Hopeaphenol

Hopeaphenol
Names

Other names (-)-hopeaphenol
Identifiers
CAS Registry Number	17912-85-5^Y
ChemSpider	10277817^N
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
Jmol-3D images	Image
PubChem	495605
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
Molecular formula	C₅₆H₄₂O₁₂
Molar mass	906.93 g·mol⁻¹
Except where noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
N verify (what is: Y/N?)
Infobox references

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]

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

References

↑ The structure of hopeaphenol. P. Coggon, T. J. King and S. C. Wallwork, Chem. Commun. (London), 1966, pages 439-440, doi:10.1039/C19660000439
↑ 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)
↑ Habiba Amira Guebailia, Kleopatra Chira, Tristan Richard, Teguiche Mabrouk, Aurélie Furiga, Xavier Vitrac, Jean-Pierre Monti, Jean-Claude Delaunay and 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.
↑ 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

Dimers

Trimers

Tetramers:

Higher polymers
(five units or more)

Oligomeric forms
of resveratrol

Dimers	Amurensin A and H Ampelopsin A B D and F Balanocarpol Cyphostemmin A and B δ-viniferin ε-viniferin Gnetin A and C Leachinol F Malibatol A Pallidol Parthenocissin A Quadrangularin A Restrytisol A, B and C Vitisinol D

Trimers	α-viniferin Ampelopsin C Amurensin C, D and G Hopeanolin Malaysianol A Miyabenol C Resviniferin A and B trans-diptoindonesin B

Tetramers	Ampelopsin H Amurensin K Caraphenol B Carasinol B Flexuosol A Hopeaphenol Kobophenol A Miyabenol A Vaticanol B and C Vaticaphenol A Vitisin A B and C β-viniferin (cyclic resveratrol tetramer)

Pentamers	Amurensin E and F

Hexamers	Chunganenol

Higher polymers	γ-viniferin Valeriaphenol A

Glycosides or conjugates