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

Natural antifouling products have been the subject of considerable attention. We screened marine algae for antifouling activity and discovered omaezallenes, the new bromoallene‐containing natural products isolated from the red alga Laurencia sp. Described is the isolation, structure elucidation, and...

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Published inAngewandte Chemie Vol. 126; no. 15; pp. 3990 - 3993
Main Authors 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
Format Journal Article
LanguageEnglish
German
Published Weinheim WILEY-VCH Verlag 07.04.2014
WILEY‐VCH Verlag
Wiley Subscription Services, Inc
Subjects
Algae
Allene
Antifouling
Antifouling substances
Bewuchshemmung
Chemistry
Laurencia
Marine
Natural products
Naturstoffe
Strukturaufklärung
Synthesis
Totalsynthesen
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Summary:Natural antifouling products have been the subject of considerable attention. We screened marine algae for antifouling activity and discovered omaezallenes, the new bromoallene‐containing natural products isolated from the red alga Laurencia sp. Described is the isolation, structure elucidation, and total syntheses of omaezallenes. The relative and absolute configurations of natural omaezallenes were unambiguously established through total synthesis. The antifouling activities and ecotoxicity of omaezallenes were also evaluated. Ein neuer bromierter Naturstoff – das aus der Rotalge Laurencia sp. isolierte Omaezallen – wurde synthetisiert und einer NMR‐Strukturaufklärung unterzogen. Die Wirkung von Omaezallen und seinen Isomeren gegen Bewuchs durch Cyprislarven der Gestreiften Seepocke (Amphibalanus amphitrite) wurde untersucht.
Bibliography:This work was supported by the Sumitomo Foundation (to T.U.) and JSPS Kakenhi grant. We thank Dr. Y. Kumaki (High-resolution NMR Laboratory, Faculty of Science, Hokkaido University) for NOE experiments.
Sumitomo Foundation
ark:/67375/WNG-F07K60PM-1
istex:91C67473AB59A48006067456910972358BD8B857
ArticleID:ANGE201311175
JSPS
This work was supported by the Sumitomo Foundation (to T.U.) and JSPS Kakenhi grant. We thank Dr. Y. Kumaki (High‐resolution NMR Laboratory, Faculty of Science, Hokkaido University) for NOE experiments.
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ISSN:0044-8249
1521-3757
DOI:10.1002/ange.201311175