Piceatannol

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Piceatannol
Names
Systematic IUPAC name
4-[(E)-2-(3,5-Dihydroxyphenyl)ethenyl]benzene-1,2-diol
Other names
3',4',3,5-Tetrahydroxy-trans-stilbene
Astringinin
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.115.063 Edit this at Wikidata
UNII
  • InChI=1S/C14H12O4/c15-11-5-10(6-12(16)8-11)2-1-9-3-4-13(17)14(18)7-9/h1-8,15-18H/b2-1+ ☒N
    Key: CDRPUGZCRXZLFL-OWOJBTEDSA-N ☒N
  • InChI=1/C14H12O4/c15-11-5-10(6-12(16)8-11)2-1-9-3-4-13(17)14(18)7-9/h1-8,15-18H/b2-1+
    Key: CDRPUGZCRXZLFL-OWOJBTEDBC
  • C1=CC(=C(C=C1C=CC2=CC(=CC(=C2)O)O)O)O
Properties
C14H12O4
Molar mass 244.246 g·mol−1
Appearance Light tan to yellow powder
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)

Piceatannol is a stilbenoid, a type of phenolic compound.

Natural occurrences

Piceatannol and its glucoside, astringin, are phenolic compounds 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.

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.[6] In 2003, this prompted research interest in piceatannol and its effect on these diseases.[7]

Injected in rats, piceatannol shows a rapid glucuronidation and a poor bioavailability, according to a 2006 study.[8]

A 2012 Purdue University study found that fat cells in culture, in the presence of piceatannol, alters the timing of gene expressions, gene functions and insulin action, resulting in the delay or complete inhibition of adipogenesis.[9][10]

See also

References

  1. ^ 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.
  2. ^ 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.
  3. ^ 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.
  4. ^ Cunningham, Jill; Haslam, E.; Haworth, R. D. (1963). "535. The constitution of piceatannol". Journal of the Chemical Society (Resumed): 2875. doi:10.1039/JR9630002875.
  5. ^ 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)
  6. ^ 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.
  7. ^ 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.
  8. ^ 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.
  9. ^ 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.{{cite journal}}: CS1 maint: unflagged free DOI (link)
  10. ^ "Potential Method to Control Obesity: Red Wine, Fruit Compound Could Help Block Fat Cell Formation". Science Daily. April 4, 2012. Retrieved 2012-04-05.

Further reading

  • Piotrowska, Hanna; Kucinska, Malgorzata; Murias, Marek (2012). "Biological activity of piceatannol: Leaving the shadow of resveratrol". Mutation Research/Reviews in Mutation Research (review). 750 (1): 60–82. doi:10.1016/j.mrrev.2011.11.001. ISSN 1383-5742. PMID 22108298.
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