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Procyanidin B2

$275

  • Brand : BIOFRON

  • Catalogue Number : BF-P3022

  • Specification : 98%

  • CAS number : 29106-49-8

  • Formula : C30H26O12

  • Molecular Weight : 578.52

  • PUBCHEM ID : 122738

  • Volume : 25mg

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Catalogue Number

BF-P3022

Analysis Method

HPLC,NMR,MS

Specification

98%

Storage

-20℃

Molecular Weight

578.52

Appearance

Off-white crystalline powder

Botanical Source

Eriobotrya japonica,Vitis vinifera,Lindera aggregata,Tripterygium wilfordii,Areca catechu

Structure Type

Flavonoids

Category

Standards;Natural Pytochemical;API

SMILES

C1C(C(OC2=C1C(=CC(=C2C3C(C(OC4=CC(=CC(=C34)O)O)C5=CC(=C(C=C5)O)O)O)O)O)C6=CC(=C(C=C6)O)O)O

Synonyms

Proanthocyanidin B3/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/(2R,3S)-2-(3,4-dihydroxyphenyl)-8-[(2R,3S,4S)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2H-chromen-4-yl]-3,4-dihydro-2H-chromene-3,5,7-triol/4,8"-Bi-[(+)-epicatechin]/PROCYANIDINDIMERB2/EPICATECHIN(4BETA->8)EPICATECHIN/Procyanidol B2/(-)epicatechin-(-)-epicatechin/Procyanidin B2/EPICATECHIN(4B-8)EPICATECHIN/ProcyanidinB2/PROCYANIDIN B1(P)/Procyanidin B-3/Proanthocyanidin/4,8'-BI-[(+)-EPICATECHIN]/2,3-trans-proanthocyanidin/[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)-

IUPAC Name

(2R,3R)-2-(3,4-dihydroxyphenyl)-8-[(2R,3R,4R)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2H-chromen-4-yl]-3,4-dihydro-2H-chromene-3,5,7-triol

Applications

Procyanidin B2 is a natural flavonoid, with anti-cancer, antioxidant activities.

Density

1.7±0.1 g/cm3

Solubility

Methanol

Flash Point

531.6±34.3 °C

Boiling Point

955.3±65.0 °C at 760 mmHg

Melting Point

197-198ºC

InChl

InChl Key

WGK Germany

RID/ADR

HS Code Reference

2932990000

Personal Projective Equipment

Correct Usage

For Reference Standard and R&D, Not for Human Use Directly.

Meta Tag

provides coniferyl ferulate(CAS#:29106-49-8) MSDS, density, melting point, boiling point, structure, formula, molecular weight etc. Articles of coniferyl ferulate are included as well.>> amp version: coniferyl ferulate

PMID

30142454

Abstract

Procyanidin B2, a naturally occurring phenolic compound, has been reported to exert multiple beneficial functions. However, the effect of procyanidin B2 on free fatty acids (FFAs)-induced hepatic steatosis remains obscure. The present study is therefore aimed to elucidate the protective effect of procyanidin B2 against hepatic steatosis and its underlying mechanism. Herein, we reported that procyanidin B2 attenuated FFAs-induced lipid accumulation and its associated oxidative stress by scavenging excessive ROS and superoxide anion radicals, blocking loss of mitochondrial membrane potential, restoring glutathione content, and increasing activity of antioxidant enzymes (GPx, SOD and CAT) in hepatocytes. Procyanidin B2 mechanistically promoted lipid degradation via modulation of transcription factor EB (TFEB), a master regulator of lysosomal pathway. Molecular docking analysis indicated a possible ligand-binding position of procyanidin B2 with TFEB. In addition, administration of procyanidin B2 resulted in a significant reduction of hepatic fat accumulation in high-fat diet (HFD)-induced obese mice, and also ameliorated HFD-induced metabolic abnormalities, including hyperlipidemia and hyperglycemia. It was confirmed that procyanidin B2 prevented HFD-induced hepatic fat accumulation through down-regulating lipogenesis-related gene expressions (PPARγ, C/EBPα and SREBP-1c), inhibiting pro-inflammatory cytokines production (IL-6 and TNF-α) and increasing antioxidant enzymes activity (GPx, SOD and CAT). Moreover, hepatic fatty acids analysis indicated that procyanidin B2 caused a significant increase in the levels of palmitic acid, oleic acid and linoleic acid. Intriguingly, procyanidin B2 restored the decreased nuclear TFEB expression in HFD-induced liver steatosis and up-regulated its target genes involved in lysosomal pathway (Lamp1, Mcoln, Uvrag), which suggested a previously unrecognized mechanism of procyanidin B2 on ameliorating HFD-induced hepatic steatosis. Taken together, our results demonstrated that procyanidin B2 attenuated FFAs-induced hepatic steatosis through regulating TFEB-mediated lysosomal pathway and redox state, which had important implications that modulation of TFEB might be a potential therapeutic strategy for hepatic steatosis and procyanidin B2 could represent a promising novel agent in the prevention and treatment of non-alcoholic fatty liver disease (NAFLD).

