Elucidating the modes of incorporation of the ferulic acid amides feruloyltyramine and feruloyloctopamine into the lignin-suberin fraction of potato periderms

del Río, José C.; Ralph, John; Benítez, José J.; Guzman-Puyol, Susana; Heredia-Guerrero, José A.; Rencoret, Jorge

doi:10.1016/j.ijbiomac.2025.145570

Elucidating the modes of incorporation of the ferulic acid amides feruloyltyramine and feruloyloctopamine into the lignin-suberin fraction of potato periderms

Journal Article · Thu Jun 26 00:00:00 EDT 2025 · International Journal of Biological Macromolecules

DOI:https://doi.org/10.1016/j.ijbiomac.2025.145570· OSTI ID:2574010

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Instituto de Recursos Naturales y Agrobiología de Sevilla (Spain)
University of Wisconsin-Madison, WI (United States)
Instituto de Ciencia de Materiales de Sevilla (Spain)
Instituto de Hortofruticultura Subtropical y Mediterránea La Mayora, Consejo Superior de Investigaciones Científicas-Universidad de Málaga (IHSM, CSIC-UMA), Malaga (Spain)

Ferulic acid amides are naturally present in the cell walls of potato (Solanum tuberosum) periderms. In this study, we investigated their modes of incorporation into the periderm cell wall polymers. A lignin/suberin-enriched fraction was isolated and analyzed by GPC, DFRC, and 2D-NMR. The analyses revealed that the lignin domain of this fraction was predominantly composed of G-lignin units, with an H:G:S ratio of 2:70:28 (S/G ratio of 0.40). More importantly, the data also indicated the presence of two ferulic acid amides, feruloyltyramine and feruloyloctopamine, that are incorporated into the lignin/suberin structure of potato periderms through a variety of linkages, including 8-O-4' and 4-O-beta' ether linkages, as well as 8-5' linkages forming a phenylcoumaran structure involving the ferulate moiety. Although the phenolic groups of the tyramine and octopamine moieties could theoretically undergo oxidation, potentially creating additional sites for radical coupling, our research indicates that these groups remain predominantly as free phenolic entities that do not participate in radical coupling. On the other hand, all the phenolic groups of the ferulate moieties are bound through ether linkages reinforcing the conclusion that the feruloyltyramine and feruloyloctopamine moieties are linked to lignin/suberin within the cell wall via radical coupling reactions.

View Accepted Manuscript (DOE)

Research Organization:: University of Wisconsin-Madison, WI (United States)

Sponsoring Organization:: USDOE Office of Science (SC), Biological and Environmental Research (BER)

Grant/Contract Number:: SC0018409

OSTI ID:: 2574010

Journal Information:: International Journal of Biological Macromolecules, Journal Name: International Journal of Biological Macromolecules Vol. 319; ISSN 0141-8130

Publisher:: ElsevierCopyright Statement

Country of Publication:: United States

Language:: English

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59 BASIC BIOLOGICAL SCIENCES
DFRC
Feruloyloctopamine
Feruloyltyramine
Lignin
NMR
Potato periderm
Suberin

Elucidating the modes of incorporation of the ferulic acid amides feruloyltyramine and feruloyloctopamine into the lignin-suberin fraction of potato periderms

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References (59)

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