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Peer-reviewedCC BYJournal of agricultural and food chemistry

Flavoglycans: Evidence for Covalent Proanthocyanidin-Polysaccharide Linkages in Western Redcedar Bark.

  • Gio Ferson M Bautista1,2
  • Oliver Musl3
  • Markus Bacher3
  • Zhicheng Xia1
  • Julia L Azzi2,4
  • Antje Potthast3
  • Thomas Rosenau3
  • Orlando J Rojas1,2,4,5
5 affiliations
  1. 1Department of Chemistry, The University of British Columbia, 2036 Main Mall, Vancouver, BCV6T 1Z1, Canada.
  2. 2Bioproducts Institute, The University of British Columbia, 2385 East Mall, Vancouver, BCV6T 1Z4, Canada.
  3. 3Department of Natural Sciences and Sustainable Resources, Institute of Chemistry of Renewable Resources, BOKU University, Konrad-Lorenz-Strasse 24, 3430Tulln, Austria.
  4. 4Department of Chemical and Biological Engineering, The University of British Columbia, 2360 East Mall, Vancouver, BCV6T 1Z3, Canada.
  5. 5Department of Wood Science, The University of British Columbia, 2424 Main Mall #2900, Vancouver, BCV6T 1Z1, Canada.
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Abstract

We investigated covalent linkages between proanthocyanidins (PAs) and cell wall polysaccharides in western redcedar bark (Thuja plicata Donn), a tannin-rich forestry co-product that has potential as a functional food ingredient. An alcohol-insoluble residue (AIR; 1.0% w/w relative to oven-dried bark) recovered from aqueous extracts contained both PAs (≥1.46% w/w of AIR) and polysaccharides (∼30% w/w of AIR) and resisted fractionation by inert solvents, consistent with recalcitrant PA-carbohydrate association. Acidic butanol hydrolysis coupled with LC-MS revealed diagnostic C-glycosylated anthocyanidins, including 6-C-pentosylcyanidin, 8-C-(deoxyhexosyl)cyanidin, and X-C-(deoxyhexosyl)-Y-C-pentosyldelphinidin. NMR analysis supported the presence of PA-polysaccharide conjugates, implicating hemicelluloses and pectins as the carbohydrate partners. These "flavoglycans" provide a chemical basis for incomplete tannin extractability from bark matrices and suggest that carbohydrate conjugation can modulate PA accessibility and interfacial interactions in aqueous systems relevant to bioactive recovery from bark matrices. Overall, this research provides converging lines of experimental evidence suggestive of C-glycosyl crosslinking between proanthocyanidins and carbohydrates in bark.

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Cite

BibTeXRIS
BibTeX
@article{bautista2026flavoglycans,
  title = {{Flavoglycans: Evidence for Covalent Proanthocyanidin-Polysaccharide Linkages in Western Redcedar Bark.}},
  author = {Gio Ferson M Bautista and Oliver Musl and Markus Bacher and Zhicheng Xia and Julia L Azzi and Antje Potthast and Thomas Rosenau and Orlando J Rojas},
  journal = {Journal of agricultural and food chemistry},
  year = {2026},
  month = sep,
  doi = {10.1021/acs.jafc.6c03146},
  url = {https://europepmc.org/article/MED/42916546},
  note = {CC BY},
}
RIS
TY  - JOUR
TI  - Flavoglycans: Evidence for Covalent Proanthocyanidin-Polysaccharide Linkages in Western Redcedar Bark.
AU  - Gio Ferson M Bautista
AU  - Oliver Musl
AU  - Markus Bacher
AU  - Zhicheng Xia
AU  - Julia L Azzi
AU  - Antje Potthast
AU  - Thomas Rosenau
AU  - Orlando J Rojas
PY  - 2026
DA  - 2026/09/01
JO  - Journal of agricultural and food chemistry
DO  - 10.1021/acs.jafc.6c03146
UR  - https://europepmc.org/article/MED/42916546
AB  - We investigated covalent linkages between proanthocyanidins (PAs) and cell wall polysaccharides in western redcedar bark (Thuja plicata Donn), a tannin-rich forestry co-product that has potential as a functional food ingredient. An alcohol-insoluble residue (AIR; 1.0% w/w relative to oven-dried bark) recovered from aqueous extracts contained both PAs (≥1.46% w/w of AIR) and polysaccharides (∼30% w/w of AIR) and resisted fractionation by inert solvents, consistent with recalcitrant PA-carbohydrate association. Acidic butanol hydrolysis coupled with LC-MS revealed diagnostic C-glycosylated anthocyanidins, including 6-C-pentosylcyanidin, 8-C-(deoxyhexosyl)cyanidin, and X-C-(deoxyhexosyl)-Y-C-pentosyldelphinidin. NMR analysis supported the presence of PA-polysaccharide conjugates, implicating hemicelluloses and pectins as the carbohydrate partners. These "flavoglycans" provide a chemical basis for incomplete tannin extractability from bark matrices and suggest that carbohydrate conjugation can modulate PA accessibility and interfacial interactions in aqueous systems relevant to bioactive recovery from bark matrices. Overall, this research provides converging lines of experimental evidence suggestive of C-glycosyl crosslinking between proanthocyanidins and carbohydrates in bark.
SN  - 0021-8561
SN  - 1520-5118
ER  -