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. 2020 Oct 20;25(20):4823.
doi: 10.3390/molecules25204823.

A Revised Structure and Assigned Absolute Configuration of Theissenolactone A

Affiliations

A Revised Structure and Assigned Absolute Configuration of Theissenolactone A

Melissa M Cadelis et al. Molecules. .

Abstract

Antimicrobial bioassay-guided fractionation of Microcera larvarum led to the isolation of a γ-lactone with a furo[3,4-b]pyran-5-one bicyclic ring system (1) and three known compounds, (3S,4R)-4-hydroxymellein (2), (3S,4S)-4-hydroxymellein (3) and 7-hydroxy-3-(1-hydroxyethyl)isobenzofuran-1(3H)-one (4). Structure elucidation was conducted by NMR spectroscopic methods. Absolute configuration of 1 (2R, 3S, 5S, 7S, 8R) was established using the chiral derivatizing agent MPA and was fully supported by calculated specific rotation and ECD spectra. The spectroscopic data observed for 1 were identical to those previously reported for theissenolactone A (7), necessitating a correction of the latter (from C-5/C-8 trans ring fusion to cis). Compounds 1-4 were evaluated for antimicrobial activity against a panel of pathogens.

Keywords: antimicrobial; fungi; lactone; natural product.

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Conflict of interest statement

The authors declare no conflict of interest.

Figures

Figure 1
Figure 1
Structures of natural products 14.
Figure 2
Figure 2
Structures of reported γ-lactones 58.
Figure 3
Figure 3
Selected COSY (bold), HMBC (red arrows) and NOESY (blue arrows) correlations for 1.
Figure 4
Figure 4
ΔδH values obtained for (S)-MPA and (R)-MPA ester derivatives (1a and 1b, respectively) of 1 in CDCl3.
Figure 5
Figure 5
The experimental ECD spectrum (orange), and the calculated ECD spectrum of 1 (blue) (blue shift = −6).

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