Miyabenol C

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Miyabenol C
Miyabenol C.svg
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
PubChem CID
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

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.

Related Research Articles

Grape Edible berry of a flowering plant in the family Vitaceae

A grape is a fruit, botanically a berry, of the deciduous woody vines of the flowering plant genus Vitis.

Resveratrol Chemical compound

Resveratrol (3,5,4′-trihydroxy-trans-stilbene) is a stilbenoid, a type of natural phenol, and a phytoalexin produced by several plants in response to injury or when the plant is under attack by pathogens, such as bacteria or fungi. Sources of resveratrol in food include the skin of grapes, blueberries, raspberries, mulberries, and peanuts.

<i>Vitis vinifera</i> Species of flowering plant in the grape vine family Vitaceae

Vitis vinifera, the common grape vine, is a species of flowering plant, native to the Mediterranean region, Central Europe, and southwestern Asia, from Morocco and Portugal north to southern Germany and east to northern Iran. There are currently between 5,000 and 10,000 varieties of Vitis vinifera grapes though only a few are of commercial significance for wine and table grape production.

Phytoalexin

Phytoalexins are antimicrobial substances, some of which are antioxidative as well. They are defined, not by their having any particular chemical structure or character, but by the fact that they are defensively synthesized de novo by plants that produce the compounds rapidly at sites of pathogen infection. In general phytoalexins are broad spectrum inhibitors; they are chemically diverse, and different chemical classes of compounds are characteristic of particular plant taxa. Phytoalexins tend to fall into several chemical classes, including terpenoids, glycosteroids and alkaloids, however the term applies to any phytochemicals that are induced by microbial infection.

<i>Gnetum gnemon</i> Species of plant

Gnetum gnemon is a species of Gnetum native to southeast Asia and the western Pacific Ocean islands, from Mizoram and Assam in India, south and east through Indonesia and Malaysia to the Philippines, Fiji, and Hawaii in the United States. Common names include gnetum, joint fir, two leaf, melinjo, belinjo, bago, and tulip.

Piceatannol Chemical compound

Piceatannol is a stilbenoid, a type of phenolic compound.

Phenolic content in wine Wine chemistry

The phenolic content in wine refers to the phenolic compounds—natural phenol and polyphenols—in wine, which include a large group of several hundred chemical compounds that affect the taste, color and mouthfeel of wine. These compounds include phenolic acids, stilbenoids, flavonols, dihydroflavonols, anthocyanins, flavanol monomers (catechins) and flavanol polymers (proanthocyanidins). This large group of natural phenols can be broadly separated into two categories, flavonoids and non-flavonoids. Flavonoids include the anthocyanins and tannins which contribute to the color and mouthfeel of the wine. The non-flavonoids include the stilbenoids such as resveratrol and phenolic acids such as benzoic, caffeic and cinnamic acids.

Procyanidin C2 Chemical compound

Procyanidin C2 is a B type proanthocyanidin trimer, a type of condensed tannin.

<i>epsilon</i>-Viniferin Chemical compound

ε-Viniferin is a naturally occurring phenol, belonging to the stilbenoids family. It is a resveratrol dimer.

<i>alpha</i>-Viniferin Chemical compound

α-Viniferin is a stilbene trimer. It can be isolated from Caragana chamlagu and from Caragana sinica and from the stem bark of Dryobalanops aromatica. It is also present in relation to resistance to Botrytis cinerea and Plasmopara viticola in Vitis vinifera and Vitis riparia.

Kobophenol A Chemical compound

Kobophenol A is a stilbenoid. It is a tetramer of resveratrol. It can be isolated from Caragana chamlagu, from Caragana sinica and from Carex folliculata seeds.

Tetramer

A tetramer (tetra-, "four" + -mer, "parts") is an oligomer formed from four monomers or subunits. The associated property is called tetramery. An example from inorganic chemistry is titanium methoxide with the empirical formula Ti(OCH3)4, which is tetrameric in solid state and has the molecular formula Ti4(OCH3)16. An example from organic chemistry is kobophenol A, a substance that is formed by combining four molecules of resveratrol.

<i>Caragana sinica</i> Species of legume

Caragana sinica is a species belonging to the genus Caragana.

Carasinol B Chemical compound

Carasinol B is a stilbenoid tetramer found in Caragana sinica.

Astringin Chemical compound

Astringin is a stilbenoid, the 3-β-D-glucoside of piceatannol. It can be found in the bark of Picea sitchensis or Picea abies.

Amurensin may refer to:

<i>delta</i>-Viniferin Chemical compound

δ-Viniferin is a resveratrol dehydrodimer. It is an isomer of epsilon-viniferin. It can be isolated from stressed grapevine leaves. It is also found in plant cell cultures and wine. It can also be found in Rheum maximowiczii.

Ampelopsin may refer to:

Isorhapontigenin Chemical compound

Isorhapontigenin is a tetrahydroxylated stilbenoid with a methoxy group. It is an isomer of rhapontigenin and an analog of resveratrol. It is found in the Chinese herb Gnetum cleistostachyum, in Gnetum parvifolium and in the seeds of the palm Aiphanes aculeata.

Foeniculoside I Chemical compound

Foeniculoside I is a stilbenoid. It is a glucoside of the stilbene trimer cis-miyabenol C. It can be found in Foeniculi fructus.

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. 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.