Evidence map›Paper›PMID 34662399›Full record

ArticlePlant physiology2022

Flavonoids naringenin chalcone, naringenin, dihydrotricin, and tricin are lignin monomers in papyrus.

Jorge Rencoret, Mario J Rosado, Hoon Kim, Vitaliy I Timokhin, Ana Gutiérrez, Florian Bausch, Thomas Rosenau, Antje Potthast, John Ralph, José C Del Río

Open access · hybridAbstract read
In one paragraph

Article in Plant physiology, 2022. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 16 papers.

0numbers the graph read from it
0cells of the map it votes in
16citing papers in PubMed
2.9field-weighted citation impact, top 9% of its field
1 · What the graph read from it

What it found

Each row is one number read from the abstract, on the scale the paper reported it, with its interval. Left of the dashed line favours the treatment, right favours the comparator. Under each row is the sentence it came from. New to these charts? A ten-minute tutorial.

The abstract states no effect estimate the extractor could read, or names no intervention and outcome on the map, so this paper lights no cell and moves no belief. It is still indexed, cited and linked below.

2 · The registry

The trial behind it

Trials whose registry record cites this paper, or whose number appears in the abstract. A trial that started after this paper was published is citing it as background, not reporting it.

Neither the registry nor the abstract names a trial number. If this is a trial report, that itself is worth knowing.

3 · Its place in the literature

Who cites it

16 citing papers in PubMed, 52 citations in OpenAlex.

  1. Article
  2. Article
  3. Review
  4. Article
  5. Article
  6. Review
  7. Article
  8. Article
  9. Lignin, the Lignification Process, and Advanced, Lignin-Based Materials.International journal of molecular sciences · 2023
    Review
  10. Article
  11. Article
  12. Article
  13. Article
  14. Article
  15. Article
  16. The Sorghum (Frontiers in plant science · 2021
    Article
4 · The record

Corrections and comments

PubMed lists nothing against this paper. Absence here is not a guarantee, only a check that was made.

5 · Who and what money

Authors and funding

10 authors at 3 institutions in 3 countries.

Jorge RencoretInstituto de Recursos Naturales y Agrobiología de Sevilla (IRNAS), CSIC, Avda. Reina Mercedes, 10, 41012-Seville, Spain.ORCID 0000-0003-2728-7331
Mario J RosadoInstituto de Recursos Naturales y Agrobiología de Sevilla (IRNAS), CSIC, Avda. Reina Mercedes, 10, 41012-Seville, Spain.ORCID 0000-0001-6313-1890
Hoon KimDepartment of Energy Great Lakes Bioenergy Research Center, The Wisconsin Energy Institute, University of Wisconsin-Madison, Madison, Wisconsin 53726, USA.ORCID 0000-0001-7425-7464
Vitaliy I TimokhinDepartment of Energy Great Lakes Bioenergy Research Center, The Wisconsin Energy Institute, University of Wisconsin-Madison, Madison, Wisconsin 53726, USA.ORCID 0000-0002-6978-1242
Ana GutiérrezInstituto de Recursos Naturales y Agrobiología de Sevilla (IRNAS), CSIC, Avda. Reina Mercedes, 10, 41012-Seville, Spain.ORCID 0000-0002-8823-9029
Florian BauschInstitute of Chemistry of Renewable Resources, University of Natural Resources and Life Sciences Vienna (BOKU), Konrad-Lorenz-Straße 24, A-3430 Tulln, Austria.ORCID 0000-0002-7076-2356
Thomas RosenauInstitute of Chemistry of Renewable Resources, University of Natural Resources and Life Sciences Vienna (BOKU), Konrad-Lorenz-Straße 24, A-3430 Tulln, Austria.ORCID 0000-0002-6636-9260
Antje PotthastInstitute of Chemistry of Renewable Resources, University of Natural Resources and Life Sciences Vienna (BOKU), Konrad-Lorenz-Straße 24, A-3430 Tulln, Austria.ORCID 0000-0003-1981-2271
John RalphDepartment of Energy Great Lakes Bioenergy Research Center, The Wisconsin Energy Institute, University of Wisconsin-Madison, Madison, Wisconsin 53726, USA.ORCID 0000-0002-6093-4521
José C Del RíoInstituto de Recursos Naturales y Agrobiología de Sevilla (IRNAS), CSIC, Avda. Reina Mercedes, 10, 41012-Seville, Spain.ORCID 0000-0002-3040-6787
Instituto de Recursos Naturales y Agrobiología de Sevilla · ESBOKU University · ATUniversity of Wisconsin–Madison · US

Funding

No grant is acknowledged in the PubMed record.

6 · The paper itself

Abstract

Recent studies demonstrate that several polyphenolic compounds produced from beyond the canonical monolignol biosynthetic pathways can behave as lignin monomers, participating in radical coupling reactions and being incorporated into lignin polymers. Here, we show various classes of flavonoids, the chalconoid naringenin chalcone, the flavanones naringenin and dihydrotricin, and the flavone tricin, incorporated into the lignin polymer of papyrus (Cyperus papyrus L.) rind. These flavonoids were released from the rind lignin by Derivatization Followed by Reductive Cleavage (DFRC), a chemical degradative method that cleaves the β-ether linkages, indicating that at least a fraction of each was integrated into the lignin as β-ether-linked structures. Due to the particular structure of tricin and dihydrotricin, whose C-3' and C-5' positions at their B-rings are occupied by methoxy groups, these compounds can only be incorporated into the lignin through 4'-O-β bonds. However, naringenin chalcone and naringenin have no substituents at these positions and can therefore form additional carbon-carbon linkages, including 3'- or 5'-β linkages that form phenylcoumaran structures not susceptible to cleavage by DFRC. Furthermore, Nuclear Magnetic Resonance analysis indicated that naringenin chalcone can also form additional linkages through its conjugated double bond. The discovery expands the range of flavonoids incorporated into natural lignins, further broadens the traditional definition of lignin, and enhances the premise that any phenolic compound present at the cell wall during lignification could be oxidized and potentially integrated into the lignin structure, depending only on its chemical compatibility. This study indicates that papyrus lignin has a unique structure, as it is the only lignin known to date that integrates such a diversity of phenolic compounds from different classes of flavonoids. This discovery will open up new ways to engineer and design lignins with specific properties and for enhanced value.

Indexed as

Binding SitesMolecular StructureBiosynthetic PathwaysCyperusEgyptFlavonoidsLigninFlavonoidsLignin

Identifiers

PMID34662399
PMCPMC8774827
OpenAlexW3205111568

What OpenQuestion holds

Textmetadata
LicenceCC BY-NC-ND
Read underepoch 390

Registered trials

None linked

Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.