Substitution pattern elucidation of hydroxypropyl Pinus pinaster (Ait.) bark polyflavonoid derivatives by ESI(-)-MS/MS - Université de Lorraine Accéder directement au contenu
Article Dans Une Revue Journal of Mass Spectrometry Année : 2014

Substitution pattern elucidation of hydroxypropyl Pinus pinaster (Ait.) bark polyflavonoid derivatives by ESI(-)-MS/MS

Résumé

The structure of condensed tannins (CTs) from Pinus pinaster bark extract and their hydroxypropylated derivatives with four degrees of substitution (DS 1, 2, 3 and 4) has been characterized for the first time using negative-ion mode electrospray ionization tandem mass spectrometry (ESI(-)-MS/MS). The results showed that P. pinaster bark CTs possess structural homogeneity in terms of monomeric units (C-15, catechin). The oligomer sizes were detected to be dimers to heptamers. The derivatives showed typical phenyl-propyl ether mass fragmentation by substituent elimination (58amu) and inherent C-15 flavonoid fissions. The relative abundance of the product ions revealed a preferential triple, tetra-/penta- and octa- hydroxypropylation substitution pattern in the monomer, dimer and trimer derivatives, respectively. A defined order of -OH reactivity towards propylene oxide was established by means of multistage experiments (A-ringB-ring>C-ring). A high structural heterogeneity of the modified oligomers was detected.

Dates et versions

hal-01597793 , version 1 (28-09-2017)

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Danny E. Garcia Marrero, Wolfgang G. Glasser, Antonio Pizzi, Sebastian Paczkowski, Marie-Pierre G. Laborie. Substitution pattern elucidation of hydroxypropyl Pinus pinaster (Ait.) bark polyflavonoid derivatives by ESI(-)-MS/MS. Journal of Mass Spectrometry, 2014, 49 (10), pp.1050-1058. ⟨10.1002/jms.3431⟩. ⟨hal-01597793⟩
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