Procyanidin B2

Procyanidin B2
Names
IUPAC name
(2R,2ʼR,3R,3ʼR,4R)-2,2ʼ-bis(3,4-dihydroxyphenyl)-3,3ʼ,4,4ʼ-tetrahydro-2H,2ʼH-4,8ʼ-bichromene-3,3ʼ,5,5ʼ,7,7ʼ-hexol
Other names
Procyanidin-B2
(−)-Epicatechin-(4β→8)-(−)-epicatechin
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
Properties
C30H26O12
Molar mass 578.52 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

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),[1] in Litchi chinensis (litchi, in the pericarp),[2] in the apple,[3] and in Ecdysanthera utilis.[4]

Procyanidin B2 can be converted into procyanidin A2 by radical oxidation using 1,1-diphenyl-2-picrylhydrazyl (DPPH) radicals under neutral conditions.[5]

Procyanidin B2 has been shown to inhibit the formation of the advanced glycation end-products pentosidine, carboxymethyllysine (CML), and methylglyoxal (MGO).[6]

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.
  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: 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.


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