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. 2019 May 10;24(9):1817.
doi: 10.3390/molecules24091817.

Seven new Drimane-Type Sesquiterpenoids from a Marine-Derived Fungus Paraconiothyrium sporulosum YK-03

Li-Hua Zhang  1   2 , Gang Chen  3 , Yi Sun  4 , Hai-Feng Wang  5 , Jiao Bai  6 , Hui-Ming Hua  7 , Yue-Hu Pei  8
Affiliations

Seven new Drimane-Type Sesquiterpenoids from a Marine-Derived Fungus Paraconiothyrium sporulosum YK-03

Li-Hua Zhang et al. Molecules. .

Abstract

Seven new drimane-type sesquiterpenoids, namely the sporulositols A-D (1-4), 6-hydroxydiaporol (5), seco-sporulositol (6) and sporuloside (7) were isolated from the ethyl acetate extract of fermentation broth for a marine-derived fungus Paraconiothyrium sporulosum YK-03. Their structures were elucidated by analysis of extensive spectroscopic data, and the absolute configurations were established by crystal X-ray diffraction analysis and comparisons of circular dichroism data. Among them, sporulositols A-E (1-4) and seco-sporulositol (6) represent the first five examples of a unique class of drimanic mannitol derivatives, while compounds 6 and 7 may represent two new series of natural drimanes, possessing an aromatic ring with a rare 4,5-secodrimanic skeleton and an unusual CH3-15 rearranged drimanic α-D-glucopyranside, respectively. Furthermore, the origin of mannitol moiety was investigated by reliable HPLC and NMR analyses.

Keywords: Paraconiothyrium; Paraconiothyrium sporulosum; drimane-type sesquiterpenoid; seco-sporulositol; sporuloside; sporulositol.

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Conflict of interest statement

The authors declare no conflict of interest.

Figures

Figure 1
Figure 1
The structures of 1–7.
Figure 2
Figure 2
The key HMBC correlations for 1–7.
Figure 3
Figure 3
Selected NOE correlations for 1–7.
Figure 4
Figure 4
Acid hydrolysis of 2 and 3.
Figure 5
Figure 5
Diamond plot for X-ray crystal structures of 2a and 7.
Figure 6
Figure 6
Experimental CD spectra of 1–5 in CH3CN.
Figure 7
Figure 7
Analysis of the reference compounds 1–3 and metabolites of P. sporulosum YK-03 in different mediums using HPLC and NMR methods. (A) HPLC Analysis of the reference compounds 1–3 and metabolites of P. sporulosum YK-03 in different mediums: (a) compound 1; (b) compound 2; (c) compound 3; (d) metabolites from blank group (medium with-No mannitol); (e) metabolites from control group (Normal medium, mannitol-contained medium); (f) metabolites from experimental group (medium with mannitol replaced by sorbitol); 1H-NMR (B) and 13C-NMR (C) spectra of compound 2 isolated from the experimental and control groups: (a) experimental group; (b) control group.
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References

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