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α-Viniferin

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α-Viniferin
Names
Preferred IUPAC name (1R,5bR,6R,10bS,11S,15bR)-1,6,11-Tris(4-hydroxyphenyl)-1,5b,6,10b,11,15b-hexahydrocyclononatris(benzofuran)-4,9,14-triol
Other names α-Viniferin; (+)-α-Viniferin
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • 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/h1-18,37-48HKey: KUTVNHOAKHJJFL-UHFFFAOYSA-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/h1-18,37-48HKey: KUTVNHOAKHJJFL-UHFFFAOYAE
SMILES
  • OC(C=C1)=CC=C12(C3=C4C(O(C5=CC=C(O)C=C5)4C6=C(7(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
Chemical formula C42H30O9
Molar mass 678.693 g·mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

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

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)
Acetylcholine metabolism and transport modulators
Enzyme
(modulators)
ChATTooltip Choline acetyltransferase
AChETooltip Acetylcholinesterase
BChETooltip Butyrylcholinesterase
Transporter
(modulators)
CHTTooltip Choline transporter
VAChTTooltip Vesicular acetylcholine transporter
Release
(modulators)
Inhibitors
Enhancers
See also
Receptor/signaling modulators
Muscarinic acetylcholine receptor modulators
Nicotinic acetylcholine receptor modulators
Oligostilbenoids and their glycosides
Dimers
Trimers
Tetramers:
Higher polymers
(five units or more)
Oligomeric forms
of resveratrol
Dimers
Trimers
Tetramers
Pentamers
Hexamers
Higher polymers
Glycosides or conjugates


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