{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,10,23]],"date-time":"2026-10-23T19:43:11Z","timestamp":1792784591043,"version":"4.5.0"},"reference-count":73,"publisher":"American Chemical Society (ACS)","issue":"37","license":[{"start":{"date-parts":[[2026,9,10]],"date-time":"2026-09-10T00:00:00Z","timestamp":1788998400000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"DOI":"10.13039\/501100000196","name":"Canada Foundation for Innovation","doi-asserted-by":"publisher","award":["38623"],"award-info":[{"award-number":["38623"]}],"id":[{"id":"10.13039\/501100000196","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100002784","name":"Canada Excellence Research Chairs, Government of Canada","doi-asserted-by":"publisher","award":["CERC-2018-00006"],"award-info":[{"award-number":["CERC-2018-00006"]}],"id":[{"id":"10.13039\/501100002784","id-type":"DOI","asserted-by":"publisher"}]},{"name":"British Columbia Ministry of Forests"},{"name":"Pacific Economic Development Canada","id":[{"id":"https:\/\/ror.org\/03pkrdc36","id-type":"ROR","asserted-by":"crossref"}]},{"name":"County of Lower Austria"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":[],"published-print":{"date-parts":[[2026,9,23]]},"abstract":"<jats:title>Abstract<\/jats:title>\n                  <jats:p>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 (\u22651.46% w\/w of AIR) and polysaccharides (\u223c30% w\/w of AIR) and resisted fractionation by inert solvents, consistent with recalcitrant PA\u2013carbohydrate association. Acidic butanol hydrolysis coupled with LC\u2013MS 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\u2013polysaccharide conjugates, implicating hemicelluloses and pectins as the carbohydrate partners. These \u201cflavoglycans\u201d 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.<\/jats:p>","DOI":"10.1021\/acs.jafc.6c03146","type":"journal-article","created":{"date-parts":[[2026,9,11]],"date-time":"2026-09-11T02:01:33Z","timestamp":1789092093000},"page":"29020-29032","source":"Crossref","is-referenced-by-count":0,"title":["Flavoglycans: Evidence\nfor Covalent Proanthocyanidin\u2013Polysaccharide\nLinkages in Western Redcedar Bark"],"prefix":"10.1021","volume":"74","author":[{"ORCID":"https:\/\/orcid.org\/0000-0002-1815-5284","authenticated-orcid":true,"given":"Gio Ferson M.","family":"Bautista","sequence":"first","affiliation":[{"name":"The University of British Columbia , , 2036 Main Mall , , ,","place":["Vancouver, BC, Canada, V6T 1Z1"]},{"name":"The University of British Columbia , , 2385 East Mall , , ,","place":["Vancouver, BC, Canada, V6T 1Z4"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-8430-1684","authenticated-orcid":true,"given":"Oliver","family":"Musl","sequence":"additional","affiliation":[{"name":"BOKU University , , Konrad-Lorenz-Strasse 24 , ,","place":["Tulln, Austria, 3430"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-4307-4849","authenticated-orcid":true,"given":"Markus","family":"Bacher","sequence":"additional","affiliation":[{"name":"BOKU University , , Konrad-Lorenz-Strasse 24 , ,","place":["Tulln, Austria, 3430"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Zhicheng","family":"Xia","sequence":"additional","affiliation":[{"name":"The University of British Columbia , , 2036 Main Mall , , ,","place":["Vancouver, BC, Canada, V6T 1Z1"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Julia L.","family":"Azzi","sequence":"additional","affiliation":[{"name":"The University of British Columbia , , 2385 East Mall , , ,","place":["Vancouver, BC, Canada, V6T 1Z4"]},{"name":"The University of British Columbia , , 2360 East Mall , , ,","place":["Vancouver, BC, Canada, V6T 1Z3"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-1981-2271","authenticated-orcid":true,"given":"Antje","family":"Potthast","sequence":"additional","affiliation":[{"name":"BOKU University , , Konrad-Lorenz-Strasse 24 , ,","place":["Tulln, Austria, 