SMB00956

trans-Resveratrol 4′-O-β-D-glucuronide

≥95% (HPLC)

• Synonym(e): Resveratrol 4′-O-glucuronide, Resveratrol-4′-O-D-Glucuronide, trans-Resveratrol 4′-O-glucuronide, trans-Resveratrol 4′-glucuronide
• Empirische Formel (Hill-System): C₂₀H₂₀O₉
• CAS-Nummer: 387372-20-5
• Molekulargewicht: 404.37
• UNSPSC-Code: 12352201
• NACRES: NA.25

Eigenschaften

• Qualitätsniveau: 200
• Assay: ≥95% (HPLC)
• Form: solid
• Farbe: white to beige
• Lagertemp.: 2-8°C
• InChI: 1S/C20H20O9/c21-12-7-11(8-13(22)9-12)2-1-10-3-5-14(6-4-10)28-20-17(25)15(23)16(24)18(29-20)19(26)27/h1-9,15-18,20-25H,(H,26,27)
• InChIKey: CDEBVTGYVFHDMA-UHFFFAOYSA-N

Beschreibung

Allgemeine Beschreibung

Trans-Resveratrol 4′-O-glucuronide is a stilbenoid glycoside often present in red wine and various foods. This compound is produced through the glucuronidation process, where the enzyme UDP-glucuronosyltransferase (UGT), specifically the UGT1A9 isoform, conjugates it with glucuronic acid. It serves as a phase II metabolite of the antioxidant trans-resveratrol.

Anwendung

Resveratrol is a plant-derived polyphenol reported to be an anticancer, antidiabetic, anti-obesity, anti-oxidant, anti-inflammatory, and anti-AD agent, among others. Some of these beneficial properties may be indirectly related to its phase II metabolism. 3-O-b-D-glucuronide (3-OG) and 4′-O-b-D-glucuronide (4OG) metabolites are more potent than resveratrol against the growth of human adenocarcinoma Caco-2. Oral resveratrol administration results in high levels of 3-OG, 4′-OG and 3-sulfate metabolites in the colorectum of colon cancer patients.

Biochem./physiol. Wirkung

Current research indicates that trans-resveratrol 4′-O-β-D-glucuronide demonstrates its anticancer effects by activating adenosine receptors located on cancer cells, ultimately triggering apoptosis. It acts as an agonist of the adenosine A3 receptor, particularly in high concentrations, resulting in apoptosis in human colon cancer cells. Moreover, this compound effectively hinders colon carcinogenesis by suppressing cell proliferation and promoting apoptosis, making it a promising agent for combating colon cancer.

Sonstige Hinweise

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Sicherheitshinweise

• Lagerklassenschlüssel: 11 - Combustible Solids
• WGK: WGK 3