PICEATANNOL

Description

Piceatannol (10083-24-6) is a naturally occurring analog of resveratrol (Cat.# 10-1057). Inhibits nonreceptor kinases Syk and Lyk (IC50 approximately 10 μM).1 Piceatannol stimulates Sirt1.2

Chemical properties

yellow to golden or green crystalline powder

The Uses of PICEATANNOL

A human metabolite of Resveratrol (R150000). Piceatannol is strong anti-oxidant.

The Uses of PICEATANNOL

Piceatannol has been used:

• to study its effect on Ataxia-Telangiectasia Mutated (ATM) protein kinase
• as an inhibitor of ZAP-70 (ζ-chain-associated protein kinase 70)
• as an inhibitor of MRP1-mediated 2′,7′-bis-(carboxypropyl)-5(6)-carboxyfluorescein (BCPCF) transport in intact human erythrocytes and inside-out erythrocyte vesicles (IOVs)

What are the applications of Application

Piceatannol is an inhibitor of Syk and NF-κB activation

Definition

ChEBI: A stilbenol that is trans-stilbene in which one of the phenyl groups is substituted by hydroxy groups at positions 3 and 4, while the other phenyl group is substituted by hydroxy groups at positions 3 and 5.

General Description

A cell-permeable, substrate competitive and reversible plant metabolite that inhibits the activity of rat liver protein kinase A catalytic subunit (IC₅₀ = 3 μM), PKC (IC₅₀ = 8 μM), MLCK (IC₅₀ = 12 μM). In RBL-2H3 cells, the selective inhibition of Syk by piceatannol results in inhibition of FceR1-mediated signaling. Also inhibits wheat embryo Ca²⁺-dependent protein kinase (CDPK) (IC₅₀ = 19 μM), and p72^syk (IC₅₀ = 10 μM), a non-receptor tyrosine kinase, relative to Lyn in isolated enzyme preparations. Also possesses anti-leukemic properties. Reported to activate sirtuins and promote the survival of eukaryotic cells.

Biological Activity

Anti-inflammatory, immunomodulatory and antiproliferative agent. Inhibits p56 lck and syk protein tyrosine kinases and inhibits TNF-induced NF- κ B activation and gene expression. Synthesis results from conversion of resveratrol (5-[(1E)-2-(4-Hydroxyphenyl)ethenyl]-1,3,benzenediol ) by cytochrome P450 1B1.

Biochem/physiol Actions

Cell permeable: yes

Storage

+4°C

References

1) Seow et al. (2002), Piceatannol, a Syk-selective tyrosine kinase inhibitor, attenuated antigen challenge of guinea pig airways in vitro; Eur. J. Pharmacol., 443 189 2) Howitz et al. (2003), Small molecule activators of sirtuins extend Saccharomyces cerevisiae lifespan; Nature, 425 191