Misplaced Pages

Procyanidin B2

Article snapshot taken from Wikipedia with creative commons attribution-sharealike license. Give it a read and then ask your questions in the chat. We can research this topic together.
(Redirected from Proanthocyanidin B2)
Procyanidin B2
Chemical structure of procyanidin B2
Names
IUPAC name -(4→8)-
Systematic IUPAC name (2R,2′R,3R,3′R,4R)-2,2′-Bis(3,4-dihydroxyphenyl)-3,3′,4,4′-tetrahydro-2H,2′H--3,3′,5,5′,7,7′-hexol
Other names Procyanidin-B2
(−)-Epicatechin-(4β→8)-(−)-epicatechin
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChemSpider
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C30H26O12/c31-13-7-20(37)24-23(8-13)41-29(12-2-4-16(33)19(36)6-12)27(40)26(24)25-21(38)10-17(34)14-9-22(39)28(42-30(14)25)11-1-3-15(32)18(35)5-11/h1-8,10,22,26-29,31-40H,9H2/t22-,26-,27-,28-,29-/m1/s1Key: XFZJEEAOWLFHDH-NFJBMHMQSA-N
SMILES
  • O1Cc2c(O)cc(O)c(3(O)(Oc4cc(O)cc(O)c34)c3ccc(O)c(O)c3)c2O1c1ccc(O)c(O)c1
Properties
Chemical formula C30H26O12
Molar mass 578.52 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). checkY verify (what is  ?) Infobox references
Chemical compound

Procyanidin B2 is a B type proanthocyanidin. Its structure is (−)-Epicatechin-(4β→8)-(−)-epicatechin.

Procyanidin B2 can be found in Cinchona pubescens (Chinchona: in the rind, bark, and cortex), in Cinnamomum verum (Ceylon cinnamon: in the rind, bark, and cortex), in Crataegus monogyna (Common hawthorn: in the flower and blossom), in Uncaria guianensis (Cat's claw: in the root), in Vitis vinifera (Common grape vine: in the leaf), in Litchi chinensis (litchi: in the pericarp), in the apple, and in Ecdysanthera utilis.

Procyanidin B2 can be converted into procyanidin A2 by radical oxidation using 1,1-diphenyl-2-picrylhydrazyl (DPPH) radicals under neutral conditions.

Procyanidin B2 has been shown to inhibit the formation of the advanced glycation end-products pentosidine, carboxymethyllysine (CML), and methylglyoxal (MGO).

See also

References

  1. Proanthocyanidin-B2 on liberherbarum.com
  2. Immunomodulatory and anticancer activities of flavonoids extracted from litchi (Litchi chinensis Sonn.) pericarp. Mouming Zhao; Bao Yang; Jinshui Wang; Yang Liu; Limei Yu; Yueming Jiang, 2007
  3. Proanthocyanidin-B2 on fuzing.com
  4. Lin LC (2002). "Immunomodulatory Proanthocyanidins from Ecdysanthera u tilis". Journal of Natural Products. 65 (4): 505–508. doi:10.1021/np010414l. PMID 11975489.
  5. Kondo K (2000). "Conversion of procyanidin B-type (catechin dimer) to A-type: evidence for abstraction of C-2 hydrogen in catechin during radical oxidation". Tetrahedron Letters. 41 (4): 485–488. doi:10.1016/S0040-4039(99)02097-3.
  6. Peng X, Ma J, Chao J, Sun Z, Chang RC, Tse I, Li ET, Chen F, Wang M (2010). "Beneficial effects of cinnamon proanthocyanidins on the formation of specific advanced glycation endproducts and methylglyoxal-induced impairment on glucose consumption". Journal of Agricultural and Food Chemistry. 58 (11): 6692–6696. doi:10.1021/jf100538t. PMID 20476737.
Types of procyanidins
A-type proanthocyanidins
B type proanthocyanidins
Types


Stub icon

This article about an aromatic compound is a stub. You can help Misplaced Pages by expanding it.

Categories: