Acremomannolipin A, the potential calcium signal modulator with a characteristic glycolipid structure from the filamentous fungus Acremonium strictum

Using a newly developed assay method, the glycolipid Acremomannolipin A (1), isolated from the fungus Acremonium strictum, was identified as a potential calcium signal modulator. The structure of 1 is quite novel and unique, and exhibits the properties of both lipids and sugars due to the hybridizat...

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Veröffentlicht in:Bioorganic & medicinal chemistry letters 2012-11, Vol.22 (21), p.6735-6739
Hauptverfasser: Sugiura, Reiko, Kita, Ayako, Tsutsui, Nozomi, Muraoka, Osamu, Hagihara, Kanako, Umeda, Nanae, Kunoh, Tatsuki, Takada, Hirofumi, Hirose, Dai
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Sprache:eng
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Zusammenfassung:Using a newly developed assay method, the glycolipid Acremomannolipin A (1), isolated from the fungus Acremonium strictum, was identified as a potential calcium signal modulator. The structure of 1 is quite novel and unique, and exhibits the properties of both lipids and sugars due to the hybridization of these two types of biomolecules. By the newly developed assay method, the glycolipid Acremomannolipin A (1) was isolated from a filamentous fungus Acremonium strictum as a potential calcium signal modulator. The structure of 1 elucidated on the basis of intensive spectroscopic analyses as well as its degradation studies is quite unique: the d-mannopyranose is connected to d-mannitol through a β-glycoside linkage; all the hydroxyls in the mannose are highly masked as peresters with aliphatic acids, and this moiety is made hydrophobic, whereas the mannitol part exhibits a highly hydrophilic property. The compound (1) showed the characteristic bioactivity property, enabling calcineurin deletion cells to grow in the presence of Cl−, which would be caused by calcium signal modulating. The activity was so potent as to exert the effect at a concentration of 200nM.
ISSN:0960-894X
1464-3405
DOI:10.1016/j.bmcl.2012.08.085