Piceatannol
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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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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.
Natural occurrences
[edit]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
[edit]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
[edit]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
[edit]References
[edit]- ^ Münzenberger, Babette; Heilemann, Jürgen; Strack, Dieter; Kottke, Ingrid; Oberwinkler, Franz (1990). "Phenolics of mycorrhizas and non-mycorrhizal roots of Norway spruce". Planta. 182 (1): 142–8. doi:10.1007/BF00239996. PMID 24197010. S2CID 43504838.
- ^ Lee, D; Cuendet, M; Vigo, JS; Graham, JG; Cabieses, F; Fong, HH; Pezzuto, JM; Kinghorn, AD (2001). "A novel cyclooxygenase-inhibitory stilbenolignan from the seeds of Aiphanes aculeata". Organic Letters. 3 (14): 2169–71. doi:10.1021/ol015985j. PMID 11440571.
- ^ Yao, Chun-Suo; Lin, Mao; Liu, Xin; Wang, Ying-Hong (2005). "Stilbene derivatives from Gnetum cleistostachyum". Journal of Asian Natural Products Research. 7 (2): 131–7. doi:10.1080/10286020310001625102. PMID 15621615. S2CID 37661785.
- ^ Cunningham, Jill; Haslam, E.; Haworth, R. D. (1963). "535. The constitution of piceatannol". Journal of the Chemical Society (Resumed): 2875. doi:10.1039/JR9630002875.
- ^ Piotrowska H, Kucinska M, Murias M (2012). "Biological activity of piceatannol: leaving the shadow of resveratrol". Mutat Res. 750 (1): 60–82. doi:10.1016/j.mrrev.2011.11.001. PMID 22108298.
{{cite journal}}: CS1 maint: multiple names: authors list (link) - ^ Bolton, Judy L.; Dunlap, Tareisha L.; Dietz, Birgit M. (2018). "Formation and biological targets of botanical o-quinones". Food and Chemical Toxicology. 120: 700–707. doi:10.1016/j.fct.2018.07.050. PMC 6643002. PMID 30063944. S2CID 51887182.
- ^ Geahlen RL, McLaughlin JL (1989). "Piceatannol (3,4,3',5'-tetrahydroxy-trans-stilbene) is a naturally occurring protein-tyrosine kinase inhibitor". Biochem. Biophys. Res. Commun. 165 (1): 241–5. doi:10.1016/0006-291X(89)91060-7. PMID 2590224.
- ^ Swanson-Mungerson M, Ikeda M, Lev L, Longnecker R, Portis T (2003). "Identification of latent membrane protein 2A (LMP2A) specific targets for treatment and eradication of Epstein-Barr virus (EBV)-associated diseases". J. Antimicrob. Chemother. 52 (2): 152–4. doi:10.1093/jac/dkg306. PMID 12837743.
- ^ Roupe, Kathryn A.; Yáñez, Jaime A.; Teng, Xiao Wei; Davies, Neal M. (2006). "Pharmacokinetics of selected stilbenes: Rhapontigenin, piceatannol and pinosylvin in rats". Journal of Pharmacy and Pharmacology. 58 (11): 1443–50. doi:10.1211/jpp.58.11.0004. PMID 17132206. S2CID 9538085.
- ^ Kwon, J. Y.; Seo, S. G.; Heo, Y.-S.; Yue, S.; Cheng, J.-X.; Lee, K. W.; Kim, K.-H. (2012). "Piceatannol, Natural Polyphenolic Stilbene, Inhibits Adipogenesis via Modulation of Mitotic Clonal Expansion and Insulin Receptor-dependent Insulin Signaling in Early Phase of Differentiation". Journal of Biological Chemistry. 287 (14): 11566–78. doi:10.1074/jbc.M111.259721. PMC 3322826. PMID 22298784.
- ^ "Potential Method to Control Obesity: Red Wine, Fruit Compound Could Help Block Fat Cell Formation". Science Daily. April 4, 2012. Retrieved 2012-04-05.
- ^ Matsumoto, Y.; Katano, Y. (2021). "Cardiovascular Protective Effects of Polyphenols Contained in Passion Fruit Seeds Namely Piceatannol and Scirpusin B: A Review". The Tokai Journal of Experimental and Clinical Medicine. 46 (3): 151–161. PMID 34498252.