Procyanidin B1

Names

[ CAS No. ]:
20315-25-7

[ Name ]:
Procyanidin B1

[Synonym ]:
Proanthocyanidin B2
(2R,2'R,3R,3'R,4R)-2,2'-Bis(3,4-dihydroxyphenyl)-3,3',4,4'-tetrahydro-2H,2'H-4,8'-bichromene-3,3',5,5',7,7'-hexol
Proanthocyanidin B1
4,8"-Bi-[(+)-epicatechin]
PROCYANIDINDIMERB2
ProcyanidinB1
[4,8'-Bi-2H-1-benzopyran]-3,3',5,5',7,7'-hexol, 2,2'-bis(3,4-dihydroxyphenyl)-3,3',4,4'-tetrahydro-, (2R,2'R,3R,3'S,4R)-
Procyanidin B1
Procyanidol B2
Procyanidin B2
Proanthocyanidin
UNII-L88HKE854X
(2R,2'R,3R,3'S,4R)-2,2'-Bis(3,4-dihydroxyphenyl)-3,3',4,4'-tetrahydro-2H,2'H-4,8'-bichromene-3,3',5,5',7,7'-hexol
[4,8'-Bi-2H-1-benzopyran]-3,3',5,5',7,7'-hexol, 2,2'-bis(3,4-dihydroxyphenyl)-3,3',4,4'-tetrahydro-, (2R,2'R,3R,3'R,4R)-

Biological Activity

[Description]:

Procyanidin B1 is a polyphenolic flavonoid isolated from commonly eaten fruits, binds to TLR4/MD-2 complex, and has anti-inflammatory activity.

[Related Catalog]:

Signaling Pathways >> Immunology/Inflammation >> Toll-like Receptor (TLR)

Natural Products >> Flavonoids

Research Areas >> Inflammation/Immunology

[In Vitro]

Procyanidin B1 is a polyphenolic flavonoid isolated from fruits and fruit juices, binds to TLR4/MD-2 complex, and has anti-inflammatory activity. Procyanidin B1 causes cellular toxicity at concentrations >100 μg/mL. Procyanidin B1 (100 μg/mL) inhibits LPS-induced TNF-α production, and expression of MD-2, TRAF6, NF-κB mRNA, phosphorylated p38 MAPK and NF-κB protein in THP1 cells[1]. Procyanidin B1 (50-100 µM) protects against Aβ oligomer-induced neuronal death. Procyanidin B1 potently inhibits the activation of caspase-3 at 100 µM, caspase-8 at concentrations of 30, 50, and 100 µM and caspase-9 at concentrations of 10, 30, 50, and 100 µM[2]. Procyanidin B1 (10, 20, 30 μM) significantly and dose-dependently induces expression of ACO and CPT1, with no obvious effect on mRNA expression of PPARα[3].

[Cell Assay]

To investigate the cytotoxic effect of Procyanidin B1, viability of THP1 cells is assessed using CCK8 assay. THP1 cells are treated with Procyanidin B1 for 18 h, and 10 μL of CCK8 solution is then added to each well and the cultures are incubated for 4 h at 37°C. The optical density (OD) at 450 nm is measured using an ELx808 Absorbance Microplate Reader. The Procyanidin B1 concentration tested ranges from 50 to 200 μg/mL. Each sample is tested in triplicate[1].

[References]

[1]. Xing J, 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. 2015 Sep;407(1-2):89-95.

[2]. Kanno H, et al. Protective effects of glycycoumarin and procyanidin B1, active components of traditional Japanese medicine yokukansan, on amyloid β oligomer-induced neuronal death. J Ethnopharmacol. 2015 Jan 15;159:122-8.

[3]. Shimada T, et al. Flavangenol (pine bark extract) and its major component procyanidin B1 enhance fatty acid oxidation in fat-loaded models. Eur J Pharmacol. 2012 Feb 29;677(1-3):147-53.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.7±0.1 g/cm3

[ Boiling Point ]:
955.3±65.0 °C at 760 mmHg

[ Melting Point ]:
231～232℃

[ Molecular Formula ]:
C₃₀H₂₆O₁₂

[ Molecular Weight ]:
578.520

[ Flash Point ]:
531.6±34.3 °C

[ Exact Mass ]:
578.142456

[ PSA ]:
220.76000

[ LogP ]:
0.30

[ Vapour Pressure ]:
0.0±0.3 mmHg at 25°C

[ Index of Refraction ]:
1.803

[ Storage condition ]:
2-8°C

MSDS

Click to get detail MSDS

Safety Information

[ Personal Protective Equipment ]:
Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter

[ Hazard Codes ]:
Xi

[ Risk Phrases ]:
24/25

[ Safety Phrases ]:
24/25

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
3

[ HS Code ]:
29329990

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Articles

Effects of UV exclusion on the physiology and phenolic composition of leaves and berries of Vitis vinifera cv. Graciano.

J. Sci. Food Agric. 95(2) , 409-16, (2014)

Ultraviolet (UV) radiation induces adaptive responses that can be used for plant production improvement. The aim of this study was to assess the effect of solar UV exclusion on the physiology and phen...

UHPLC-PDA-ESI/HRMSn profiling method to identify and quantify oligomeric proanthocyanidins in plant products.

J. Agric. Food Chem. 62(39) , 9387-400, (2014)

Oligomeric proanthocyanidins were successfully identified by UHPLC-PDA-HRMS(n) in a selection of plant-derived materials (jujube fruit, Fuji apple, fruit pericarps of litchi and mangosteen, dark choco...

Reliability of bond dissociation enthalpy calculated by the PM6 method and experimental TEAC values in antiradical QSAR of flavonoids.

Bioorg. Med. Chem. 18 , 28-35, (2010)

The applicability of the newly developed RM1 and PM6 methods implemented in the semiempirical quantum chemistry mopac2009 software package in modeling free radical scavenging activity of flavonoids wa...

Related Compounds

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