title: Zooxanthellamide Cs: vasoconstrictive polyhydroxylated macrolides with the largest lactone ring size from a marine dinoflagellate of Symbiodinium sp.
abstract: Zooxanthellamide Cs (ZAD-Cs), C(128)H(220)N(2)O(53)S(2) (ca. 2.7 kDa), was obtained from a cultured marine dinoflagellate of the genus Symbiodinium as an inseparable isomeric mixture of polyhydroxylated 61- to 66-membered macrolides. The chemical structures of the components were clarified by detailed 2D NMR analysis to be the macrolactonized analogues of zooxanthellamide A (ZAD-A), which had been previously isolated from the same microalgae. Chemical lability of ZAD-Cs suggests that ZAD-A is an artifact derived from ZAD-Cs during the isolation steps. Three of the components possess the largest (63-, 64-, and 66-membered) ring sizes found to date among the natural macrolides. ZAD-Cs exhibited higher vasoconstrictive activity than that of the zooxanthellatoxins, the first vasoconstrictive macrolides from Symbiodinium sp. The structure-activity relationship suggests that the huge macrolactone structure is important for biological activity. The relationship between the structures of the polyol metabolites and the phylogenetic systematics of Symbiodinium sp. is also discussed.
authors: Graduate School of Bioagricultural Sciences, Nagoya University, Chikusa-ku, Nagoya 464-8601, Japan.
authors: Ken-Ichi
authors: K
authors: Onodera
authors: Hideshi
authors: H
authors: Nakamura
authors: Yuichi
authors: Y
authors: Oba
authors: Yasushi
authors: Y
authors: Ohizumi
authors: Makoto
authors: M
authors: Ojika
mesh_terms: D000818:Animals; D004141:Dinoflagellida / Q000737:chemistry*; D018942:Macrolides / Q000138:chemical synthesis / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology; D019906:Nuclear Magnetic Resonance, Biomolecular; D011714:Pyrans / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology; D051381:Rats; D021241:Spectrometry, Mass, Electrospray Ionization; D014662:Vasoconstrictor Agents / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology
chemical_list: D018942:Macrolides; D011714:Pyrans; D014662:Vasoconstrictor Agents; C504103:Zooxanthellamide Cs