LIPID MAPS

Structure Database (LMSD)

View 3D

Download as... MDLMOL SDF CSV TSV PNG

Common Name

Piceatannol

Systematic Name

Synonyms

3,3',4'5-tetrahydroxystilbene

LM ID

LMPK13090006

Formula

C₁₄H₁₂O₄

Exact Mass

Calculate m/z

244.07356

Status

Curated

Show lipids differing only in stereochemistry/bond geometry

View NP-MRD ID(NMR) spectrum

Classification

Biological Context

Piceatannol is a stilbene that has been found in red wine and an active metabolite of trans-resveratrol , a polyphenol with diverse biological activities.¹ It is formed from trans-resveratrol by the cytochrome P450 (CYP) isoform CYP1B1.1,2 Piceatannol induces apoptosis in BJAB B cell lymphoma cells (EC50 = 25 µM).³ Dietary administration of piceatannol (0.025% w/w) improves intestinal epithelial barrier integrity, prevents decreases in colon length, and increases body weight in a mouse model of ulcerative colitis induced by dextran sodium sulfate (DSS).⁴

This information has been provided by Cayman Chemical

References

1. Rotondo, S., Rajtar, G., Manarini, S., et al. Effect of trans-resveratrol, a natural polyphenolic compound, on human polymorphonuclear leukocyte function. Br. J. Pharmacol. 123(8), 1691-1699 (1998).

2. Wieder, T., Prokop, A., Bagci, B., et al. Piceatannol, a hydroxylated analog of the chemopreventive agent resveratrol, is a potent inducer of apoptosis in the lymphoma cell line BJAB and in primary, leukemic lymphoblasts. Leukemia 15(11), 1735-1742 (2001).

3. Potter, G.A., Patterson, L.H., Wanogho, E., et al. The cancer preventative agent resveratrol is converted to the anticancer agent piceatannol by the cytochrome P450 enzyme CYPIBI. Br. J. Cancer 86(5), 774-778 (2002).

4. Lin, W.-S., Chueh, T.-L., Nagabhushanam, K., et al. Piceatannol and 3'-hydroxypterostilbene alleviate inflammatory bowel disease by maintaining intestinal epithelial integrity and regulating gut microbiota in mice. J. Agric. Food Chem. 71(4), 1994-2005 (2023).