Amphidinolides H2−H5, G2, and G3, New Cytotoxic 26- and 27-Membered Macrolides from Dinoflagellate Amphidinium sp

Six new macrolides, amphidinolides H2 (5), H3 (6), H4 (7), H5 (8), G2 (9), and G3 (10), have been isolated from a marine dinoflagellate Amphidinium sp. (strain Y-42). Cytotoxicity of five derivatives (11−15) of amphidinolide H (1) in addition to 10 amphidinolides (1−10) containing amphidinolides H (...

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Bibliographic Details
Published in:Journal of organic chemistry 2002-09, Vol.67 (19), p.6585-6592
Main Authors: Kobayashi, Jun'ichi, Shimbo, Kazutaka, Sato, Masaaki, Tsuda, Masashi
Format: Article
Language:English
Subjects:
Animals
Biological and medical sciences
Cell Survival - drug effects
Dinoflagellida - chemistry
Drug Screening Assays, Antitumor
General pharmacology
Humans
Japan
KB Cells - drug effects
Leukemia
Macrolides - chemistry
Macrolides - isolation & purification
Macrolides - pharmacology
Marine Toxins - chemistry
Marine Toxins - isolation & purification
Marine Toxins - pharmacology
Medical sciences
Mice
Molecular Conformation
Molecular Structure
Nuclear Magnetic Resonance, Biomolecular
Pharmacognosy. Homeopathy. Health food
Pharmacology. Drug treatments
Stereoisomerism
Structure-Activity Relationship
Tumor Cells, Cultured - drug effects
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Summary:Six new macrolides, amphidinolides H2 (5), H3 (6), H4 (7), H5 (8), G2 (9), and G3 (10), have been isolated from a marine dinoflagellate Amphidinium sp. (strain Y-42). Cytotoxicity of five derivatives (11−15) of amphidinolide H (1) in addition to 10 amphidinolides (1−10) containing amphidinolides H (1), G (2), B (3), and D (4) was examined, and it was found that the presence of an allyl epoxide, an S-cis-diene moiety, and the ketone at C-20 was important for the cytotoxicity of amphidinolide H (1)-type macrolides.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo016222c