23567-23-9

Usage

Uses

Used in Pharmaceutical Applications:
Procyanidin B3 is used as a specific HAT inhibitor for its diverse biological properties, which contribute to its potential as a pharmaceutical candidate.
Used in Antifungal Applications:
Extracted from Woodfordia uniflora, Procyanidin B3 is used as an antifungal agent, providing protection against various fungal infections.
Used in the Food and Beverage Industry:
Procyanidin B3 is used as a natural additive in the food and beverage industry, particularly in red wine, barley, and beer, for its health-promoting properties and contribution to the taste and quality of these products.

InChI:InChI=1/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

Upstream product

• 480-17-1 2,3-trans-flavan-3,4-diol 
• 154-23-4 catechin 
• 137550-06-2 5,7,3',4'-tetra-O-benzyl-4α-(5,7,3',4'-tetra-O-benzylcatechin)catechin 
• 20728-73-8 5,7,3',4'-tetra-O-benzyl-(+)-catechin 
• 476312-04-6 (2R,3S,4S)-5,7,3',4'-tetrabenzyloxy-3-acetoxy-4-methoxyflavan 
• 480-18-2 taxifolin 
• 777063-26-0 8-bromo-3,5,7,3',4'-penta-O-benzyl-catechin-(4α->8)-3,5,7,3',4'-penta-O-benzyl-catechin 
• 1217257-69-6 3’,4’,5,7-tetra-O-benzyl-4β-O-propargylcatechin 
• 294203-72-8 (2R,3S,4S)-5,7,3',4'-tetrabenzyloxy-4-methoxyflavan-3-ol 
• 223387-51-7 (2R,3S,4S)-5,7,3',4'-tetrabenzyloxy-4-(2-hydroxyethyloxy)flavan-3-ol 
• 256236-21-2 5,7,3',4'-tetra-O-benzyl-8-bromocatechin 
• 923565-00-8 3’,4’,5,7-tetra-O-benzyl-4β-(2-hydroxyethyloxy)-8-bromocatechin 
• 476312-06-8 [4,8']-2,3-trans-3,4-trans:2',3'-trans-octa-O-benzyl-3-O-acetyl-bi-(+)-catechin 
• 923565-04-2 3’,4’,5,7-tetra-O-benzyl-8-bromocatechin-(4α8)-3’,4’,5,7-tetra-O-benzylcatechin 

Downstream Products

• 37126-92-4 5,7,3',4',5'',7'',3''',4'''-octa-O-methylprocyanidin B-3 
• 21179-22-6 [4,8]-2,3-trans-3,4-trans:2,3-trans-deca-O-acetyl-bi-(+)-catechin 
• 154-23-4 catechin 
• 51079-25-5 (2R,3S)-(+)-catechin 3',4',5,7-tetramethyl ether 
• 37064-31-6 catechin-(4α <*> 8)-catechin-(4α <*> 8)-catechin (C2) 
• 58065-35-3 (+)-catechin tetramethyl ether acetate 
• 128428-20-6 8,9-cis-9,10-trans-3,4,9,10-tetrahydro-2H,8H-pyrano<2,3-h>chromene 
• 128428-22-8 (2R,3R,4S,2'R,3'S)-4,2'-Bis-(3,4-dihydroxy-phenyl)-3,4,3',4'-tetrahydro-2H,2'H-[2,8']bichromenyl-3,5,7,3',5',7'-hexaol 
• 128428-28-4 (2R,3R,4S,2'S,3'S)-4,2'-Bis-(3,4-dihydroxy-phenyl)-3,4,3',4'-tetrahydro-2H,2'H-[2,6']bichromenyl-3,5,7,3',5',7'-hexaol 
• 128428-25-1 (2R,3R,4S,2'R,3'S)-4,2'-Bis-(3,4-dihydroxy-phenyl)-3,4,3',4'-tetrahydro-2H,2'H-[2,6']bichromenyl-3,5,7,3',5',7'-hexaol 
• 13306-05-3 cyanidin 
• 490-46-0 (2R,3R)-2-(3,4-dihydroxyphenyl)-3,4-dihydro-1[2H]-benzopyran-3,5,7-triol 

