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Matrix‐assisted laser desorption/ionization time‐of‐flight/time‐of‐flight tandem mass spectrometry (negative ion mode) of French Oak lignin: A novel series of lignin and tricin derivatives attached to carbohydrate and shikimic acid moieties
Author(s) -
Mikhael Abanoub,
Jurcic Kristina,
Fridgen Travis D.,
Delmas Michel,
Banoub Joseph
Publication year - 2020
Publication title -
rapid communications in mass spectrometry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.528
H-Index - 136
eISSN - 1097-0231
pISSN - 0951-4198
DOI - 10.1002/rcm.8841
Subject(s) - tricin , chemistry , lignin , shikimic acid , organic chemistry , carbohydrate , coniferyl alcohol , flavonoid , antioxidant
Rationale We report the top‐down lignomic analysis of the virgin released lignin (VRL) small oligomers obtained from French Oak wood. Methods We have used MALDI‐TOF‐MS in the negative ion mode for the analysis of the complex mixture of lignin oligomers extracted from French Oak wood. High‐energy CID‐TOF/TOF‐MS/MS analyses were used to support the postulated precursor ion structures. Results Twenty compounds were identified using MALDI‐TOF‐MS/MS of the VRL extracted from French Oak wood: seven tricin derivatives and/or flavonoids, three syringylglycerol derivatives, two syringol derivatives, two flavonolignin derivatives, and six miscellaneous compounds: luteoferol, lariciresinol isomer, 5‐hydroxy guaiacyl derivative, syringyl ‐C 10 H 10 O 2 dimer, trihydroxy benzaldehyde derivative, and aryl tetralin lignan derivative. Most of the identified compounds were in the form of carbohydrate and/or shikimic acid complexes. Conclusions The analysis of this complex mixture led to the identification of a series of lignin dimers, novel lignin‐carbohydrate complexes (LCC), and unique tricin derivatives linked to different types of carbohydrates and shikimic acid moieties. This finding supports the presence of lignin‐carbohydrate complexes in the isolated VRL. These analyses also showed that French Oak lignin is abundant in syringol moieties present in the lignin syringyl units or tricin derivatives. Moreover, the identification of some lignin‐carbohydrate and/or flavonoid‐shikimic acid complexes could provide new insight into the relationship between the biosynthesis of lignin and tricin.