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. 2023 Aug 2;12(8):1273.
doi: 10.3390/antibiotics12081273.

Bioactive Naphtho-α-Pyranones from Two Endophytic Fungi of the Genus Polyphilus

Jan-Peer Wennrich  1   2 , Ellen Sepanian  1 , Sherif S Ebada  1   3 , Natalia A Llanos-Lopez  1 , Samad Ashrafi  4   5 , Wolfgang Maier  4 , Tibor Kurtán  6 , Marc Stadler  1   2
Affiliations

Bioactive Naphtho-α-Pyranones from Two Endophytic Fungi of the Genus Polyphilus

Jan-Peer Wennrich et al. Antibiotics (Basel). .

Abstract

In the course of our survey to study the metabolic potential of two species of a new helotialean genus Polyphilus, namely P. frankenii and P. sieberi, their crude extracts were obtained using different cultivation techniques, which led to the isolation and characterization of two new naphtho-α-pyranone derivatives recognized as a monomer (1) and its 6,6'-homodimer (2) together with two known diketopiperazine congeners, outovirin B (3) and (3S,6S)-3,6-dibenzylpiperazine-2,5-dione (4). The structures of isolated compounds were determined based on extensive 1D and 2D NMR and HRESIMS. The absolute configuration of new naphtho-α-pyranones was determined using a comparison of their experimental ECD spectra with those of related structural analogues. 6,6'-binaphtho-α-pyranone talaroderxine C (2) exhibited potent cytotoxic activity against different mammalian cell lines with IC50 values in the low micromolar to nanomolar range. In addition, talaroderxine C unveiled stronger antimicrobial activity against Bacillus subtilis rather than Staphylococcus aureus with MIC values of 0.52 µg mL-1 (0.83 µM) compared to 66.6 µg mL-1 (105.70 µM), respectively.

Keywords: Ascomycota; Helotiales; Polyphilus; antimicrobial; naphthopyranones.

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Conflict of interest statement

The authors declare no conflict of interest.

Figures

Figure 1
Figure 1
Chemical structures of 1–4.
Figure 2
Figure 2
Key COSY, HMBC, and ROESY correlations of 1 and 2.
See this image and copyright information in PMC

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