Amphidinolide Y, a Novel 17-Membered Macrolide from Dinoflagellate Amphidinium sp.:  Plausible Biogenetic Precursor of Amphidinolide X

A novel cytotoxic 17-membered macrolide, amphidinolide Y (1), has been isolated from a marine dinoflagellate Amphidinium sp., and it was elucidated to exist as a 9:1 equilibrium mixture of 6-keto- and 6(9)-hemiacetal forms (1a and 1b, respectively) on the basis of 2D NMR data and chemical means. The...

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Bibliographic Details
Published in:Journal of organic chemistry 2003-11, Vol.68 (23), p.9109-9112
Main Authors: Tsuda, Masashi, Izui, Naoko, Shimbo, Kazutaka, Sato, Masaaki, Fukushi, Eri, Kawabata, Jun, Kobayashi, Jun'ichi
Format: Article
Language:English
Subjects:
Analytical, structural and metabolic biochemistry
Animals
Aromatic and heterocyclic compounds
Biological and medical sciences
Dinoflagellida - chemistry
Fundamental and applied biological sciences. Psychology
Heterocyclic compounds, pigments
Macrolides - chemistry
Macrolides - isolation & purification
Magnetic Resonance Spectroscopy
Molecular Structure
Other biological molecules
Spectrometry, Mass, Fast Atom Bombardment
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Summary:A novel cytotoxic 17-membered macrolide, amphidinolide Y (1), has been isolated from a marine dinoflagellate Amphidinium sp., and it was elucidated to exist as a 9:1 equilibrium mixture of 6-keto- and 6(9)-hemiacetal forms (1a and 1b, respectively) on the basis of 2D NMR data and chemical means. The feeding experiments with 13C-labeled acetates suggested that amphidinolide Y (1) may be a biogenetic precursor of 16-membered macrodiolide, amphidinolide X (2).
ISSN:0022-3263
1520-6904
DOI:10.1021/jo035278z