Marine Phenolics: Extraction and Purification, Identification, Characterization and Applications

A special issue of Marine Drugs (ISSN 1660-3397).

Deadline for manuscript submissions: closed (31 July 2020) | Viewed by 65154

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Centro de Investigaciones Biomédicas (CINBIO), Departamento de Enxeñería Química, Universidade de Vigo (Campus Ourense), Edificio Politécnico, As Lagoas, 32004 Ourense, Spain
Interests: bioactive compounds; macroalgae; vegetal biomass; environmentally-friendly extraction technologies; membranes; waste valorisation
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Departamento de Ingeniería Química y Bioprocesos, Pontificia Universidad Católica de Chile, Santiago, Chile
Interests: extraction; purification; natural products; polyphenols; mathematical modelling
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Dear Colleagues,

Phenolic compounds are an extremely diverse class of ubiquitous secondary metabolites produced by a variety of organisms playing different biological roles. They have shown several bioactivities, including antioxidant, antimicrobial, anti-inflammatory, antitumoral, immunomodulator, neuroprotective, cardioprotective, and antidiabetic. Marine organisms produce a vast collection of unique phenolic structures, some of them not found in terrestrial habitats. Progress in different aspects is rapidly advancing, and this Special Issue will provide updated information and recent studies on marine phenolics. Specially, this Issue is focused on their chemical characterization, elucidation of their structures, evaluation of their biological properties and mechanisms of action, efficient extraction and purification technologies, development of value-added applications, as well as formulation of novel products.

Prof. Dr. Herminia Domínguez
Prof. Dr. José Ricardo Pérez-Correa
Guest Editors

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Keywords

  • phenolic compounds
  • characterization
  • extraction
  • purification
  • biological properties
  • antioxidant
  • antimicrobial
  • anti-inflammatory
  • food
  • cosmetics
  • pharmacological or therapeutic agents

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Related Special Issue

Published Papers (8 papers)

