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A Revised Structure and Assigned Absolute Configuration of Theissenolactone A.

ABSTRACT: Antimicrobial bioassay-guided fractionation of Microcera larvarum led to the isolation of a ?-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.

SUBMITTER: Cadelis MM

PROVIDER: S-EPMC7587954 | biostudies-literature | 2020 Oct

REPOSITORIES: biostudies-literature

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A Revised Structure and Assigned Absolute Configuration of Theissenolactone A.

Cadelis Melissa M MM Geese Soeren S Gris Lauren L Weir Bevan S BS Copp Brent R BR Wiles Siouxsie S

Molecules (Basel, Switzerland) 20201020 20

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< ...[more]

PMID: 33092217

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