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The Quest for Phenolic Compounds from Macroalgae: a Review of Extraction and Identification Methodologies

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The Quest for Phenolic Compounds from Macroalgae: a Review of Extraction and Identification Methodologies biomolecules Review The Quest for Phenolic Compounds from Macroalgae: A Review of Extraction and Identification Methodologies 1, , 2, 1 3 Sónia A. O. Santos * y , Rafael Félix y , Adriana C. S. Pais ,Sílvia M. Rocha and Armando J. D. Silvestre 1 1 CICECO—Aveiro Institute of Materials, Department of Chemistry, University of Aveiro, 3810-193 Aveiro, Portugal; [email protected] (A.C.S.P.); [email protected] (A.J.D.S.) 2 On Leave MARE—Marine and Environmental Sciences Centre, ESTM, Instituto Politécnico de Leiria, 2520-620 Peniche, Portugal; [email protected] 3 QOPNA/LAQV-REQUIMTE, Department of Chemistry, University of Aveiro, 3810-193 Aveiro, Portugal; [email protected] * Correspondence: [email protected]; Tel.: +351-234-370-084 These authors contributed equally for this work. y Received: 19 September 2019; Accepted: 25 November 2019; Published: 9 December 2019 Abstract: The current interest of the scientific community for the exploitation of high-value compounds from macroalgae is related to the increasing knowledge of their biological activities and health benefits. Macroalgae phenolic compounds, particularly phlorotannins, have gained particular attention due to their specific bioactivities, including antioxidant, antiproliferative, or antidiabetic. Notwithstanding, the characterization of macroalgae phenolic compounds is a multi-step task, with high challenges associated with their isolation and characterization, due to the highly complex and polysaccharide-rich matrix of macroalgae. Therefore, this fraction is far from being fully explored. In fact, a critical revision of the extraction and characterization methodologies already used in the analysis of phenolic compounds from macroalgae is lacking in the literature, and it is of uttermost importance to compile validated methodologies and discourage misleading practices. The aim of this review is to discuss the state-of-the-art of phenolic compounds already identified in green, red, and brown macroalgae, reviewing their structural classification, as well as critically discussing extraction methodologies, chromatographic separation techniques, and the analytical strategies for their characterization, including information about structural identification techniques and key spectroscopic profiles. For the first time, mass spectrometry data of phlorotannins, a chemical family quite exclusive of macroalgae, is compiled and discussed. Keywords: bioactive compounds; extraction; characterization; macroalgae; phenolic compounds; phlorotannins; mass spectrometry; seaweed 1. Introduction Phenolic compounds constitute one of the most numerous and widespread groups of secondary metabolites. These components are important to the normal growth and development of algae and terrestrial plants, providing defense mechanisms against infections, injuries, and environmental aggressions. As part of both animal and human diet, the nutraceutical properties assigned to phenolic compounds are almost endless [1]. Therefore, in recent years, there has been an outstanding demand for the search for phenolic compounds from natural sources, with a focus on plants [2], fruits [3], or ensuing agro-industrial biomass residues [4]. Marine macroalgae (seaweeds) have been seen in the last years as a valuable source of bioactive components, including phenolic compounds [5], which Biomolecules 2019, 9, 847; doi:10.3390/biom9120847 www.mdpi.com/journal/biomolecules Biomolecules 2019, 9, 847 2 of 56 Biomolecules 2019, 9, 847 2 of 58 in some cases are quite exclusive to macroalgae, e.g., phlorotannins. Despite the growing number of studiesthe regardinggrowing number the analysis of studies ofthe regarding phenolic the fraction analysis ofof macroalgaethe phenolic [fraction6,7], including of macroalgae the optimization [6,7], of extractionincluding conditionsthe optimization [8,9] of and extraction analysis conditions [10] of such [8,9] components, and analysis [10] a detailed of such and components, comprehensive a revisiondetailed of their and phenoliccomprehensive composition revision as of well their as pheno of thelic extraction composition and as analytical well as of methodologiesthe extraction and applied to theiranalytical detailed methodologies characterization, applied has to nottheir been detailed available characterization, so far. Actually, has not and been despite available the so increasing far. Actually, and despite the increasing interest from the scientific community, the bioprospection of interest from the scientific community, the bioprospection of phenolic compounds from macroalgae phenolic compounds from macroalgae has been a challenging issue. The large size and