Zooxanthellactone, a Novel .GAMMA.-Lactone-type Oxylipine from Dinoflagellates of Symbiodinium sp.: Structure, Distribution, and Biological Activity

• ONODERA Ken-ichi

  Graduate School of Bioagricultural Sciences, Nagoya University

• FUKATSU Takuya

  Graduate School of Bioagricultural Sciences, Nagoya University

• KAWAI Nozomi

  Graduate School of Bioagricultural Sciences, Nagoya University

• YOSHIOKA Yukio

  Graduate School of Biomedical Sciences, Hiroshima University

• OKAMOTO Tetsuji

  Graduate School of Biomedical Sciences, Hiroshima University

• NAKAMURA Hideshi

  Graduate School of Bioagricultural Sciences, Nagoya University

• OJIKA Makoto

  Graduate School of Bioagricultural Sciences, Nagoya University

Bibliographic Information

Other Title

• Zooxanthellactone, a Novel γ-Lactone-type Oxylipine from Dinoflagellates of Symbiodinium sp.: Structure, Distribution, and Biological Activity
• Zooxanthellactone a Novel ガンマ Lactone type Oxylipine from Dinoflagellates of Symbiodinium sp Structure Distribution and Biological Activity
• Zooxanthellactone, a Novel γ-Lactone-type Oxylipine from Dinoflagellates of<i>Symbiodinium</i>sp.: Structure, Distribution, and Biological Activity

Abstract

A novel fatty acid derivative named zooxanthellactone (ZL) was isolated from several strains of symbiotic microalgae, dinoflagellates of the genus Symbiodinium. The metabolite is structurally related to docosahexaenoic acid (DHA) and seems to be biosynthesized by oxidation and subsequent lactonization. The absolute stereochemistry was determined from the specific rotation of the perhydro derivative. The distribution of ZL within several Symbiodinium isolates was quantitatively analyzed by HPLC techniques and suggested a relationship between the productivity of this metabolite and the Symbiodinium phylogeny. The cytotoxicity of ZL was evaluated by using human squamous cell carcinoma cell lines in comparison with that of DHA and other common fatty acids, suggesting that the long unsaturated chain was important rather than the γ-lactone moiety.

Journal

• Bioscience, Biotechnology, and Biochemistry

  Bioscience, Biotechnology, and Biochemistry 68 (4), 848-852, 2004

  Japan Society for Bioscience, Biotechnology, and Agrochemistry

Keywords

• zooxanthellactone
• oxylipine
• cytotoxic
• dinoflagellate
• <I>Symbiodinium</I>

Details

• CRID: 1390001206473738624
• NII Article ID: 10013143782
• NII Book ID: AA10824164
• DOI: 10.1271/bbb.68.848
• ISSN: 13476947
• ISSN: 09168451
• NDL BIB ID: 6930307
• PubMed: 15118313
• Web Site: https://ndlsearch.ndl.go.jp/books/R000000004-I6930307
• Web Site: http://www.tandfonline.com/doi/pdf/10.1271/bbb.68.848
• Text Lang: en
• Data Source:
  • JaLC
  • NDL
  • Crossref
  • PubMed
  • CiNii Articles
• Abstract License Flag: Disallowed