Piceatannol
Chemical compound From Wikipedia, the free encyclopedia
Piceatannol is the organic compound with the formula ((HO)2C6H3)2CH)2. Classified as a stilbenoid and a phenol, it is a white solid, although samples often are yellow owing to impurities.
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| Names | |
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| Preferred IUPAC name
4-[(E)-2-(3,5-Dihydroxyphenyl)ethen-1-yl]benzene-1,2-diol | |
| Other names
3',4',3,5-Tetrahydroxy-trans-stilbene Astringinin | |
| Identifiers | |
3D model (JSmol) |
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| ChEBI | |
| ChemSpider | |
| ECHA InfoCard | 100.115.063 |
PubChem CID |
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| UNII | |
CompTox Dashboard (EPA) |
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| Properties | |
| C14H12O4 | |
| Molar mass | 244.246 g·mol−1 |
| Appearance | white solid |
| Melting point | 215–217 °C (419–423 °F; 488–490 K) |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Natural occurrences
Piceatannol and its glucoside, astringin, are found in mycorrhizal and non-mycorrhizal roots of Norway spruces (Picea abies).[1] It can also be found in the seeds of the palm Aiphanes horrida[2] and in Gnetum cleistostachyum.[3] The chemical structure of piceatannol was established by Cunningham et al. as being an analog of resveratrol.[4]
In food
Piceatannol is a metabolite of resveratrol found in red wine, grapes, passion fruit, white tea, and Japanese knotweed.[5] Astringin, a piceatannol glucoside, is also found in red wine. The formation of piceatannol from resveratrol is catalyzed by cytochrome P450.[6]
Biochemical study
A 1989 in vitro study found that piceatannol blocked LMP2A, a viral protein-tyrosine kinase implicated in leukemia, non-Hodgkin's lymphoma and other diseases associated with Epstein–Barr virus.[7] In 2003, this prompted research interest in piceatannol and its effect on these diseases.[8]
Injected in rats, piceatannol shows a rapid glucuronidation and a poor bioavailability, according to a 2006 study.[9]
Piceatannol affect gene expressions, gene functions and insulin action, resulting in the delay or complete inhibition of adipogenesis.[10][11]
Passion fruit seeds are rich in piceatannol and scirpusin B (dimer of piceatannol) as polyphenols, both of which have been reported to have vasodilating effects in the thoracic aorta and coronary artery of rats.[12] Furthermore, these polyphenols did not increase heart rate (i.e., these polyphenols did not increase oxygen consumption).
See also
References
Further reading
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