Molecules (Oct 2020)

A Revised Structure and Assigned Absolute Configuration of Theissenolactone A

  • Melissa M. Cadelis,
  • Soeren Geese,
  • Lauren Gris,
  • Bevan S. Weir,
  • Brent R. Copp,
  • Siouxsie Wiles

DOI
https://doi.org/10.3390/molecules25204823
Journal volume & issue
Vol. 25, no. 20
p. 4823

Abstract

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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.

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