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Research

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15 pages, 1287 KiB  
Article
Microwave-Assisted Extraction of Phlorotannins from Fucus vesiculosus
by Sónia J. Amarante, Marcelo D. Catarino, Catarina Marçal, Artur M. S. Silva, Rita Ferreira and Susana M. Cardoso
Mar. Drugs 2020, 18(11), 559; https://doi.org/10.3390/md18110559 - 15 Nov 2020
Cited by 46 | Viewed by 3600
Abstract
Microwave-assisted extraction (MAE) was carried out to maximize the extraction of phlorotannins from Fucus vesiculosus using a hydroethanolic mixture as a solvent, as an alternative to the conventional method with a hydroacetonic mixture. Optimal MAE conditions were set as ethanol concentration of 57% [...] Read more.
Microwave-assisted extraction (MAE) was carried out to maximize the extraction of phlorotannins from Fucus vesiculosus using a hydroethanolic mixture as a solvent, as an alternative to the conventional method with a hydroacetonic mixture. Optimal MAE conditions were set as ethanol concentration of 57% (v/v), temperature of 75 °C, and time of 5 min, which allowed a similar recovery of phlorotannins from the macroalgae compared to the conventional extraction. While the phlorotannins richness of the conventional extract was slightly superior to that of MAE (11.1 ± 1.3 vs. 9.8 ± 1.8 mg PGE/g DWextract), both extracts presented identical phlorotannins constituents, which included, among others, tetrafucol, pentafucol, hexafucol, and heptafucol structures. In addition, MAE showed a moderate capacity to scavenge ABTS•+ (IC50 of 96.0 ± 3.4 µg/mL) and to inhibit the activity of xanthine oxidase (IC50 of 23.1 ± 3.4 µg/mL) and a superior ability to control the activity of the key metabolic enzyme α-glucosidase compared to the pharmaceutical drug acarbose. Full article
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16 pages, 2590 KiB  
Article
Extraction, Enrichment, and LC-MSn-Based Characterization of Phlorotannins and Related Phenolics from the Brown Seaweed, Ascophyllum nodosum
by J. William Allwood, Huw Evans, Ceri Austin and Gordon J. McDougall
Mar. Drugs 2020, 18(9), 448; https://doi.org/10.3390/md18090448 - 27 Aug 2020
Cited by 26 | Viewed by 4557
Abstract
Phenolic components from the edible brown seaweed, Ascophyllum nodosum, have been associated with considerable antioxidant activity but also bioactivities related to human health. This study aims to select and identify the main phlorotannin components from this seaweed which have been previously associated [...] Read more.
Phenolic components from the edible brown seaweed, Ascophyllum nodosum, have been associated with considerable antioxidant activity but also bioactivities related to human health. This study aims to select and identify the main phlorotannin components from this seaweed which have been previously associated with potential health benefits. Methods to enrich phenolic components then further select phlorotannin components from ethanolic extracts of Ascophyllum nodosum were applied. The composition and phenolic diversity of these extracts were defined using data dependent liquid chromatography mass spectroscopic (LC-MSn) techniques. A series of phlorotannin oligomers with apparent degree of polymerization (DP) from 10 to 31 were enriched by solid phase extraction and could be selected by fractionation on Sephadex LH-20. Evidence was also obtained for the presence of dibenzodioxin linked phlorotannins as well as sulphated phlorotannins and phenolic acids. As well as diversity in molecular size, there was evidence for potential isomers at each DP. MS2 fragmentation analyses strongly suggested that the phlorotannins contained ether linked phloroglucinol units and were most likely fucophlorethols and MS3 data suggested that the isomers may result from branching within the chain. Therefore, application of these LC-MSn techniques provided further information on the structural diversity of the phlorotannins from Ascophyllum, which could be correlated against their reported bioactivities and could be further applied to phlorotannins from different seaweed species. Full article
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12 pages, 3594 KiB  
Article
Bioactive Polyphenols from Southern Chile Seaweed as Inhibitors of Enzymes for Starch Digestion
by Luz Verónica Pacheco, Javier Parada, José Ricardo Pérez-Correa, María Salomé Mariotti-Celis, Fernanda Erpel, Angara Zambrano and Mauricio Palacios
Mar. Drugs 2020, 18(7), 353; https://doi.org/10.3390/md18070353 - 8 Jul 2020
Cited by 23 | Viewed by 4668
Abstract
The increment of non-communicable chronic diseases is a constant concern worldwide, with type-2 diabetes mellitus being one of the most common illnesses. A mechanism to avoid diabetes-related hyperglycemia is to reduce food digestion/absorption by using anti-enzymatic (functional) ingredients. This research explored the potential [...] Read more.
