LIPID MAPS

Structure Database (LMSD)

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Common Name

Procyanidin B1

Systematic Name

Synonyms

Epicatechin-(4beta->8)-ent-epicatechin

LM ID

LMPK12030001

Formula

C₃₀H₂₆O₁₂

Exact Mass

Calculate m/z

578.142431

Status

Curated

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Classification

Biological Context

Procyanidin B1 is a polyphenol flavonoid existing as a dimer of (+)-catechin and (−)-epicatechin . It inhibits hepatitis C virus RNA replication (EC50 = 72 µM), while (+)-catechin and (−)-epicatechin do not, up to concentrations of 200 µM.¹ Procyanidin B1 (10 µg/ml) prevents phosphorylation of ERK1/2 and the production of reactive oxygen species (ROS) in THP-1 cells.² It decreases TNF-α, phosphorylated p38 MAPK, and NF-κB levels following LPS administration.³

This information has been provided by Cayman Chemical

References

1. Li, S., Kodama, E.N., Inoue, Y., et al. Procyanidin B1 purified from Cinnamomi cortex suppresses hepatitis C virus replication. Antivir. Chem. Chemother. 20(6), 239-248 (2010).

2. Terra, X., Palozza, P., Fernandez-Larrea, J., et al. Procyanidin dimer B1 and trimer C1 impair inflammatory response signalling in human monocytes. Free Radic. Res. 45(5), 611-619 (2011).

3. Xing, J., Li, R., Li, N., et al. Anti-inflammatory effect of procyanidin B1 on LPS-treated THP1 cells via interaction with the TLR4-MD-2 heterodimer and p38 MAPK and NF-κB signaling. Mol. Cell. Biochem. 407(1-2), 89-95 (2015).

String Representations

InChiKey (Click to copy)

XFZJEEAOWLFHDH-UKWJTHFESA-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+/m0/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