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. 2023 Jul 13;13(7):848.
doi: 10.3390/metabo13070848.

Panapophenanthrin, a Rare Oligocyclic Diterpene from Panus strigellus

Natalia A Llanos-López  1   2 , Sherif Saeed Ebada  1   3 , Aída M Vasco-Palacios  4 , Laura M Sánchez-Giraldo  5 , Lina López  6 , Luisa F Rojas  6 , Attila Mándi  7 , Tibor Kurtán  7 , Yasmina Marin-Felix  1   2
Affiliations

Panapophenanthrin, a Rare Oligocyclic Diterpene from Panus strigellus

Natalia A Llanos-López et al. Metabolites. .

Abstract

During the course of our search for biologically active secondary metabolites from fungal cultures, a new oligocyclic diterpenoidal derivative, panapophenanthrin (1), was isolated from Panus strigellus. In addition, two known metabolites, panepophenanthrin (2) and dihydrohypnophilin (3), were also obtained. The chemical structures of the isolated compounds were elucidated based on extensive 1D and 2D NMR spectral analyses together with high-resolution electrospray ionization mass spectrometry (HR-ESI-MS). The absolute configuration was determined through TDDFT-ECD calculations. All of the compounds were assessed for their antimicrobial and cytotoxic activities. Compounds 1 and 3 showed moderate to weak activities in the performed antimicrobial assays, while compound 1 exhibited potent cytotoxic activity against the mammalian cell lines mouse fibroblast (L929) and human endocervical adenocarcinoma (KB3.1).

Keywords: antimicrobial; basidiomycota; cytotoxicity; secondary metabolites; white rot fungi.

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Conflict of interest statement

The authors declare no conflict of interest.

Figures

Figure 1
Figure 1
Chemical structures of 1–3.
Figure 2
Figure 2
Key COSY, HMBC and ROESY correlations of 1.
Figure 3
Figure 3
(a) Experimental ECD spectrum of 1 in MeOH compared with the BH&HLYP/TZVP PCM/MeOH ECD spectrum of (2R,3R,3aR,5aS,10R,10aS,10bS,10cR,11S)-1 calculated for the ωB97X/TZVP PCM/MeOH conformers. (b) Low-energy ωB97X/TZVP PCM/MeOH conformers of (2R,3R,3aR,5aS,10R,10aS,10bS,10cR,11S)-1.
See this image and copyright information in PMC

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