Miyabenol C

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Miyabenol C
Other names

Z-miyabenol C
E-cis-miyabenol C[1]

Identifiers
CAS number 109605-83-6

 Jmol-3D images {{#if:Oc1ccc(cc1)/C=C/c7cc(O)cc8O[C@H](c2ccc(O)cc2)[C@@H](c6cc4c(O[C@@H](c3ccc(O)cc3)[C@@H]4c5cc(O)cc(O)c5)c(O)c6)c78|Image 1
Properties
Molecular formula C42H32O9
Molar mass 680.69 g/mol
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

Miyabenol C is a stilbenoid and a resveratrol trimer. It is found in Vitis vinifera (grape),[2] in Foeniculi fructus (fruit of Foeniculum vulgare),[3] in Caragana sinica and shows protein kinase C inhibitor activity.[4]

See also

References

  1. ↑ Mattivi, F.; Vrhovsek, U.; Malacarne, G.; Masuero, D.; Zulini, L.; Stefanini, M.; Moser, C.; Velasco, R.; Guella, G. (2011). "Profiling of Resveratrol Oligomers, Important Stress Metabolites, Accumulating in the Leaves of Hybrid Vitis vinifera (Merzling × Teroldego) Genotypes Infected with Plasmopara viticola". Journal of Agricultural and Food Chemistry 59 (10): 110503144447002. doi:10.1021/jf200771y. 
  2. ↑ Barjot, C.; Tournaire, M.; Castagnino, C.; Vigor, C.; Vercauteren, J.; Rossi, J. F. O. (2007). "Evaluation of antitumor effects of two vine stalk oligomers of resveratrol on a panel of lymphoid and myeloid cell lines: Comparison with resveratrol". Life Sciences 81 (23–24): 1565–1574. doi:10.1016/j.lfs.2007.08.047. PMID 18001803. 
  3. ↑ Four new glycosides of stilbene trimer from Foeniculi fructus (fruit of Foeniculum vulgare MILLER). Ono M, Ito Y, Kinjo J, Yahara S, Nohara T and Niiho Y, Chemical and pharmaceutical bulletin, 1995, vol. 43, no5, pages 868-871, INIST:3610745
  4. ↑ Kulanthaivel, P.; Janzen, W.; Ballas, L.; Jiang, J.; Hu, C. Q.; Darges, J.; Seldin, J.; Cofield, D.; Adams, L. (2007). "Naturally Occurring Protein Kinase C Inhibitors; II. Isolation of Oligomeric Stilbenes from Caragana sinica". Planta Medica 61 (1): 41–44. doi:10.1055/s-2006-957996. PMID 7700990. 

External links

Aglycones
Dihydroxylated
Trihydroxylated
Tetrahydroxylated
O-methylated
  • 4-Methoxyresveratrol
  • Gnetucleistol D (2-methoxyoxyresveratrol)
  • Gnetucleistol E (3-methoxy-isorhapontigenin)
  • Isorhapontigenin (3,4',5-trihydroxy-3'-methoxystilbene)
  • Pterostilbene
  • Rhapontigenin (3,3',5-trihydroxy-4'-methoxystilbene)
Combretastatins:
carboxylated
other acetylations
Glycosides
  • Astringin (Piceatannol 3-O-glucoside)
  • Foeniculoside I, II, III and IV
  • Isorhapontin (Isorhapontigenin glucoside)
  • Mulberroside A (Oxyresveratrol diglucoside)
of resveratrol
of rhapontigenin
  • Rhapontigenin 3-O-rutinoside
    • 4'-Methoxy-(E)-resveratrol 3-O-rutinoside
  • Rhaponticin (Rhapontigenin glucoside)
Oligomeric forms
  • Ampelopsin C, E and H
  • Amurensin A, B, G and H
  • Balanocarpol
  • Carasinol B
  • Dibalanocarpol
  • Diptoindonesin C
  • Diptoindonesin F
  • Flexuosol A
  • Gnetin H
  • Hemsleyanol D
  • Isohopeaphenol
  • Kobophenol A
  • Laetevirenol A, B, C, D and E
  • Malibatol A and B
  • Suffruticosol A and B
  • Vaticanol C
  • Viniferal
  • E-ω-viniferin
  • Z-ω-viniferin
Tetramers:
  • Laetevirenol F and G
of resveratrol
Dimers
Trimers
Tetramers
  • Amurensin E
  • F and K
  • Gnetuhainin R (isorhapontigenin tetramer)
  • Hopeaphenol
  • Vaticanol B
  • Vitisin A
  • B and C
  • β-viniferin (cyclic resveratrol tetramer)
Pentamers
  • Amurensin E and F
Higher polymers
  • γ-viniferin
Oligomeric forms
glycosides or conjugates
  • Diptoindonesin A
  • Laevifonol (an ε-viniferin-ascorbic acid hybrid compound)
  • Laevifoside (O-glucoside of ampelopsin A)
Synthetic
  • Stilbenoid drugs


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