American Chemical Society
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Potential Cancer Chemopreventive in Vitro Activities of Monomeric Xanthone Derivatives from the Marine Algicolous Fungus Monodictys putredinis#

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journal contribution
posted on 2020-04-02, 15:31 authored by Anja Krick, Stefan Kehraus, Clarissa Gerhäuser, Karin Klimo, Martin Nieger, Armin Maier, Heinz-Herbert Fiebig, Iuliana Atodiresei, Gerhard Raabe, Jörg Fleischhauer, Gabriele M. König
Investigation of the fungal strain Monodictys putredinis isolated from the inner tissue of a marine green alga led to the isolation of four new monomeric xanthones and a benzophenone. All structures were elucidated by extensive spectroscopic measurements. The relative configuration of compound 1 was determined by X-ray crystal structure analysis, while for 2 and 3 configurations were confirmed by NOE experiments. Absolute configurations for compounds 13 were deduced by comparing experimental circular dichroism spectroscopic data with those calculated employing quantum-chemical time-dependent density functional theory (TDDFT). The compounds were examined for their cancer chemopreventive potential. Xanthone 2 was shown to inhibit cytochrome P450 1A activity with an IC50 value of 3.0 μM. Compounds 2 and 3 displayed moderate activity as inducers of NAD(P)H:quinone reductase (QR) in cultured mouse Hepa 1c1c7 cells, with CD values (concentration required to double the specific activity of QR) of 12.0 and 12.8 μM, respectively. Compound 3 showed weak inhibition of aromatase activity.