Isolation of polyphenols with anticancer activity from the Baltic Sea brown seaweed Fucus vesiculosus using bioassay-guided fractionation

Zenthoefer, Marion; Geisen, Ulf; Hofmann-Peiker, Karsten; Fuhrmann, Markus; Kerber, Jannik; Kirchhöfer, Renate; Hennig, Steffen; Peipp, Matthias; Geyer, Roland; Piker, Levent; Kalthoff, Holger

doi:10.1007/s10811-017-1080-z

Cited by 47 publications

(36 citation statements)

References 76 publications

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“…A different SLr effect was observed on the phlorotannin extraction from Fucus vesiculosus, for which 1:70 was the optimal value (in a range between 1:10 and 1:110) [9]. Finally, the conventional SLE of phenolic compounds from macroalgae has also been commonly assisted by stirring [9,28,62,69,86,88,91] in order to increase molecular diffusion.…”

Section: Conventional Solid-liquid Extractionmentioning

confidence: 99%

“…NMR allows a more detailed (albeit still very unspecific) analysis of complex mixtures, being widely used in the analysis if crude extracts or enriched fractions [7,8,25,34,61,64,91,[144][145][146][147][148][149] Indeed, 1 H NMR has been used to confirm the presence of phenolic constituents [8] as well as to detect [145] and quantify [147,149] phlorotannins. The protons from phenolic units have characteristic chemical shifts that can be used to detect the presence of phenolic moieties.…”

Section: Direct Spectroscopic Analysis Of Crude Extractsmentioning

confidence: 99%

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

et al. 2019

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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.

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Section: Conventional Solid-liquid Extractionmentioning

confidence: 99%

Section: Direct Spectroscopic Analysis Of Crude Extractsmentioning

confidence: 99%

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

et al. 2019

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“…Another major difference in the extraction conditions are the temperature and time of extraction. The majority of extraction conditions involve room temperature conditions and overnight extractions . However, these conditions could vary from laboratory to laboratory, based on the room temperature in that part of the world.…”

Section: Total Phenolic Content Assays – Quantitative Techniquesmentioning

confidence: 99%

“…The majority of extraction conditions involve room temperature conditions and overnight extractions. 32,38,47 However, these conditions could vary from laboratory to laboratory, based on the room temperature in that part of the world. It is also known that the phlorotannins in brown seaweeds readily undergo oxidation and hence overnight extraction could lead to depleted results.…”

Section: Total Phenolic Content Assays -Quantitative Techniquesmentioning

confidence: 99%

A critical review of analytical methods used for the chemical characterisation and quantification of phlorotannin compounds in brown seaweeds

Ford

Theodoridou

Sheldrake

et al. 2019

Phytochemical Analysis

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IntroductionPhlorotannins, the phenolic compounds found in brown seaweeds, are a unique and diverse class of compounds showing a huge potential for food and pharmaceutical applications.ObjectiveThis review will give an account of the colorimetric assays used and a discussion of their quantitative and qualitative analytical shortcomings. It will also discuss other more complex and modern analytical chemistry methods that are currently being developed to study phlorotannins. The purpose of this review is to increase awareness of these bioactive compounds and promote further development of robust analytical methods for use in biology, food science, pharmacology and biomedical and cosmeceutical sciences.ResultsWhilst the biological activity and huge commercial potential of the phlorotannins has been widely reported throughout the literature, the chemical structures and reactivity of these compounds is still not well understood. The phlorotannin content of seaweed is usually characterised using colorimetric assays. However, although these methods give a reasonable overall estimation of the total phenolic content, they lack precision and specificity.ConclusionThis review highlights the strengths and weaknesses of commonly used colorimetric assays. Novel techniques are highlighted using more selective chemistry to identify this class of compounds.

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“…Due to their important roles in the physiology of brown algae, these compounds attracted a lot of research interest, with many studies addressing their isolation [26][27][28][29]. Moreover, as reviewed by Imbs and Zvyagintseva [30], there were a high number of studies describing the important in vitro activities of phlorotannins including anti-inflammatory, antitumor, and antibacterial activities, among others, which led researchers to advance the study of these compounds, trying to prove their biological activities in vivo.…”

Section: Phlorotanninsmentioning

confidence: 99%

Seaweed Secondary Metabolites with Beneficial Health Effects: An Overview of Successes in In Vivo Studies and Clinical Trials

et al. 2019

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Macroalgae are increasingly viewed as a source of secondary metabolites with great potential for the development of new drugs. In this development, in vitro studies are only the first step in a long process, while in vivo studies and clinical trials are the most revealing stages of the true potential and limitations that a given metabolite may have as a new drug. This literature review aims to give a critical overview of the secondary metabolites that reveal the most interesting results in these two steps. Phlorotannins show great pharmaceutical potential in in vivo models and, among the several examples, the anti-dyslipidemia activity of dieckol must be highlighted because it was more effective than lovastatin in an in vivo model. The IRLIIVLMPILMA tridecapeptide that exhibits an in vivo level of activity similar to the hypotensive clinical drug captopril should still be stressed, as well as griffithsin which showed such stunning results over a variety of animal models and which will probably move onto clinical trials soon. Regarding clinical trials, studies with pure algal metabolites are scarce, limited to those carried out with kahalalide F and fucoxanthin. The majority of clinical trials currently aim to ascertain the effect of algae consumption, as extracts or fractions, on obesity and diabetes.Studies focusing on the preparation of macroalgae extracts and their chemical characterization revealed a large range of seaweed compounds with very interesting biological activities including antitumor, anti-inflammatory, antimicrobial, antidiabetic, antivirus, antihypertensive, fat-lowering, and neuroprotective activities [12][13][14][15].The large volume of studies proving the seaweed compound activities in in vitro systems [16][17][18][19] hints the need for further advancements in the knowledge about macroalgae compound efficiency in living systems (in vivo) and their use in the development of pharmaceuticals. In vitro studies are very relevant and yield very important information, but they only represent the first step of a long process, and the results obtained rarely reveal anything about the effects of a compound in vivo, because the responses observed in vitro can be magnified, diminished, or totally different in a more complex and integrated system. In fact, in vivo studies and clinical trials are those which contribute most to truly understanding the real potential of compounds as future pharmaceuticals.In this regard, the present work intends to present insight into the results obtained in the last few years regarding secondary metabolites, such as phlorotannins, halogenated compounds, fucoxanthin, and fucosterol isolated from macroalgae, involved in in vivo studies and clinical trials, identifying the research opportunities and knowledge gaps, to valorize these compounds and their natural resources. The intention is not to present an exhaustive survey of all published works, but rather a selection of authors based on the following criteria: in-depth studies involving pure compounds most characteristic f...

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Isolation of polyphenols with anticancer activity from the Baltic Sea brown seaweed Fucus vesiculosus using bioassay-guided fractionation

Cited by 47 publications

References 76 publications

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

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

A critical review of analytical methods used for the chemical characterisation and quantification of phlorotannin compounds in brown seaweeds

Seaweed Secondary Metabolites with Beneficial Health Effects: An Overview of Successes in In Vivo Studies and Clinical Trials

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