (B) UHPH 240 Mpa; (C) UHPH 270 Mpa; (D) UHPH 300 MPa; Cabernet Sauvignon (Vitis vinifera L.); (E) Control 0.1 Mpa; (F) UHPH 300 MPa. Cabernet Sauvignon (Vitis vinifera L.); (E) Control 0.1 Mpa; (F) UHPH 300 MPa. 5. HHP Applying vs. UHPH UHPH produces in the Extraction a highly effective nano-fragmentation and Stability of Anthocyanins of the plant tissues and The cells,use releasing the anthocyanins from of HHP has the advantage of allowing the them and facilitating processing highofand rapid solids; extraction therefore, it (Figure 5) [22]. Therefore, the application of UHPH is a powerful, is possible to process grapes, grape pomace, or even bunches. The only limitation is that gentle technology not only the to of size eliminate the product microorganisms to be treatedbut must also beto releasethan smaller pigments [22], thus the diameter andprotecting length of the the color [51,52] vessel. Large andHHPother nutrients, machines withantioxidants, a diameter ofand 0.38nutraceutical m can be found compounds on the market [51–55].today. Several significant works have been carried out on (https://www.hiperbaric.com/en/ (accessed on 24 August 2023)). Therefore, treating the use of High-Pressure Homog- enization whole (HPH) grape destemmed or UHPH berriesfor the processing or bunches is perfectly of possible juices or on plant-based an industrial beverages scale [25], [21,23,34,49–51,56–58], but not too much in the processing as well as processing by-products such as pomace [26]. The extraction of red grape juice or berries of solids canrich be in anthocyanins. However, there are some recent works at obtained from the whole raw material and can be higher than in the case of UHPH, where 150–300 MPa with important aresults, previousincluding the release pre-extraction of anthocyanins is needed. However,from afterplant cells or fragments, the pre-extraction, the the protection intense nano- of color and the fragmentation control caused by of UHPHbrowning, in the the specific colloids effect ona acylated guarantees anthocyanins, better release of anthocyaninsthe in- activation from of PPOsplant the colloidal and the preservation fragments [22]. Inof addition, antioxidant theactivity (Tablenature continuous 3) [22,59,60], of UHPH to- gether with effective control of microbial loads. processing makes it more efficient from an industrial perspective. Conversely, a 33–38% reduction in antho- cyanins was observed Concerning in mulberry anthocyanin juice processed oxidation, the main at 200 MPa with disadvantage of aHHP pilotisUHPH system the variable at a flow effect rate on the of 10 L/h, which inactivation the authors of oxidative enzymes associate with uncontrolled [16,27,32,33]. The protective peroxidase or pol- effect of UHPH yphenol on oxidase, anthocyanin but is color which due to canitsbe avoided gentle actionwith onascorbic them but acid also[61]. Most to the of the highly studies effective reporting control a reduction of PPOs in anthocyanin [21,23,56], which can be content work more considered at lower pressures intense than in (50–200 MPa) and HHP treatment, in multi-cycle where inactivationmode (2–5 passes) is usually [60,62,63], variable and under which increases stronger the possibilities conditions [64–70]. of oxidation and damage by mechanical effects during several passes through the UHPH valve. Fur- 6. Environmental thermore, Impacts at a pressure andMPa of 200 Research or less,Needs we are at the limit of UHPH and work more in Lastly,range. the HPH the UHPH technology In these conditions, is environmentally the inactivationmore of PPOssustainable is lowerthan[20].HHP due to the An intense in- low consumption activation of PPOs of(>90%, water used[21])for hasprocessing been observed and cleaning. at 300 MPa, Sustainability and therefore, is currently a key the oxidative parameter damage toinanthocyanins the wine industry will [71–75]. be moreThe waterespecially intense, consumption in atolonger produce 1 kg of grapes multipass process. is about 550 L [76]. In a more recent study, the water food print The design shape and nanocoating of the valve and seat valve is another key aspect to for a 0.75 L bottle has 632 L [77]. Only in the enhance theindustry, mechanical winemaking effects and andinactivation cleaning consume [20,31].inFrom the range of 0.2–8 L ofworking our experience, water per at 1300 L of wine, MPa in adepending single pass,onthe several parameters, inactivation of PPOs, especially the size ofeffect, the antimicrobial the winery and the [73,74,78]. stability With UHPH, the are of anthocyanins need for cleaning optimal, with strongproducts is lowerofbecause protection the colorofand the better small antioxidant volume of pipelines. activity [22].Typical consumption In general, several is 750 Lhave works of water observedfor 35 ah of processing clear with 3000 effect on particle sizeL/h and UHPH systems, which means less than 0.018 L of water per viscosity