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Deciphering the Unique Structure and Acylation Pattern of Posidonia oceanica Lignin

AuthorsRencoret, Jorge ; Marques, Gisela ; Serrano, Oscar ; Kaal, Joeri ; Martínez, Ángel T. ; Río Andrade, José Carlos del ; Gutiérrez Suárez, Ana
2D-NMR experiments
Organic chemistry
Issue Date24-Jul-2020
PublisherAmerican Chemical Society
CitationACS Sustainable Chemistry and Engineering 8(33): 12521–12533 (2020)
AbstractLignins from different parts of the seagrass Posidonia oceanica—namely sheaths, rhizome, and roots—as well as from fibrous balls from P. oceanica detritus were isolated and thoroughly characterized by pyrolysis coupled with gas chromatography/mass spectrometry, derivatization followed by reductive cleavage, two-dimensional nuclear magnetic resonance spectroscopy, and gel permeation chromatography. The lignins of P. oceanica were enriched in guaiacyl (G) over syringyl (S) units, with S/G ratios ranging from 0.1 (fibrous balls) to 0.5 (rhizome). β–O–4′ ethers and phenylcoumarans were the most abundant lignin substructures, followed by resinols, and minor amounts of dibenzodioxocins and spirodienones. Moreover, all lignins were found to be highly γ-acylated (up to 44% of total units), mainly with p-hydroxybenzoates but also, to a lesser extent, with acetates. The data indicated that this acylation extensively occurred in both G- and S-lignin units, contrary to what happens in palms, poplar, and willow, where p-hydroxybenzoates overwhelmingly appear at the γ-position of S-units.
Description13 páginas.- 6 figuras.- 3 tablas.- 49 referencias.- The Supporting Information is available free of charge at https://pubs.acs.org/doi/10.1021/acssuschemeng.0c03502
Publisher version (URL)http://dx.doi.org/10.1021/acssuschemeng.0c03502
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