Omaezallene from Red Alga <i>Laurencia</i> sp.: Structure Elucidation, Total Synthesis, and Antifouling Activity

Umezawa, Taiki; Oguri, Yuko; Matsuura, Hiroshi; Yamazaki, Shohei; Suzuki, Masahiro; Yoshimura, Erina; Furuta, Takeshi; Nogata, Yasuyuki; Serisawa, Yukihiko; Matsuyama‐Serisawa, Kazuyo; Abe, Tsuyoshi; Matsuda, Fuyuhiko; Suzuki, Minoru; Okino, Tatsufumi

doi:10.1002/ange.201311175

Cited by 9 publications

(5 citation statements)

References 24 publications

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“…Marine microalgae are also the main biofouling organism influencing biofilm formation after the initial fouling stage in the marine environment. [34,35] The effect of these antifouling coatings on the algae attachment of representative Phaeodactylum tricornutum and Nitzschia closterium forma minutissima was further explored to confirm the antifouling effect.…”

Section: Bactericidal Activity and Anti-microalgae Adhesion Performancementioning

confidence: 99%

Bio‐Based Anti‐Biofoulant with Copper(II) as Intramolecular Catalyst for Radicals Formation

Chen

Hao

et al. 2023

Adv Materials Inter

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but was completely banned by the International Maritime Organization in 2002 due to its ability to form enrichment effect in organisms through the food chain, affecting food safety. [9,10] At present, copper oxide, organic copper or a combination of several copper-based antifoulants are the mainstream anti-biofoulants used in antifouling coatings. [11,12] Copper oxide is the most widely used antifouling agent due to its low cost and broadspectrum bactericidal effect. [13] However, it has become evident that copper is highly toxic to marine invertebrates in the marine environment, especially to their larvae. Some research have shown that CuCl 2 at a concentration of 0.38 µmol L −1 in the environment can cause complete arrest of oyster (Crassostrea gigas) larvae, while the semi-lethal concentration (LC 50 ) and absolute lethal concentration (LC 100 ) for Virginia oyster (Crassostrea virginica) embryos are 0.78 and 0.98 µmol L −1 , respectively. [14] For crustaceans, copper was able to kill 50% of different crustacean species after 48 h of exposure to the environment, and juveniles were more sensitive than adults. According to statistics, more than 3000 metric tons of copper are currently imported from the coating into seawater each year. [15] Especially in some bays or closed water bodies where water exchange is poor, copper-containing antifouling coating has a significant effect on the copper content of the water body. [13] In addition to copper-containing antifoulants, chlorothalonil, Irgarol 1051, Sea-Nine 211, diuron, zinc dioxane, etc., are commonly used as eco-friendly antifoulants, but these antifoulants are still required to be combined with cuprous oxide or other copper-containing antifoulants because of their weak inhibitory effect on large fouling organisms. [16][17][18] Therefore, the development of efficient and eco-friendly antifoulants that can replace and significantly reduce of copper-containing antifoulants is crucial for antifouling coatings.Oxime compounds are one of the most important precursors for the preparation of biologically active antibacterial, [19] and copper ions can initiate oxime to produce iminoxyl radicals via the homolytic cleavage of OH bonds, [20] which have highly reactive free radicals in exerting effective antibacterial activity in vitro against most Gram-negative organisms. [21] In the early experiment, some of the antifouling coatings were accidentally contaminated by 2,5-diformylfuran dioxime (DFFD) and its metal chelates. These contaminated antifouling coatings were free from any microorganisms, while some control coatings containing antimicrobial agents showed different degree of microbial growth. Additionally, the solubility of DFFD is Highly efficient and eco-friendly antimicrobial agents are crucial to the development of future marine antifouling coatings. A high efficient and low bio-toxicity bio-based anti-biofoulant, 2,5-diformylfuran dioxime chelating with copper ions (E-DFFD-Cu), is evaluated. Its minimal bactericidal concentration and the concentration for 50%...

