Disease relevance of BRN 1675863

• The in vivo efficacy of procyanidin B dimers was evaluated in an aromatase-transfected MCF-7 breast cancer xenograft model [1].
• The procyanidin-rich French maritime pine bark extract Pycnogenol (PBE) has been investigated for its effect in protecting human skin against solar UV-simulated light-induced erythema [2].
• Procyanidin trimers to pentamers fractionated from apple inhibit melanogenesis in B16 mouse melanoma cells [3].
• We have investigated the effects of three types of procyanidin isolated from apple (Rosaceae Malus pumila) on DNA of human stomach cancer KATO III cells [4].
• Only TP-6, a procyanidin-rich fraction, significantly reduced viability in HepG2 human liver cancer cells, yet unlike resveratrol, caused no cytotoxicity to non-cancerous PK15 pig kidney cells [5].

High impact information on BRN 1675863

• Because mutations at Asp-309, Ser-378, and His-480 of aromatase significantly affected the binding of the procyanidin B dimer, these active site residues are thought to be important residues that interact with this phytochemical [1].
• These in vitro and in vivo studies demonstrated that procyanidin B dimers in red wine and grape seeds could be used as chemopreventive agents against breast cancer by suppressing in situ estrogen biosynthesis [1].
• Thus, in this study we investigated the capacity of a hexameric procyanidin fraction (Hex) isolated from cocoa to protect Caco-2 cells from deoxycholic (DOC)-induced cytotoxicity, cell oxidant increase, and loss of monolayer integrity [6].
• The procyanidin-rich maritime pine bark extract Pycnogenol has well-documented antioxidant and anti-inflammatory activity [7].
• OBJECTIVE: This study sought to evaluate whether 28 d of supplementation with cocoa flavanols and related procyanidin oligomers would modulate human platelet reactivity and primary hemostasis and reduce oxidative markers in vivo [8].

Chemical compound and disease context of BRN 1675863

• A second objective was to assess the effects of select purified cocoa flavonoids, epicatechin, catechin, the procyanidin Dimer B2 and one of its major metabolites, 3'-O-methyl epicatechin, on free radical-induced erythrocyte hemolysis in vitro [9].
• In vitro, the flavanols and the procyanidin oligomers exhibited dose-dependent protection against 2,2'-azo-bis (2-amidinopropane) dihydrochloride (AAPH)-induced erythrocyte hemolysis between concentrations of 2.5 and 40 microM [10].
• Polyphenolic constituent structures of Zanthoxylum piperitum fruit and the antibacterial effects of its polymeric procyanidin on methicillin-resistant Staphylococcus aureus [11].

Biological context of BRN 1675863

• Fractions V-VIII, however, caused significant growth inhibition and apoptosis with the highest activity present in the later fractions that contained procyanidin trimers and GA esters of dimers and trimers [12].
• In addition, the position of linkage between inter-flavan units also influences lipid peroxidation activity; procyanidin isomers with a 4-6 linkage showed stronger inhibitory activity than isomers with a 4-8 linkage [13].
• In contrast, procyanidin trimers, pentamers and DRW inhibited the platelet activation in response to epinephrine [14].
• In the presence of PHA, gene expression also seemed to be most affected by the larger procyanidin fractions [15].
• For the purpose of examining the hair-growing mechanisms of procyanidin B-3, we examined its relationship to the TGF-beta signal pathway, which is known to be a regulator of catagen induction [16].

Anatomical context of BRN 1675863

• After the in vitro procyanidin treatments, aortic endothelial cells synthesized twice as much 6-keto-prostaglandin F(1alpha) (P<0.01) and 16% less leukotriene (P<0.05) as did control cells [17].
• In skin constituent cells, only epithelial cells such as hair keratinocytes or epidermal keratinocytes respond to procyanidin oligomers [18].
• Procyanidin oligomers selectively and intensively promote proliferation of mouse hair epithelial cells in vitro and activate hair follicle growth in vivo [18].
• In addition, in unstimulated RAW 264.7 macrophages, both procyanidin C2 and Pycnogenol increased TNF-alpha secretion in a concentration- and time-dependent manner [19].
• Epicatechin is the primary bioavailable form of the procyanidin dimers B2 and B5 after transfer across the small intestine [20].

Associations of BRN 1675863 with other chemical compounds

• A sharp increase in the inhibition of epidermal lipid peroxidation was also evident when a gallate group was linked at the 3'-hydroxy position of a procyanidin dimer [13].
• This paper describes the characterization of procyanidin mixtures by acid depolymerization in the presence of cysteine (thiolysis with cysteine) and micellar electrokinetic chromatography (MEKC) [21].
• The above data support the theories that in healthy adults, 1) a positive relationship exists between procyanidin consumption and plasma procyanidin concentration and 2) the rise in plasma epicatechin contributes to the ability of plasma to scavenge free radicals and to inhibit lipid peroxidation [22].
• Anthocyanidin synthase from Gerbera hybrida catalyzes the conversion of (+)-catechin to cyanidin and a novel procyanidin [23].
• By means of mass spectrometry, 1H-NMR, and 13C-NMR analyses, one substance was revealed to be procyanidin B-3 and the other substance was identified as (+)-catechin [16].

Gene context of BRN 1675863

• Potentiation of apple procyanidin-triggered apoptosis by the polyamine oxidase inactivator MDL 72527 in human colon cancer-derived metastatic cells [24].
• RESULTS: The elm extract and the procyanidin oligomer (100-1,000 microg/ml) exhibited potent inhibitory effects on the MMPs in GCF (chiefly MMP-8 and MMP-9), the pro and active forms of MMP-2, and secreted and trypsin-like enzymes from T. denticola and P. gingivalis [25].
• Procyanidin oligomers counteract TGF-beta1- and TGF-beta2-induced apoptosis in hair epithelial cells: an insight into their mechanisms [26].
• We speculate that the hair-growing activity of procyanidin oligomers is at least linked to their growth-promoting effects on hair epithelial cells that follow MEK activation and their protective action on TGF-beta(1)- or TGF-beta(2)-induced apoptosis that is assumed to trigger catagen induction in the hair cycle [26].
• For the purpose of examining the hair-growing mechanisms of procyanidin oligomers, we examined their relationship to the TGF-beta signal pathway, known to be a regulator of catagen induction, and the mitogen-activated protein kinase cascade linked to cell proliferation [26].

Analytical, diagnostic and therapeutic context of BRN 1675863

• Using UV absorbance analysis, high-performance liquid chromatography profiling, accurate mass-mass spectrometry, and nanospray tandem mass spectrometry, most of the compounds in our red wine fraction were identified as procyanidin B dimers that were shown to be aromatase inhibitors [1].
• Procyanidin oligomers eluting in HPLC Fractions 2 and 3 were obtained in larger quantities by separating GSE into eight fractions (I-VIII) on a gel filtration column [12].
• The MEKC procedures here reported, are cheap, reliable and fast, and their potential in the determination of the size and composition in procyanidin mixtures has been shown [21].
• Perfusion of isolated small intestine with the procyanidin dimers B2 and B5 extracted from cocoa indicated that both forms of dimer are transferred to the serosal side of enterocytes but only to a very small extent (<1% of the total transferred flavanol-like compounds) [20].
• Using the patch-clamp technique, we measured the effects of Crataegus extract (10 mg/l; flavonoid content: 2.25%, total procyanidin content: 11.3 +/- 0.4%) on the inward rectifier and the delayed rectifier potassium current in isolated guinea pig ventricular myocytes [27].

References