Understanding the Biosynthesis of Paxisterol in Lichen-Derived Penicillium aurantiacobrunneum for Production of Fluorinated Derivatives |
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| Authors: | Yoshi Yamano Harinantenaina L. Rakotondraibe |
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| Affiliation: | 1.Division of Medicinal Chemistry and Pharmacognosy, College of Pharmacy, The Ohio State University, Columbus, OH 43210, USA;2.Graduate School of Biomedical and Health Sciences, Pharmaceutical Sciences, Hiroshima University, Hiroshima 739-8527, Japan;3.Infectious Diseases Institute, The Ohio State University, Columbus, OH 43210, USA;4.Center for Applied Plant Sciences, The Ohio State University, Columbus, OH 43210, USA |
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| Abstract: | 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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| Keywords: | lichen Penicillium fluorinated metabolite antiproliferative |
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