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Miyabenol C

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Miyabenol C
Names
Other names
Z-miyabenol C
E-cis-miyabenol C[1]
Identifiers
3D model (JSmol)
ChEBI
  • 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
Properties
C42H32O9
Molar mass 680.69 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

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

It shows protein kinase C inhibitor activity.[4]

Foeniculoside I is a glucoside of cis-miyabenol C.

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. ^ a b 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.

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