Synthesis of maculalactone A and derivatives for environmental fate tracking studies

Bader, Samuel L.; Luescher, Michael U.; Gademann, Karl

doi:10.1039/c4ob02042a

Cited by 16 publications

(13 citation statements)

References 53 publications

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“…Further studies on AF characteristics of DIM and DIM-Ph-4-OH, such as the anti-algal activity against fouling algae, anti-biofilm activity against fouling bacteria, the evaluation of toxicity toward nontarget organisms, AF mechanism using proteomic methods, and so on are in progress in our laboratory. Two diketopiperazines (DKPs) (Figure 7), (6S,3S)-6-benzyl-3-methyl-2,5-diketopiperazine (bmDKP) (45) and (6S, 3S)-6-isobutyl-3-methyl-2,5-diketopiperazine (imDKP) (46), were obtained from a seaweed Undaria pinnatifida-derived Streptomyces praecox 291-11. Both bmDKP and imDKP could inhibit zoospore settlement of the seaweed U. pertusa with EC50 values of 2.2 and 3.1 μg/mL and the growth of the diatom N. annexa with EC50 values of 0.8 and 1.1 μg/mL, respectively.…”

Section: Alkaloidsmentioning

confidence: 99%

Anti-Larval and Anti-Algal Natural Products from Marine Microorganisms as Sources of Anti-Biofilm Agents

et al. 2022

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Bacteria growing inside biofilms are more resistant to hostile environments, conventional antibiotics, and mechanical stresses than their planktonic counterparts. It is estimated that more than 80% of microbial infections in human patients are biofilm-based, and biofouling induced by the biofilms of some bacteria causes serious ecological and economic problems throughout the world. Therefore, exploring highly effective anti-biofilm compounds has become an urgent demand for the medical and marine industries. Marine microorganisms, a well-documented and prolific source of natural products, provide an array of structurally distinct secondary metabolites with diverse biological activities. However, up to date, only a handful of anti-biofilm natural products derived from marine microorganisms have been reported. Meanwhile, it is worth noting that some promising antifouling (AF) compounds from marine microbes, particularly those that inhibit settlement of fouling invertebrate larvae and algal spores, can be considered as potential anti-biofilm agents owing to the well-known knowledge of the correlations between biofilm formation and the biofouling process of fouling organisms. In this review, a total of 112 anti-biofilm, anti-larval, and anti-algal natural products from marine microbes and 26 of their synthetic analogues are highlighted from 2000 to 2021. These compounds are introduced based on their microbial origins, and then categorized into the following different structural groups: fatty acids, butenolides, terpenoids, steroids, phenols, phenyl ethers, polyketides, alkaloids, flavonoids, amines, nucleosides, and peptides. The preliminary structure-activity relationships (SAR) of some important compounds are also briefly discussed. Finally, current challenges and future research perspectives are proposed based on opinions from many previous reviews.

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Section: Alkaloidsmentioning

confidence: 99%

Anti-Larval and Anti-Algal Natural Products from Marine Microorganisms as Sources of Anti-Biofilm Agents

et al. 2022

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“…Maculalactones, having γ-butyrolactone core, gained much interest because of its significant bioactivities. [24] In 2015, synthesis of γ-butyrolactone derivatives by a multi-component microwave reaction of aryl bromide, a carbonyl compound and dimethyl itaconate catalyzed by cobalt bromide and Zn powder at 60°C in acetonitrile medium was established by Donate et al [25] Different stereoisomers of γ-butyrolactones were obtained in 80-96 % yields under argon atmosphere (Scheme 6).…”

Section: G S Susan Treesa Was Born In 1994 Inmentioning

confidence: 99%

Cobalt‐Catalyzed Multi‐Component Reactions: Recent Advances and Perspectives in Organic Synthesis

et al. 2020

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This review focuses on the recent achievements in the field of cobalt-catalyzed multi-component reactions that could access a wide range of acyclic compounds, carbocyclic compounds and heterocyclic compounds. Multi-component reactions (MCRs) gained significant interest in organic synthesis since they could be utilized to achieve complex products from readily available starting materials in an environment-friendly manner. This review covers the literature up to 2019 and is the first one that emphasizes on cobalt-catalyzed one-pot multi-component reactions.

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“…Unfortunately, most of the biocides, like Cu 2 O/CuO, ZnO, zinc pyrithione and copper pyrithione, tributyltin, diuron, and irgarol, are not environmentally friendly [198][199][200][201][202]. Due to increasing environmental concerns, many previously used biocides have been, or are going to be banned [203,204], which is stimulating the development of new biocide-releasing coatings. Coating developers have to seek for new environmentally friendly additives or biocides, such as antibiotics, quaternary ammonium ions, and some inorganic ions, compounds or particles [205][206][207][208][209].…”

Section: Antifouling Coatingsmentioning

confidence: 99%

Modification, Degradation and Evaluation of a Few Organic Coatings for Some Marine Applications

Song

Feng

2020

CMD

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Organic coatings for marine applications must have great corrosion protection and antifouling performance. This review presents an overview of recent investigations into coating microstructure, corrosion protection performance, antifouling behavior, and evaluation methods, particularly the substrate effect and environmental influence on coating protectiveness, aiming to improve operational practice in the coating industry. The review indicates that the presence of defects in an organic coating is the root cause of the corrosion damage of the coating. The protection performance of a coating system can be enhanced by proper treatment of the substrate and physical modification of the coating. Environmental factors may synergistically accelerate the coating degradation. The long-term protection performance of a coating system is extremely difficult to predict without coating defect information. Non-fouling coating and self-repairing coatings may be promising antifouling approaches. Based on the review, some important research topics are suggested, such as the exploration of rapid evaluation methods, the development of long-term cost-effective antifouling coatings in real marine environments.

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Synthesis of maculalactone A and derivatives for environmental fate tracking studies

Cited by 16 publications

References 53 publications

Anti-Larval and Anti-Algal Natural Products from Marine Microorganisms as Sources of Anti-Biofilm Agents

Anti-Larval and Anti-Algal Natural Products from Marine Microorganisms as Sources of Anti-Biofilm Agents

Cobalt‐Catalyzed Multi‐Component Reactions: Recent Advances and Perspectives in Organic Synthesis

Modification, Degradation and Evaluation of a Few Organic Coatings for Some Marine Applications

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