Polybrominated Diphenyl Ethers: Structure Determination and Trends in Antibacterial Activity

Liu, Hongbing; Lohith, Katheryn; Rosario, Margaret E.; Pulliam, Thomas H.; O’Connor, Robert; Bell, Lori J.; Bewley, Carole A.

doi:10.1021/acs.jnatprod.6b00229

Cited by 33 publications

(34 citation statements)

References 28 publications

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“…The 13 C-NMR ( Table 1) and HMQC spectra displayed twelve aromatic carbons, including seven quaternary carbons (δ(C) 149.8 (C(1)), 138.7 (C(2)), 117.4 (C(3)), 82.9 (C(6)), 152.3 (C(1')), 112.7 (C(2')), and 115.8 (C(4'))), and five methine carbons (δ(C) 126.5 (C(4)), 136.3 (C(5)), 136.1 (C(3')), 131.4 (C(5')), and 116.0 (C(6'))). These NMR data of 1 were similar to those of the polybrominated diphenyl ethers isolated from Lamellodysidea herbacea, [12] Dysidea granulosa, [9,13] Lamellodysidea sp., [13] and Dysidea sp. [14] Polybrominated diphenyl ethers were also isolated from an Australian marine sponge, belonging to the same family (Callyspongiidae) as the Arenosclera sp.…”

Section: Resultssupporting

confidence: 70%

Brominated Diphenyl Ethers Including a New Tribromoiododiphenyl Ether from the Vietnamese Marine Sponge Arenosclera sp. and Their Antibacterial Activities

Awouafack

Wong

et al. 2019

Chemistry & Biodiversity

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A new tribromoiododiphenyl ether (1) and eight known brominated diphenyl ethers (2–9) were isolated from the MeOH extract of the sponge Arenosclera sp. collected in Vietnam, using repeated open column chromatography and preparative thin layer chromatography. The chemical structure of the new compound 1 was determined by analyses of spectroscopic (1D‐ and 2D‐NMR, and MS) data and by comparison of our data with those reported in the literature. Compounds 1, 3, and 8 exhibited strong antibacterial activities against the Gram‐positive bacteria Bacillus subtilis and Staphylococcus aureus and the Gram‐negative bacterium Klebsiella pneumoniae with MIC values ranging from 0.8 to 6.3 μm, while compounds 5 and 7 only displayed activities against Gram‐positive bacteria with MIC values from 0.5 to 3.1 μm. Compound 2 showed activities against the four tested bacteria with MIC values ranging from 0.5 to 6.3 μm.

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Section: Resultssupporting

confidence: 70%

Brominated Diphenyl Ethers Including a New Tribromoiododiphenyl Ether from the Vietnamese Marine Sponge Arenosclera sp. and Their Antibacterial Activities

Awouafack

Wong

et al. 2019

Chemistry & Biodiversity

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“…and Dysidea granulosa (2)) from Papua New Guinea led the researchers to identify fourteen polybrominated, diphenyl ethers, including a new methoxy-containing compound (8). These compounds displayed strong to moderate antimicrobial activity against test pathogens (Table 2) [123].…”

Section: Marine-derived Antimicrobial Compounds From Invertebratesmentioning

confidence: 99%

Antibiotics Development and the Potentials of Marine-Derived Compounds to Stem the Tide of Multidrug-Resistant Pathogenic Bacteria, Fungi, and Protozoa

et al. 2020

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As the search for new antibiotics continues, the resistance to known antimicrobial compounds continues to increase. Many researchers around the world, in response to antibiotics resistance, have continued to search for new antimicrobial compounds in different ecological niches such as the marine environment. Marine habitats are one of the known and promising sources for bioactive compounds with antimicrobial potentials against currently drug-resistant strains of pathogenic microorganisms. For more than a decade, numerous antimicrobial compounds have been discovered from marine environments, with many more antimicrobials still being discovered every year. So far, only very few compounds are in preclinical and clinical trials. Research in marine natural products has resulted in the isolation and identification of numerous diverse and novel chemical compounds with potency against even drug-resistant pathogens. Some of these compounds, which mainly came from marine bacteria and fungi, have been classified into alkaloids, lactones, phenols, quinones, tannins, terpenes, glycosides, halogenated, polyketides, xanthones, macrocycles, peptides, and fatty acids. All these are geared towards discovering and isolating unique compounds with therapeutic potential, especially against multidrug-resistant pathogenic microorganisms. In this review, we tried to summarize published articles from 2015 to 2019 on antimicrobial compounds isolated from marine sources, including some of their chemical structures and tests performed against drug-resistant pathogens.

