Vitisin A (stilbenoid)

For other uses, see Vitisin A.
Vitisin A
Chemical structure of vitisin A
Names
Preferred IUPAC name
(21S,26R,27S,4E,62S,63S)-27,62-Bis(4-hydroxyphenyl)-21,26,27,211b,62,63-hexahydro-2(1,6)-benzo[6,7]cyclohepta[1,2,3-cd][1]benzofurana-6(4,3)-[1]benzofurana-1,7(1),3(1,3)-tribenzenaheptaphan-4-ene-14,24,28,210,36,66,73,75-octol
Other names
R2-Viniferin[1]
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
UNII
  • InChI=1S/C56H42O12/c57-33-10-4-28(5-11-33)49-51(42-23-40(64)26-47-53(42)54(43-22-39(63)24-45(66)52(43)49)56(68-47)30-8-14-35(59)15-9-30)41-17-27(2-16-44(41)65)1-3-31-18-38(62)25-46-48(31)50(32-19-36(60)21-37(61)20-32)55(67-46)29-6-12-34(58)13-7-29/h1-26,49-51,54-66H/b3-1+/t49-,50+,51+,54+,55-,56-/m1/s1
    Key: XAXVWWYPKOGXSY-DBHYGPPCSA-N
  • InChI=1/C56H42O12/c57-33-10-4-28(5-11-33)49-51(42-23-40(64)26-47-53(42)54(43-22-39(63)24-45(66)52(43)49)56(68-47)30-8-14-35(59)15-9-30)41-17-27(2-16-44(41)65)1-3-31-18-38(62)25-46-48(31)50(32-19-36(60)21-37(61)20-32)55(67-46)29-6-12-34(58)13-7-29/h1-26,49-51,54-66H/b3-1+/t49-,50+,51+,54+,55-,56-/m1/s1
    Key: XAXVWWYPKOGXSY-DBHYGPPCBS
  • c1cc(ccc1[C@H]2c3c(cc(cc3O)O)[C@H]4c5c(cc(cc5O[C@@H]4c6ccc(cc6)O)O)[C@@H]2c7cc(ccc7O)/C=C/c8cc(cc9c8[C@@H]([C@H](O9)c1ccc(cc1)O)c1cc(cc(c1)O)O)O)O
Properties
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).
checkY verify (what is checkY☒N ?)

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

  1. ^ Poster at 1st International Conference of Resveratrol and Health, Jean-Claude Izard, 2010
  2. ^ a b 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. S2CID 22844861.
  3. ^ 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.
  4. ^ 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.


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