How 3-O-Glucosylation Modulates Resveratrol Radical Scavenging: A QM-ORSA Study of Polydatin/Piceid, a Stilbenoid Glucoside.
- 1Department of Organic Chemistry and Pharmaceutical Technology, Faculty of Pharmacy, Wroclaw Medical University, Wroclaw50-556, Poland.
- 2Department of Chemistry and Chemical Technologies, Università della Calabria, Rende87036, Italy.
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).
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BibTeX
@article{spiegel20263oglucosylation,
title = {{How 3-O-Glucosylation Modulates Resveratrol Radical Scavenging: A QM-ORSA Study of Polydatin/Piceid, a Stilbenoid Glucoside.}},
author = {Maciej Spiegel and Nino Russo},
journal = {The journal of physical chemistry. B},
year = {2026},
month = sep,
doi = {10.1021/acs.jpcb.6c03897},
url = {https://europepmc.org/article/MED/42917562},
note = {CC BY},
}
RIS
TY - JOUR
TI - How 3-O-Glucosylation Modulates Resveratrol Radical Scavenging: A QM-ORSA Study of Polydatin/Piceid, a Stilbenoid Glucoside.
AU - Maciej Spiegel
AU - Nino Russo
PY - 2026
DA - 2026/09/01
JO - The journal of physical chemistry. B
DO - 10.1021/acs.jpcb.6c03897
UR - https://europepmc.org/article/MED/42917562
AB - 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).
SN - 1520-6106
SN - 1520-5207
ER -