29106-49-8Relevant articles and documents
Synthesis of procyanidin B1, B2, and B4 and their anti-inflammatory activity: The effect of 4-alkoxy group of catechin and/or epicatechin electrophiles for condensation
Katoh,Oizumi,Mohri,Hirota,Makabe
scheme or table, p. 233 - 238 (2012/07/28)
Abstract: Procyanidin B1, B2, and B3 were synthesized based on a Yb(OTf)3 catalyzed equimolar condensation using methoxy and/or 4-(2-ethoxyethoxy) drivatives as electrophiles. The anti-inflammatory effect of synthetic procyanidin B1, B2, and B4 on 12-O-tetradecanoylphorbol-13-acetate (TPA)-induced inflammation of mouse ears was examined. Procyanidin B1, B2, B 4 suppressed TPA-induced inflammation of mouse ears by 48%, 34%, and 29%, respectively, at a dose of 200 μg. Their activities are stronger than those of indomethacin and glycyrrhetinic acid, the normally used antiinflammatory agent.
Total synthesis of 14C-labeled procyanidin B2
Viton, Florian,Landreau, Cyrille,Rustidge, David,Little, Gill,Robert, Fabien,Williamson, Gary,Barron, Denis
scheme or table, p. 371 - 374 (2011/05/05)
During the last decades, many in vitro and in vivo studies have shown the beneficial effects on health of procyanidins. However, their absorption and metabolism is still not fully understood and some aspects are still controversial. In order to have a clearer picture of the metabolism of procyanidins, the use of labelled compounds is essential. In this context, the enantioselective synthesis of 14C-radiolabelled procyanidin B2 was developed in our laboratories. It was achieved in fourteen 'hot' steps, involving as key steps the Sharpless dihydroxylation of an elaborated alkene, a stereoselective intramolecular cyclization to benzylated (+)-catechin and the condensation of two (-)-epicatechin units. 11 mCi of protected procyanidin B2 were obtained from 524 mCi of potassium [14C]cyanide. Copyright
Preparation of dimeric procyanidins B1, B2, B5, and B7 from a polymeric procyanidin fraction of black chokeberry (Aronia melanocarpa)
Esatbeyoglu, Tuba,Winterhalter, Peter
experimental part, p. 5147 - 5153 (2011/07/29)
A semisynthetic approach has been used for the preparative formation of dimeric procyanidins B1, B2, B5, and B7. As starting material for the semisynthesis, polymeric procyanidins from black chokeberry were applied. These polymers were found to consist almost exclusively of (-)-epicatechin units. Under acidic conditions the interflavanoid linkages of the polymeric procyanidins are cleaved and the liberated (-)-epicatechin can react with nucleophiles, such as (+)-catechin or (-)-epicatechin. In this way, the polymeric procyanidins are degraded while dimeric procyanidins are formed. During this reaction only dimeric procyanidins are formed that contain (-)-epicatechin in the upper unit, that is, B1 [(-)-EC-4β→8-(+)-C)], B2 [(-)-EC-4β→8-(-)-EC], B5 [(-)-EC-4β→6-(-)-EC], and B7 [(-)-EC-4β→6-(+)-C]. The reaction mixtures of the semisynthesis can be successfully fractionated with high-speed countercurrent chromatography (HSCCC), and it is possible to isolate pure procyanidins B1, B2, B5, and B7 on a preparative scale.
An efficient synthesis of procyanidins using equimolar condensation of catechin and/or epicatechin catalyzed by ytterbium triflate
Mohri, Yoshihiro,Sagehashi, Masayoshi,Yamada, Taiji,Hattori, Yasunao,Morimura, Keiji,Hamauzu, Yasunori,Kamo, Tsunashi,Hirota, Mitsuru,Makabe, Hidefumi
experimental part, p. 549 - 563 (2009/12/07)
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.
First total synthesis of14C-labeled procyanidin B2 - A milestone toward understanding cocoa polyphenol metabolism
Viton, Florian,Landreau, Cyrille,Rustidge, David,Robert, Fabien,Williamson, Gary,Barron, Denis
supporting information; experimental part, p. 6069 - 6078 (2009/05/27)
The idea that foods consumed for pure pleasure could provide health benefits received much recognition in the recent years. Among these foods, cocoa and dark chocolate are particularly rich in procyanidins, one of the major dietary families of polyphenols. We developed the first asymmetric total synthesis of procyanidin B2 and applied it to the preparation of a regioselectively radiolabeled 14C-analogue, which will be used to strengthen our knowledge on the metabolism of procyanidins. Wiley-VCH Verlag GmbH & Co. KGaA, 2008.
