{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,10,24]],"date-time":"2026-10-24T04:22:21Z","timestamp":1792815741214,"version":"4.5.0"},"reference-count":48,"publisher":"MDPI AG","issue":"24","license":[{"start":{"date-parts":[[2024,12,10]],"date-time":"2024-12-10T00:00:00Z","timestamp":1733788800000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"name":"French region R\u00e9gion Hauts-de-France"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>Flavonoids have been documented to have good antioxidant activities in vitro. In recent years, reports on the antioxidant activities of flavone C-glycosides, a subclass of flavonoids, have attracted great attention. Despite the wealth of information on this subject, the correlation between structure and function is not well understood. In this work, the relationship between the structure and the antioxidant activity of 12 flavone C-glycosides extracted from the aerial part of winter linseed (Linum usitatissimum L.) was studied to fill the current gaps. Orientin, isoorientin, vitexin, isovitexin, swertisin, swertiajaponin, carlinoside, schaftoside, lucenin-1, lucenin-2, vicenin-1, and vicenin-2 were purified by preparative HPLC and by the drowning-out crystallization method. Then, the control of the purity and the confirmation of the chemical structures were assessed by LC-MS and NMR analyses. The antioxidant activity was evaluated using ABTS, CUPRAC, FRAP, and iron chelating activity in vitro assays. Luteolin and its flavone C-glycoside derivatives exhibited higher antioxidant activity than apigenin and its flavone C-glycosides derivatives. This could be attributed to the ortho-dihydroxyl groups at C-3\u2032 and C-4\u2032 of the B ring in the flavonoid skeleton, which seemed to play an important role in antioxidant behavior. These results indicate that the antioxidant activity of these compounds, derived from apigenin and luteolin, can be closely related to their structural characteristics, including the position and nature of the sugars, the number of hydroxyl groups, and the presence of methyl group.<\/jats:p>","DOI":"10.3390\/molecules29245829","type":"journal-article","created":{"date-parts":[[2024,12,10]],"date-time":"2024-12-10T11:17:20Z","timestamp":1733829440000},"page":"5829","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":24,"title":["Relationship Between the Structure of the Flavone C-Glycosides of Linseed (Linum usitatissimum L.) and Their Antioxidant Activity"],"prefix":"10.3390","volume":"29","author":[{"ORCID":"https:\/\/orcid.org\/0009-0000-6743-8136","authenticated-orcid":false,"given":"Imen","family":"Ghozzi","sequence":"first","affiliation":[{"name":"UMRT INRAE 1158 BioEcoAgro, BIOlogie des Plantes et Innovation (BIOPI), Universit\u00e9 de Picardie Jules Verne, IUT GB, Avenue des Facult\u00e9s, Le Bailly, 80025 Amiens, France"},{"name":"LR22ES04 Bioresources Environment Biotechnology, Institut Sup\u00e9rieur des Sciences Biologiques Appliqu\u00e9es de Tunis, Facult\u00e9 des Sciences de Tunis, Universit\u00e9 Tunis-El Manar, Tunis 2092, Tunisia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-8189-9238","authenticated-orcid":false,"given":"Jean-Xavier","family":"Fontaine","sequence":"additional","affiliation":[{"name":"UMRT INRAE 1158 BioEcoAgro, BIOlogie des Plantes et Innovation (BIOPI), Universit\u00e9 de Picardie Jules Verne, IUT GB, Avenue des Facult\u00e9s, Le Bailly, 80025 Amiens, France"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-4399-8838","authenticated-orcid":false,"given":"Roland","family":"Molini\u00e9","sequence":"additional","affiliation":[{"name":"UMRT INRAE 1158 BioEcoAgro, BIOlogie des Plantes et Innovation (BIOPI), Universit\u00e9 de Picardie Jules Verne, IUT GB, Avenue des Facult\u00e9s, Le Bailly, 80025 Amiens, France"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-5772-8030","authenticated-orcid":false,"given":"Redouan","family":"Elboutachfaiti","sequence":"additional","affiliation":[{"name":"UMRT INRAE 1158 BioEcoAgro, BIOlogie des Plantes et Innovation (BIOPI), Universit\u00e9 de Picardie Jules Verne, IUT GB, Avenue des Facult\u00e9s, Le Bailly, 80025 Amiens, France"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Lylia","family":"Akkouche","sequence":"additional","affiliation":[{"name":"UMRT INRAE 1158 BioEcoAgro, BIOlogie des Plantes et Innovation (BIOPI), Universit\u00e9 de Picardie Jules Verne, IUT GB, Avenue des Facult\u00e9s, Le Bailly, 80025 Amiens, France"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-8691-9576","authenticated-orcid":false,"given":"Khaled","family":"Sebei","sequence":"additional","affiliation":[{"name":"LR22ES04 Bioresources Environment Biotechnology, Institut Sup\u00e9rieur des Sciences Biologiques Appliqu\u00e9es de Tunis, Facult\u00e9 des Sciences de Tunis, Universit\u00e9 Tunis-El Manar, Tunis 2092, Tunisia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-5478-3029","authenticated-orcid":false,"given":"David","family":"Mathiron","sequence":"additional","affiliation":[{"name":"Plate-Forme Analytique, Universit\u00e9 de Picardie Jules Verne, 33 rue Saint Leu, 80039 Amiens, France"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-9938-0151","authenticated-orcid":false,"given":"Christophe","family":"Hano","sequence":"additional","affiliation":[{"name":"Institut de Chimie 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