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

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

Department of Science and Technological Innovation

Research output: Contribution to journal › Article › peer-review

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.

Original language	English
Pages (from-to)	192-198
Number of pages	7
Journal	Phytochemistry
Volume	93
DOIs	https://doi.org/10.1016/j.phytochem.2013.03.019
Publication status	Published - 2013

Keywords

Absolute configuration
CD
Cadinane
Lyophyllaceae
Lyophyllum transforme
Sesquiterpenes
Structure elucidation
TD-DFT calculations

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10.1016/j.phytochem.2013.03.019

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@article{c97dc07bbbcf4a4991daa8a9ef093366,

title = "Cadinane sesquiterpenes from the mushroom Lyophyllum transforme",

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",

author = "Marco Clericuzio and Roberto Negri and Maurizio Cossi and Gianluca Gilardoni and Davide Gozzini and Giovanni Vidari",

note = "Funding Information: We thank Prof. Mariella Mella, the University of Pavia, for NMR measurements and the Italian MIUR (Funds PRIN 2009 ) for partial financial support. All data concerning the reported compounds are included in LIBIOMOL, a chemical library of natural and synthetic bioactive molecules, accessible at the website http://www.libiomol.unina.it . ",

year = "2013",

doi = "10.1016/j.phytochem.2013.03.019",

language = "English",

volume = "93",

pages = "192--198",

journal = "Phytochemistry",

issn = "0031-9422",

publisher = "Elsevier Ltd.",

}

TY - JOUR

T1 - Cadinane sesquiterpenes from the mushroom Lyophyllum transforme

AU - Clericuzio, Marco

AU - Negri, Roberto

AU - Cossi, Maurizio

AU - Gilardoni, Gianluca

AU - Gozzini, Davide

AU - Vidari, Giovanni

N1 - Funding Information: We thank Prof. Mariella Mella, the University of Pavia, for NMR measurements and the Italian MIUR (Funds PRIN 2009 ) for partial financial support. All data concerning the reported compounds are included in LIBIOMOL, a chemical library of natural and synthetic bioactive molecules, accessible at the website http://www.libiomol.unina.it .

PY - 2013

Y1 - 2013

N2 - 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.

AB - 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.

KW - Absolute configuration

KW - CD

KW - Cadinane

KW - Lyophyllaceae

KW - Lyophyllum transforme

KW - Sesquiterpenes

KW - Structure elucidation

KW - TD-DFT calculations

UR - https://www.scopus.com/pages/publications/84884909699

U2 - 10.1016/j.phytochem.2013.03.019

DO - 10.1016/j.phytochem.2013.03.019

M3 - Article

SN - 0031-9422

VL - 93

SP - 192

EP - 198

JO - Phytochemistry

JF - Phytochemistry

ER -

Cadinane sesquiterpenes from the mushroom Lyophyllum transforme

Abstract

Keywords

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