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“…Tandem mass spectrometry-based molecular networking of extracts of Theonella swinhoei and enriched cell fractions of the sponge's symbiotic filamentous bacteria "Candidatus Entotheonella" suggested the presence of unrecognized chemical diversity and previously unknown types of metabolites in the sponge (Wilson et al 2014). Coupling mass spectrometry-guided fractionation of sponge extracts with the characterization of natural product chemical structures based on molecular fragmentation expanded the diversity of polybrominated diphenyl ethers (PBDEs) known from the Dysideidae family of sponges (Agarwal et al 2015), a class of natural products that has been intensively studied for more than four decades from multiple geographical locations (Sharma and Vig 1972;Carte and Faulkner 1981;Calcul et al 2009;Agarwal et al 2015;Liu et al 2016). Liquid chromatography mass spectrometry (LC-MS) datasets for marine sponge extracts are starting to be made accessible on metabolome mining tools, such as the Global Natural Products Social (GNPS) Molecular Networking platform, which enables a communitywide effort to curate natural products, dereplicate previously known natural products, and discover novel natural products based on chemical similarity to known natural product structures (Wang et al 2016).…”

Section: Sponge-derived Natural Products Chemistrymentioning

confidence: 99%

Chemical Ecology of Marine Sponges: New Opportunities through “-Omics”

Paul

Freeman

Agarwal

2019

Integrative and Comparative Biology

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The chemical ecology and chemical defenses of sponges have been investigated for decades; consequently, sponges are among the best understood marine organisms in terms of their chemical ecology, from the level of molecules to ecosystems. Thousands of natural products have been isolated and characterized from sponges, and although relatively few of these compounds have been studied for their ecological functions, some are known to serve as chemical defenses against predators, microorganisms, fouling organisms, and other competitors. Sponges are hosts to an exceptional diversity of microorganisms, with almost 40 microbial phyla found in these associations to date. Microbial community composition and abundance are highly variable across host taxa, with a continuum from diverse assemblages of many microbial taxa to those that are dominated by a single microbial group. Microbial communities expand the nutritional repertoire of their hosts by providing access to inorganic and dissolved sources of nutrients. Not only does this continuum of microorganism–sponge associations lead to divergent nutritional characteristics in sponges, these associated microorganisms and symbionts have long been suspected, and are now known, to biosynthesize some of the natural products found in sponges. Modern “omics” tools provide ways to study these sponge–microbe associations that would have been difficult even a decade ago. Metabolomics facilitate comparisons of sponge compounds produced within and among taxa, and metagenomics and metatranscriptomics provide tools to understand the biology of host–microbe associations and the biosynthesis of ecologically relevant natural products. These combinations of ecological, microbiological, metabolomic and genomics tools, and techniques provide unprecedented opportunities to advance sponge biology and chemical ecology across many marine ecosystems.

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Polybrominated Diphenyl Ethers: Structure Determination and Trends in Antibacterial Activity

Cited by 33 publications

References 28 publications

Brominated Diphenyl Ethers Including a New Tribromoiododiphenyl Ether from the Vietnamese Marine Sponge Arenosclera sp. and Their Antibacterial Activities

Brominated Diphenyl Ethers Including a New Tribromoiododiphenyl Ether from the Vietnamese Marine Sponge Arenosclera sp. and Their Antibacterial Activities

Antibiotics Development and the Potentials of Marine-Derived Compounds to Stem the Tide of Multidrug-Resistant Pathogenic Bacteria, Fungi, and Protozoa

Chemical Ecology of Marine Sponges: New Opportunities through “-Omics”

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