Miyabenol C

Miyabenol C
Names

Other names Z-miyabenol C E-cis-miyabenol C^[1]
Identifiers
CAS Number	109605-83-6
ChEBI	CHEBI:76193
Jmol interactive 3D	Image
SMILES 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
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

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): 110503144447002. doi:10.1021/jf200771y.
↑ 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.
↑ 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
1 2 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

Glycosides or conjugates

Diptoindonesin A (C-glucoside of ε-viniferin)
Foeniculoside I (glucoside of miyabenol C), II, III and IV
Laevifonol (an ε-viniferin-ascorbic acid hybrid compound)
Laevifoside (O-glucoside of ampelopsin A)

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