Piceatannol

Piceatannol

Names
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
CAS Number	10083-24-6  Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:28814  N
ChemSpider	581006  N
ECHA InfoCard	100.115.063
PubChem CID	667639
UNII	6KS3LS0D4F  N
CompTox Dashboard (EPA)	DTXSID6040587
InChI 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
SMILES C1=CC(=C(C=C1C=CC2=CC(=CC(=C2)O)O)O)O
Properties
Chemical formula	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). N  verify  (what is  YN ?) Infobox references

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

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

Piceattanol acts as an inhibitor of the tyrosine kinase Syk and some related tyrosine kinases. ^[7] In the early 2000s, this prompted research interest in piceatannol and its effect on immune or inflammatory 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

• Pterostilbene
• List of phytochemicals in food

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. Bibcode:1990Plant.182..142M. doi:10.1007/BF00239996. PMID   24197010. S2CID   43504838.
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. Bibcode:2005JANPR...7..131Y. doi:10.1080/10286020310001625102. PMID   15621615. S2CID   37661785.
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. Bibcode:2012MRRMR.750...60P. doi:10.1016/j.mrrev.2011.11.001. PMID   22108298.
6. 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.
7. 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.
8. 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.
9. 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.
10. 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.
11. "Potential Method to Control Obesity: Red Wine, Fruit Compound Could Help Block Fat Cell Formation". Science Daily. April 4, 2012. Retrieved 2012-04-05.
12. 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.

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. Bibcode:2012MRRMR.750...60P. doi:10.1016/j.mrrev.2011.11.001. ISSN   1383-5742. PMID   22108298.