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Computational Structural Revision of a 4-Hydroxy-3-(1′-angeloyloxy-2′,3′-epoxy-3′-methyl)butylacetophenone Compound from Ageratina grandifolia
- Source :
- Journal of Natural Products. 84:2043-2047
- Publication Year :
- 2021
- Publisher :
- American Chemical Society (ACS), 2021.
-
Abstract
- The structure of the reported compound 4-hydroxy-3-((S)-1'-angeloyloxy-(R)-2',3'-epoxy-3'-methyl)butylacetophenone (1), isolated from Ageratina grandifolia, has been revised through the use of DFT computational predictions. Re-examination of the reported experimental and DFT computed chemical shifts has led to the proposal of a chromane skeleton rather than the original epoxide derivative. Empirical predictions of the 13C and 1H NMR shifts showed a much better fit for the chromane structure than for the epoxide. The relative configuration of the molecule was established using CASE-3D methodology on the basis of new DFT chemical shielding and J-coupling predictions, allowing the proposal of a new rel-2,2-dimethyl-3R-hydroxy-4S-(1-angeloyloxy)chromane structure (2) for the isolated compound. However, DFT prediction of the optical rotation for the CASE-3D selected configuration/conformations did not provide a conclusive answer for the absolute configuration.
- Subjects :
- Pharmacology
Ageratina
biology
010405 organic chemistry
Chemical shift
Organic Chemistry
Absolute configuration
Pharmaceutical Science
Epoxide
biology.organism_classification
01 natural sciences
0104 chemical sciences
Analytical Chemistry
010404 medicinal & biomolecular chemistry
chemistry.chemical_compound
Complementary and alternative medicine
chemistry
Computational chemistry
Drug Discovery
Proton NMR
Molecular Medicine
Chromane
Molecule
Derivative (chemistry)
Subjects
Details
- ISSN :
- 15206025 and 01633864
- Volume :
- 84
- Database :
- OpenAIRE
- Journal :
- Journal of Natural Products
- Accession number :
- edsair.doi...........5089e67620fd4849d58c521c2f01adc0