Assignment of stereochemistry in open-chain steroidal saponins

Challinor, Victoria L. and De Voss, James J. (2012) Assignment of stereochemistry in open-chain steroidal saponins. Pure and Applied Chemistry, 84 6: 1469-1478.


Author Challinor, Victoria L.
De Voss, James J.
Title Assignment of stereochemistry in open-chain steroidal saponins
Journal name Pure and Applied Chemistry   Check publisher's open access policy
ISSN 0033-4545
1365-3075
Publication date 2012
Sub-type Article (original research)
DOI 10.1351/PAC-CON-11-09-12
Volume 84
Issue 6
Start page 1469
End page 1478
Total pages 10
Editor Anthony R. Carroll
Place of publication Research Triangle Park, NC, United States
Publisher International Union of Pure and Applied Chemistry
Collection year 2013
Language eng
Formatted abstract The major phytochemical constituents of the widely used medicinal herb Chamaelirium luteum ("false unicorn") are open-chain cholesterol-derived steroidal saponins. These are unusual in lacking the extra ring(s) derived from the steroidal side chain that are characteristic of the more commonly isolated furostanol and spirostanol saponins. The structures of the major steroidal saponins of C. luteum were determined using a combination of multistage mass spectrometry (MSn), 1D and 2D NMR experiments, and chemical degradation. The flexible nature of the steroidal side chain in these saponins necessitated determination of their absolute stereochemistry via total synthesis and X-ray crystallography.
Keyword Natural products
Steroidal saponins
Structure elucidation
Total synthesis
Q-Index Code C1
Q-Index Status Confirmed Code
Institutional Status UQ
Additional Notes Special issue: 27th International Symposium on the Chemistry of Natural Products and the 7th International Conference on Biodiversity (ISCNP-27 & ICOB-7). 14 papers based upon lectures presented at ISCNP-27/ICOB-7.

Document type: Journal Article
Sub-type: Article (original research)
Collections: Official 2013 Collection
School of Chemistry and Molecular Biosciences
 
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Created: Tue, 05 Jun 2012, 08:44:00 EST by Lucy O'Brien on behalf of School of Chemistry & Molecular Biosciences