SMB00956

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

≥95% (HPLC)

• 동의어(들): Resveratrol 4′-O-glucuronide, Resveratrol-4′-O-D-Glucuronide, trans-Resveratrol 4′-O-glucuronide, trans-Resveratrol 4′-glucuronide
• 실험식(Hill 표기법): C₂₀H₂₀O₉
• CAS Number: 387372-20-5
• Molecular Weight: 404.37
• UNSPSC 코드: 12352201
• NACRES: NA.25

속성

• Quality Level: 200
• 분석: ≥95% (HPLC)
• 양식: solid
• 색상: white to beige
• 저장 온도: 2-8°C
• SMILES string: O1C(C(C(C(C1C(=O)O)O)O)O)Oc2ccc(cc2)C=Cc3cc(cc(c3)O)O
• 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)
• InChI key: CDEBVTGYVFHDMA-UHFFFAOYSA-N

설명

일반 설명

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.

애플리케이션

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.

생화학적/생리학적 작용

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.

기타 정보

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안전성 정보

• Storage Class Code: 11 - Combustible Solids
• WGK: WGK 3