| Revision as of 19:22, 19 May 2011 editNono64 (talk | contribs)Autopatrolled, Pending changes reviewers, Rollbackers96,246 editsm opposite effect to hopeaphenol← Previous edit |
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{{Other uses|Vitisin A (disambiguation)}} |
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{{Other uses|Vitisin A (disambiguation){{!}}Vitisin A}} |
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{{chembox |
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{{chembox |
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| Watchedfields = changed |
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| verifiedrevid = 422979796 |
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| verifiedrevid = 429928505 |
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| Name = Vitisin A |
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| Name = Vitisin A |
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| ImageFile = Vitisin A.png |
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| ImageFile = Vitisin A (stilbenoid).png |
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| ImageSize = 200px |
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| ImageSize = 200px |
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| ImageName = Chemical structure of vitisin A |
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| ImageName = Chemical structure of vitisin A |
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| ImageAlt = Chemical structure of vitisin A |
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| ImageAlt = Chemical structure of vitisin A |
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| PIN = (2<sup>1</sup>''S'',2<sup>6</sup>''R'',2<sup>7</sup>''S'',4''E'',6<sup>2</sup>''S'',6<sup>3</sup>''S'')-2<sup>7</sup>,6<sup>2</sup>-Bis(4-hydroxyphenyl)-2<sup>1</sup>,2<sup>6</sup>,2<sup>7</sup>,2<sup>11b</sup>,6<sup>2</sup>,6<sup>3</sup>-hexahydro-2(1,6)-benzocycloheptabenzofurana-6(4,3)-benzofurana-1,7(1),3(1,3)-tribenzenaheptaphan-4-ene-1<sup>4</sup>,2<sup>4</sup>,2<sup>8</sup>,2<sup>10</sup>,3<sup>6</sup>,6<sup>6</sup>,7<sup>3</sup>,7<sup>5</sup>-octol |
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| IUPACName = |
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| OtherNames = R2-Viniferin<ref></ref> |
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| OtherNames = |
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|Section1= {{Chembox Identifiers |
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|Section1={{Chembox Identifiers |
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| CASNo = 142449-89-6 |
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| CASNo = 142449-89-6 |
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| CASNo_Ref = |
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| CASNo_Ref = {{cascite|correct|??}}= |
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| CASOther = |
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| CASNoOther = |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII = 832N5294M6 |
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| PubChem = 16131430 |
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| PubChem = 16131430 |
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| ChemSpiderID = 17288137 |
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| 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 |
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| SMILES = c1cc(ccc12c3c(cc(cc3O)O)4c5c(cc(cc5O4c6ccc(cc6)O)O)2c7cc(ccc7O)/C=C/c8cc(cc9c8((O9)c1ccc(cc1)O)c1cc(cc(c1)O)O)O)O |
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| InChI = |
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| 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 |
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| InChIKey = XAXVWWYPKOGXSY-DBHYGPPCBS |
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| StdInChI = 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 |
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| StdInChIKey = XAXVWWYPKOGXSY-DBHYGPPCSA-N |
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| MeSHName = |
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| MeSHName = |
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| ChEMBL = 507409 |
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|Section2= {{Chembox Properties |
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|Section2={{Chembox Properties |
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| Formula = C<sub>56</sub>H<sub>42</sub>O<sub>12</sub> |
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| Formula = C<sub>56</sub>H<sub>42</sub>O<sub>12</sub> |
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| MolarMass = 906.92 g/mol |
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| MolarMass = 906.92 g/mol |
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| ExactMass = 906.267627 u |
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| Appearance = |
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| Appearance = |
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| Density = |
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| Density = |
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| MeltingPt = <!-- °C --> |
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| MeltingPt = |
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| BoilingPt = <!-- °C --> |
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| BoilingPt = |
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| Solubility = |
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| Solubility = |
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}} |
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| Section3 = {{Chembox Hazards |
