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Hopeaphenol

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Hopeaphenol
Chemical structure of hopeaphenol
Names
Other names (-)-hopeaphenol
Identifiers
CAS Number
3D model (JSmol)
ChEMBL
ChemSpider
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C56H42O12/c57-29-9-1-25(2-10-29)45-47-37(17-33(61)21-41(47)65)53-49-39(19-35(63)23-43(49)67-55(53)27-5-13-31(59)14-6-27)51(45)52-40-20-36(64)24-44-50(40)54(56(68-44)28-7-15-32(60)16-8-28)38-18-34(62)22-42(66)48(38)46(52)26-3-11-30(58)12-4-26/h1-24,45-46,51-66H/t45-,46-,51-,52-,53-,54-,55+,56+/m0/s1Key: YQQUILZPDYJDQJ-QWJFNKQSSA-N
  • InChI=1/C56H42O12/c57-29-9-1-25(2-10-29)45-47-37(17-33(61)21-41(47)65)53-49-39(19-35(63)23-43(49)67-55(53)27-5-13-31(59)14-6-27)51(45)52-40-20-36(64)24-44-50(40)54(56(68-44)28-7-15-32(60)16-8-28)38-18-34(62)22-42(66)48(38)46(52)26-3-11-30(58)12-4-26/h1-24,45-46,51-66H/t45-,46-,51-,52-,53-,54-,55+,56+/m0/s1Key: YQQUILZPDYJDQJ-QWJFNKQSBW
SMILES
  • OC(C=C1)=CC=C12OC3=CC(O)=CC4=C32()C(C=C(O)C=C5O)=C5(C6=CC=C(O)C=C6)4()7()(C8=CC=C(O)C=C8)C9=C(C=C(O)C=C9O)%10()C%11=C7C=C(O)C=C%11O%10C%12=CC=C(O)C=C%12
Properties
Chemical formula C56H42O12
Molar mass 906.940 g·mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

Hopeaphenol is a stilbenoid. It is a resveratrol tetramer. It has been first isolated from Dipterocarpaceae like Shorea ovalis. It has also been isolated from wines from North Africa.

It shows an opposite effect to vitisin A on apoptosis of myocytes isolated from adult rat heart.

See also

References

  1. The structure of hopeaphenol. P. Coggon, T. J. King and S. C. Wallwork, Chem. Commun. (London), 1966, pages 439-440, doi:10.1039/C19660000439
  2. The Isolation of Hopeaphenol, a Tetramer Stilbene, from Shorea ovalis Blume. Advances in Natural & Applied Sciences, January–April 2009, Volume 3, Issue 1, page 107 (abstract)
  3. Habiba Amira Guebailia; Kleopatra Chira; Tristan Richard; Teguiche Mabrouk; Aurélie Furiga; Xavier Vitrac; Jean-Pierre Monti; Jean-Claude Delaunay; Jean-Michel Mérillon (2006). "Hopeaphenol: The First Resveratrol Tetramer in Wines from North Africa". J. Agric. Food Chem. 54 (25): 9559–9564. doi:10.1021/jf062024g. PMID 17147446.
  4. Seya, Kazuhiko; Kanemaru, Kouta; Sugimoto, Chiharu; Suzuki, Megumi; Takeo, Teruko; et al. (2008-10-16). "Opposite Effects of Two Resveratrol (trans-3,5,4′-Trihydroxystilbene) Tetramers, Vitisin A and Hopeaphenol, on Apoptosis of Myocytes Isolated from Adult Rat Heart". Journal of Pharmacology and Experimental Therapeutics. 328 (1). American Society for Pharmacology & Experimental Therapeutics (ASPET): 90–98. doi:10.1124/jpet.108.143172. ISSN 0022-3565. PMID 18927354. S2CID 22844861.
Oligostilbenoids and their glycosides
Dimers
Trimers
Tetramers:
Higher polymers
(five units or more)
Oligomeric forms
of resveratrol
Dimers
Trimers
Tetramers
Pentamers
Hexamers
Higher polymers
Glycosides or conjugates
Categories: