Abstract

European Journal of Mass Spectrometry
Volume 15 Issue 2, Pages 221–230 (2009)
doi: 10.1255/ejms.969

Gas-phase reactivity of acylphenols in electrospray and matrix- assisted laser desorption ionization mass spectrometry

Isabelle Schmitz-Afonso,^a Vincent Guérineau,^a Alessandra Maia- Grondard,^a Khalijah Awang,^b Marc Litaudon,^a Françoise Guéritte^a and Olivier Laprévote^a,*
aCNRS, UPR2301–ICSN Mass Spectrometry Laboratory, Avenue de la Terrasse, Bat 27, 91198 Gif-sur- Yvette cedex, France. E-mail: olivier.laprevote@icsn.cnrs-gif.fr
^bDepartment of Chemistry, University of Malaya, Pantai Valley, Kuala Lumpur, Malaysia

Acylphenols from Myristica crassa were identified based on liquid chromatography high-resolution mass spectrometry and liquid chromatography tandem mass spectrometry (MS/MS) experiments. Two types of compound were found in the extract of the plant: monomeric (malabaricone B and C) and dimeric compounds (C–C bonded biphenyl and C–C bonded phenyl–linear carbon chain). Evidence of formation of covalent dimeric ions during the electrospray ionization and matrix-assisted laser desorption ionization (MALDI) processes was established. [2M–3H]^– dimeric ions were detected on the mass spectra of each monomeric compound during high-performance liquid chromatography separation. The MS/MS spectra of those species were compared to the MS/MS spectra obtained for the dimeric compounds synthesized by the plant. Fragmentation pathways were studied for the two classes of dimer. The dimeric ions formed in the ion source were C–C bonded biphenyl compounds. Further evidence was obtained from MALDI experiments: increase in the extraction delay time leads to an increase of the dimeric ions relative abundance. Their formation is based on the high reactivity of phenols or phenolate ions which are easily oxidized yielding phenoxy radicals.

Keywords: acylphenols, Myristicaceae, gas-phase reactions, mass spectrometry, oxidative coupling

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