Understanding the Biosynthesis of Paxisterol in Lichen-Derived Penicillium aurantiacobrunneum for Production of Fluorinated Derivatives.

Understanding the Biosynthesis of Paxisterol in Lichen-Derived Penicillium aurantiacobrunneum for Production of Fluorinated Derivatives.
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DOI:
10.3390/molecules27051641
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发表时间:
2022-03-02
期刊:
Molecules (Basel, Switzerland)
影响因子:
--
通讯作者:
Rakotondraibe HL
Rakotondraibe HL
中科院分区:
其他
文献类型:
--
作者:
Yamano Y;Rakotondraibe HL

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The U.S. endemic lichen (Niebla homalea)-derived Penicillium aurantiacobrunneum produced a cytotoxic paxisterol derivative named auransterol (2) and epi-citreoviridin (6). Feeding assay using 13C1-labelled sodium acetate not only produced C-13-labelled paxisterol but also confirmed the biosynthetic origin of the compound. The fluorination of bioactive compounds is known to improve pharmacological and pharmacokinetic effects. Our attempt to incorporate the fluorine atom in paxisterol and its derivatives using the fluorinated precursor sodium monofluoroacetate resulted in the isolation of 7-monofluoroacetyl paxisterol (7). The performed culture experiment, as well as the isolation and structure elucidation of the new fluorinated paxisterol, is discussed herein.
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