Vitisin B (stilbenoid)

For other uses, see Vitisin B.

Vitisin B

IUPAC name 5-[(2R,3R)-6-[(2R,3R)-5-[(E)-2-[(2R,3R)-3-(3, 5-dihydroxyphenyl)-6-hydroxy-2-(4-hydroxyphenyl)-2,3-dihydro-1-benzofuran-4-yl]ethenyl]-2-(4-hydroxyphenyl)-2,3-dihydro-1-benzofuran-3-yl]-4-hydroxy-2-(4-hydroxyphenyl)-2,3-dihydro-1-benzofuran-3-yl]benzene-1,3-diol
Other names R-Viniferin^[1]
Identifiers
PubChem	16133855
Jmol-3D images	Image 1
SMILES C1=CC(=CC=C1C2C(C3=C(O2)C=CC(=C3)C=CC4=CC(=CC5=C4C(C(O5)C6=CC=C(C=C6)O)C7=CC(=CC(=C7)O)O)O)C8=CC9=C(C(C(O9)C1=CC=C(C=C1)O)C1=CC(=CC(=C1)O)O)C(=C8)O)O
Properties
Molecular formula	C₅₆H₄₂O₁₂
Molar mass	906.92 g/mol
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

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

References

^ 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

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Stilbenoids and their glycosides

Aglycones

Dihydroxylated : Pinosylvin | 3,4′-Dihydroxystilbene
Trihydroxylated : Resveratrol
Tetrahydroxylated : Oxyresveratrol | Piceatannol

O-methylated	4-Methoxyresveratrol \| Gnetucleistol D (2-methoxyoxyresveratrol) \| Gnetucleistol E (3-methoxy-isorhapontigenin) \| Isorhapontigenin (3,4',5-trihydroxy-3'-methoxystilbene) \| Pterostilbene \| Rhapontigenin (3,3',5-trihydroxy-4'-methoxystilbene) Combretastatins : Combretastatin A-1 \| Combretastatin A-4

carboxylated	Hydrangeic acid

other acetylations	3,5-Dihydroxy-4-isopropyl-trans-stilbene

Glycosides

Astringin (Piceatannol 3-O-glucoside) | Foeniculoside I, II, III and IV | Isorhapontin (Isorhapontigenin glucoside) | Mulberroside A (Oxyresveratrol diglucoside)

of resveratrol	Piceid (trans-Resveratrol-3-O-glucoside) \| trans-Resveratrol-3-O-glucuronide \| Resveratroloside (trans-resveratrol-4'-O-beta-D-glucopyranoside)

of rhapontigenin	Rhapontigenin 3-O-rutinoside (4'-Methoxy-(E)-resveratrol 3-O-rutinoside) \| Rhaponticin (Rhapontigenin glucoside)

Oligomeric forms

of resveratrol

Dimers : Amurensin A and H, Ampelopsin A, B, D and F, δ-viniferin, ε-viniferin, Leachinol F, Pallidol, Parthenocissin A, Quadrangularin A, Restrytisol A, B and C
Trimers : α-viniferin, Amurensin C, D and G, Malaysianol A, Miyabenol C, Resviniferin A and B, trans-diptoindonesin B
Tetramers : Amurensin E, F and K | Gnetuhainin R (isorhapontigenin tetramer), Hopeaphenol, Vaticanol B, Vitisin A, B and C, β-viniferin (cyclic resveratrol tetramer)
Pentamers : Amurensin E and F | More highly polymerized oligomers : γ-viniferin

Oligomeric forms glycosides or conjugates

Diptoindonesin A | Laevifonol (an ε-viniferin-ascorbic acid hybrid compound) | Laevifoside (O-glucoside of ampelopsin A)

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Last modified on 18 May 2013, at 06:42