213007-61-5

Upstream product

• 100-53-8 phenylmethanethiol 
• 1235753-24-8 epicatechin-(4β->8,2β->O->7)-[epicatechin-(4β->8)-epicatechin-(4β->6)]-epicatechin-(4β->8)-epicatechin 
• 88038-15-7 epicatechin-(4β->6)-epicatechin-(2β->O->7, 4β->8)-epicatechin-(4β->8)-epicatechin 
• 88038-12-4 Cinnamtannin B₁ 
• 29106-49-8 procyanidin B₂ 
• 20315-25-7 procyanidin B₁ 

Downstream Products

• 51196-02-2 5,7,3',4'-tetra-O-methylepicatechin 
• 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

Biotransformation of procyanidins by a purified fungal dioxygenase: Identification and characterization of the products using mass spectrometry

Procyanidins commonly known as condensed tannins are a type of polyphenol with wide abundance naturally. They are commonly known as potent anti-oxidants with powerful free radical scavenging activity as well as anti-tumor-promoting activity. Little is known about the enzymatic mechanisms/pathways involved in the microbial biotransformation of these polyphenolic molecules. The extracellular enzyme, dioxygenase produced by Aspergillus fumigatus was used as in vitro tools to study the degradation pathway of a model procyanidin dimer, namely procyanidin B2. The enzyme was purified to homogeneity by a two step process of anion-exchange chromatography coupled with FPLC followed by gel-filtration chromatography coupled with HPLC and the molecular mass estimated. In addition, the different biotransformed products resulted from the dioxygenase action on PB2 were purified using Reversed-Phase-High Performance Liquid Chromatography prior to their identification and characterization by structural elucidation using Electrospray Ionization-Mass Spectrometry. Subsequently, the mechanism of dioxygenase action on procyanidin dimer was defined.

Immunomodulatory proanthocyanidins from Ecdysanthera utilis

Two new A-type proanthocyanidins have been isolated from Ecdysanthera utilis and identified as epicatechin-(4β→8,2β→O→7)- epicatechin-(4β→8)-epicatechin (5) and epicatechin-(4β→8)-epicatechin- (4β→8,2β→O→7)-epicatechin- (4β→8)-epicatechin (6), respectively. The structure-related components epicatechin (1), procyanidin B2 (2), proanthocyanidin A1 (3), proanthocyanidin A2 (4), and aesculitannin C (7) were also isolated. All of these compounds were identified and evaluated for immunopharmacological activity. Human peripheral blood mononuclear cells (PBMC) were used as target cells, and cell proliferation was determined by 3H-thymidine uptake. The results indicated that compound 3 suppressed PBMC proliferation activated with phytohemagglutinin (PHA). The inhibitory mechanisms may involve the blocking of interleukin-2 (IL-2) and interferon-γ (IFN-γ) production, since compound 3 attenuated IL-2 and IFN-γ production of PBMC in a dose-dependent manner. Therefore, it is suggested that immunomodulatory agents are present in E. utilis.

Anticancer activities of proanthocyanidins from the plant Urceola huaitingii and their synergistic effects in combination with chemotherapeutics

Phytochemical investigation of the stem of Urceola huaitingii resulted in the isolation of nine proanthocyanidins (1-9), including a new compound (9). Their chemical structures were determined by UV, (HR) ESI-MS, 1D-, 2D-NMR, and CD spectra in combination with chemical derivatization. Determination of the absolute configuration of proanthocyanidins were discussed, which suggested that positive Δ? values at 245 nm can be applied to determine the absolute configuration of them. In addition, anticancer activities of proanthocyanidins (1-9) and their synergistic anticancer effects in combination with chemotherapeutics were evaluated. The results showed that some proanthocyanidins, especially compound 7 possessing two doubly interflavonoid linkages, exhibited significant synergistic anticancer effects with some chemotherapeutics in multiple cancer cell lines.

