Homopetasinic acid isolated from Diaporthe sp. strain 1308-05

[Display omitted] Homopetasinic acid (1) was isolated from fungi of the Diaporthe sp. strain 1308-05. NMR spectroscopic structural analysis revealed a petasol (3) substructure and a (4E,6E)-7-carboxy-3-hydroxy-2-methylhepta-4,6-dienoate side chain. The absolute configuration of the petasol moiety wa...

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Bibliographic Details
Published in:Tetrahedron letters 2016-03, Vol.57 (10), p.1117-1119
Main Authors: Ito, Atsushi, Kumagai, Ikuya, Maruyama, Miku, Maeda, Hayato, Tonouchi, Akio, Nehira, Tatsuo, Kimura, Ken-ichi, Hashimoto, Masaru
Format: Article
Language:English
Subjects:
Chains
Chemical correlation
Cytotoxicity
Electron circular dichroism analysis
Homopetasinic acid
Hydrolysis
Nuclear magnetic resonance
Spectra
Strain
Structural analysis
Substructures
Tetrahedrons
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Summary:[Display omitted] Homopetasinic acid (1) was isolated from fungi of the Diaporthe sp. strain 1308-05. NMR spectroscopic structural analysis revealed a petasol (3) substructure and a (4E,6E)-7-carboxy-3-hydroxy-2-methylhepta-4,6-dienoate side chain. The absolute configuration of the petasol moiety was established by the specific rotation value after basic hydrolysis. The (2′S,3′S)-configuration of the side chain was determined by NMR empirical methods as well as comparison of the spectral data with related model compounds. The absolute structure of the side chain moiety was established on the basis of ECD spectral analyses involving theoretical calculations. The biological activities of 1 are also discussed.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2016.01.095