Structure Database (LMSD)

Common Name
Procyanidin B2
Systematic Name
Synonyms
LM ID
LMPK12030002
Formula
Exact Mass
Calculate m/z
578.14243
Status
Curated


Classification

Biological Context

Procyanidin B2 is a phenol and a dimer of (–)-epicatechin (Item No. 11807) that has been found in apple pomace and has diverse biological activities.1,2,3,4 It inhibits MCF-7 breast cancer cell proliferation (IC50 = 19.2 µM).1 Procyanidin B2 scavenges 2,2-diphenyl-1-picrylhydrazyl (DPPH; Item No. 14805) and superoxide anion radicals in cell-free assays.2 It inhibits LDL oxidation in vitro by 79.5 and 98% when used at concentrations of 5 and 10 µM, respectively.3 Procyanidin B2 (100 mg/kg) prevents carbon tetrachloride-induced increases in serum aspartate aminotransferase (AST) and alanine aminotransferase (ALT) activities and hepatic injury in mice.4

This information has been provided by Cayman Chemical

References

1. Avelar, M.M., and Gouvêa, C.M.C.P. Procyanidin B2 cytotoxicity to MCF-7 human breast adenocarcinoma cells. Indian J. Pharm. Sci. 74(4), 351-355 (2012).
2. Lu, Y., and Foo, L.Y. Antioxidant and radical scavenging activities of polyphenols from apple pomace. Food Chem. 68(1), 81-85 (2000).
3. Teissedre, P.L., Frankel, E.N., Waterhouse, A.L., et al. Inhibition of in vitro human LDL oxidation by phenolic antioxidants from grapes and wines. J. Sci. Food Agric. 70(1), 55-61 (1996).
4. Yang, B.-Y., Zhang, X.-Y., Guan, S.-W., et al. Protective effect of procyanidin B2 against CCl4-induced acute liver injury in mice. Molecules 20(7), 12250-12265 (2015).

String Representations

InChiKey (Click to copy)
XFZJEEAOWLFHDH-NFJBMHMQSA-N
InChi (Click to copy)
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/s1
SMILES (Click to copy)
C1(O)=CC2O[C@H](C3C=CC(O)=C(O)C=3)[C@H](O)[C@@H](C3=C(O)C=C(O)C4C[C@@H](O)[C@@H](C5C=CC(O)=C(O)C=5)OC=43)C=2C(O)=C1

Other Databases

Wikipedia
KEGG ID
HMDB ID
CHEBI ID
PubChem CID
Cayman ID

Calculated Physicochemical Properties

Heavy Atoms 42
Rings 6
Aromatic Rings 4
Rotatable Bonds 3
Van der Waals Molecular Volume 483.60
Topological Polar Surface Area 224.90
Hydrogen Bond Donors 10
Hydrogen Bond Acceptors 12
logP 3.57
Molar Refractivity 144.41

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Updated at
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