Piceatannol

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Piceatannol
Piceatannol.svg
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
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.115.063 OOjs UI icon edit-ltr-progressive.svg
PubChem CID
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+ X mark.svgN
    Key: CDRPUGZCRXZLFL-OWOJBTEDSA-N X mark.svgN
  • 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
Appearancewhite 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.

Contents

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

Related Research Articles

<span class="mw-page-title-main">Grape</span> Fruit growing on woody vines in clusters

A grape is a fruit, botanically a berry, of the deciduous woody vines of the flowering plant genus Vitis. Grapes are a non-climacteric type of fruit, generally occurring in clusters.

<span class="mw-page-title-main">Resveratrol</span> Polyphenol with a stilbene skeleton

Resveratrol (3,5,4′-trihydroxy-trans-stilbene) is a stilbenoid, a type of natural phenol, and a phytoalexin produced by several plants in response to injury or when the plant is under attack by pathogens, such as bacteria or fungi. Sources of resveratrol in food include the skin of grapes, blueberries, raspberries, mulberries, and peanuts.

<i>Gnetum gnemon</i> Species of plant

Gnetum gnemon is a gymnosperm species of Gnetum, its native area spans from Mizoram and Assam in India down south through Malay Peninsula, Malay Archipelago and the Philippines in southeast Asia to the western Pacific islands. Common names include gnetum, joint fir, two leaf, melinjo, belinjo, bago, and tulip.

<span class="mw-page-title-main">Stilbenoid</span> Class of chemical compounds

Stilbenoids are hydroxylated derivatives of stilbene. They have a C6–C2–C6 structure. In biochemical terms, they belong to the family of phenylpropanoids and share most of their biosynthesis pathway with chalcones. Most stilbenoids are produced by plants, and the only known exception is the antihelminthic and antimicrobial stilbenoid, 2-isopropyl-5-[(E)-2-phenylvinyl]benzene-1,3-diol, biosynthesized by the Gram-negative bacterium Photorhabdus luminescens.

<i>p</i>-Coumaric acid Chemical compound

p-Coumaric acid is an organic compound with the formula HOC6H4CH=CHCO2H. It is one of the three isomers of hydroxycinnamic acid. It is a white solid that is only slightly soluble in water but very soluble in ethanol and diethyl ether.

<span class="mw-page-title-main">Pinosylvin</span> Chemical compound

Pinosylvin is an organic compound with the formula C6H5CH=CHC6H3(OH)2. A white solid, it is related to trans-stilbene, but with two hydroxy groups on one of the phenyl substituents. It is very soluble in many organic solvents, such as acetone.

<span class="mw-page-title-main">Piceid</span> Chemical compound

Piceid is a stilbenoid glucoside and is a major resveratrol derivative in grape juices. It can be found in the bark of Picea sitchensis. It can also be isolated from Reynoutria japonica, the Japanese knotweed.

<span class="mw-page-title-main">Sirtuin 1</span> Protein

Sirtuin 1, also known as NAD-dependent deacetylase sirtuin-1, is a protein that in humans is encoded by the SIRT1 gene.

<span class="mw-page-title-main">Phenolic content in wine</span> Wine chemistry

The phenolic content in wine refers to the phenolic compounds—natural phenol and polyphenols—in wine, which include a large group of several hundred chemical compounds that affect the taste, color and mouthfeel of wine. These compounds include phenolic acids, stilbenoids, flavonols, dihydroflavonols, anthocyanins, flavanol monomers (catechins) and flavanol polymers (proanthocyanidins). This large group of natural phenols can be broadly separated into two categories, flavonoids and non-flavonoids. Flavonoids include the anthocyanins and tannins which contribute to the color and mouthfeel of the wine. The non-flavonoids include the stilbenoids such as resveratrol and phenolic acids such as benzoic, caffeic and cinnamic acids.

<span class="mw-page-title-main">Phlorizin</span> Chemical compound

Phlorizin is a glucoside of phloretin, a dihydrochalcone. A white solid, samples often appear yellowing to impurities. It is of sweet taste and contains four molecules of water in the crystal. Above 200 °C, it decomposes to give rufin. It is poorly soluble in ether and cold water, but soluble in ethanol and hot water. Upon prolonged exposure to aqueous solutions phlorizin hydrolyzes to phloretin and glucose.

ε-Viniferin Chemical compound

ε-Viniferin is a naturally occurring phenol, belonging to the stilbenoids family. It is a resveratrol dimer.

<span class="mw-page-title-main">Astringin</span> Chemical compound

Astringin is a stilbenoid, the 3-β-D-glucoside of piceatannol. It can be found in the bark of Picea sitchensis or Picea abies.

<i>trans</i>-Resveratrol-3-<i>O</i>-glucuronide Chemical compound

trans-Resveratrol-3-O-glucuronide is a metabolite of resveratrol and trans-resveratrol-3-O-glucoside (piceid).

<i>delta</i>-Viniferin Chemical compound

δ-Viniferin is a resveratrol dehydrodimer. It is an isomer of epsilon-viniferin. It can be isolated from stressed grapevine leaves. It is also found in plant cell cultures and wine. It can also be found in Rheum maximowiczii.

<span class="mw-page-title-main">Miyabenol C</span> Chemical compound

Miyabenol C is a stilbenoid. It is a resveratrol trimer. It is found in Vitis vinifera (grape), in Foeniculi fructus, in Caragana sinica.

<span class="mw-page-title-main">Rhapontigenin</span> Chemical compound

Rhapontigenin is a stilbenoid. It can be isolated from Vitis coignetiae or from Gnetum cleistostachyum.

<span class="mw-page-title-main">Isorhapontigenin</span> Chemical compound

Isorhapontigenin is a tetrahydroxylated stilbenoid with a methoxy group. It is an isomer of rhapontigenin and an analog of resveratrol. It is found in the Chinese herb Gnetum cleistostachyum, in Gnetum parvifolium and in the seeds of the palm Aiphanes aculeata.

<span class="mw-page-title-main">Stilbenolignan</span>

Stilbenolignans are phenolic compounds formed from a stilbenoid and a lignan.

Gnetum cleistostachyum is a liana species in the Sessiles subsection of the genus Gnetum described from South East Yunnan.

<span class="mw-page-title-main">Isorhapontin</span> Chemical compound

Isorhapontin is a stilbenoid. It is the glucoside of isorhapontigenin. It can be found in mycorrhizal and non-mycorrhizal roots of Norway spruces, in the bark of Picea sitchensis or in white spruce.

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. 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. 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. doi:10.1016/j.mrrev.2011.11.001. PMID   22108298.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  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