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(+)- and (-)-Xanthostones A-D: Four Pairs of Enantiomeric Cinnamoyl-β-Triketone Derivatives from Xanthostemon chrysanthus.
- Source :
-
Chemistry & biodiversity [Chem Biodivers] 2022 Jun; Vol. 19 (6), pp. e202200356. Date of Electronic Publication: 2022 Jun 02. - Publication Year :
- 2022
-
Abstract
- Four pairs of cinnamoyl-β-triketone derivative enantiomers, (+)- and (-)-xanthostones A-D ((+)- and (-)-1-4), were isolated from Xanthostemon chrysanthus. Compounds 1 and 2 feature a new rearranged cinnamoyl-phloroglucinol scaffold fused with a cinnamyl-β-triketone framework. Compounds 1, 3, and 4 are the first examples of natural products with a peculiar phenethyl-pyranone acid unit. Their structures with absolute configurations were determined by spectroscopic data, X-ray diffraction analysis and electronic circular dichroism (ECD) calculation. Interestingly, these novel compounds showed a tautomeric behavior in solution, which was revealed by NMR spectroscopy and density functional theory calculation. A plausible biosynthetic pathway toward xanthostones A-D was proposed. Additionally, the anti-inflammatory and antibacterial activities of xanthostones A-D were evaluated.<br /> (© 2022 Wiley-VHCA AG, Zurich, Switzerland.)
Details
- Language :
- English
- ISSN :
- 1612-1880
- Volume :
- 19
- Issue :
- 6
- Database :
- MEDLINE
- Journal :
- Chemistry & biodiversity
- Publication Type :
- Academic Journal
- Accession number :
- 35581725
- Full Text :
- https://doi.org/10.1002/cbdv.202200356