after (U)HPH, which affects the extraction of molecules such as anthocyanins, liter of product in a regular production phenolic aroma,cycle. and Additionally, it has aaslower other nutrients, well asconsumption the colloidalofstability energy andof theis not juicenecessary [62]. The Antioxidants 2023, 12, 1746 10 of 14 for steam as processing or cleaning fluid. The main power consumption for UHPH is the motor of the UHPH pump, which is 11–18 kW for 60–150 L/h. The consumption for an industrial system of 3000 L/h is 290 kW/h. In terms of environmental impact, high-pressure extraction is superior to conventional methods and comparable to pulsed electric fields (PEFs), as reported in the literature [79], which is also another continuous emerging non-thermal technology used to increase the extraction of anthocyanins [80] and to accelerate the maceration of red wines [35,81–86]. Moreover, a better bioprotective capacity is obtained [87]. Therefore, UHPH and HHP are similar to PEF in anthocyanin protection and antioxidant activity [20,88]. All techniques accelerate the extraction of anthocyanins compared to conventional methods [81–84]. UHPH and PEF are continuous technologies and can, therefore, be applied to the product more efficiently [20,81]. HHPs and PEFs can be used in crushed grapes, but UHPH only in liquid juice [20,22]. At the same time, the commonly used packaging materials in HHP processing, i.e., polyethylene terephthalate, ethylene–vinyl alcohol copolymer, polyethylene, and polypropylene, could be a negative aspect of this extraction from a sustainability and environmental viewpoint, compared to other emerging extraction technologies such as UHPH [20], or moderate electric field [89]. Further enhancement of high-pressure processing sustainability could be a topic for future studies, which can be achieved by exploring the possibility of using biodegradable packaging materials or developing strategies for re-using and recycling high-pressure processing packaging material. Additionally, there are limited reports on combining high- pressure extraction and other techniques [90]. The possible effects of such combined approaches based on HPP and UHPH on anthocyanin extraction and stability could be considered in future research. At the same time, the bioavailability of the anthocyanins extracted by HPP and UHPH is among the information encouraged to be revealed by researchers [91]. This expected research can help provide information that can further promote the commercialization of HPP and UHPH so that the industry and consumers can benefit from high-pressure-based extracted anthocyanins. 7. Conclusions High-pressure techniques are a powerful processing tool to enhance extraction in a gentle manner, protecting sensitive molecules such as anthocyanins and maintaining their stability during storage. The inactivation of oxidative enzymes and the absence of oxidation are key process parameters to achieve optimal conditions. As mentioned above, the main advantages of UHPH are its higher antimicrobial efficacy, better control of PPO enzymes, continuous processing, and low consumption of water, detergents, and energy. Conversely, the main disadvantage is the need to process liquid products and the impossibility of processing whole or crushed berries with skins. With regard to HHP, the most interesting processing feature is the possibility to process juice, crushed berries, or whole berries, which is optimal for the extraction of anthocyanins from skins to juice. The main disadvantage is a more variable behavior in the inactivation of enzymes, a less optimal batch process, and a higher consumption of water and energy. These HP technologies open up new opportunities to obtain highly sensitive pigments with nutraceutical properties, such as anthocyanins, or to increase their content in juices, smoothies, purees, or derived beverages, even fermented as wines. The appropriate inactivation of oxidative enzymes, the high antimicrobial effect, and the gentle action allow us to reduce chemical additives such as SO2 and obtain food products with clean labels. Author Contributions: Conceptualization, A.M.; methodology, A.M. and C.L.; writing—original draft preparation, A.M., J.M.d.F., C.L. and F.P.; writing—review and editing, A.M., M.G., B.G., J.M.d.F., C.L. and F.P.; funding acquisition, A.M. All authors have read and agreed to the published version of the manuscript. Antioxidants 2023, 12, 1746 11 of 14 Funding: This research was funded by MINISTERIO DE CIENCIA E INNOVACIÓN, project ENOINNOVAPRESS—PID2021-124250OB-I00 Ministerio de Ciencia e Innovación. This work was partially supported by the State Program to Promote Scientific-Technical Research and its Transfer of the Spanish Ministry of Science and Innovation through the MALTA CONSOLIDER TEAM Research Network (RED2022-134388-T). Institutional Review Board Statement: Not applicable. 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