Isolation and Potential Biological Applications of Haloaryl Secondary Metabolites from Macroalgae

Jesus, Ana; Correia-da-Silva, Marta; Afonso, Carlos; Pinto, Madalena; Cidade, Honorina

doi:10.3390/md17020073

Cited by 44 publications

(51 citation statements)

References 61 publications

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“…The search for novel compounds from marine organisms in recent years has produced a number of novel secondary metabolites with pharmaceutical, cosmetics, traditional, and industrial applications [9]. Among these natural products of marine origin, the isolation of halogenated derivatives, especially the bromophenols from seaweeds and macro-algae has been exhaustively reported [10,11]. Recent studies showed that the marine BPs demonstrated a wide range of biological activities [12][13][14][15][16], and therefore the novel BPs have attracted much attention in the field of pharmaceutical agents and functional foods [11].…”

Section: Introductionmentioning

confidence: 99%

α-Glucosidase Inhibition and Molecular Docking Studies of Natural Brominated Metabolites from Marine Macro Brown Alga Dictyopteris hoytii

et al. 2019

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Bioassay guided isolation of the methanolic extract of marine macro brown alga Dictyopteris hoytii afforded one new metabolite (ethyl methyl 2-bromobenzene 1,4-dioate, 1), one new natural metabolite (diethyl-2-bromobenzene 1,4-dioate, 2) along with six known metabolites (3–8) reported for the first time from this source. The structure elucidation of all these compounds was achieved by extensive spectroscopic techniques including 1D (1H and 13C) and 2D (NOESY, COSY, HMBC and HSQC) NMR and mass spectrometry and comparison of the spectral data of known compounds with those reported in literature. The in vitro α-glucosidase inhibition studies confirmed compound 7 to be the most active against α-glucosidase enzyme with IC50 value of 30.5 ± 0.41 μM. Compounds 2 and 3 demonstrated good inhibition with IC50 values of 234.2 ± 4.18 and 289.4 ± 4.91 μM, respectively, while compounds 1, 5, and 6 showed moderate to low inhibition. Furthermore, the molecular docking studies of the active compounds were performed to examine their mode of inhibition in the binding site of the α-glucosidase enzyme.

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Section: Introductionmentioning

confidence: 99%

α-Glucosidase Inhibition and Molecular Docking Studies of Natural Brominated Metabolites from Marine Macro Brown Alga Dictyopteris hoytii

et al. 2019

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“…Halogenated compounds are also an interesting set of bioactive macroalgae secondary metabolites [17,[110][111][112][113]. Among these, halogenated terpenes and bromophenols are those whose in vivo studies revealed the greatest potential for new drug development, as discussed below.…”

Section: Halogenated Secondary Metabolitesmentioning

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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“…It is therefore important to discover compounds that inhibit the AI-2 system for control of bacterial virulence and biofilm formation. Several compounds have been shown to inhibit AI-2 based QS of Vibrio spp., including halogenated furanones, cinnamaldehyde, and their derivatives [9][10][11].…”

Section: Introductionmentioning

confidence: 99%

“…Seaweed is one of the most available sources of bioactive compounds in the marine plant kingdom [12]. Seaweed produces a diversity of bioactive compounds, such as saturated and polyunsaturated fatty acids, vitamins, amino acids, polyphenol, alkaloids, halogenated compounds, and polysaccharides such as agar, carrageenan, proteoglycans, alginate, laminaran, rhamnan sulfate, and fucoidan [9,13]. Gracilaria genus is a macroalgae group with more than 300 species, of which 160 have been accepted taxonomically [14].…”

Section: Introductionmentioning

confidence: 99%

Purification and Evaluation of N-benzyl Cinnamamide from Red Seaweed Gracilaria fisheri as an Inhibitor of Vibrio harveyi AI-2 Quorum Sensing

et al. 2020

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Previously, we reported that the ethanol extract from red seaweed Gracilaria fisheri effectively decreased biofilm formation of Vibrio harveyi. In this study, the anti-biofilm active compounds in the ethanol extract were isolated and their structures identified. The anti-biofilm fractionation assay for minimum inhibitory concentration (MIC) produced two fractions which possessed maximal inhibitory activities toward the biofilm formation of V. harveyi strains 1114 and BAA 1116. Following chromatographic separation of the bioactive fractions, two pure compounds were isolated, and their structures were elucidated using FTIR, NMR, and HR-TOF-MS. The compounds were N-benzyl cinnamamide and α-resorcylic acid. The in vitro activity assay demonstrated that both compounds inhibited the biofilm formation of V. harveyi and possessed the anti-quorum sensing activity by interfering with the bioluminescence of the bacteria. However, the N-benzyl cinnamamide was more potent than α-resorcylic acid with a 10-fold lesser MIC. The present study reveals the beneficial property of the N-benzyl cinnamamide from the ethanol extract as a lead anti-microbial drug against V. harveyi.

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Isolation and Potential Biological Applications of Haloaryl Secondary Metabolites from Macroalgae

Cited by 44 publications

References 61 publications

α-Glucosidase Inhibition and Molecular Docking Studies of Natural Brominated Metabolites from Marine Macro Brown Alga Dictyopteris hoytii

α-Glucosidase Inhibition and Molecular Docking Studies of Natural Brominated Metabolites from Marine Macro Brown Alga Dictyopteris hoytii

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

Purification and Evaluation of N-benzyl Cinnamamide from Red Seaweed Gracilaria fisheri as an Inhibitor of Vibrio harveyi AI-2 Quorum Sensing

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