Piceatannol Explained

Piceatannol is the organic compound with the formula . Classified as a stilbenoid and a phenol, it is a white solid, although samples often are yellow owing to impurities.

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

Further reading

Notes and References

  1. 10.1007/BF00239996 . Phenolics of mycorrhizas and non-mycorrhizal roots of Norway spruce . 1990 . Münzenberger . Babette . Heilemann . Jürgen . Strack . Dieter . Kottke . Ingrid . Oberwinkler . Franz . Planta . 182 . 1 . 24197010 . 142–8. 43504838 .
  2. 11440571 . 2001 . Lee . D . Cuendet . M . Vigo . JS . Graham . JG . Cabieses . F . Fong . HH . Pezzuto . JM . Kinghorn . AD . A novel cyclooxygenase-inhibitory stilbenolignan from the seeds of Aiphanes aculeata . 3 . 14 . 2169–71 . Organic Letters . 10.1021/ol015985j.
  3. 10.1080/10286020310001625102 . 15621615 . Stilbene derivatives from Gnetum cleistostachyum . 2005 . Yao . Chun-Suo . Lin . Mao . Liu . Xin . Wang . Ying-Hong . Journal of Asian Natural Products Research . 7 . 2 . 131–7. 37661785 .
  4. 10.1039/JR9630002875 . 535. The constitution of piceatannol . 1963 . Cunningham . Jill . Haslam . E. . Haworth . R. D. . Journal of the Chemical Society (Resumed) . 2875.
  5. Piotrowska H, Kucinska M, Murias M. Biological activity of piceatannol: leaving the shadow of resveratrol. . Mutat Res . 2012 . 750 . 1 . 60–82 . 22108298 . 10.1016/j.mrrev.2011.11.001 .
  6. 10.1016/j.fct.2018.07.050. Formation and biological targets of botanical o-quinones . 2018 . Bolton . Judy L. . Dunlap . Tareisha L. . Dietz . Birgit M. . Food and Chemical Toxicology . 120 . 700–707 . 30063944 . 6643002 . 51887182 . free .
  7. Geahlen RL, McLaughlin JL . Piceatannol (3,4,3',5'-tetrahydroxy-trans-stilbene) is a naturally occurring protein-tyrosine kinase inhibitor . Biochem. Biophys. Res. Commun. . 165 . 1 . 241–5 . 1989 . 2590224 . 10.1016/0006-291X(89)91060-7.
  8. Swanson-Mungerson M, Ikeda M, Lev L, Longnecker R, Portis T . 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 . 2003 . 12837743 . 10.1093/jac/dkg306.
  9. 10.1211/jpp.58.11.0004 . Pharmacokinetics of selected stilbenes: Rhapontigenin, piceatannol and pinosylvin in rats . 2006 . Roupe . Kathryn A. . Yáñez . Jaime A. . Teng . Xiao Wei . Davies . Neal M. . Journal of Pharmacy and Pharmacology . 58 . 11 . 1443–50 . 17132206. 9538085 . free .
  10. 10.1074/jbc.M111.259721 . Piceatannol, Natural Polyphenolic Stilbene, Inhibits Adipogenesis via Modulation of Mitotic Clonal Expansion and Insulin Receptor-dependent Insulin Signaling in Early Phase of Differentiation . 2012 . Kwon . J. Y. . Seo . S. G. . Heo . Y.-S. . Yue . S. . Cheng . J.-X. . Lee . K. W. . Kim . K.-H. . Journal of Biological Chemistry . 287 . 14 . 11566–78 . 22298784 . 3322826. free .
  11. Web site: Potential Method to Control Obesity: Red Wine, Fruit Compound Could Help Block Fat Cell Formation . April 4, 2012. . 2012-04-05.
  12. 34498252. 2021. Matsumoto. Y.. Katano. Y.. 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.

This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article "Piceatannol".

Except where otherwise indicated, Everything.Explained.Today is © Copyright 2009-2024, A B Cryer, All Rights Reserved. Cookie policy.