{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,24]],"date-time":"2026-09-24T13:02:51Z","timestamp":1790254971143,"version":"4.1.0"},"reference-count":45,"publisher":"American Chemical Society (ACS)","issue":"38","license":[{"start":{"date-parts":[[2026,9,14]],"date-time":"2026-09-14T00:00:00Z","timestamp":1789344000000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":[],"published-print":{"date-parts":[[2026,9,24]]},"abstract":"<jats:title>Abstract<\/jats:title>\n                  <jats:p>The antioxidant properties of polydatin\/piceid (3-O-\u03b2-D-glucopyranosyl-resveratrol), a stilbenoid polyphenol widely found in Vitaceae, Liliaceae, and Leguminosae plants and used in traditional medicine, have been investigated against the \u2022OOH radical by means of a density functional theory-based QM-ORSA protocol. The central mechanistic question addressed is how 3-O-glucosylation modulates the primary antiradical activity. To provide a biologically meaningful answer, its mechanisms of action were studied in both aqueous solution at physiological pH and in a lipid-like environment. Conformational analysis performed at the outset confirmed that the trans isomer is preferred over the cis form by 4.9 kcal\u00b7mol\u20131, and species distribution calculations show that the neutral form dominates at pH 7.4 (98.6%). The para-hydroxyl of ring B emerges as the dominant contributor to anti-\u2022OOH activity regardless of the milieu; however, the activity trends show that while polydatin reacts faster than Trolox in the modeled lipid-like phase (9.78 \u00d7 103 vs. 3.40 \u00d7 103 M\u20131\u00b7s\u20131), in water its apparent rate constant (4.12 \u00d7 104 M\u20131\u00b7s\u20131) falls below both trans-resveratrol (1.42 \u00d7 105 M\u20131\u00b7s\u20131) and Trolox (8.96 \u00d7 104 M\u20131\u00b7s\u20131).<\/jats:p>","DOI":"10.1021\/acs.jpcb.6c03897","type":"journal-article","created":{"date-parts":[[2026,9,15]],"date-time":"2026-09-15T04:02:25Z","timestamp":1789444945000},"page":"9981-9988","source":"Crossref","is-referenced-by-count":0,"title":["How 3-\n                    <i>O<\/i>\n                    -Glucosylation\nModulates Resveratrol Radical Scavenging: A QM-ORSA Study of Polydatin\/Piceid,\na Stilbenoid Glucoside"],"prefix":"10.1021","volume":"130","author":[{"ORCID":"https:\/\/orcid.org\/0000-0002-8012-1026","authenticated-orcid":true,"given":"Maciej","family":"Spiegel","sequence":"first","affiliation":[{"name":"Wroclaw Medical University , , ,","place":["Wroclaw, Poland, 50-556"]},{"name":"Universita\u0300 della Calabria , , ,","place":["Rende, Italy, 87036"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-3826-3386","authenticated-orcid":true,"given":"Nino","family":"Russo","sequence":"additional","affiliation":[{"name":"Universita\u0300 della Calabria , , ,","place":["Rende, Italy, 87036"]}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"316","published-online":{"date-parts":[[2026,9,14]]},"reference":[{"issue":"19","key":"2026092408092039600_cit1","doi-asserted-by":"publisher","first-page":"6474","DOI":"10.3390\/molecules27196474","article-title":"Polydatin: Pharmacological\nMechanisms, Therapeutic Targets, Biological Activities, and Health\nBenefits","volume":"27","author":"Karami","year":"2022","journal-title":"Molecules"},{"key":"2026092408092039600_cit2","doi-asserted-by":"publisher","first-page":"22","DOI":"10.1016\/j.jchromb.2019.04.005","article-title":"Comprehensive Metabolism\nStudy of\nPolydatin in Rat Plasma and Urine Using Ultra-High Performance Liquid\nChromatography Coupled with High-Resolution Mass Spectrometry","volume":"1117","author":"Mei","year":"2019","journal-title":"J. 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Mechanistic Insights into Antiradical\nActivity of Eckol","volume":"26","author":"Spiegel","year":"2025","journal-title":"Int. J. Mol. Sci"},{"issue":"9","key":"2026092408092039600_cit42","doi-asserted-by":"publisher","first-page":"3257","DOI":"10.1021\/acs.joc.4c02837","article-title":"A Comprehensive Experimental and Theoretical Investigation\nof the Antioxidant Properties of Hispidin and Isohispidin","volume":"90","author":"Boulebd","year":"2025","journal-title":"J. Org. Chem"},{"issue":"13","key":"2026092408092039600_cit43","doi-asserted-by":"publisher","first-page":"4642","DOI":"10.1039\/c3cp43319f","article-title":"A Physicochemical Examination\nof the Free Radical Scavenging Activity of Trolox: Mechanism, Kinetics\nand Influence of the Environment","volume":"15","author":"Alberto","year":"2013","journal-title":"Phys. Chem.\nChem. 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