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Highly acylated (acetylated and/or p-coumaroylated) native lignins from diverse herbaceous plants

AuthorsRío Andrade, José Carlos del ; Rencoret, Jorge ; Marques, Gisela ; Gutiérrez Suárez, Ana ; Ibarra, David ; Santos, José Ignacio ; Jiménez-Barbero, Jesús ; Zhang, L.; Martínez, Ángel T.
Herbaceous plants
Sinapyl acetate
Sinapyl p-coumarate
Issue Date2008
PublisherAmerican Chemical Society
CitationJournal of Agricultural and Food Chemistry 56: 9525-9534 (2008)
AbstractThe structure of lignins isolated from the herbaceous plants sisal (Agave sisalana), kenaf (Hibiscus cannabinus), abaca (Musa textilis) and curaua (Ananas erectifolius) has been studied upon spectroscopic (2D-NMR) and chemical degradative (Derivatization Followed by Reductive Cleavage) methods. The analyses demonstrate that the structure of the lignins from these plants is highly remarkable, being extensively acylated at the γ-carbon of the lignin side-chain (up to 80% acylation) with acetate and/or p-coumarate groups, and preferentially over syringyl units. While the lignins from sisal and kenaf are γ-acylated exclusively with acetate groups, the lignins from abaca and curaua are esterified with acetate and p-coumarate groups. The structures of all these highly-acylated lignins are characterized by a very high syringyl/guaiacyl ratio, a large predominance of β-O-4´ linkages (up to 94% of all linkages) and a strikingly low proportion of traditional β-β´linkages, which indeed are completely absent in the lignins from abaca and curaua. The occurrence of β-β´ homo-coupling and cross-coupling products of sinapyl acetate in the lignins from sisal and kenaf indicates that sinapyl alcohol is acetylated at monomer stage and that, therefore, sinapyl acetate should be considered as a real monolignol involved in the lignification reactions.
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