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/anie.201311175

Cited by 53 publications

(32 citation statements)

References 24 publications

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“…At present, one omaezallene and four polyether triterpenoids are reported with anti-macrofouling activity from Laurencia sp. and L. viridis, respectively [73]. Dai Nippon Ink and Chemical Company from Japan extracted a blue phycocyanin from S. platensis and sold to the market as a natural blue pigment called "lina blue" which is commercially used in food preparation and cosmetic products.…”

Section: Paint Printing and Dying Industrymentioning

confidence: 99%

A Review on Marine Algae and Its Applications

Veluchamy

Palaniswamy²

2020

Asian J Pharm Clin Res

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The ocean is the major essential source of structurally unique natural products that are mainly present in living organisms. The essential products extracted from marine microbes and marine algae are highly analyzed areas in instinctive product research. Marine algae are the novel food with potential nutritional values used for multiple purposes in industry and medicine. They show pharmacological activities which are helpful for the invention of bioactive compounds. Furthermore, marine algae have shown to provide an abundant source of natural bioactive compounds with antidiabetic, anti-inflammatory, antiviral, antifungal, hypolipidemic, antioxidant, anti-hypercholesterolemia, antibacterial, and antineoplastic properties. They produce new secondary metabolites that possess biological activities and have the potential to be developed as therapeutic agents. Macroalgal lectins, fucoidans, kainoids, and other substances have been routinely used in the research of biomedical and also have biological activities. The potential pharmaceutical, medicinal, and research applications of these compounds are discussed.

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Section: Paint Printing and Dying Industrymentioning

confidence: 99%

A Review on Marine Algae and Its Applications

Veluchamy

Palaniswamy²

2020

Asian J Pharm Clin Res

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“…As far as we know, the two syntheses described above are the only ones using the recent halogen substitution methodologies. Although, several syntheses were realized thanks to bromoetherification reactions, using NBS [51][52][53] or the tetrabromocyclohexadienone (TBCO). 54 Thus, the formal synthesis of Obstusallenes II and IV proceeded using TBCO, 54 and the total syntheses of Gambieric Acid A, 52 the unnatural Omaezallene 53 and Laureatin 51 were attempted using NBS.…”

Section: Scheme 14: Chloropolyol Cyclization Into Thfmentioning

confidence: 99%

Recent advances in the synthesis of tetrahydrofurans and applications in total synthesis

et al. 2016

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Mousseron. His research interests include the total synthesis of oxygenated cyclic and non cyclic metabolites of polyunsaturated fatty acids, mainly leukotrienes, iso-, phyto-and neuroprostanes, as well as dihydroxylated PUFAs and more recently lipophenols and the understanding of the role of such bioactive lipids and lipophenols by developing collaborations with chemists, biochemists, biologists and clinicians across the world. Jean-Marie Galano studied chemistry at Paul Cézanne Université Marseille and obtained his PhD under the supervision of Honoré Monti in 2001. He then moved to the University of Oxford to pursue a postdoctoral fellowship with David H. Hodgson on the development of new methods for the total synthesis of natural products. In October 2005 he joined the CNRS as a Chargé de Recherche at Université of Montpellier. His research focuses on the total synthesis and discovery of new lipid metabolites, and to discover their potential implications in human health. AbstractMany natural products contain tetrahydrofuran (THF) moieties. Those molecules, often biologically active, may be structurally diverse, e.g. cis or trans THF, mono-, di-, tri-or tetrasubstituted on the furan ring. Thus, the construction of THF is of great interest for the community of organic chemists; especially in developing new methodologies, and applying them in the total synthesis of natural products. The aim of this review is to report recent advances in the field of THF synthesis, as well as the application of these methods to the synthesis of bioactive compounds.

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“…The ecotoxicity of omaezallene (709) against the marine crustacean Tigriopus japonicus was quite low (LC 50 ¼ 2.5 μg/cm 3 in 48 h), especially when compared to that of commercial antifoulants [584]. Omaezallene (709) and 710 showed potent settlement inhibition against B. amphitrite cyprids with ED 50 values of 0.22 and 0.30 μg/cm 3 , respectively, while the activity of 711 was moderate (ED 50 ¼ 1.5 μg/cm 3 ).…”

Section: Antifouling Activitymentioning

confidence: 99%