Miyabenol C

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
CAS Number	109605-83-6^Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:76193
ChemSpider	4977560
PubChem CID	5388319
UNII	78H44UGJ85^Y
CompTox Dashboard (EPA)	DTXSID20745441
InChI 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
SMILES 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
Chemical formula	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

Chemical compound

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

^ 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.
^ 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.
^ 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.
^ ^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.

External links

Miyabenol C at www.plant-expert.com

Oligostilbenoids and their glycosides

Diptoindonesin C
Diptoindonesin F
Gnetin H
Hemsleyanol D
Isohopeaphenol
Laetevirenol A, B, C, D and E
Suffruticosol A and B
Viniferal
E-ω-viniferin
Z-ω-viniferin

Dimers

Diptoindonesin G
Jezonodione
B
Scirpusin A
Tibeticanol (piceatannol dimer)

Trimers

Amurensin B
Gnetin E
Gneyulin A
Johorenol A
Ampelopsin E
Vaticanol G

Tetramers:

Dibalanocarpol
Gnetin J (3"-hydroxygnetin E)
Gnetin K (3"-methoxygnetin E)
Gnetuhainin R (isorhapontigenin tetramer)
Laetevirenol F and G

Higher polymers
(five units or more)

Vaticanol D, H, I and J

Oligomeric forms
of resveratrol

Dimers	Amurensin A and H Ampelopsin A B D and F Balanocarpol Cyphostemmin A and B δ-viniferin ε-viniferin Gnetin A and C Leachinol F Malibatol A Pallidol Parthenocissin A Quadrangularin A Restrytisol A, B and C Vitisinol D
Trimers	α-viniferin Ampelopsin C Amurensin C, D and G Hopeanolin Malaysianol A Miyabenol C Resviniferin A and B trans-diptoindonesin B
Tetramers	Ampelopsin H Amurensin K Caraphenol B Carasinol B Flexuosol A Hopeaphenol Kobophenol A Miyabenol A Vaticanol B and C Vaticaphenol A Vitisin A B and C β-viniferin (cyclic resveratrol tetramer)
Pentamers	Amurensin E and F
Hexamers	Chunganenol
Higher polymers	γ-viniferin Valeriaphenol A