Cadinane sesquiterpenes from the mushroom Lyophyllum transforme

Marco Clericuzio; Roberto Negri; Maurizio Cossi; Gianluca Gilardoni; Davide Gozzini; Giovanni Vidari

doi:10.1016/j.phytochem.2013.03.019

Cadinane sesquiterpenes from the mushroom Lyophyllum transforme

Phytochemistry. 2013 Sep:93:192-8. doi: 10.1016/j.phytochem.2013.03.019. Epub 2013 May 2.

Authors

Marco Clericuzio¹, Roberto Negri, Maurizio Cossi, Gianluca Gilardoni, Davide Gozzini, Giovanni Vidari

Affiliation

¹ Università del Piemonte Orientale, Dipartimento di Scienze e Innovazione Tecnologica, Via T. Michel 11, 15121 Alessandria, Italy.

PMID: 23642390
DOI: 10.1016/j.phytochem.2013.03.019

Abstract

Two rare cadinane-type sesquiterpenes, lyophyllone A (1) and lyophyllanetriol A (2), were isolated from the mushroom Lyophyllum transforme. The structures were elucidated on the basis of exhaustive NMR techniques, together with MS, UV-Vis and molecular modelling. The absolute configuration of lyophyllone A was determined by ab initio theoretical CD calculation performed by Density Functional Theory (DFT) using the B3PW91/6-31G(d,p) basis set. The experimental CD were found to be in good agreement with the corresponding population-weighted theoretical CD spectra, allowing for the determination of the absolute stereochemistry of the compound.

Keywords: Absolute configuration; CD; Cadinane; Lyophyllaceae; Lyophyllum transforme; Sesquiterpenes; Structure elucidation; TD-DFT calculations.

Publication types

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

MeSH terms

Agaricales / chemistry*
Magnetic Resonance Spectroscopy
Molecular Conformation
Quantum Theory
Sesquiterpenes / chemistry
Sesquiterpenes / isolation & purification*

Substances

Sesquiterpenes
lyophyllanetriol A
lyophyllone A