Isolation and pharmacological activities of bromophenols fromRhodomela confervoides

Han, Lijun; Xu, Nianjun; Jiangong, Shi; Yan, Xiaojun; Chengkui, Zheng

doi:10.1007/bf02894243

Cited by 32 publications

(10 citation statements)

References 12 publications

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“…It is a new natural product and we named this new bromophenol Vertebratol. The nmR data of the known bromophenolic compounds 2 to 7 (see Table S1, Supplementary Materials) were in good agreement with values from the literature [13][14][15][16].…”

Section: Structural Elucidation Of Compoundsupporting

confidence: 82%

“…Pure standards were isolated from the methanolic extract of a sample collected in Brittany (France) by using various chromatographic techniques followed by structural elucidation of all isolated compounds by nmR spectroscopy and MS. The isolated standards include one new bromophenolic substance and six that have previously been reported from other red algae [13][14][15][16]. Their content was determined in Vertebrata lanosa from different collection years and sampling sites.…”

Section: Introductionmentioning

confidence: 99%

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Development and Validation of an HPLC Method for the Quantitative Analysis of Bromophenolic Compounds in the Red Alga Vertebrata lanosa

et al. 2019

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Bromophenols are a class of compounds occurring in red algae that are thought to play a role in chemical protection; however, their exact function is still not fully known. In order to investigate their occurrence, pure standards of seven bromophenols were isolated from a methanolic extract of the epiphytic red alga Vertebrata lanosa collected in Brittany, France. The structures of all compounds were determined by NMR and MS. Among the isolated substances, one new natural product, namely, 2-amino-5-(3-(2,3-dibromo-4,5-dihydroxybenzyl)ureido)pentanoic acid was identified. An HPLC method for the separation of all isolated substances was developed using a Phenomenex C8(2) Luna column and a mobile phase comprising 0.05% trifluoroacetic acid in water and acetonitrile. Method validation showed that the applied procedure is selective, linear (R2 ≥ 0.999), precise (intra-day ≤ 6.28%, inter-day ≤ 5.21%), and accurate (with maximum displacement values of 4.93% for the high spikes, 4.80% for the medium spikes, and 4.30% for the low spikes). For all standards limits of detection (LOD) were lower than 0.04 μg/mL and limits of quantification (LOQ) lower than 0.12 μg/mL. Subsequently, the method was applied to determine the bromophenol content in Vertebrata lanosa samples from varying sampling sites and collection years showing values between 0.678 and 0.005 mg/g dry weight for different bromophenols with significant variations between the sampling years. Bioactivity of seven isolated bromophenols was tested in agar diffusion tests against Staphylococcus aureus and Escherichia coli bacteria. Three compounds showed a small zone of inhibition against both test organisms at a concentration of 100 µg/mL.

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Section: Structural Elucidation Of Compoundsupporting

confidence: 82%

Section: Introductionmentioning

confidence: 99%

Development and Validation of an HPLC Method for the Quantitative Analysis of Bromophenolic Compounds in the Red Alga Vertebrata lanosa

et al. 2019

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“…Still, the identification and quantification of phlorotannins is usually performed by RP-HPLC with methanol/acetonitrile and water (buffer) solvent combinations and the detection in the UV range of the spectrum [ 16 ]. For instance, in a study conducted with the red seaweed Rhodomela confervoides , the RP-HPLC method provided bromophenols’ identification and characterization (3-bromo-4, 5-dihydroxy benzoic acid methyl ester and 3-bromo-4,5-dihydroxy- benzaldehyde) [ 130 ].…”

Section: Phenolic Compounds Extractions and Purification Methodolomentioning

confidence: 99%

“…Therefore, the phenolic compound can be cytotoxic to normal cell lines, such as the human embryo lung fibroblast (HELF), because the compounds can have low selectivity and can be counter-productive in their application, so a full batch of assays is needed to have a secure anticancer compound available. For this case, chemical modification can be needed to enhance the molecule selectivity [33,130,311], and more research will be necessary until a commercial product is released.…”

Section: Anticancer Propertiesmentioning

confidence: 99%

Seaweed Phenolics: From Extraction to Applications

et al. 2020

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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.

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“…Some of these algae are sources of foods or traditional medicines [1], while others may serve as important resources for bioactive natural products [2,3,4]. Red algae of the Rhodomelaceae (Ceramiales) family are rich sources of several monoaryl, diaryl, and triaryl bromocatechol structural types with various biological activities, including anticancer, antioxidative, antimicrobial, and anti-thrombotic effects [5,6,7,8,9]. However, there have been no reports describing the characterization of compounds derived from Neorhodomela aculeata (L.P. Perestenko) Masuda.…”

Section: Introductionmentioning

confidence: 99%

Anti-Human Rhinoviral Activity of Polybromocatechol Compounds Isolated from the Rhodophyta, Neorhodomela aculeata

et al. 2012

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An extract of the red alga, Neorhodomela aculeata, exhibited antiviral activity against human rhinoviruses. Bioassay-guided purification was performed to yield six compounds, which were subsequently identified as lanosol (1) and five polybromocatechols (2–6) by spectroscopic methods, including 1D and 2D NMR and mass spectrometric analyses. Structurally, all of these compounds, except compound 5, contain one or two 2,3-dibromo-4,5-dihydroxyphenyl moieties. In a biological activity assay, compound 1 was found to possess antiviral activity with a 50% inhibitory concentration (IC50) of 2.50 μg/mL against HRV2. Compound 3 showed anti-HRV2 activity, with an IC50 of 7.11 μg/mL, and anti-HRV3 activity, with an IC50 of 4.69 μg/mL, without demonstrable cytotoxicity at a concentration of 20 μg/mL. Collectively, the results suggest that compounds 1 and 3 are candidates for novel therapeutics against two different groups of human rhinovirus.

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Isolation and pharmacological activities of bromophenols fromRhodomela confervoides

Cited by 32 publications

References 12 publications

Development and Validation of an HPLC Method for the Quantitative Analysis of Bromophenolic Compounds in the Red Alga Vertebrata lanosa

Development and Validation of an HPLC Method for the Quantitative Analysis of Bromophenolic Compounds in the Red Alga Vertebrata lanosa

Seaweed Phenolics: From Extraction to Applications

Anti-Human Rhinoviral Activity of Polybromocatechol Compounds Isolated from the Rhodophyta, Neorhodomela aculeata

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