title: Zooxanthellactone, a novel gamma-lactone-type oxylipine from dinoflagellates of Symbiodinium 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 gamma-lactone moiety.
authors.affiliation: Graduate School of Bioagricultural Sciences, Nagoya University, Japan.
authors.forename: Ken-ichi
authors.initials: K
authors.lastname: Onodera
authors.forename: Takuya
authors.initials: T
authors.lastname: Fukatsu
authors.forename: Nozomi
authors.initials: N
authors.lastname: Kawai
authors.forename: Yukio
authors.initials: Y
authors.lastname: Yoshioka
authors.forename: Tetsuji
authors.initials: T
authors.lastname: Okamoto
authors.forename: Hideshi
authors.initials: H
authors.lastname: Nakamura
authors.forename: Makoto
authors.initials: M
authors.lastname: Ojika
mesh_terms: D000818:Animals; D016923:Cell Death / Q000187:drug effects; D045744:Cell Line, Tumor; D004141:Dinoflagellida / Q000737:chemistry*; D004281:Docosahexaenoic Acids / Q000737:chemistry; D006801:Humans; D007783:Lactones / Q000737:chemistry* / Q000302:isolation & purification / Q000633:toxicity*; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure
chemical_list: D007783:Lactones; D004281:Docosahexaenoic Acids