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Beccaridiol, an unusual 28-nortriterpenoid from the leaves of Diplectria beccariana.
- Source :
-
Phytochemistry [Phytochemistry] 2006 Aug; Vol. 67 (16), pp. 1832-7. Date of Electronic Publication: 2006 Jan 19. - Publication Year :
- 2006
-
Abstract
- A C29-triterpene, beccaridiol (1), a dihydrochalcone natural product, 2',4'-dihydroxy-3-(4-methoxyphenyl)-propiophenone (2), as well as three known compounds, 4'-hydroxy-1',2'-dihydro-beta-ionone, 4'-O-methyldavidigenin (3), and ursolic acid, have been isolated from an EtOAc-soluble extract of the leaves of Diplectria beccariana. Beccaridiol (1) was characterized as an ursane-type 28-nortriterpene possessing an unusual aromatic E-ring by spectroscopic data interpretation. The relative configuration of this unusual isolate was established by analyzing the observed NOESY NMR correlations, and the absolute stereochemistry of 1 was then determined based on the circular dichroism (CD) spectrum of its 2,3-di-p-bromobenzoate (1b) derivative. All isolates were evaluated for their potential cancer chemopreventive properties utilizing a cell culture assay to determine quinone reductase induction.
- Subjects :
- Enzyme Induction
NAD(P)H Dehydrogenase (Quinone) biosynthesis
Nuclear Magnetic Resonance, Biomolecular
Spectrometry, Mass, Electrospray Ionization
Spectrophotometry, Ultraviolet
Spectroscopy, Fourier Transform Infrared
Triterpenes chemistry
Melastomataceae chemistry
Plant Leaves chemistry
Triterpenes isolation & purification
Subjects
Details
- Language :
- English
- ISSN :
- 0031-9422
- Volume :
- 67
- Issue :
- 16
- Database :
- MEDLINE
- Journal :
- Phytochemistry
- Publication Type :
- Academic Journal
- Accession number :
- 16426647
- Full Text :
- https://doi.org/10.1016/j.phytochem.2005.11.026