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. 2023 Nov 24;86(11):2457-2467.
doi: 10.1021/acs.jnatprod.3c00525. Epub 2023 Nov 1.

Neurite Outgrowth-Inducing Drimane-Type Sesquiterpenoids Isolated from Cultures of the Polypore Abundisporus violaceus MUCL 56355

Winnie Chemutai Sum  1   2 , Sherif S Ebada  1   3 , Marco Kirchenwitz  4 , Lucy Wanga  5 , Cony Decock  6 , Theresia E B Stradal  4 , Josphat Clement Matasyoh  7 , Attila Mándi  8 , Tibor Kurtán  8 , Marc Stadler  1   2
Affiliations

Neurite Outgrowth-Inducing Drimane-Type Sesquiterpenoids Isolated from Cultures of the Polypore Abundisporus violaceus MUCL 56355

Winnie Chemutai Sum et al. J Nat Prod. .

Abstract

Abundisporin A (1), together with seven previously undescribed drimane sesquiterpenes named abundisporins B-H (2-8), were isolated from a polypore, Abundisporus violaceus MUCL 56355 (Polyporaceae), collected in Kenya. Chemical structures of the isolated compounds were elucidated based on exhaustive 1D and 2D NMR spectroscopic measurements and supported by HRESIMS data. The absolute configurations of the isolated compounds were determined by using Mosher's method for 1-4 and TDDFT-ECD calculations for 4 and 5-8. None of the isolated compounds exhibited significant activities in either antimicrobial or cytotoxicity assays. Notably, all of the tested compounds demonstrated neurotrophic effects, with 1 and 6 significantly increasing outgrowth of neurites when treated with 5 ng/mL NGF.

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Conflict of interest statement

The authors declare no competing financial interest.

Figures

Chart 1
Chart 1
Figure 1
Figure 1
Key 1H–1H COSY, HMBC, and ROESY correlations of 1–4.
Figure 2
Figure 2
ΔδSR values of (S)/(R)-MTPA esters obtained from abundisporin A (1) diagnostic for (11R), abundisporins B (2) and C (3) diagnostic for (7S), and abundisporin D (4) diagnostic for (1S).
Figure 3
Figure 3
Experimental ECD spectrum of 4 (black) compared with the CAM-B3LYP/TZVP PCM/MeOH ECD spectrum of (1S,4R,5R,10R)-4 (dark yellow). Level of DFT optimization: ωB97X/TZVP PCM/MeOH.
Figure 4
Figure 4
Key 1H–1H COSY, HMBC, and ROESY correlations of 5–8.
Figure 5
Figure 5
Experimental ECD spectrum of 5 (black) compared with the B3LYP/TZVP PCM/MeOH ECD spectrum of (4R,5R,10S)-5 (red). Level of DFT optimization: ωB97X/TZVP PCM/MeOH.
Figure 6
Figure 6
Experimental ECD spectrum of 6 (black) compared with the CAM-B3LYP/TZVP PCM/MeOH ECD spectrum of (4R,5R,9S,10S)-6 (dark yellow). Level of DFT optimization: ωB97X/TZVP PCM/MeOH.
Figure 7
Figure 7
Experimental ECD spectrum of 7 (black) compared with the PBE0/TZVP PCM/MeOH ECD spectrum of (4R,5R,9R,10S)-7 (purple). Level of DFT optimization: ωB97X/TZVP PCM/MeOH.
Figure 8
Figure 8
Experimental ECD spectrum of 8 (black) compared with the PBE0/TZVP PCM/MeOH ECD spectrum of (4R,5R,10S)-8 (purple). Level of DFT optimization: ωB97X/TZVP PCM/MeOH.
Figure 9
Figure 9
Neurite outgrowth activity of drimane-type sesquiterpenoid compounds at 5 μg/mL. PC-12 cells were treated with 5 ng/mL of NGF and (A) DMSO and (B–G) drimane-type sesquiterpenoid compounds 1–6. Phase contrast images show the neurite outgrowth after 48 h in PC-12 cells. (H) Data shown in bar graph originate from five independent experiments ± s.e.m. *p < 0.1, one-tailed t-test.
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