An efficient synthesis of procyanidins. Rare earth metal Lewis acid catalyzed equimolar condensation of catechin and epicatechin
Mohri, Yoshihiro,Sagehashi, Masayoshi,Yamada, Taiji,Hattori, Yasunao,Morimura, Keiji,Kamo, Tsunashi,Hirota, Mitsuru,Makabe, Hidefumi
, p. 5891 - 5894 (2008/02/09)
Stereoselective synthesis of catechin and epicatechin dimers under intermolecular condensation is achieved by an equimolar amount of coupling catalyzed by Yb(OTf)3. The coupled products were successfully converted to procyanidin B1, B2, B3, and B4.
An improved synthesis of procyanidin dimers: Regio- and stereocontrol of the interflavan bond
Tarascou, Isabelle,Barathieu, Karine,Andre, Yann,Pianet, Isabelle,Dufourc, Erick J.,Fouquet, Eric
, p. 5367 - 5377 (2007/10/03)
A direct and general synthesis of procyanidin dimers B1, B2, B3 and B4 (10a-d) is presented. The approach is based on the stoichiometric coupling of two protected monomeric units (the nucleophilic 2a-b and electrophilic 4a-b partners) and deals with the regio- and stereocontrol of the C4-C8 interflavan bond as well as the control of the degree of oligomerization. The synthesis involves a five-step pathway starting from the native catechin (1a) or epicatechin (1b) to the fully deprotected dimers 10a-d. Furthermore, the process appears to be iterative as the coupling intermediates 9a-d themselves can be readily used in further selective syntheses of trimers or higher oligomers. Wiley-VCH Verlag GmbH & Co. KGaA, 2006.
Compositions and methods of use of dimer digallates
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Page/Page column 13, (2010/02/15)
The invention relates to compositions, such as pharmaceuticals, foods, food additives, or dietary supplements, containing dimer digallates, and methods of use thereof, for prophylactic or therapeutic treatment of a human or a veterinary animal to treat or prevent NO-responsive health conditions, treat hypertension, cardiovascular disease, coronary artery disease, diabetes, cognitive dysfunction or disorder and/or vascular circulation disorders, prevent or reduce the risk of heart attack, stroke, congestive heart failure and/or kidney failure, or to improve blood flow, for example renal blood flow. The composition may optionally contain an additional NO modulating agent and/or a vascular-protective or therapeutic agent, or may be administered in combination with such an agent.
Synthetic studies of proanthocyanidins. Part 5.1 Highly stereoselective synthesis and inhibitory activity of Maillard reaction of 3,4-trans catechin and epicatechin dimers, procyanidin B1, B2, B3, B4 and their acetates
Saito, Akiko,Nakajima, Noriyuki,Matsuura, Nobuyasu,Tanaka, Akira,Ubukata, Makoto
, p. 479 - 489 (2007/10/03)
TMSOTf-catalyzed condensation of a potential electrophile with a nucleophile was achieved with a high level of 3,4-trans condensation, and we succeeded in the stereoselective synthesis of procyanidin B2 and its peracetate. Studies on the inhibitory activity of the Maillard reaction of four 3,4-trans series of catechin and epicatechin dimers, procyanidin B1, B2, B3 and B4, and their peracetates were also carried out.
ISOLATION, PURIFICATION AND SYNTHESIS OF PROCYANIDIN B2 AND USES THEREOF
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Page 45, (2008/06/13)
Methods for the synthesis, isolation, and purification of procyanidin B2 are disclosed. The synthetic methods utilize epicatechin as a starting material and produce procyanidin BZ in high yields. The isolation methods extract procyanidin B2 from a sample of bark powder from plant matter of the genus Uncaria. The isolated and/or synthesized procyanidin B2 is used to treat amyloid disease, such as Alzheimer's disease and Parkinson's disease. Pharmaceutical compositions containing the synthesized and/or isolated procyanidin B2 are also disclosed.
