Journal
MOLECULES
Volume 17, Issue 7, Pages 7769-7781Publisher
MDPI AG
DOI: 10.3390/molecules17077769
Keywords
Hymenoscyphus pseudoalbidus; Chalara fraxinea; B-norsteroids; secondary metabolites; structure elucidation
Funding
- Swedish Research Council FORMAS [2010-1344]
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Two viridin-related B-norsteroids, B-norviridiol lactone (1) and B-norviridin enol (2), both possessing distinct unprecedented carbon skeletons, were isolated from a liquid culture of the ash dieback-causing fungus Hymenoscyphus pseudoalbidus. Compound 2 was found to degrade to a third B-norsteroidal compound, 1 beta-hydroxy-2 alpha-hydro-asterogynin A (3), which was later detected in the original culture. The proposed structure of 1 is, regarding connectivity, identical to the original erroneous structure for TAEMC161, which was later reassigned as viridiol. Compound 2 showed an unprecedented H-1-C-13 HMBC correlation through an intramolecular hydrogen bond. The five-membered B-ring of compounds 1-3 was proposed to be formed by a benzilic acid rearrangement. The known compound asterogynin A was found to be formed from 3 by a beta-elimination of water. All compounds were characterized by NMR spectroscopy, LC-HRMS and polarimetry.
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