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Deep Eutectic Solvents As Extraction Media for Valuable Flavonoids from Natural Sources

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Deep Eutectic Solvents As Extraction Media for Valuable Flavonoids from Natural Sources applied sciences Review Deep Eutectic Solvents as Extraction Media for Valuable Flavonoids from Natural Sources Dimitris Skarpalezos and Anastasia Detsi * Laboratory of Organic Chemistry, Department of Chemical Sciences, School of Chemical Engineering, National Technical University of Athens, 15780 Zografou, Athens, Greece; [email protected] * Correspondence: [email protected] Received: 31 July 2019; Accepted: 30 September 2019; Published: 4 October 2019 Abstract: The present review article attempts to summarize the use of deep eutectic solvents in the extraction of flavonoids, one of the most important classes of plant secondary metabolites. All of the applications reviewed have reported success in isolation and extraction of the target compounds; competitive, if not superior, extraction rates compared with conventional solvents; and satisfactory behavior of the extract in the latter applications (such as direct analysis, synthesis, or catalysis), wherever attempted. Keywords: flavonoids; extraction; deep eutectic solvents (DES); natural deep eutectic solvents (NaDES) 1. Introduction The global turn towards green chemistry is an integral approach towards conventional chemical practices. Following this trend, both raw materials and processes are being re-evaluated from the ground up, combining the research for naturally, sustainably sourced raw materials with eco-friendly, cost effective, and lean processes. Research on multiple compound groups is being carried out globally, aiming at isolating substances with significant health, well-being, or other benefits from natural sources, through green methods. The present review focuses on the extraction of flavonoids, an immense category of compounds found in plants and natural products. Furthermore, the review is dedicated to conventional and novel extraction methods using classic or natural deep eutectic solvents, a new category of green solvents with exceptional solvent properties, as well as generally green behavior. An inclusive overview of the current research being carried out on the extraction of flavonoids using deep eutectic solvents is provided. The main conclusions, issues, and trends are analyzed in order to comprise a solid foundation for further research or more focused application. 1.1. Flavonoids Flavonoids are a category of naturally occurring organic compounds found in fruits, vegetables, or grains. Flavonoids, as a group, include upwards of 8000 different identified compounds, which are responsible for a number of functions within plants, such as the coloration of the different parts of fruits or vegetables (leaves, flower, peel), as well as shielding against UV rays or external threats, such as pathogens. They can be located in other subsystems as well, such as the bark or the roots of the plant, where they might serve similar or different purposes [1]. The interest around extraction of flavonoids stems from the multiple health benefits they provide. Cardiovascular benefits, anticancer activity, and neurological system fortification are only some of the many actions this group. Flavonoid intake has been involuntarily pursued in medicine since ancient times. Herbal medicine, such as traditional Chinese or Mediterranean medicine, has helped breed Appl. Sci. 2019, 9, 4169; doi:10.3390/app9194169 www.mdpi.com/journal/applsci Appl.Appl. Sci. 2019,, 9,, 41694169 22 of of 2322 since ancient times. Herbal medicine, such as traditional Chinese or Mediterranean medicine, has plantshelped that breed are plants considerably that are rich considerably in flavonoids. rich This in flavonoids. legacy has fueledThis legacy much has of the fueled research much listed of the in thisresearch project, listed directing in this greenproject, extraction directing towards green extraction traditional towards herbs, fruits, traditional or common herbs, foodsfruits, in or the common hopes offoods isolating in the useful hopes substances,of isolating includinguseful substances, flavonoids including [2,3]. flavonoids [2,3]. From a chemical structure standpoint, all flavonoidsflavonoids stem from a main skeleton that they share, and didifferentiatefferentiate fromfrom eacheach otherother basedbased onon thethe substituentssubstituents attached to any part ofof thethe structurestructure (Figure(Figure1 1).). TheyThey possesspossess phenolicphenolic andand pyranepyrane ringsrings inin theirtheir structuresstructures andand havehave manymany subclasses,subclasses, such asas flavanols,flavanols, flavones,flavones, flavanones,flavanones, chalcones,chalcones, andand anthocyanidines.anthocyanidines. The flavonoidflavonoid skeleton isis comprised ofof anan aromatic aromatic ring ring linked linked on on one one side side with with a six-membered a six-membered heterocyclic heterocyclic ring, whichring, which bears anbears oxygen an oxygen atom instead atom instead of carbon of carbon next to thenext common to the common side. The side. two The rings two connect rings toconnect another to aromatic another ringaromatic to form ring the to skeleton,form the asskeleton, shown as below: shown below: Figure 1. Flavonoid skeleton and general structures of the main flavonoidflavonoid categories.categories. 