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Absolute configuration of tropane alkaloids from Schizanthus species by vibrational circular dichroism.
- Source :
-
Phytochemistry [Phytochemistry] 2010 May; Vol. 71 (7), pp. 810-5. Date of Electronic Publication: 2010 Feb 26. - Publication Year :
- 2010
-
Abstract
- The absolute configuration (AC) of 6beta-hydroxy-3alpha-senecioyloxytropane (1), 3alpha-hydroxy-6beta-tigloyloxytropane (2), 3alpha-hydroxy-6beta-senecioyloxytropane (3), and 3alpha-hydroxy-6beta-angeloyloxytropane (4) was assigned as (1R,3R,5S,6R) using density functional theory (DFT) calculations at the B3LYP/DGDZVP level of theory in combination with experimental vibrational circular dichroism (VCD) measurements and comparison with the spectra of similar tropanes. The AC of 1 followed from a sample isolated from Schizanthus grahamii, while those of the mixture of 2 and 3, isolated from the same source, were determined by comparing the VCD measurement to a weighted calculation of the individual VCD spectra according to a 69:31 ratio of 2:3 determined by (1)H NMR signal integration. In turn, Schizanthus pinnatus provided a 7:3 mixture of 1:4 whose AC was determined using the experimental VCD absorptions in the 1150-950 cm(-1) spectral region which were compared with those observed for 1-3 and with those described for other 3alpha,6beta-tropanediol derivatives.<br /> (Copyright 2010 Elsevier Ltd. All rights reserved.)
Details
- Language :
- English
- ISSN :
- 1873-3700
- Volume :
- 71
- Issue :
- 7
- Database :
- MEDLINE
- Journal :
- Phytochemistry
- Publication Type :
- Academic Journal
- Accession number :
- 20189614
- Full Text :
- https://doi.org/10.1016/j.phytochem.2010.02.004