Identification of lignans by liquid chromatography‐electrospray ionization ion‐trap mass spectrometry

Abstract

The fragmentation pattern of 30 compounds belonging to different classes of the lignan family was studied by liquid chromatography-electrospray ionization ion-trap mass spectrometry. On the basis of the observed fragmentation patterns, identification of different types of lignans was achieved. For example, dibenzylbutyrolactone lignans showed a characteristic fragmentation pathway by the loss of 44 Da (CO(2)) from the lactone moiety, whereas dibenzylbutanediols showed a loss of 48 Da by a combined loss of formaldehyde and water from the 1,4-butanediol moiety. Lignan glycosides readily lost the sugar residue to give the parent lignan as their primary product ion. In addition, several compound-specific fragmentations were observed and used for identification of individual compounds.A versatile method for analyses of lignans was developed using LC separation on a C8 column followed by fragmentation and detection of ions produced in the ion trap.

LC‐DAD/ESI‐MS/MS study of phenolic compounds in ash (Fraxinus excelsior L. and F. americana L.) heartwood. Effect of toasting intensity at cooperage

“…Another dilignol belonging to the 8-8´link-age group is compound 32, tentatively identified as syringaresinol since their [M-H] -and fragmentation ions were consistent with data previously reported in the literature. [31,32] Syringaresinol was also detected in ash thermal treated wood (200 C, 4 h) using GC-MS 15 , and in the phloem of F. americana by LC-MS. [12] On the basis of the fragmentation patterns, compounds 13, 15 and 22 were characterized as b-aryl ether dilignols. [31] Consecutive losses of formaldehyde and water and A -and B -products ions allowed the characterization of the bonding structure and the aromatic units involved in these dimers (m/z 195 or m/z 179 for guaiacyl A or B ions, respectively; m/z 225 for syringyl A -ion, and m/z 223 for unit derived for sinapaldehyde).…”

“…Peaks 9, 11,13,15,22,26,27,32,33,34,36,38,39,46,48, 50, 52, 54 and 55 were identified as dilignols or oligolignols, using literature data for UV/Vis absorbance and mass spectra when standards were not available. Among them, different class of dilignols and oligolignols were identified.…”

A Key Role for Apoplastic H2O2 in Norway Spruce Phenolic Metabolism

“…Metabolic conversion types were selected from the list given by Morreel et al (2014) based on their prevalence in CSPP networks and presumed presence in gymnosperms. Structural elucidation of the multiplestage mass spectrometry fragmentation MS n spectra was based on Eklund et al (2008) and Morreel et al (2004Morreel et al ( , 2010aMorreel et al ( , 2010b for the (neo)lignans/oligolignols, on Cuyckens and Claeys (2004), Fabre et al (2001), Hughes et al (2001), Morreel et al (2006), and Hvattum and Ekeberg (2003) for the flavonoids, on Zhou et al (2013) and Abu-Reidah et al (2014) for the C-glycosylated flavanones, on Morreel et al (2014) for the phenylpropanoids/benzenoids, and on Gu et al (2003) and Jaiswal et al (2012) for the condensed tannins. Shorthand names for the oligolignols are as explained by Morreel et al (2004).…”

Simultaneous quantification of lignans in Arabidopsis thaliana by highly sensitive capillary liquid chromatography-electrospray ionization-ion trap mass spectrometry

“…Recently, a combination of liquid chromatography and electrospray ionization mass spectrometry (LC-ESI-MS) has become a sensitive method for lignan analysis (Eklund et al 2008;). Since the sensitivity of LC-ESI-MS can be increased by lowering the flow rate of the mobile phase, capillary LC-ESI-MS systems with narrow diameter LC columns are more sensitive than conventional LC-ESI-MS systems (Abian et al 1999;Hopfgartner et al 1993).…”