Antibacterial Oligomeric Polyphenols from the Green Alga <i>Cladophora socialis</i>

Lavoie, Serge; Sweeney-Jones, Anne Marie; Mojib, Nazia; Dale, Brandon; Gagaring, Kerstin; McNamara, Case W.; Quave, Cassandra L.; Soapi, Katy M.; Kubanek, Julia

doi:10.1021/acs.joc.8b03218

Cited by 23 publications

(19 citation statements)

References 33 publications

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“…In more recent studies, the C. socialis phenolic compounds, such as 2,3,8,9-tetrahydroxybenzo [c]chromen-6-one, 3,4,3 ,4 -tetrahydroxy-1,1 -biphenyl, and cladophorol have been identified with interesting antibacterial activity against methicillin-resistant Staphylococcus aureus [147].…”

Section: Green Seaweedsmentioning

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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Section: Green Seaweedsmentioning

confidence: 99%

Seaweed Phenolics: From Extraction to Applications

et al. 2020

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“…Cladophorol C exhibits strong antibacterial activity against MRSA with a MIC of 1.4 μg/mL (control is vancomycin with a MIC of 4 μg/mL). Other cladophorols have lower activity [ 69 , 70 ].…”

Section: Interaction Of Algal Polyphenols With Methicillin-resistamentioning

confidence: 99%

Algae Polyphenolic Compounds and Modern Antibacterial Strategies: Current Achievements and Immediate Prospects

et al. 2020

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The increasing drug resistance of pathogenic microorganisms raises concern worldwide and necessitates the search for new natural compounds with antibacterial properties. Marine algae are considered a natural and attractive biotechnological source of novel antibiotics. The high antimicrobial activity of their polyphenolic compounds is a promising basis for designing innovative pharmaceuticals. They can become both a serious alternative to traditional antimicrobial agents and an effective supplement to antibiotic therapy. The present review summarizes the results of numerous studies on polyphenols from algae and the range of biological activities that determine their biomedical significance. The main focus is put on a group of the polyphenolic metabolites referred to as phlorotannins and, particularly, on their structural diversity and mechanisms of antimicrobial effects. Brown algae are an almost inexhaustible resource with a high biotechnological potential for obtaining these polyfunctional compounds. An opinion is expressed that the effectiveness of the antibacterial activity of phlorotannins depends on the methods of their extraction aimed at preserving the phenolic structure. The use of modern analytical tools opens up a broad range of opportunities for studying the metabolic pathways of phlorotannins and identifying their structural and functional relationships. The high antimicrobial activity of phlorotannins against both Gram-positive and Gram-negative bacteria provides a promising framework for creating novel drugs to be used in the treatment and prevention of infectious diseases.

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“…59 The calculated 1 H and 13 C NMR shielding tensors were scaled against experimental 1 H and 13 C NMR chemical shift values. 60…”

Section: Experimental Proceduresmentioning

confidence: 99%

Peyssonnosides A–B, Unusual Diterpene Glycosides with a Sterically Encumbered Cyclopropane Motif: Structure Elucidation Using an Integrated Spectroscopic and Computational Workflow

et al. 2019

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Two sulfated diterpene glycosides featuring a highly substituted and sterically encumbered cyclopropane ring have been isolated from the marine red alga Peyssonnelia sp. Combination of a wide array of 2D NMR spectroscopic experiments, in a systematic structure elucidation workflow, revealed that peyssonnosides A–B (1–2) represent a new class of diterpene glycosides with a tetracyclo [7.5.0.01,10.05,9] tetradecane architecture. A salient feature of this workflow is the unique application of quantitative interproton distances obtained from the rotating frame Overhauser effect spectroscopy (ROESY) NMR experiment, wherein the β-d-glucose moiety of 1 was used as an internal probe to unequivocally determine the absolute configuration, which was also supported by optical rotatory dispersion (ORD). Peyssonnoside A (1) exhibited promising activity against liver stage Plasmodium berghei and moderate antimethicillin-resistant Staphylococcus aureus (MRSA) activity, with no cytotoxicity against human keratinocytes. Additionally, 1 showed strong growth inhibition of the marine fungus Dendryphiella salina indicating an antifungal ecological role in its natural environment. The high natural abundance and novel carbon skeleton of 1 suggests a rare terpene cyclase machinery, exemplifying the chemical diversity in this phylogenetically distinct marine red alga.

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Antibacterial Oligomeric Polyphenols from the Green Alga Cladophora socialis

Cited by 23 publications

References 33 publications

Seaweed Phenolics: From Extraction to Applications

Seaweed Phenolics: From Extraction to Applications

Algae Polyphenolic Compounds and Modern Antibacterial Strategies: Current Achievements and Immediate Prospects

Peyssonnosides A–B, Unusual Diterpene Glycosides with a Sterically Encumbered Cyclopropane Motif: Structure Elucidation Using an Integrated Spectroscopic and Computational Workflow

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