High molecular weight persimmon (Diospyros kaki L.) proanthocyanidin: A highly galloylated, a-linked tannin with an unusual flavonol terminal unit, myricetin

MALDI-TOF MS suggested that the high molecular weight proanthocyanidin (condensed tannin) from persimmon (Diospyros kaki L.) pulp comprised a heteropolyflavanol series with flavan-3-O-galloylated extenders, flavan-3-ol and flavonol terminal units, and A-type interflavan linkages. Thiolysis-HPLC-ESI-MS with DAD, electrochemical, and ESI-MS detection confirmed a previously unreported terminal unit, the flavonol myricetin, in addition to the typical flavan-3-ols catechin and epigallocatechin gallate. The extender units were epicatechin, epigallocatechin, (epi)gallocatechin-3-O-gallate, and (epi)catechin-3-O-gallate. The crude tannin had a high prodelphinidin content (65%) and a high degree of 3-O-galloylation (72%). The material was fractionated on Toyopearl TSK-HW-50-F to yield fractions distinguished by degree of polymerization (DP). Thiolysis suggested that the persimmon tannin was composed of polymers ranging from 7 to 20 kDa (DP 19-47), but sizes estimated by GPC were 50-70% smaller. The crude material was chemically degraded with acid to yield products that were amenable to NMR and ESI-MS analysis, which were used to establish for the first time that persimmon tannin has a mixture of B-type and A-type linkages. 2010 American Chemical Society.

REMEDY FOR AUTOIMMUNE DISEASES

In the present invention, there are disclosed a therapeutic agent for the treatment of a disease in which the suppression of Th1 cytokine production is therapeutically effective and/or a disease in which the suppression of autoantibody production is therapeutically effective, a therapeutic agent for the eradicative treatment of these diseases, and an agent for inhibiting the progress of these diseases, comprising (i) a proanthocyanidin with a polymerization degree of at least 4 or (ii) a plant material extract containing a proanthocyanidin as an active ingredient.

Polyphenols from peanut skins and their free radical-scavenging effects

Separation of the water-soluble fraction of peanut skins led to the isolation of five proanthocyanidins. Based on the spectroscopic investigation and partial acid catalyzed degradation, their structures were determined to be epicatechin-(2β→O→7, 4β→6)-[epicatechin- (4β→8)]-catechin (1), epicatechin-(2β→O→7, 4β→8) epicatechin-(4β→8)-catechin-(4β→8)- epicatechin (2), and procyanidins B2 (3), B3 (4) and B4 (5). The absolute configuration of the new compounds was determined from their circular dichroism curves and the 1H NMR spectra of analysis of flavan-3-ols formed by thiolytic degradation of 1 and 2 in the presence of a chiral dirhodium complex (dirhodium tetra-(R)-(trifluoromethyl) phenyl acetate).

POLYPHENOLIC COMPOUNDS FROM CROTON LECHLERI

The blood-red sap of Croton lechleri was found to contain proanthocyanidins as major constituents which accounted for up to 90percent of the dried weight.In addition to (+)-catechin, (-)-epicatechin, (+)-gallocatechin, (-)-epigallocatechin and dimeric procyanidins B-1 and B-4, five novel dimers and trimers were isolated and characterized as catechin-(4α->8-epigallocatechin, gallocatechin-(4α->8)-epicatechin, gallocatechin-(4α->6)-epigallocatechin, catechin-(4α->8)-gallocatechin-(4α->8)-gallocatechin and gallocatechin-(4α->8)-gallocatechin-(4α->8)-epigallocatechin.Higher oligomers were also obtained.A new procedure combining chemical degradation with 1H NMR spectroscopy has been developed for determination of the composition and molecular size of oligomeric/polymeric proanthocyanidins.The oligomers of the sap were shown to have the mean degree of polymerization of 4,5-6 and 6-7, respectively, and Mr up to 2130.The heterogeneity of the oligomers was clearly indicated by the presence of a variety of flavan-3-ols as extension and terminal units.An exceptionally high content of gallocatechin and epigallocatechin in the oligomers was observed.Key Word Index: Croton lechleri; Euphorbiaceae; Sangre de Grado; Dragon's blood; polyphenol; proanthocyanidins; flavan-3-ols; procyanidins; prodelphinidins.