Vitisin A (stilbenoid)

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
Identifiers
CAS Number	142449-89-6 =;
3D model (JSmol)	Interactive image;
ChEMBL	ChEMBL507409;
ChemSpider	17288137;
PubChem CID	16131430;
UNII	832N5294M6 ;
CompTox Dashboard (EPA)	DTXSID901029696 ;
	InChI 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;
	SMILES 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
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). verify (what is ?) 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
^ ^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.
^ 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.

External links

Website of the Schröder group

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

[Seya-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. 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.

[2]

[1]

[3]

[4]

Names

Preferred IUPAC name (2¹S,2⁶R,2⁷S,4E,6²S,6³S)-2⁷,6²-Bis(4-hydroxyphenyl)-2¹,2⁶,2⁷,2^11b,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
CAS Number	142449-89-6^Y=
3D model (JSmol)	Interactive image
ChEMBL	ChEMBL507409
ChemSpider	17288137
PubChem CID	16131430
UNII	832N5294M6^Y
CompTox Dashboard (EPA)	DTXSID901029696
InChI 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
SMILES 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
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