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Hopeaphenol

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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
UNII	8K2E6922LC^Y
CompTox Dashboard (EPA)	DTXSID801029736
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

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[edit]

^ 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; 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.

^ 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:

Dibalanocarpol
Gnetin J (3"-hydroxygnetin E)
Gnetin K (3"-methoxygnetin E)
Gnetuhainin R (isorhapontigenin tetramer)
Laetevirenol F and G

Higher polymers
(five units or more)

Vaticanol D, H, I and J

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

Diptoindonesin A (C-glucoside of ε-viniferin)
Foeniculoside I (glucoside of miyabenol C), II, III and IV
Laevifonol (an ε-viniferin-ascorbic acid hybrid compound)
Laevifoside (O-glucoside of ampelopsin A)

Retrieved from "https://en.wikipedia.org/w/index.php?title=Hopeaphenol&oldid=1145171104" Categories: ●Resveratrol oligomers ●Natural phenol tetramers ●Wine chemistry Hidden categories: ●Articles without KEGG source ●Articles with changed EBI identifier ●Articles with changed ChemSpider identifier ●Articles with changed InChI identifier ●Articles containing unverified chemical infoboxes ●Chembox image size set ●Articles with short description ●Short description matches Wikidata ●This page was last edited on 17 March 2023, at 16:46 (UTC). ●Text is available under the Creative Commons Attribution-ShareAlike License 4.0; additional terms may apply. By using this site, you agree to the Terms of Use and Privacy Policy. Wikipedia® is a registered trademark of the Wikimedia Foundation, Inc., a non-profit organization. ●Privacy policy ●About Wikipedia ●Disclaimers ●Contact Wikipedia ●Code of Conduct ●Developers ●Statistics ●Cookie statement ●Mobile view