SMB00956

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

≥95% (HPLC)

• Sinônimo(s): Resveratrol 4′-O-glucuronide, Resveratrol-4′-O-D-Glucuronide, trans-Resveratrol 4′-O-glucuronide, trans-Resveratrol 4′-glucuronide
• Fórmula empírica (Notação de Hill): C₂₀H₂₀O₉
• Número CAS: 387372-20-5
• Peso molecular: 404.37
• Código UNSPSC: 12352201
• NACRES: NA.25

Propriedades

• Nível de qualidade: 200
• Ensaio: ≥95% (HPLC)
• Formulário: solid
• cor: white to beige
• temperatura de armazenamento: 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)
• chave InChI: CDEBVTGYVFHDMA-UHFFFAOYSA-N

Descrição

Descrição geral

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.

Aplicação

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.

Ações bioquímicas/fisiológicas

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.

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Informações de segurança

• Código de classe de armazenamento: 11 - Combustible Solids
• Classe de risco de água (WGK): WGK 3