KEYWORDS

Hepatic steatosis; Molecular docking; Procyanidin B2; Redox state; Transcriptional factor EB.

Title

Procyanidin B2 Ameliorates Free Fatty Acids-Induced Hepatic Steatosis Through Regulating TFEB-mediated Lysosomal Pathway and Redox State

Author

Hongming Su 1 , Yuting Li 1 , Dongwen Hu 1 , Lianghua Xie 1 , Huihui Ke 1 , Xiaodong Zheng 1 , Wei Chen 2

Publish date

2018 Oct

PMID

30025709

Abstract

Paraquat is a commonly used heterocyclic herbicide and has high toxicity by causing acute lung injury. There is no effective treatment for paraquat poisoning. We evaluated the effects of procyanidin B2, a natural dietary phytochemical, on paraquat-induced lung injury in rats. Paraquat was used to induce acute lung injury of rats, which were administered with procyanidin B2. The lung injury was evaluated by measuring the lung/body weight ratio, the histology and PMNs count. The oxidative stress was assessed by detecting ROS-mediated indices in the BALF. The expression of IL-1β and IL-18 were detected by RT-PCR and ELISA. The levels of NLRP3 inflammasome components including NLRP3, ASC and caspase-1 were detected by western blot. The lung injury in the paraquat-induced models in NLRP3 gene silenced animals was compared with the same lung injury model treated with procyanidin B2. Administration of procyanidin B2 significantly reduced paraquat-induced lung injury with lower BALF PMNs count, MPO activity, MDA level and elevated SOD activity. Procyanidin B2 suppressed expression of IL-1β and IL-18 at both RNA and protein levels, similar to the NLRP3 gene silenced rats. Compared to paraquat-induced group, procyanidin B2 showed remarkably decreased NLRP3, ASC and caspase-1 signals in the lung tissues in a dose-dependent manner. Procyanidin B2 significantly suppressed the activation of NLRP3 inflammasome in the lung tissue induced by paraquat in the rat model. This finding revealed a novel mechanism by which procyanidin B2 exerts anti-inflammatory effects and their clinical benefits in health.

KEYWORDS

Hepatic steatosis; Molecular docking; Procyanidin B2; Redox state; Transcriptional factor EB.

Title

Procyanidin B2 Protects Rats From Paraquat-Induced Acute Lung Injury by Inhibiting NLRP3 Inflammasome Activation

Author

Yinling Jiang 1 , Wanchun Yang 1 , Shuyu Gui 2

Publish date

2018 Oct

PMID

29751077

Abstract

To elucidate the possible mechanisms for the preventive effect of procyanidin B2 on aging, a combined analysis of metabolic profile and gut microbiome was carried out in the present study. The mimetic aged mice induced by d-galactose injection (500 mg/kg, sc daily), and the preventive group was fed with the diet plus 0.2% procyanidin B2. After 7 weeks of treatment, the spatial memory was assayed using the Morris water maze test. Procyanidin B2 significantly ameliorated the impaired memory and antioxidant abilities induced by d-galactose. Furthermore, metabolomics analysis of plasma based on LC/Q-TOF-MS demonstrated that phosphatidyl cholines, oleic acid, linoleic acid, carnitine, pantothenic acid, and taurocholic acid were significantly increased in the mice treated with procyanidin B2, and pyruvic acid, hydroxybutyric acid, hippuric acid, and cholic acid were decreased significantly. Together, gut microbiome analysis using Illumina sequencing showed that there were significant differences in the Firmicutes/Bacteroidetes ratio and abundance of Roseburia, Lachnospiraceae, and Bifidobacterium between the aging and supplemental procyanidin B2 groups. In summary, procyanidin B2 possessed potential prevention of the cognitive and oxidative impairment via the metabolic pathway regulation related to citrate cycle, fatty acid, and bile acid in the aged mice, accompanied by remodeling the gut flora.

KEYWORDS

Anti-aging; Gut microbiota; Metabolomics; Procyanidin B2.

Title

Procyanidin B2 Protects Against D-Galactose-Induced Mimetic Aging in Mice: Metabolites and Microbiome Analysis

Author

Ying Xiao 1 , Jialin Dong 2 , Zhiting Yin 2 , Qiguo Wu 2 , Yiming Zhou 2 , Xiaoli Zhou 3

Publish date

2018 Sep