Zooxanthellamide D, a polyhydroxy polyene amide from a marine dinoflagellate, and chemotaxonomic perspective of the Symbiodinium polyols.
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.
Fukatsu
Takuya
T
Graduate School of Bioagricultural Sciences, Nagoya University, Chikusa-ku, Nagoya 464-8601, Japan.
Onodera
Ken-ichi
K
Ohta
Yuichiro
Y
Oba
Yuichi
Y
Nakamura
Hideshi
H
Shintani
Tomoaki
T
Yoshioka
Yukio
Y
Okamoto
Tetsuji
T
ten Lohuis
Michael
M
Miller
David J
DJ
Kawachi
Masanobu
M
Ojika
Makoto
M
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
D000577:Amides; D011090:Polyenes; D011108:Polymers; C024617:polyol; C519057:zooxanthellamide D