biostudies-literaturede Fatima AConselho Nacional de Desenvolvimento Cient?fico e Tecnol?gicoBLRD VAOffice of Dietary SupplementsNCCIH NIH HHSUniversity of North TexasNational Center for Complementary and Integrative HealthU.S. Department of Veterans Affairs8222-8330https://www.ebi.ac.uk/biostudies/studies/S-EPMC6590917biostudies-literatureUnknown4(5)Bioactive dietary polyphenols have health benefits against a variety of disorders, but some benefits of polyphenols may be not directly related to them, but rather to their metabolites. Recently, we have identified the brain-available phenol glucuronide metabolite deoxyrhapontigenin-3-<i>O</i>-<i>β</i>-D-glucuronide (<b>5</b>) in perfused rat brains following sub-acute treatment with the stilbene resveratrol (<b>1</b>). However, the role of such a metabolite in the neuroprotective activity of resveratrol (<b>1</b>) is not understood, in part due to the non-commercial availability of <b>5</b> for performing biological evaluation in animal models of Alzheimer's disease or other neurological disorders. Here, we describe a concise chemical synthesis of deoxyrhapontigenin-3-<i>O</i>-<i>β</i>-D-ACS omegaAn Efficient Synthesis of Deoxyrhapontigenin-3-<i>O</i>-<i>β</i>-D-glucuronide, a Brain-targeted Derivative of Dietary Resveratrol, and its Precursor 4'-<i>O</i>-Me-Resveratrol.PMC6590917P50 AT008661-01IK6 BX003785204106/2017-6P50 AT008661Docampo-Palacios MAlvarez-Hernandez Ade Fatima APasinetti GMDixon RAfalseAn Efficient Synthesis of Deoxyrhapontigenin-3-<i>O</i>-<i>β</i>-D-glucuronide, a Brain-targeted Derivative of Dietary Resveratrol, and its Precursor 4'-<i>O</i>-Me-Resveratrol.Bioactive dietary polyphenols have health benefits against a variety of disorders, but some benefits of polyphenols may be not directly related to them, but rather to their metabolites. Recently, we have identified the brain-available phenol glucuronide metabolite deoxyrhapontigenin-3-<i>O</i>-<i>β</i>-D-glucuronide (<b>5</b>) in perfused rat brains following sub-acute treatment with the stilbene resveratrol (<b>1</b>). However, the role of such a metabolite in the neuroprotective activity of resveratrol (<b>1</b>) is not understood, in part due to the non-commercial availability of <b>5</b> for performing biological evaluation in animal models of Alzheimer's disease or other neurological disorders. Here, we describe a concise chemical synthesis of deoxyrhapontigenin-3-<i>O</i>-<i>β</i>-D-2019-01-01T00:00:00Z2019 May2025-04-04T21:00:41.927Z2019-07-24T07:27:22ZS-EPMC65909173123652610.1021/acsomega.9b00722