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{{chembox |
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| verifiedrevid = 423484890 |
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| Name = Procyanidin B2 |
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| verifiedrevid = 410666400 |
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| Reference = |
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| Name = Proanthocyanidin B2 |
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| ImageFile = Structure_of_Procyanidin_B2.png |
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| Reference = |
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| ImageName = Chemical structure of procyanidin B2 |
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| ImageFile = Procyanidin B2.svg |
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| ImageSize = 200px |
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| ImageName = Chemical structure of proanthocyanidin B2 |
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| IUPACName = -(4→8)- |
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| ImageSize = 200px |
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| SystematicName = (2''R'',2′''R'',3''R'',3′''R'',4''R'')-2,2′-Bis(3,4-dihydroxyphenyl)-3,3′,4,4′-tetrahydro-2''H'',2′''H''--3,3′,5,5′,7,7′-hexol |
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| IUPACName = |
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| OtherNames = Procyanidin-B2<br>(−)-]-(4β→8)-(−)-epicatechin |
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| OtherNames = Procyanidin-B2<br>(−)-]-(4β→8)-(−)-epicatechin |
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| Section1= {{Chembox Identifiers |
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|Section1={{Chembox Identifiers |
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| CASNo = 29106-49-8 |
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| CASNo = 29106-49-8 |
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| CASOther = |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| PubChem = 122738 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| SMILES = |
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| UNII = L88HKE854X |
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| PubChem = 122738 |
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| ChEBI = 75632 |
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| SMILES = O1Cc2c(O)cc(O)c(3(O)(Oc4cc(O)cc(O)c34)c3ccc(O)c(O)c3)c2O1c1ccc(O)c(O)c1 |
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| ChemSpiderID = 109417 |
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| StdInChI = 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/s1 |
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| StdInChIKey = XFZJEEAOWLFHDH-NFJBMHMQSA-N |
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|Section2= {{Chembox Properties |
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|Section2={{Chembox Properties |
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| Formula = C<sub>30</sub>H<sub>26</sub>O<sub>12</sub> |
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| Formula = C<sub>30</sub>H<sub>26</sub>O<sub>12</sub> |
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| MolarMass = 578.52 g/mol |
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| MolarMass = 578.52 g/mol |
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| Appearance= |
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| ExactMass = 578.142426 u |
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|Section3= {{Chembox Hazards |
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|Section3={{Chembox Hazards |
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'''Proanthocyanidin B2''' is a ] ((−)-]-(4β→8)-(−)-epicatechin). |
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'''Procyanidin B2''' is a ]. Its structure is (−)-]-(4β→8)-(−)-epicatechin. |
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Procyanidin B2 can be found in '']'' (Chinchona: in the rind, bark, and cortex), in '']'' (Ceylon cinnamon: in the rind, bark, and cortex), in '']'' (Common hawthorn: in the flower and blossom), in '']'' (Cat's claw: in the root), in '']'' (Common grape vine: in the leaf),<ref></ref> in '']'' (litchi: in the pericarp),<ref name="Mouming"></ref> in the ],<ref></ref> and in '']''.<ref name="Lie-Chwen">{{cite journal|doi=10.1021/np010414l | volume=65 | issue=4 | title=Immunomodulatory Proanthocyanidins from Ecdysanthera u tilis | year=2002 | journal=Journal of Natural Products | pages=505–508 | vauthors=Lin LC | pmid=11975489}}</ref> |
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Procyanidin B2 can be converted into ] by radical oxidation using ] (DPPH) radicals under neutral conditions.<ref>{{cite journal | doi = 10.1016/S0040-4039(99)02097-3 | volume=41 | title=Conversion of procyanidin B-type (catechin dimer) to A-type: evidence for abstraction of C-2 hydrogen in catechin during radical oxidation | year=2000 | journal=Tetrahedron Letters | pages=485–488 | vauthors=Kondo K| issue=4 }}</ref> |
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Procyanidin B2 has been shown to inhibit the formation of the ]s ], ] (CML), and ] (MGO).<ref>{{cite journal |vauthors=Peng X, Ma J, Chao J, Sun Z, Chang RC, Tse I, Li ET, Chen F, Wang M | title=Beneficial effects of cinnamon proanthocyanidins on the formation of specific advanced glycation endproducts and methylglyoxal-induced impairment on glucose consumption| journal= Journal of Agricultural and Food Chemistry | volume=58 | issue=11 | year=2010 | pages=6692–6696 | pmid=20476737 | doi=10.1021/jf100538t}}</ref> |
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== See also == |
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Proanthocyanidin B2 can be found in '']'' (Chinchona, in the rind, bark and cortex), in '']'' (Ceylon cinnamon, in the rind, bark and cortex), in '']'' (Common hawthorn, in the flower and blossom), in '']'' (Cat's claw, in the root), in '']'' (Common grape vine, in the leaf)<ref></ref>, in '']'' (litchi, in the pericarp)<ref name="Mouming"></ref>, in the ]<ref></ref>, and in '']''<ref name="Lie-Chwen"></ref>. |
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* ] |
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== References == |
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Proanthocyanidin B2 has been shown to inhibit the formation of the ]s ], ] (CML), and ] (MGO).<ref>{{cite journal | author=Peng X, Ma J, Chao J, Sun Z, Chang RC, Tse I, Li ET, Chen F, Wang M | title=Beneficial effects of cinnamon proanthocyanidins on the formation of specific advanced glycation endproducts and methylglyoxal-induced impairment on glucose consumption| journal= JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY | volume=58 | issue=11 | year=2010 | pages=6692–6696 | id= | pmid=20476737}}</ref> |
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{{reflist|2}} |
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{{procyanidin}} |
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==References== |
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{{reflist}} |
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] |
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{{proanthocyanidin}} |
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] |
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{{Natural-phenol-stub}} |
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{{Aromatic-stub}} |