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Section: Bactericidal Activity and Anti-microalgae Adhesion Performancementioning

confidence: 99%

Bio‐Based Anti‐Biofoulant with Copper(II) as Intramolecular Catalyst for Radicals Formation

Chen

Hao

et al. 2023

Adv Materials Inter

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“…Studies on omaezallene [( R CCC )- 8 ] 19 and other synthetic allenes such as ( R )- 9 and ( R )- 10 finally enabled us to investigate the properties of the VCD signal for the antisymmetric C=C=C stretching. The VCD intensity of the C=C=C stretching mode of ( R CCC )- 8 (ε = 15, Δε = +0.002), which was barely above the noise level, was 100 times smaller than those observed for carbodiimides 6 and 7 (Figure 4 ).…”

Section: Axially Chiral Allenesmentioning

confidence: 99%

Vibrational Circular Dichroism Studies on Axially Chiral Carbodiimides and Allenes

Taniguchi

2023

Synlett

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The axial chirality of molecules with two consecutive double bonds (X=Y=Z) has not been studied well because of the lack of analysis methods and because of difficulties in their preparation in an enantiomerically pure form. This Synpacts article describes the use of VCD spectroscopy to study the stereochemistry of carbodiimides and allenes. A strategy to obtain carbodiimides with one-handed chirality using conformationally restrained systems is also discussed. 1 Introduction 2 Carbodiimides with Partially-Biased Axial Chirality and One-Handed Axial Chirality 3 Axially Chiral Allenes 4 Conclusions

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“…Polyether triterpenoids such as dehydrothyrsiferol and saiyacenols B and C isolated from the Laurencia viridis showed high inhibitory activity against marine biofouling organisms (Cen-Pacheco et al 2015). Furthermore, omaezallenes, a newly discovered natural product from the red alga Laurencia sp., effectively inhibit the fouling marine organism (Umezawa et al 2014). It is no doubt that marine macroalgae harbor rich amount of biofouling compounds; however, extraction, isolation, and commercialization are critical, expensive, and laborious.…”

Section: Macroalgaementioning

confidence: 99%

Antibiofilm, Antifouling, and Anticorrosive Biomaterials and Nanomaterials for Marine Applications

Anbalagan

Mnif

Subramani

2020

Nanotechnology in the Life Sciences

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Formation of biofilms is one of the most serious problems affecting the integrity of marine structures both onshore and offshore. These biofilms are the key reasons for fouling of marine structures. Biofilm and biofouling cause severe economic loss to the marine industry. It has been estimated that around 10% of fuel is additionally spent when the hull of ship is affected by fouling. However, the prevention and control treatments for biofilms and biofouling of marine structures often involve toxic materials which pose severe threat to the marine environment and are strictly regulated by international maritime conventions. In this context, biomaterials for the treatment of biofilms, fouling, and corrosion of marine structures assume much significance. In recent years, due to the technological advancements, various nanomaterials and nanostructures have revolutionized many of the biological applications including antibiofilm, antifouling, and anticorrosive applications in marine environment. Many of the biomaterials such as furanones and some polypeptides are found to have antibiofilm, antifouling, and anticorrosive potentials. Many of the nanomaterials such as metal (titanium, silver, zinc, copper, etc.) nanoparticles, nanocomposites, bioinspired nanomaterials, and metallic nanotubes were found to exhibit antifouling and anticorrosive applications in marine environment. Both biomaterials and nanomaterials have been used in the control and prevention of biofilms, biofouling, and corrosion in marine structures. In recent years, the biomaterials and nanomaterials were also characterized to have the ability to inhibit bacterial quorum sensing and thereby control biofilm formation, biofouling, and corrosion in marine structures. This chapter would provide an overview of the biomaterials from diverse sources and various category of nanomaterials for their use in antibiofilm, antifouling, and anticorrosion treatments with special reference to marine applications.

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Omaezallene from Red Alga Laurencia sp.: Structure Elucidation, Total Synthesis, and Antifouling Activity

Cited by 9 publications

References 24 publications

Bio‐Based Anti‐Biofoulant with Copper(II) as Intramolecular Catalyst for Radicals Formation

Bio‐Based Anti‐Biofoulant with Copper(II) as Intramolecular Catalyst for Radicals Formation

Vibrational Circular Dichroism Studies on Axially Chiral Carbodiimides and Allenes

Antibiofilm, Antifouling, and Anticorrosive Biomaterials and Nanomaterials for Marine Applications

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