Vitisin A (stilbenoid)

For other uses, see Vitisin A.

Vitisin A
Names

Other names R2-Viniferin^[1]
Identifiers
CAS Number	142449-89-6^Y=
3D model (Jmol)	Interactive image
PubChem	16131430
SMILES C1=CC(=CC=C1C2C(C3=CC(=CC4=C3C(C(O4)C5=CC=C(C=C5)O)C6=CC(=CC(=C26)O)O)O)C7=C(C=CC(=C7)C=CC8=CC(=CC9=C8C(C(O9)C1=CC=C(C=C1)O)C1=CC(=CC(=C1)O)O)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).
Y verify (what is ^YN ?)
Infobox references

Vitisin A is a resveratrol tetramer found in plants of the genus Vitis. It is a complex of two resveratrol dimers, (+)-epsilon-viniferin and ampelopsin B.^[2]

It shows an opposite effect to hopeaphenol on apoptosis of myocytes isolated from adult rat heart.^[2]^[3]^[4]

References

↑ Poster at 1st International Conference of Resveratrol and Health, Jean-Claude Izard, 2010
1 2 Seya, K.; Kanemaru, K.; Sugimoto, C.; Suzuki, M.; Takeo, T.; Motomura, S.; Kitahara, H.; Niwa, M.; Oshima, Y.; Furukawa, K. -I. (2008). "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): 90–98. doi:10.1124/jpet.108.143172. PMID 18927354.
↑ Kim, S. H.; Park, H. S.; Lee, M. S.; Cho, Y. J.; Kim, Y. S.; Hwang, J. T.; Sung, M. J.; Kim, M. S.; Kwon, D. Y. (2008). "Vitisin a inhibits adipocyte differentiation through cell cycle arrest in 3T3-L1 cells". Biochemical and Biophysical Research Communications. 372 (1): 108–113. doi:10.1016/j.bbrc.2008.04.188. PMID 18482581.
↑ Mi Jeong Sung, S.; Davaatseren, M.; Kim, W.; Sung Kwang, P.; Kim, S. H.; Haeng Jeon, H.; Myung Sunny, K.; Kim, Y. S.; Dae Young, K. (2009). "Vitisin a suppresses LPS-induced NO production by inhibiting ERK, p38, and NF-κB activation in RAW 264.7 cells". International Immunopharmacology. 9 (3): 319–323. doi:10.1016/j.intimp.2008.12.005. PMID 19135555. INIST:21253190.

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

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