complexity has been a challenging issue. The large size and complexity of their structures, together with the high of their structures, together with the high abundance of polysaccharides on the macroalgae matrix, abundancemake the of isolation polysaccharides and characterization on the macroalgae of phenolic matrix, fraction makequite difficult. the isolation On this and vein, characterization a multi-step of phenolicstrategy fraction (Figure quite 1), diincludingfficult. Ondifferent this vein, fractionation a multi-step techniques strategy after (Figure phenolic1), including compounds di ff erent fractionationextraction, techniques has been done after by phenolicdifferent scientists, compounds which extraction, influenced has afterward been done the effectiveness by different of scientists, the whichstructural influenced characterization. afterward the effectiveness of the structural characterization. Figure 1. Schematic representation of the multi-step strategy applied to the identification of macroalgae Figure 1. Schematic representation of the multi-step strategy applied to the identification of phenolicmacroalgae compounds. phenolic compounds. Therefore,Therefore, the aimthe aim of this of reviewthis review is to provideis to pr aovide comprehensive a comprehensive overview overview of published of published information on theinformation phenolic on composition the phenolic ofcomposition green, red, of green, and brownred, and macroalgae, brown macroalgae, reviewing reviewing their their structural classification,structural classification, as well as critically as well as discuss critically extraction discuss extraction methodologies, methodologies, chromatographic chromatographic separation methodologies,separation methodologies, and structural and identification structural identification techniques techniques and key and spectroscopic key spectroscopic profiles profiles of identified of phenolicidentified compounds. phenolic compounds. Due to the well-knownDue to the well-known significant significant inter- oreither inter- intra-speciesor either intra-species variability of macroalgaevariability composition, of macroalgae depending composition, on depending both macroalgae on both macroalgae characteristics characteristics (e.g., age, (e.g., size, age, tissue size, type) andtissue abiotic type) factors and (e.g., abiotic nutrients, factors (e.g., salinity, nutrients, light, salinity, season), light, phenolic season), content phenolic values content will notvalues be discussedwill not be discussed in detail here. Most studies here revised have reported total phenolic (TPC) or in detail here. Most studies here revised have reported total phenolic (TPC) or phlorotannins contents phlorotannins contents (TPhC) only based on spectrophotometric methods, as will be discussed (TPhC) only based on spectrophotometric methods, as will be discussed below, for which the possible below, for which the possible co-extraction of, e.g., polysaccharides may have a significant co-extractioncontribution. of, e.g., polysaccharides may have a significant contribution. ThisThis appraisal appraisal can can constitute constitute aa landmarklandmark on on th thee systematization systematization of the of themulti-step multi-step procedures procedures usedused to study to study macroalgae, macroalgae, fostering fostering research research and and the the valorization valorization of of a verya very abundant abundant source source of of natural compounds,natural compounds, representing, representing, therefore, therefore, an important an important contribution contribution to the to development the development of the of so-calledthe blueso-called biotechnology, blue biotechnology, one of the most one important of the most areas forimportant the sustainable areas for world the sustainable development. world development. 2. Wide Chemical Diversity of Phenolic Compounds Present in Macroalgae 2. Wide Chemical Diversity of Phenolic Compounds Present in Macroalgae Structurally, phenolic compounds present in macroalgae vary from simple molecules, such as Structurally, phenolic compounds present in macroalgae vary from simple molecules, such as phenolic and cinnamic acids or flavonoids, to the more complex phlorotannin polymeric structures. phenolic and cinnamic acids or flavonoids, to the more complex phlorotannin polymeric structures. 2.1. Simple Phenolic Compounds 2.1. Simple Phenolic Compounds Hydroxybenzoic acid derivatives, such as gallic acid (Figure2), are commonly reported as constituents of different green, red, and brown macroalgae species [11–14]. Flavan-3-ol derivatives, such as epicatechin or epigallocatechin (Figure2), have been one of the major class of phenolic Biomolecules 2019, 9, 847 3 of 56 components detected in green, red, and brown macroalgae [11,15]. Other flavonoids, such as rutin, quercitrin, hesperidin, myricetin, morin, kaempferol, and cirsimaritin (Figure2),
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