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By-Products of Agri-Food Industry As Tannin-Rich Sources: a Review of Tannins’ Biological Activities and Their Potential for Valorization

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By-Products of Agri-Food Industry As Tannin-Rich Sources: a Review of Tannins’ Biological Activities and Their Potential for Valorization foods Review By-Products of Agri-Food Industry as Tannin-Rich Sources: A Review of Tannins’ Biological Activities and Their Potential for Valorization María Fraga-Corral 1,2 , Paz Otero 1,3 , Javier Echave 1 , Paula Garcia-Oliveira 1,2 , Maria Carpena 1 , Amira Jarboui 1, Bernabé Nuñez-Estevez 1,2 , Jesus Simal-Gandara 1,* and Miguel A. Prieto 1,2,* 1 Nutrition and Bromatology Group, Analytical and Food Chemistry Department, Faculty of Food Science and Technology, Ourense Campus, University of Vigo, 32004 Ourense, Spain; [email protected] (M.F.-C.); [email protected] (P.O.); [email protected] (J.E.); [email protected] (P.G.-O.); [email protected] (M.C.); [email protected] (A.J.); [email protected] (B.N.-E.) 2 Centro de Investigação de Montanha (CIMO), Campus de Santa Apolonia, Instituto Politécnico de Bragança, 5300-253 Bragança, Portugal 3 Department of Pharmacology, Pharmacy and Pharmaceutical Technology, Faculty of Veterinary, University of Santiago of Compostela, 27002 Lugo, Spain * Correspondence: [email protected] (J.S.-G.); [email protected] (M.A.P.) Abstract: During recent decades, consumers have been continuously moving towards the substi- tution of synthetic ingredients of the food industry by natural products, obtained from vegetal, animal or microbial sources. Additionally, a circular economy has been proposed as the most efficient production system since it allows for reducing and reutilizing different wastes. Current agriculture is responsible for producing high quantities of organic agricultural waste (e.g., discarded fruits and Citation: Fraga-Corral, M.; Otero, P.; vegetables, peels, leaves, seeds or forestall residues), that usually ends up underutilized and accu- Echave, J.; Garcia-Oliveira, P.; mulated, causing environmental problems. Interestingly, these agri-food by-products are potential Carpena, M.; Jarboui, A.; Nuñez-Estevez, B.; Simal-Gandara, J.; sources of valuable bioactive molecules such as tannins. Tannins are phenolic compounds, secondary Prieto, M.A. By-Products of metabolites of plants widespread in terrestrial and aquatic natural environments. As they can be Agri-Food Industry as Tannin-Rich found in plenty of plants and herbs, they have been traditionally used for medicinal and other pur- Sources: A Review of Tannins’ poses, such as the leather industry. This fact is explained by the fact that they exert plenty of different Biological Activities and Their biological activities and, thus, they entail a great potential to be used in the food, nutraceutical and Potential for Valorization. Foods 2021, pharmaceutical industry. Consequently, this review article is directed towards the description of the 10, 137. https://doi.org/10.3390/ biological activities exerted by tannins as they could be further extracted from by-products of the foods10010137 agri-food industry to produce high-added-value products. Received: 2 December 2020 Keywords: tannins; valorization; circular economy; biological properties; health benefits Accepted: 31 December 2020 Published: 11 January 2021 Publisher’s Note: MDPI stays neu- 1. Introduction tral with regard to jurisdictional clai- ms in published maps and institutio- 1.1. Tannins as Target Compounds nal affiliations. Tannins are a diverse group within phenolic compounds widely distributed in nature. They are secondary metabolites of plants usually produced as a result of stress and they exert a protective role, including photoprotection against UV rays and free radicals or defense against other organisms and environmental conditions, such as dryness [1–3]. Copyright: © 2021 by the authors. Li- Tannins are a heterogeneous group, having molecular weights between 500 and 20,000 Da censee MDPI, Basel, Switzerland. and very different chemical structures [4]. Tannins have been demonstrated to exert dif- This article is an open access article ferent biological activities, such as antioxidant activity. This property is related to their distributed under the terms and con- ditions of the Creative Commons At- chemical structure as they possess phenolic rings able to bind to a wide range of molecules tribution (CC BY) license (https:// and act as electron scavengers to trap ions and radicals [2,4]. Generally, tannins possess creativecommons.org/licenses/by/ about 12–16 phenolic groups and five to seven aromatic rings per 1000 Da [5]. They also 4.0/). present plenty of hydroxyl groups, which confer on them hydrophilic properties, solubility Foods 2021, 10, 137. https://doi.org/10.3390/foods10010137 https://www.mdpi.com/journal/foods Foods 2021, 10, x FOR PEER REVIEW 2 of 23 Foods 2021, 