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|Section3={{Chembox Hazards |
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| MainHazards = |
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| MainHazards = |
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| FlashPt = |
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| FlashPt = |
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| Autoignition = |
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| AutoignitionPt = |
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| RPhrases = <!-- {{R10}}, {{R23}}, {{R34}}, {{R50}} etc. --> |
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| GHS_ref =<!-- no GHS data in PubChem Dec2021 --> |
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| SPhrases = <!-- {{S1/2}}, {{S9}}, {{S16}}, {{S26}}, {{S36/37/39}}, {{S45}}, {{S61}} etc. --> |
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'''Vitisin A''' is a ] ] found in plants of the genus '']''. It is a complex of two resveratrol dimers, (+)-] and ].<ref name=Seya>{{Cite journal | last1 = Seya | first1 = K. | last2 = Kanemaru | first2 = K. | last3 = Sugimoto | first3 = C. | last4 = Suzuki | first4 = M. | last5 = Takeo | first5 = T. | last6 = Motomura | first6 = S. | last7 = Kitahara | first7 = H. | last8 = Niwa | first8 = M. | last9 = Oshima | first9 = Y. | doi = 10.1124/jpet.108.143172 | last10 = Furukawa | first10 = K. -I. | title = 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 = Journal of Pharmacology and Experimental Therapeutics | volume = 328 | issue = 1 | pages = 90–98 | year = 2008 | pmid = 18927354| s2cid = 22844861 }}</ref> |
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'''Vitisin A''' is a ] ] found in '']''. |
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It shows an opposite effect to ] on apoptosis of myocytes isolated from adult rat heart.<ref>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}}</ref><ref>Vitisin A inhibits adipocyte differentiation through cell cycle arrest in 3T3-L1 cells. Soon-hee Kim, Hee-Sook Park, Myoung-su Lee, Yong-Jin Cho, Young-Sup Kim, Jin-Taek Hwang, Mi Jeong Sung, Myung Sunny Kim and Dae Young Kwon, Biochemical and Biophysical Research Communications, Volume 372, Issue 1, 18 July 2008, Pages 108-113 {{doi|10.1016/j.bbrc.2008.04.188}}, {{PMID|18482581}}</ref><ref>Vitisin A suppresses LPS-induced NO production by inhibiting ERK, p38, and NF-KB activation in RAW 264.7 cells. Mi Jeong Sung, Davaatseren Munkhtugs, Kim Won, Sung Kwang Park, Kim Soon-Hee, Haeng Jeon Hur, Myung Sunny Kim, Kim Young-Sup and Dae Young Kwon, International immunopharmacology, 2009, vol. 9, no3, pp. 319-323, {{INIST|21253190}}</ref> |
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It shows an opposite effect to ] on apoptosis of myocytes isolated from adult rat heart.<ref name=Seya/><ref>{{Cite journal | last1 = Kim | first1 = S. H. | last2 = Park | first2 = H. S. | last3 = Lee | first3 = M. S. | last4 = Cho | first4 = Y. J. | last5 = Kim | first5 = Y. S. | last6 = Hwang | first6 = J. T. | last7 = Sung | first7 = M. J. | last8 = Kim | first8 = M. S. | last9 = Kwon | first9 = D. Y. | doi = 10.1016/j.bbrc.2008.04.188 | title = Vitisin a inhibits adipocyte differentiation through cell cycle arrest in 3T3-L1 cells | journal = Biochemical and Biophysical Research Communications | volume = 372 | issue = 1 | pages = 108–113 | year = 2008 | pmid = 18482581}}</ref><ref>{{Cite journal |
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| last1 = Mi Jeong Sung | first1 = S. |
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| last2 = Davaatseren | first2 = M. |
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| last3 = Kim | first3 = W. |
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| last4 = Sung Kwang | first4 = P. |
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| last5 = Kim | first5 = S. H. |
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| last6 = Haeng Jeon | first6 = H. |
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| last7 = Myung Sunny | first7 = K. |
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| last8 = Kim | first8 = Y. S. |
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| last9 = Dae Young | first9 = K. |
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| title = Vitisin a suppresses LPS-induced NO production by inhibiting ERK, p38, and NF-κB activation in RAW 264.7 cells |
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| doi = 10.1016/j.intimp.2008.12.005 |
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| journal = International Immunopharmacology |
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| volume = 9 |
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| issue = 3 |
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| pages = 319–323 |
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| year = 2009 |
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| pmid = 19135555 |
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| id = {{INIST|21253190}} |
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}}</ref> |
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==References== |
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== References == |
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{{reflist}} |
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{{Reflist}} |
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==External links== |
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== External links == |
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{{Stilbenoids}} |
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{{Oligostilbenoid}} |
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{{Natural-phenol-stub}} |
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{{aromatic-stub}} |