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

Abstract : 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.
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https://hal.univ-lorraine.fr/hal-01597793
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Submitted on : Thursday, September 28, 2017 - 5:19:16 PM
Last modification on : Tuesday, March 20, 2018 - 10:17:42 AM

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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, Wiley-Blackwell, 2014, 49 (10), pp.1050-1058. ⟨10.1002/jms.3431⟩. ⟨hal-01597793⟩

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