The increment of non-communicable chronic diseases is a constant concern worldwide, with type-2 diabetes mellitus being one of the most common illnesses. A mechanism to avoid diabetes-related hyperglycemia is to reduce food digestion/absorption by using anti-enzymatic (functional) ingredients. This research explored the potential of six common Chilean seaweeds to obtain anti-hyperglycemic polyphenol extracts, based on their capacity to inhibit key enzymes related with starch digestion. Ethanol/water hot pressurized liquid extraction (HPLE), which is an environmentally friendly method, was studied and compared to conventional extraction with acetone. Total polyphenols (TP), antioxidant activity, cytotoxicity and inhibition capacity on α-glucosidase and α-amylase were analyzed. Results showed that the Durvillaea antarctica (cochayuyo) acetone extract had the highest TP content (6.7 ± 0.7 mg gallic acid equivalents (GAE)/g dry seaweed), while its HPLE ethanol/water extract showed the highest antioxidant activity (680.1 ± 11.6 μmol E Trolox/g dry seaweed). No extract affected cell viability significantly. Only cochayuyo produced extracts having relevant anti-enzymatic capacity on both studied enzymes, showing a much stronger inhibition to α-glucosidase (even almost 100% at 1000 µg/mL) than to α-amylase. In conclusion, from the Chilean seaweeds considered in this study, cochayuyo is the most suitable for developing functional ingredients to moderate postprandial glycemic response (starchy foods), since it showed a clear enzymatic inhibition capacity and selectivity. Full article
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21 pages, 953 KiB  
Article
LC-ESI-QTOF-MS/MS Characterization of Seaweed Phenolics and Their Antioxidant Potential
by Biming Zhong, Nicholas A. Robinson, Robyn D. Warner, Colin J. Barrow, Frank R. Dunshea and Hafiz A.R. Suleria
Mar. Drugs 2020, 18(6), 331; https://doi.org/10.3390/md18060331 - 24 Jun 2020
Cited by 114 | Viewed by 9492
Abstract
Seaweed is an important food widely consumed in Asian countries. Seaweed has a diverse array of bioactive compounds, including dietary fiber, carbohydrate, protein, fatty acid, minerals and polyphenols, which contribute to the health benefits and commercial value of seaweed. Nevertheless, detailed information on [...] Read more.
Seaweed is an important food widely consumed in Asian countries. Seaweed has a diverse array of bioactive compounds, including dietary fiber, carbohydrate, protein, fatty acid, minerals and polyphenols, which contribute to the health benefits and commercial value of seaweed. Nevertheless, detailed information on polyphenol content in seaweeds is still limited. Therefore, the present work aimed to investigate the phenolic compounds present in eight seaweeds [Chlorophyta (green), Ulva sp., Caulerpa sp. and Codium sp.; Rhodophyta (red), Dasya sp., Grateloupia sp. and Centroceras sp.; Ochrophyta (brown), Ecklonia sp., Sargassum sp.], using liquid chromatography electrospray ionization quadrupole time-of-flight mass spectrometry (LC-ESI-QTOF-MS/MS). The total phenolic content (TPC), total flavonoid content (TFC) and total tannin content (TTC) were determined. The antioxidant potential of seaweed was assessed using a 2,2-diphenyl-1-picrylhydrazyl (DPPH) free radical scavenging assay, a 2,2′-azino-bis-3-ethylbenzothiazoline-6-sulfonic acid (ABTS) free radical scavenging assay and a ferric reducing antioxidant power (FRAP) assay. Brown seaweed species showed the highest total polyphenol content, which correlated with the highest antioxidant potential. The LC-ESI-QTOF-MS/MS tentatively identified a total of 54 phenolic compounds present in the eight seaweeds. The largest number of phenolic compounds were present in Centroceras sp. followed by Ecklonia sp. and Caulerpa sp. Using high-performance liquid chromatography-photodiode array (HPLC-PDA) quantification, the most abundant phenolic compound was p-hydroxybenzoic acid, present in Ulva sp. at 846.083 ± 0.02 μg/g fresh weight. The results obtained indicate the importance of seaweed as a promising source of polyphenols with antioxidant properties, consistent with the health potential of seaweed in food, pharmaceutical and nutraceutical applications. Full article
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15 pages, 1604 KiB  
Article
Optimisation of Ultrasound Frequency, Extraction Time and Solvent for the Recovery of Polyphenols, Phlorotannins and Associated Antioxidant Activity from Brown Seaweeds
by Viruja Ummat, Brijesh K Tiwari, Amit K Jaiswal, Kevin Condon, Marco Garcia-Vaquero, John O’Doherty, Colm O’Donnell and Gaurav Rajauria
Mar. Drugs 2020, 18(5), 250; https://doi.org/10.3390/md18050250 - 11 May 2020
Cited by 112 | Viewed by 7777
Abstract
This study investigates ultrasound assisted extraction (UAE) process parameters (time, frequency and solvent) to obtain high yields of phlorotannins, flavonoids, total phenolics and associated antioxidant activities from 11 brown seaweed species. Optimised UAE conditions (35 kHz, 30 min and 50% ethanol) significantly improved [...] Read more.
This study investigates ultrasound assisted extraction (UAE) process parameters (time, frequency and solvent) to obtain high yields of phlorotannins, flavonoids, total phenolics and associated antioxidant activities from 11 brown seaweed species. Optimised UAE conditions (35 kHz, 30 min and 50% ethanol) significantly improved the extraction yield from 1.5-fold to 2.2-fold in all seaweeds investigated compared to solvent extraction. Using ultrasound, the highest recovery of total phenolics (TPC: 572.3 ± 3.2 mg gallic acid equivalent/g), total phlorotannins (TPhC: 476.3 ± 2.2 mg phloroglucinol equivalent/g) and total flavonoids (TFC: 281.0 ± 1.7 mg quercetin equivalent/g) was obtained from Fucus vesiculosus seaweed. While the lowest recovery of TPC (72.6 ± 2.9 mg GAE/g), TPhC (50.3 ± 2.0 mg PGE/g) and TFC (15.2 ± 3.3 mg QE/g) was obtained from Laminaria digitata seaweed. However, extracts from Fucus serratus obtained by UAE exhibited the strongest 1,1-diphenyl-2-picryl-hydrazyl (DPPH) scavenging activity (29.1 ± 0.25 mg trolox equivalent/g) and ferric reducing antioxidant power (FRAP) value (63.9 ± 0.74 mg trolox equivalent/g). UAE under optimised conditions was an effective, low-cost and eco-friendly technique to recover biologically active polyphenols from 11 brown seaweed species. Full article
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Review