Relevant academic research and scientific papers

New procyanidin B3-human salivary protein complexes by mass spectrometry. Effect of salivary protein profile, tannin concentration, and time stability

Several factors could influence the tannin-protein interaction such as the human salivary protein profile, the tannin tested, and the tannin/protein ratio. The goal of this study aims to study the effect of different salivas (A, B, and C) and different tannin concentrations (0.5 and 1 mg/mL) on the interaction process as well as the complex's stability over time. This study is focused on the identification of new procyanidin B3-human salivary protein complexes. Thus, 48 major B3-human salivary protein aggregates were identified regardless of the saliva and tannin concentration tested. A higher number of aggregates was found at lower tannin concentration. Moreover, the number of protein moieties involved in the aggregation process was higher when the tannin concentration was also higher. The selectivity of the different groups of proteins to bind tannin was also confirmed. It was also verified that the B3-human salivary protein complexes formed evolved over time.

Influence of carbohydrates on the interaction of procyanidin B3 with trypsin

The biological properties of procyanidins, in particular their inhibition of digestive enzymes, have received much attention in the past few years. Dietary carbohydrates are an environmental factor that is known to affect the interaction of procyanidins with proteins. This work aimed at understanding the effect of ionic food carbohydrates (polygalacturonic acid, arabic gum, pectin, and xanthan gum) on the interaction between procyanidins and trypsin. Physical-chemical techniques such as saturation transfer difference-NMR (STD-NMR) spectroscopy, fluorescence quenching, and nephelometry were used to evaluate the interaction process. Using STD-NMR, it was possible to identify the binding of procyanidin B3 to trypsin. The tested carbohydrates prevented the association of procyanidin B3 and trypsin by a competition mechanism in which the ionic character of carbohydrates and their ability to encapsulate procyanidins seem crucial leading to a reduction in STD signal and light scattering and to a recovery of the proteins intrinsic fluorescence. On the basis of these results, it was possible to grade the carbohydrates in their aggregation inhibition ability: XG > PA > AG ? PC. These effects may be relevant since the coingestion of procyanidins and ionic carbohydrates are frequent and furthermore since these might negatively affect the antinutritional properties ascribed to procyanidins in the past.

Unambiguous assignments for free dimeric proanthocyanidin phenols from 2D NMR

Characterization of proanthocyanidin oligomers proceeds commonly through investigation of NMR data of their peracetates or methyl ether acetates, in conjunction with FAB-mass spectrometry and circular dichroism. Since such an approach is unsuitable in bioassay-guided isolations, we applied two dimensional NMR techniques for the identification of dimeric proanthocyanidins. This afforded not only a powerful probe for distinction between the different procyanidin isomers, but also allowed full assignments, even for both major rotameric forms, whenever present, without the need for derivatisation. Moreover, discrimination between the crucial 6- and 8- protons and carbons was achieved after addition of traces of cadmium nitrate, resulting in the separation of the broad phenolic signals into sharp singlets. As an example of the general strategy followed in the assignment and combination of data of the different spectra available, complete analysis of underivatised procyanidin B3 or catechin-(4α → 8)-catechin is discussed for the first time.

COMPOSITION FOR PROMOTING EXPRESSION OF AQUAPORIN 3, AND USE THEREOF

The purpose of the present invention is to provide a specific composition for promoting expression of aquaporin 3, and use thereof. The present invention relates to a composition for promoting expression of aquaporin 3, the composition including a galloyl group-containing flavan-3-ol monomer and/or a galloyl group-containing flavan-3-ol polymer as an active ingredient.

Molecular Interaction between Salivary Proteins and Food Tannins

Polyphenols interaction with salivary proteins (SP) has been related with organoleptic features such as astringency. The aim of this work was to study the interaction between some human SP and tannins through two spectroscopic techniques, fluorescence quenching, and saturation transfer difference-nuclear magnetic resonance (STD-NMR). Generally, the results showed a significant interaction between SP and both condensed tannins and ellagitannins. Herein, STD-NMR proved to be a useful tool to map tannins' epitopes of binding, while fluorescence quenching allowed one to discriminate binding affinities. Ellagitannins showed the greatest binding constants values (KSV from 20.1 to 94.1 mM-1 KA from 0.7 to 8.3 mM-1) in comparison with procyanidins (KSV from 5.4 to 40.0 mM-1 KA from 1.1 to 2.7 mM-1). In fact, punicalagin was the tannin that demonstrated the highest affinity for all three SP. Regarding SP, P-B peptide was the one with higher affinity for ellagitannins. On the other hand, cystatins showed in general the lower KSV and KA values. In the case of condensed tannins, statherin was the SP with the highest affinity, contrasting with the other two SP. Altogether, these results are evidence that the distinct SP present in the oral cavity have different abilities to interact with food tannins class.

