Beyond Solanaceae: Incorporation of Feruloyltyramine and Feruloyloctopamine into Cannabaceae Lignins

Journal Article · Mon Apr 13 00:00:00 EDT 2026 · Plant Physiology

DOI:https://doi.org/10.1093/plphys/kiag202· OSTI ID:3029012

Rencoret, Jorge ^[1]; Martín-Alvarado, David ^[1]; Ralph, John ^[2]; del Río, José C ^[1]

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1. Instituto de Recursos Naturales y Agrobiología de Sevilla, CSIC , Avda. Reina Mercedes, 10, 41012-Seville ,
2. Department of Energy Great Lakes Bioenergy Research Center, the Wisconsin Energy Institute, University of Wisconsin-Madison , Madison, WI 53726 ,; Department of Biochemistry, University of Wisconsin-Madison , Madison, WI 53706 ,

Abstract The ferulic acid amides feruloyltyramine and feruloyloctopamine have been widely reported as integral constituents in the lignins in several species of Solanaceae in which they function as authentic lignin monomers. In the present study, we demonstrate that these ferulic acid amides are likewise incorporated into the lignins of species within Cannabaceae, including hemp (Cannabis sativa), hops (Humulus lupulus), and European nettle tree (Celtis australis). Structural analyses using Derivatization Followed by Reductive Cleavage (DFRC) and two-dimensional Nuclear Magnetic Resonance (2D-NMR) spectroscopy revealed that these ferulic acid amides are incorporated via 4−O- and 8−O-ether linkages, as well as through 8−5′ linkages forming phenylcoumaran structures. Examination of a broad phylogenetic range of plant families demonstrated the absence of these ferulic acid amides from the lignins of all families studied except Solanaceae and Cannabaceae. Given the distant phylogenetic relationship between Solanaceae and Cannabaceae, the recruitment of these ferulic acid amides as lignin monomers in both lineages likely constitutes a case for convergent evolution at the level of lignin biosynthetic pathways. The significance of these ferulic acid amides lies in their unique role as the sole nitrogen-containing phenolic compounds known to participate in lignin formation.

• Research Organization: Great Lakes Bioenergy Research Center (GLBRC) (GLBRC)
• Sponsoring Organization: USDOE Office of Science (SC), Biological and Environmental Research (BER)
• Grant/Contract Number: SC0018409
• OSTI ID: 3029012
• Journal Information: Plant Physiology, Journal Name: Plant Physiology; ISSN 0032-0889; ISSN 1532-2548
• Publisher: Oxford University Press (OUP)
• Country of Publication: United States
• Language: English

Related Subjects

Cannabaceae
European nettle tree
Feruloyltyramine
hemp
hops
lignin