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58 pages, 2171 KiB  
Review
Bioactive Properties of Marine Phenolics
by Raquel Mateos, José Ricardo Pérez-Correa and Herminia Domínguez
Mar. Drugs 2020, 18(10), 501; https://doi.org/10.3390/md18100501 - 30 Sep 2020
Cited by 73 | Viewed by 7534
Abstract
Phenolic compounds from marine organisms are far less studied than those from terrestrial sources since their structural diversity and variability require powerful analytical tools. However, both their biological relevance and potential properties make them an attractive group deserving increasing scientific interest. The use [...] Read more.
Phenolic compounds from marine organisms are far less studied than those from terrestrial sources since their structural diversity and variability require powerful analytical tools. However, both their biological relevance and potential properties make them an attractive group deserving increasing scientific interest. The use of efficient extraction and, in some cases, purification techniques can provide novel bioactives useful for food, nutraceutical, cosmeceutical and pharmaceutical applications. The bioactivity of marine phenolics is the consequence of their enzyme inhibitory effect and antimicrobial, antiviral, anticancer, antidiabetic, antioxidant, or anti-inflammatory activities. This review presents a survey of the major types of phenolic compounds found in marine sources, as well as their reputed effect in relation to the occurrence of dietary and lifestyle-related diseases, notably type 2 diabetes mellitus, obesity, metabolic syndrome, cancer and Alzheimer’s disease. In addition, the influence of marine phenolics on gut microbiota and other pathologies is also addressed. Full article
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22 pages, 566 KiB  
Review
Emerging Technologies for the Extraction of Marine Phenolics: Opportunities and Challenges
by Adane Tilahun Getachew, Charlotte Jacobsen and Susan Løvstad Holdt
Mar. Drugs 2020, 18(8), 389; https://doi.org/10.3390/md18080389 - 27 Jul 2020
Cited by 63 | Viewed by 5409
Abstract
Natural phenolic compounds are important classes of plant, microorganism, and algal secondary metabolites. They have well-documented beneficial biological activities. The marine environment is less explored than other environments but have huge potential for the discovery of new unique compounds with potential applications in, [...] Read more.
Natural phenolic compounds are important classes of plant, microorganism, and algal secondary metabolites. They have well-documented beneficial biological activities. The marine environment is less explored than other environments but have huge potential for the discovery of new unique compounds with potential applications in, e.g., food, cosmetics, and pharmaceutical industries. To survive in a very harsh and challenging environment, marine organisms like several seaweed (macroalgae) species produce and accumulate several secondary metabolites, including marine phenolics in the cells. Traditionally, these compounds were extracted from their sample matrix using organic solvents. This conventional extraction method had several drawbacks such as a long extraction time, low extraction yield, co-extraction of other compounds, and usage of a huge volume of one or more organic solvents, which consequently results in environmental pollution. To mitigate these drawbacks, newly emerging technologies, such as enzyme-assisted extraction (EAE), microwave-assisted extraction (MAE), ultrasound-assisted extraction (UAE), pressurized liquid extraction (PLE), and supercritical fluid extraction (SFE) have received huge interest from researchers around the world. Therefore, in this review, the most recent and emerging technologies are discussed for the extraction of marine phenolic compounds of interest for their antioxidant and other bioactivity in, e.g., cosmetic and food industry. Moreover, the opportunities and the bottleneck for upscaling of these technologies are also presented. Full article
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47 pages, 5184 KiB  
Review
Seaweed Phenolics: From Extraction to Applications
by João Cotas, Adriana Leandro, Pedro Monteiro, Diana Pacheco, Artur Figueirinha, Ana M. M. Gonçalves, Gabriela Jorge da Silva and Leonel Pereira
Mar. Drugs 2020, 18(8), 384; https://doi.org/10.3390/md18080384 - 24 Jul 2020
Cited by 298 | Viewed by 20854
Abstract
Seaweeds have attracted high interest in recent years due to their chemical and bioactive properties to find new molecules with valuable applications for humankind. Phenolic compounds are the group of metabolites with the most structural variation and the highest content in seaweeds. The [...] Read more.
Seaweeds have attracted high interest in recent years due to their chemical and bioactive properties to find new molecules with valuable applications for humankind. Phenolic compounds are the group of metabolites with the most structural variation and the highest content in seaweeds. The most researched seaweed polyphenol class is the phlorotannins, which are specifically synthesized by brown seaweeds, but there are other polyphenolic compounds, such as bromophenols, flavonoids, phenolic terpenoids, and mycosporine-like amino acids. The compounds already discovered and characterized demonstrate a full range of bioactivities and potential future applications in various industrial sectors. This review focuses on the extraction, purification, and future applications of seaweed phenolic compounds based on the bioactive properties described in the literature. It also intends to provide a comprehensive insight into the phenolic compounds in seaweed. Full article
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