Structure and absolute configuration of methyl (3R)-malonyl-(13S)-hydroxycheilanth-17-en-19-oate, a sesterterpene derivative from the roots of Aletris farinosa

Victoria L Challinor; Sonet Chap; Reginald P Lehmann; Paul V Bernhardt; James J De Voss

doi:10.1021/np400035n

Structure and absolute configuration of methyl (3R)-malonyl-(13S)-hydroxycheilanth-17-en-19-oate, a sesterterpene derivative from the roots of Aletris farinosa

J Nat Prod. 2013 Apr 26;76(4):485-8. doi: 10.1021/np400035n. Epub 2013 Mar 21.

Authors

Victoria L Challinor¹, Sonet Chap, Reginald P Lehmann, Paul V Bernhardt, James J De Voss

Affiliation

¹ School of Chemistry and Molecular Biosciences, The University of Queensland, Brisbane 4072, Australia.

PMID: 23514637
DOI: 10.1021/np400035n

Abstract

We report the isolation and structure elucidation of a new cheilanthane sesterterpene from the roots of Aletris farinosa that possesses an unusual malonate half-ester functional group. The structure of 1 was determined via mass spectrometry and 1D and 2D NMR spectroscopy, while its absolute configuration was determined via X-ray crystallographic analysis performed on its methyl ester derivative 2.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Crystallography, X-Ray
Molecular Conformation
Molecular Structure
Nuclear Magnetic Resonance, Biomolecular
Plant Roots / chemistry
Plants, Medicinal / chemistry*
Sesterterpenes / chemistry*
Sesterterpenes / isolation & purification*

Substances

Sesterterpenes
methyl (3R)-malonyl-(13S)-hydroxycheilanth-17-en-19-oate