{
  "abstract": "The antioxidant properties of polydatin/piceid (3-O-β-D-glucopyranosyl-resveratrol), a stilbenoid polyphenol widely found in Vitaceae, Liliaceae, and Leguminosae plants and used in traditional medicine, have been investigated against the •OOH 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·mol-1, 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-•OOH 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 × 103 vs. 3.40 × 103 M-1·s-1), in water its apparent rate constant (4.12 × 104 M-1·s-1) falls below both trans-resveratrol (1.42 × 105 M-1·s-1) and Trolox (8.96 × 104 M-1·s-1).",
  "abstract_shown": true,
  "affiliations": [
    "Department of Organic Chemistry and Pharmaceutical Technology, Faculty of Pharmacy, Wroclaw Medical University, Wroclaw50-556, Poland.",
    "Department of Chemistry and Chemical Technologies, Università della Calabria, Rende87036, Italy."
  ],
  "article_type": "research article",
  "arxiv": null,
  "author_total": 2,
  "authors": [
    {
      "affs": [
        0,
        1
      ],
      "name": "Maciej Spiegel",
      "orcid": "0000-0002-8012-1026"
    },
    {
      "affs": [
        1
      ],
      "name": "Nino Russo",
      "orcid": "0000-0003-3826-3386"
    }
  ],
  "bibtex": "https://research.draconitic.com/paper/bqrx9gmw6zmbj.bib",
  "cited_by": 0,
  "doi": "10.1021/acs.jpcb.6c03897",
  "fulltext_url": "https://europepmc.org/articles/PMC13618030",
  "id": "bqrx9gmw6zmbj",
  "issns": [
    "1520-6106",
    "1520-5207"
  ],
  "landing_url": "https://europepmc.org/article/MED/42917562",
  "language": "eng",
  "licence": "CC-BY",
  "licence_label": "CC BY",
  "licence_source": "article",
  "licence_url": "https://creativecommons.org/licenses/by/4.0/",
  "metadata_licence": null,
  "native_subjects": [
    [
      "openalex",
      "1605|Free Radicals and Antioxidants"
    ]
  ],
  "openalex": "W7213316989",
  "pdf_url": "https://europepmc.org/articles/PMC13618030?pdf=render",
  "pmcid": "PMC13618030",
  "pmid": "42917562",
  "published": "2026-09-01",
  "publisher": null,
  "ris": "https://research.draconitic.com/paper/bqrx9gmw6zmbj.ris",
  "sources": [
    {
      "first_seen": "2026-10-30T12:21:02Z",
      "native_id": "MED:42917562",
      "source": "europepmc",
      "url": "https://europepmc.org/article/MED/42917562"
    }
  ],
  "subjects": [
    {
      "field": "chemistry",
      "origin": "openalex:1605|Free Radicals and Antioxidants",
      "subfield": "organic"
    }
  ],
  "title": "How 3-O-Glucosylation Modulates Resveratrol Radical Scavenging: A QM-ORSA Study of Polydatin/Piceid, a Stilbenoid Glucoside.",
  "title_text": "How 3-O-Glucosylation Modulates Resveratrol Radical Scavenging: A QM-ORSA Study of Polydatin/Piceid, a Stilbenoid Glucoside.",
  "type": "peer-reviewed",
  "updated_at": "2026-10-30T12:21:02Z",
  "url": "https://research.draconitic.com/paper/bqrx9gmw6zmbj",
  "venue": "The journal of physical chemistry. B",
  "versions": []
}