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Vitisin B (stilbenoid)

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Vitisin B
Names

Preferred IUPAC name (2²R,2³R,3²R,3³R,4E,6²R,6³R)-2²,3²,6²-Tris(4-hydroxyphenyl)-2²,2³,3²,3³,6²,6³-hexahydro-2(3,6),3(3,5),6(4,3)-tris([1]benzofurana)-1,7(1)-dibenzenaheptaphan-4-ene-1³,1⁵,2⁴,6⁶,7³,7⁵-hexol
Other names R-Viniferin^[1]
Identifiers
3D model (JSmol)	Interactive image
ChemSpider	17290428^N
PubChem CID	16133855
CompTox Dashboard (EPA)	DTXSID601029954
InChI InChI=1S/C56H42O12/c57-36-10-4-29(5-11-36)54-49(35-23-45(65)53-47(24-35)67-56(31-8-14-38(59)15-9-31)52(53)34-21-41(62)26-42(63)22-34)44-17-28(2-16-46(44)66-54)1-3-32-18-43(64)27-48-50(32)51(33-19-39(60)25-40(61)20-33)55(68-48)30-6-12-37(58)13-7-30/h1-27,49,51-52,54-65H/b3-1+/t49-,51-,52-,54+,55+,56+/m1/s1^N Key: SPRFPODGXUUTIB-APEUUSFDSA-N^N
SMILES c1cc(ccc1[C@H]2[C@@H](c3cc(ccc3O2)/C=C/c4cc(cc5c4[C@H]([C@@H](O5)c6ccc(cc6)O)c7cc(cc(c7)O)O)O)c8cc(c9c(c8)O[C@H]([C@@H]9c1cc(cc(c1)O)O)c1ccc(cc1)O)O)O
Properties
Chemical formula	C₅₆H₄₂O₁₂
Molar mass	906.92 g/mol
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

Vitisin B is a resveratrol tetramer found in plants of the genus Vitis.^[2]

References[edit]

^ Poster at 1st International Conference of Resveratrol and Health, Jean-Claude Izard, 2010

^ 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

External links[edit]

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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)

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