1.2. Deep Eutectic Solvents The extraction media of choicechoice for greengreen extractionsextractions couldcould veryvery wellwell bebe DeepDeep EutecticEutectic SolventsSolvents (DES).(DES). DESDES are are solvents solvents that that occur occur when when a mixture a mixture of substances of substances has ahas melting a melting point point that is that much is lowermuch thanlower that than of that the twoof the constituents. two constituents. In order In toorder form to aform DES a system, DES system, there needsthere needs to be ato hydrogen be a hydrogen bond donorbond donor (HBD) (HBD) and a and hydrogen a hydrogen bond acceptorbond acceptor (HBA), (H whichBA), which when mixedwhen mixed at proper at proper ratios createratios acreate new “mesh”a new of“mesh” hydrogen-bond-interconnected of hydrogen-bond-interconnected molecules with molecules interesting with physicochemical interesting physicochemical properties. DES canproperties. be highly DES viscous, can be inhibiting highly viscou theirs, use inhibiting in processes their that use requirein processes diffusion that orrequire flow, however,diffusion researchor flow, intohowever, their chemicalresearch structure,into their aschemical well as thestructure, use of additivesas well as (like the water),use of additives largely alleviates (like water), this issue largely [4]. alleviatesThe potential this issue to [4]. use multiple molecules as constituents and create a fluid mixture that can be used as a solventThe potential is the firstto use key multiple interesting molecules point regarding as constituents DES. Adding and create to this a fluid notion, mixture the potential that can forbe manyused as naturally a solvent occurring is the first molecules key interesting to form point DES, regarding thus providing DES. Adding a natural to solventthis notion, system the withpotential low vaporfor many pressure; naturally low occurring cost, even molecules at larger to industrial form DES, scales; thus and providing the potential a natural to removesolvent thesystem need with for solventlow vapor retrieval pressure; (Natural low cost, DES–NaDES even at larger could indust remainrial in scales; a consumable and the endpotential product) to remove highlights the theirneed importance.for solvent retrieval The evolution (Natural of DES, DES–NaDES and more could importantly, remain NaDES, in a consumable means that end the product) design of highlights the newer solventstheir importance. can focus The on aevolution solvent that of DES, is a capable and more and importantly, biocompatible NaDES, storage means media, that a readilythe design available of the activenewer ingredient,solvents can a veryfocus e ffioncient a solvent catalyst, that or is a moleculara capable and or compound biocompatible carrier storage [5,6]. media, a readily availableCompeting active ingredient, with ionic liquidsa very efficient (ILs), another catalyst, category or a molecular of green or solvents compound so far carrier favors [5,6]. DES, since they areCompeting largely cheaper with ionic to produce, liquids (ILs), less toxic, another and category offer great of variety. green solvents Seemingly, so far NaDES favors is theDES, natural since stepthey forwardare largely from cheaper conventional to produce, ionic liquids,less toxic, since and they offer can great be formedvariety. from Seemingly, green sources, NaDES canis the be natural step forward from conventional ionic liquids, since they can be formed from green sources, Appl. Sci. 2019, 9, 4169 3 of 22 Appl. Sci. 2019, 9, 4169 3 of 22 can be polar or non-polar, hydrophilic or hydrophobic, and can be tailored for any situation. DES Appl. Sci. 2019, 9, 4169 3 of 22 couldcan be become polar or designer non-polar, solvents, hydrophilic designed or hydropand synthobic,hesized and for can every be tailored extraction for anyindividually, situation. withDES maximumcould become efficiency designer in mind. solvents, designed and synthesized for every extraction individually, with canAppl. beSci. polar 2019, 9 ,or 4169 non-polar, hydrophilic or hydrophobic, and can be tailored for any situation.3 DESof 22 maximumDES can efficiency be synthesized in mind. via a number of methods. Considering the research listed in this Appl.couldAppl. Sci. Sci. 2019 become 2019, 9, ,4169 9, 4169designer solvents, designed and synthesized for every extraction
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