3430"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-6636-9260","authenticated-orcid":true,"given":"Thomas","family":"Rosenau","sequence":"additional","affiliation":[{"name":"BOKU University , , Konrad-Lorenz-Strasse 24 , ,","place":["Tulln, Austria, 3430"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-4036-4020","authenticated-orcid":true,"given":"Orlando J.","family":"Rojas","sequence":"additional","affiliation":[{"name":"The University of British Columbia , , 2036 Main Mall , , ,","place":["Vancouver, BC, Canada, V6T 1Z1"]},{"name":"The University of British Columbia , , 2385 East Mall , , ,","place":["Vancouver, BC, Canada, V6T 1Z4"]},{"name":"The University of British Columbia , , 2360 East Mall , , ,","place":["Vancouver, BC, Canada, V6T 1Z3"]},{"name":"The University of British Columbia , , 2424 Main Mall #2900 , , ,","place":["Vancouver, BC, Canada, V6T 1Z1"]}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"316","published-online":{"date-parts":[[2026,9,10]]},"reference":[{"issue":"1","key":"2026092310072643800_cit1","doi-asserted-by":"publisher","first-page":"71","DOI":"10.1023\/A:1021115300942","article-title":"The Functions of Cell Wall Polysaccharides in Composition\nand Architecture Revealed through Mutations","volume":"247","author":"Carpita","year":"2002","journal-title":"Plant Soil"},{"key":"2026092310072643800_cit2","doi-asserted-by":"crossref","first-page":"131","DOI":"10.1002\/9781119545958.ch6","article-title":"Challenges in\nAnalyzing Bioactive Proanthocyanidins","volume-title":"Recent Adv. 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Agric. Food Chem."},{"key":"2026092310072643800_cit26","doi-asserted-by":"publisher","first-page":"1110","DOI":"10.1016\/j.foodchem.2017.07.001","article-title":"Structural Characterization of Proanthocyanidins\nfrom Adzuki Seed Coat","volume":"239","author":"Kawakami","year":"2018","journal-title":"Food Chem."},{"key":"2026092310072643800_cit27","doi-asserted-by":"crossref","first-page":"385","DOI":"10.1007\/978-1-4615-3476-1_21","article-title":"The Nature\nof Non-Proanthocyanidin Units in \u2018Condensed Tannins\u2019\nfrom Conifer Wood and Bark","volume-title":"Plant Polyphenols:\nSynthesis, Properties, Significance","author":"Hergert","year":"1992"},{"issue":"9","key":"2026092310072643800_cit28","doi-asserted-by":"publisher","first-page":"5601","DOI":"10.1021\/acs.biomac.5c00271","article-title":"Strong Association\nbetween Proanthocyanidins and Polysaccharides in the Cell Walls of\nWestern Redcedar Bark","volume":"26","author":"Bautista","year":"2025","journal-title":"Biomacromolecules"},{"issue":"1","key":"2026092310072643800_cit29","doi-asserted-by":"publisher","first-page":"223","DOI":"10.1016\/S0031-9422(00)94533-3","article-title":"The Conversion\nof Procyanidins and\nProdelphinidins to Cyanidin and Delphinidin","volume":"25","author":"Porter","year":"1985","journal-title":"Phytochemistry"},{"issue":"43","key":"2026092310072643800_cit30","doi-asserted-by":"publisher","first-page":"9471","DOI":"10.1021\/acs.jafc.5b04106","article-title":"Sodium Hydroxide Enhances Extractability\nand Analysis\nof Proanthocyanidins in Ensiled Sainfoin (Onobrychis Viciifolia)","volume":"63","author":"Ramsay","year":"2015","journal-title":"J. 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Plant Pathol."},{"issue":"1","key":"2026092310072643800_cit34","doi-asserted-by":"publisher","first-page":"5","DOI":"10.1111\/cote.12385","article-title":"Extraction of Anthocyanins from Aronia Melanocarpa\nSkin Waste as a Sustainable Source of Natural Colorants","volume":"135","author":"Wathon","year":"2019","journal-title":"Color. Technol."},{"issue":"3","key":"2026092310072643800_cit35","doi-asserted-by":"publisher","first-page":"115","DOI":"10.1016\/S0315-5463(80)73348-5","article-title":"Estimation Qualitative\net Quantitative de La Matie\u0300re Colorante Des Jus et Vins de\nFruits","volume":"13","author":"Simard","year":"1980","journal-title":"Can. Inst. Food Sci. Technol. 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