Procyanidin oligomers. A new method for 4→8 interflavan bond formation using C8-boronic acids and iterative oligomer synthesis through a boron-protection strategy

Interest in the synthesis of procyanidin (catechin or epicatechin) oligomers that contain the 4→8 interflavan linkage remains high, principally due to research into their health effects. A novel coupling utilising a C8-boronic acid as a directing group was developed in the synthesis of natural procyanidin B3 (i.e., 3,4-trans-(+)-catechin-4α→8-(+)- catechin dimer). The key interflavan bond was forged using a novel Lewis acid-promoted coupling of C4-ether 6 with C8-boronic acid 16 to provide the α-linked dimer with high diastereoselectivity. Through the use of a boron protecting group, the new coupling procedure was extended to the synthesis of a protected procyanidin trimer analogous to natural procyanidin C2.

Procyanidin B3 synthesis: a study of leaving group and Lewis acid activator effects upon interflavan bond formation

A range of electrophilic ethers were prepared via DDQ oxidation and alcoholic trapping (propanol, crotyl alcohol and propargyl alcohol) at the C4 position of (+)-catechin. The Lewis acid-mediated C4-substitution of each of these ethers was examined and it was found that the propargyl ether was the best overall electrophile. A range of Lewis acids were then examined as activators and it was found that BF3·OEt2 was the best in terms of both yield and stereochemical control at the C4 position. This newly developed set of conditions was then used to prepare the natural product nutraceutical procyanidin B3 with complete control of stereochemistry.

Synthesis of procyanidin B3 and its anti-inflammatory activity. the effect of 4-alkoxy group of catechin electrophile in the Yb(OTf)3-catalyzed condensation with catechin nucleophile

(Figure Presented) Yb(OTf)3-catalyzed equimolar condensation of the benzylated catechin with various 4-alkoxy catechin derivatives was studied. In particular, the reaction using 4-(2′′-ethoxyethoxy)flavan derivative gave good yield with excellent stereoselectivity. The condensed product was successfully converted to procyanidin B3 (1). The anti-inflammatory effect of procyanidin B3 (1) on 12-O-tetradecanoylphorbol-13-acetate (TPA)-induced inflammation of mouse ears was examined. The anti-inflammatory activity of 1 was stronger than that of indomethacin and glycyrrhetinic acid, the normally used anti-inflammatory agents.

An efficient synthesis of procyanidins using equimolar condensation of catechin and/or epicatechin catalyzed by ytterbium triflate

Stereoselective synthesis of catechin and epicatechin dimers under intermolecular condensation of equimolar amount of catechin derivatives catalyzed by Yb(OTf)3. The coupled products were successfully converted to procyanidins B1, B2, B3, and B4, respectively. Procyanidins B1, B2, B3, and B4 could be used as standard compounds for identifying the polyphenols in natural source.

Synthesis of procyanidins by stepwise- and self-condensation using 3,4-cis-4-acetoxy-3-O-acetyl-4-dehydro-5,7,3′,4′-tetra-O-ben zyl-(+)-catechin and (-)-epicatechin as a key building monomer

3,4-cis-4-Acetoxy-3-O-acetyl-4-dehydro-5,7,3′,4′-tetra-O-ben zyl-(+)-catechin (1a) or (-)-epicatechin (1b) reacted high regio- and stereo-selectively with 1.5 equiv of the 5,7,3′,4′-tetra-O-benzyloxyflavan-3-ol (4a or 4b) in the presence of 1 equiv of TMSOTf to give the corresponding procyanidins. On the other hand, the self-condensation of 1a in the presence of a catalytic amount of B(C6F5)3 afforded wide-range procyanidins from dimer to 15-mer like a biomass.