α-Viniferin

α-Viniferin is a stilbene trimer. It can be isolated from Caragana chamlagu[1] and from Caragana sinica[2] and from the stem bark of Dryobalanops aromatica.[3] It is also present in relation to resistance to Botrytis cinerea and Plasmopara viticola in Vitis vinifera and Vitis riparia.[4] It has been shown to inhibit acetylcholinesterase.[1]

α-Viniferin
Names
Preferred IUPAC name
(1R,5bR,6R,10bS,11S,15bR)-1,6,11-Tris(4-hydroxyphenyl)-1,5b,6,10b,11,15b-hexahydrocyclonona[1,2,3-cd:4,5,6-c′d′:7,8,9-c′′d′′]tris([1]benzofuran)-4,9,14-triol
Other names
α-Viniferin; (+)-α-Viniferin
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
UNII
  • InChI=1S/C42H30O9/c43-22-7-1-19(2-8-22)40-37-28-13-25(46)17-32-35(28)39(42(50-32)21-5-11-24(45)12-6-21)30-15-27(48)18-33-36(30)38(29-14-26(47)16-31(49-40)34(29)37)41(51-33)20-3-9-23(44)10-4-20/h1-18,37-48H ☒N
    Key: KUTVNHOAKHJJFL-UHFFFAOYSA-N ☒N
  • InChI=1/C42H30O9/c43-22-7-1-19(2-8-22)40-37-28-13-25(46)17-32-35(28)39(42(50-32)21-5-11-24(45)12-6-21)30-15-27(48)18-33-36(30)38(29-14-26(47)16-31(49-40)34(29)37)41(51-33)20-3-9-23(44)10-4-20/h1-18,37-48H
    Key: KUTVNHOAKHJJFL-UHFFFAOYAE
  • OC(C=C1)=CC=C1[C@@H]2[C@@H](C3=C4C(O[C@@H](C5=CC=C(O)C=C5)[C@@H]4C6=C([C@@H]7[C@H](C8=CC=C(O)C=C8)O9)C9=CC(O)=C6)=CC(O)=C3)C%10=C7C=C(O)C=C%10O2
  • Oc1ccc(cc1)C%10Oc2cc(O)cc7c2C%10c8cc(O)cc9OC(c3ccc(O)cc3)C(c5cc(O)cc6OC(c4ccc(O)cc4)C7c56)c89
Properties
C42H30O9
Molar mass 678.693 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

References
  1. Sung, Sang Hyun; Kang, So Young; Lee, Ki Yong; Park, Mi Jung; Kim, Jeong Hun; Park, Jong Hee; Kim, Young Chul; Kim, Jinwoong; Kim, Young Choong (2002). "(+)-α-Viniferin, a Stilbene Trimer from Caragana chamlague, Inhibits Acetylcholinesterase". Biological & Pharmaceutical Bulletin. 25 (1): 125–127. doi:10.1248/bpb.25.125. PMID 11824541.
  2. Shu, N; Zhou, H; Hu, C (2006). "Simultaneous determination of the contents of three stilbene oligomers in Caragana sinica collected in different seasons using an improved HPLC method". Biological & Pharmaceutical Bulletin. 29 (4): 608–12. doi:10.1248/bpb.29.608. PMID 16595888.
  3. Wibowo, A.; Ahmat, N.; Hamzah, A.S.; Sufian, A.S.; Ismail, N.H.; Ahmad, R.; Jaafar, F.M.; Takayama, H. (2011). "Malaysianol A, a new trimer resveratrol oligomer from the stem bark of Dryobalanops aromatica". Fitoterapia. 82 (4): 676–81. doi:10.1016/j.fitote.2011.02.006. PMID 21338657.
  4. Disease resistance of Vitis spp. and the production of the stress metabolites resveratrol, epsilon -viniferin, alpha -viniferin and pterostilbene. Langcake P, Physiological Plant Pathology, 1981, Vol. 18, No. 2, pages 213-226 (abstract Archived 2014-12-10 at the Wayback Machine)


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