10, 137 2 of 22 present plenty of hydroxyl groups, which confer on them hydrophilic properties, solubil- ityin aqueousin aqueous solvents solvents and and also also the abilitythe ability to form to form complexes complex withes with proteins, proteins, carbohydrates, carbohy- drates,nucleic nucleic acids and acids alkaloids and alkaloids [6,7]. Regarding [6,7]. Regarding tannin tannin classification, classification, they have they been have histor- been historicallyically classified classified into hydrolyzableinto hydrolyzable tannins tannins (HTs) (HT ands) an condensedd condensed tannins tannins (CTs), (CT ands), and the thelatter latter are alsoare also called called proanthocyanidins. proanthocyanidins. Nowadays, Nowadays, the classificationthe classification according according to their to theirchemical chemical characteristic characteristic and structuraland structural properties properties has beenhas been updated. updated. Thus, Thus, tannins tannins can canbe groupedbe grouped into in gallotannins,to gallotannins, ellagitannins, ellagitannins, CTs, CT complexs, complex tannins tannins (CoTs) (CoT ands) and phlorotan- phloro- tanninsnins (PTs, (PT ans, an exclusive exclusive class class of of tannins tannins found found in in the the algalalgal speciesspecies ofof the Phaeophyceae class)class) [1,2,8]. [1,2,8]. A A schematic schematic representation representation of of tannin tannin structural structural classification classification is is presented presented in in FigureFigure 1.. FigureFigure 1. 1. StructuralStructural classification classification of of tannins. tannins. Functional Functional groups groups are are shown shown in in circles. circles. HTHTss have have owned owned their their name name as as they they can can be behydrolyzed hydrolyzed by byweak weak acids/bases, acids/bases, produc- pro- ingducing carbohydrates carbohydrates and andphenolic phenolic acids acids because because of the of reaction the reaction [3]. They [3]. They are formed are formed by gly- by glycosylated gallic acid units [9], which can be either ellagic acid (EA) or gallic acid (GA), cosylated gallic acid units [9], which can be either ellagic acid (EA) or gallic acid (GA), forming ellagitannins (ETs) and gallotannins (GTs), respectively [3,10]. ETs are formed by forming ellagitannins (ETs) and gallotannins (GTs), respectively [3,10]. ETs are formed by simple to multiple units of hexahydroxydiphenol (HHDP) connected to a polyol core. After simple to multiple units of hexahydroxydiphenol (HHDP) connected to a polyol core. Af- hydrolysis and the breakdown of C-C bonds between suitably orientated galloyl residues of ter hydrolysis and the breakdown of C-C bonds between suitably orientated galloyl resi- glucogalloyl molecules of HHDP, they are converted into EA units [2,11,12]. The abundant dues of glucogalloyl molecules of HHDP, they are converted into EA units [2,11,12]. The variety of structure has been observed within this group, due to the different possibili- abundant variety of structure has been observed within this group, due to the different ties in the formation of oxidative linkages [7]. On the other hand, GTs are considered as possibilities in the formation of oxidative linkages [7]. On the other hand, GTs are consid- simpler HTs and are formed by galloyl or digalloyl units coupled to a polyol, catechin ered as simpler HTs and are formed by galloyl or digalloyl units coupled to a polyol, cat- or triterpenoid unit, in the form of pentagalloyl glucose (PGG). They can yield GA from echin or triterpenoid unit, in the form of pentagalloyl glucose (PGG). They can yield GA the hydrolysis reaction [2,13]. HTs can be mainly found in fruits, berries, legumes, leafy fromvegetables the hydrolysis and different reaction tree species[2,13]. HT [3,9s]. can They be havemainly been found widely in fruits, employed berries, in the legumes, leather leafyindustry vegetables and they and have different been studied tree species for their [3,9]. antioxidant They have and been antimicrobial widely employed properties in the [3]. leatherCTs industry or proanthocyanidins and they have been account studied for morefor their than antioxidant 90% of the and world antimicrobial commercial prop- pro- ertiesduction [3]. of tannins [3]. They are polymeric or oligomeric flavan-3-ols, formed by the combinationCTs or proanthocyanidins of A (phloroglucinol account or resorcinol) for more and than B (catechol90% of the or world pyrogallol) commercial rings [ 2pro-,14] duction(Figure1 of). Whentannins these [3]. compoundsThey are polymeric are heated or inoligomeric ethanol solutions flavan-3- inols, acidic formed conditions, by the com- they binationare decomposed of A (phloroglucinol into anthocyanidins or resorcinol) [7]. The and combination B (catechol ofor these pyrogallol) flavan-3-ol rings monomers [2,14] (givesFigure rise 1). toWhen the formationthese compounds of procyanidins are
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