Issue 86, 2015
From the journal:

Chemical Communications

Synthesis and discovery of phytofurans: metabolites of α-linolenic acid peroxidation†

C. Cuyamendous,a   K. S. Leung,b   T. Durand,a   J. C.-Y. Lee,*b   C. Oger*a  and  J.-M. Galano*a  

* Corresponding authors

a Institut des Biomolécules Max Mousseron (IBMM), UMR CNRS 5247 - Université de Montpellier – ENSCM Faculté de Pharmacie, 15 avenue Charles Flahault, 34093 Montpellier cedex 05, France
E-mail: camille.oger@umontpellier.fr, jean-marie.galano@umontpellier.fr

b School of Biological Sciences, The University of Hong-Kong, Pokfulam Road, Hong Kong SAR, China
E-mail: jettylee@hku.hk

Abstract

Phytofurans are novel metabolites produced by non-enzymatic peroxidation of α-linolenic acid. An unprecedented Payne rearrangement-cyclization of a C2-symmetric bis-epoxide permitted construction of the core 3-hydroxy-2,5-disubstituted tetrahydrofuran. LC-MS/MS investigation provided evidence for the presence of phytofurans in nuts and seeds for the first time.

Graphical abstract: Synthesis and discovery of phytofurans: metabolites of α-linolenic acid peroxidation

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Article information

DOI
https://doi.org/10.1039/C5CC05736A
Article type
Communication
Submitted
10 Jul 2015
Accepted
03 Sep 2015
First published
07 Sep 2015

Chem. Commun., 2015,51, 15696-15699

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Synthesis and discovery of phytofurans: metabolites of α-linolenic acid peroxidation

C. Cuyamendous, K. S. Leung, T. Durand, J. C.-Y. Lee, C. Oger and J.-M. Galano, Chem. Commun., 2015, 51, 15696 DOI: 10.1039/C5CC05736A

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