Hopeaphenol

Hopeaphenol is a stilbenoid. It is a resveratrol tetramer. It has been first isolated from Dipterocarpaceae[1] like Shorea ovalis.[2] It has also been isolated from wines from North Africa.[3]

Hopeaphenol

Names
Other names (-)-hopeaphenol
Identifiers
CAS Number	17912-85-5^Y
3D model (JSmol)	Interactive image
ChEMBL	ChEMBL1082601^N
ChemSpider	10277817^N
PubChem CID	495605
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/s1^N Key: YQQUILZPDYJDQJ-QWJFNKQSSA-N^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/s1 Key: YQQUILZPDYJDQJ-QWJFNKQSBW
SMILES OC(C=C1)=CC=C1[C@@H]2OC3=CC(O)=CC4=C3[C@@]2([H])C(C=C(O)C=C5O)=C5[C@@H](C6=CC=C(O)C=C6)[C@]4([H])[C@@]7([H])[C@H](C8=CC=C(O)C=C8)C9=C(C=C(O)C=C9O)[C@]%10([H])C%11=C7C=C(O)C=C%11O[C@H]%10C%12=CC=C(O)C=C%12
Properties
Chemical formula	C56H42O12
Molar mass	906.940 g·mol^−1
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

It shows an opposite effect to vitisin A on apoptosis of myocytes isolated from adult rat heart.[4]

See also

• Phenolic compounds in wine

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. Opposite Effects of Two Resveratrol (trans-3,5,4′-Trihydroxystilbene) Tetramers, Vitisin A and Hopeaphenol, on Apoptosis of Myocytes Isolated from Adult Rat Heart. Kazuhiko Seya, Kouta Kanemaru, Chiharu Sugimoto, Megumi Suzuki, Teruko Takeo, Shigeru Motomura, Haruo Kitahara, Masatake Niwa, Yoshiteru Oshima and Ken-Ichi Furukawa, JPET January 2009 vol. 328 no. 1 90-98, doi:10.1124/jpet.108.143172