Amphidinolide X, a novel 16-membered macrodiolide from dinoflagellate Amphidinium sp.
A novel cytotoxic 16-membered macrodiolide, amphidinolide X (1), has been isolated from a marine dinoflagellate Amphidinium sp. (strain Y-42). The gross structure of 1 was elucidated on the basis of spectroscopic data including one-bond and long-range (13)C-(13)C correlations. The relative and absolute stereochemistries were determined by combined analyses of NOESY data and (1)H-(1)H and (1)H-(13)C coupling constants of 1 and NMR data of the degradation products. Amphidinolide X (1) is the first macrodiolide consisting of polyketide-derived diacid and diol units from natural sources. The biosynthetic origins of 1 were investigated by means of feeding experiments with (13)C-labeled acetates.
Tsuda
Masashi
M
Graduate School of Pharmaceutical Sciences, Hokkaido University, Sapporo 060-0812, Japan.
Izui
Naoko
N
Shimbo
Kazutaka
K
Sato
Masaaki
M
Fukushi
Eri
E
Kawabata
Jun
J
Katsumata
Kazuhito
K
Horiguchi
Takeo
T
Kobayashi
Jun'ichi
J
D000818:Animals; D002247:Carbon Isotopes; D004141:Dinoflagellida / Q000737:chemistry*; D018942:Macrolides / Q000138:chemical synthesis / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D013237:Stereoisomerism; D000097442:Amphidinolides
D002247:Carbon Isotopes; D018942:Macrolides; C480942:amphidinolide X; D000097442:Amphidinolides