Structure Determination and Mechanism of Formation of a seco-Moreliane Derivative Supported by Computational Analysis

Pablo A Chacón Morales; Juan M Amaro-Luis; Andrei G Kutateladze

doi:10.1021/acs.jnatprod.7b00041

Structure Determination and Mechanism of Formation of a seco-Moreliane Derivative Supported by Computational Analysis

J Nat Prod. 2017 Apr 28;80(4):1210-1214. doi: 10.1021/acs.jnatprod.7b00041. Epub 2017 Mar 30.

Authors

Pablo A Chacón Morales¹, Juan M Amaro-Luis¹, Andrei G Kutateladze²

Affiliations

¹ Laboratory of Natural Products, Department of Chemistry, Faculty of Sciences, University of "Los Andes" , Mérida 5101, Venezuela.
² Department of Chemistry and Biochemistry, University of Denver , Denver, Colorado 80208, United States.

PMID: 28358484
DOI: 10.1021/acs.jnatprod.7b00041

Abstract

Basic hydrolysis of a dichloromethane extract of Stevia lucida yielded (4R,5S,7R,9R,10R,11R)-7,9-dihydroxylongipin-2-en-1-one (1), which was oxidized and subjected to acidic conditions to generate the new seco-moreliane derivative 3. The structure of 3 was established based on NMR data interpretation and confirmed computationally. A plausible mechanism for the carbocationic rearrangement of the trione 2 to the seco-moreliane 3 was supported by DFT computations.

Publication types

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

MeSH terms

Hydrolysis
Models, Molecular
Molecular Conformation
Molecular Structure
Nuclear Magnetic Resonance, Biomolecular
Oxidation-Reduction
Sesquiterpenes / chemistry
Sesquiterpenes / isolation & purification*
Stereoisomerism
Stevia / chemistry*
Venezuela

Substances

Sesquiterpenes