Miyabenol C

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]

Miyabenol C
Names
Preferred IUPAC name
(2S,2′R,3S,3′R)-3′-(3,5-Dihydroxyphenyl)-2,2′-bis(4-hydroxyphenyl)-4-[(E)-2-(4-hydroxyphenyl)ethen-1-yl]-2,2′,3,3′-tetrahydro[3,5′-bi-1-benzofuran]-6,7′-diol
Other names
Z-miyabenol C
E-cis-miyabenol C[1]
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
UNII
  • InChI=1S/C42H32O9/c43-27-9-2-22(3-10-27)1-4-25-15-32(48)20-35-37(25)40(42(50-35)24-7-13-29(45)14-8-24)34-19-33(49)21-36-39(34)38(26-16-30(46)18-31(47)17-26)41(51-36)23-5-11-28(44)12-6-23/h1-21,38,40-49H/b4-1+/t38-,40+,41+,42-/m1/s1
    Key: RKFYYCKIHVEWHX-YOBICRQBSA-N
  • c1cc(ccc1/C=C/c2cc(cc3c2[C@@H]([C@H](O3)c4ccc(cc4)O)c5cc(cc6c5[C@H]([C@@H](O6)c7ccc(cc7)O)c8cc(cc(c8)O)O)O)O)O
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).
Infobox references

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): 5364–75. doi:10.1021/jf200771y. PMID 21510709.
  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. Ono, M; Ito, Y; Kinjo, J; Yahara, S; Nohara, T; Niiho, Y (1995). "Four new glycosides of stilbene trimer from Foeniculi fructus (fruit of Foeniculum vulgare MILLER)". Chemical and Pharmaceutical Bulletin. 43 (5): 868–871. doi:10.1248/cpb.43.868. 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.


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