title: Zooxanthellamide D, a polyhydroxy polyene amide from a marine dinoflagellate, and chemotaxonomic perspective of the Symbiodinium polyols.
abstract: A long-chain polyhydroxy polyene amide, zooxanthellamide D (ZAD-D, 1, C54H83NO19), was isolated from a cultured marine dinoflagellate of the genus Symbiodinium. ZAD-D (1) is a polyhydroxy amide consisting of a C22-acid part and a C32-amine part and furnishes three tetrahydropyran rings and six isolated butadiene chromophores. The relative stereochemistry of the tetrahydropyran ring systems was elucidated by NMR techniques. This metabolite showed moderate cytotoxicity against two human tumor cell lines. A phylogenetic tree of Symbiodinium has been updated and compared with the structures of the hitherto isolated polyols of Symbiodinium, zooxanthellatoxins and zooxanthellamides, providing a promising chemotaxonomic perspective for the classification of this morphologically indistinguishable dinoflagellate.
authors.affiliation: Graduate School of Bioagricultural Sciences, Nagoya University, Chikusa-ku, Nagoya 464-8601, Japan.
authors.forename: Takuya
authors.initials: T
authors.lastname: Fukatsu
authors.forename: Ken-ichi
authors.initials: K
authors.lastname: Onodera
authors.forename: Yuichiro
authors.initials: Y
authors.lastname: Ohta
authors.forename: Yuichi
authors.initials: Y
authors.lastname: Oba
authors.forename: Hideshi
authors.initials: H
authors.lastname: Nakamura
authors.forename: Tomoaki
authors.initials: T
authors.lastname: Shintani
authors.forename: Yukio
authors.initials: Y
authors.lastname: Yoshioka
authors.forename: Tetsuji
authors.initials: T
authors.lastname: Okamoto
authors.forename: Michael
authors.initials: M
authors.lastname: ten Lohuis
authors.forename: David J
authors.initials: DJ
authors.lastname: Miller
authors.forename: Masanobu
authors.initials: M
authors.lastname: Kawachi
authors.forename: Makoto
authors.initials: M
authors.lastname: Ojika
mesh_terms: D000577:Amides; D000818:Animals; D004141:Dinoflagellida / Q000737:chemistry*; D008386:Marine Biology; D015394:Molecular Structure; D011090:Polyenes / Q000737:chemistry / Q000302:isolation & purification*; D011108:Polymers / Q000737:chemistry* / Q000145:classification
chemical_list: D000577:Amides; D011090:Polyenes; D011108:Polymers; C024617:polyol; C519057:zooxanthellamide D