Abstract: Cocoa components having enhanced levels of cocoa polyphenols, processes for producing the cocoa components while conserving a significant amount of the cocoa polyphenols, compositions containing the cocoa components or the cocoa polyphenols, and methods of using the cocoa components or the cocoa polyphenols for improving the health of a mammal are described. The cocoa components include partially and fully defatted cocoa solids, cocoa nibs and fractions derived therefrom, cocoa polyphenol extracts, cocoa butter, chocolate liquors, and mixtures thereof. The invention provides processes for extracting fat from cocoa beans and for otherwise processing cocoa beans to yield a cocoa component having conserved concentrations of polyphenols relative to the starting materials.

Abstract: This invention relates to a method of therapeutic or prophylactic treatment of periodontal disease comprising administering to a subject in need thereof a polymeric compound of formula An. Also disclosed and claimed is an article of manufacture comprising the above compounds packaged within a container with instructions for use, and methods of making thereof.

Abstract: The invention relates to a method of treating or preventing a nitric oxide (NO)-responsive disease or disorder by administering to a subject in need thereof a composition, including foods such as confectionary and pet foods, comprising nut skins and/or a procyanidin-containing nut skins extract. Said composition may further comprise cocoa polyphenol(s) and/or L-arginine.

Abstract: Cocoa components having enhanced levels of cocoa polyphenols, processes for producing the cocoa components while conserving a significant amount of the cocoa polyphenols, compositions containing the cocoa components or the cocoa polyphenols, and methods of using the cocoa components or the cocoa polyphenols for improving the health of a mammal are described. The cocoa components include partially and fully defatted cocoa solids, cocoa nibs and fractions derived therefrom, cocoa polyphenol extracts, cocoa butter, chocolate liquors, and mixtures thereof. The invention provides processes for extracting fat from cocoa beans and for otherwise processing cocoa beans to yield a cocoa component having conserved concentrations of polyphenols relative to the starting materials.

Abstract: Disclosed and claimed are flavanols, e.g. epicatechin, compositions such as pharmaceutical compositions containing an effective amount of flavanols, e.g. epicatechin, and methods of treatment or prevention of hypertension using the same.

Abstract: This invention relates to a method of improving renal function comprising administering to a subject in need thereof a composition comprising the inventive compounds. Also disclosed is a method of improving renal function where the subject is at risk of or suffering from renal failure.

Abstract: Disclosed and claimed are cocoa extracts such as polyphenols or procyanidins, methods for preparing such extracts, as well as uses for them, especially as antineoplastic agents and antioxidants. Disclosed and claimed are antineoplastic compositions containing cocoa polyphenols or procyanidins and methods for treating patients employing the compositions. Additionally disclosed and claimed is a kit for treating a patient in need of treatment with an antineoplastic agent containing cocoa polyphenols or procyanidins as well as a lyophilized antineoplastic composition containing cocoa polyphenols or procyanidins. Further, disclosed and claimed is the use of the invention in antioxidant, preservative and topoisomerase-inhibiting compositions and methods.

Abstract: This invention relates to compositions comprising epicatechin and method of use of such compositions for inducing vasodilation of blood vessels in humans and veterinary animals.

Abstract: This invention relates to an article of manufacture comprising a polymeric compound of formula An and an additional NO-modulating agent and method of use thereof. Also disclosed and claimed is a method of making an article of manufacture comprising of the polymeric compound of formula An.

Abstract: Cocoa components having enhanced levels of cocoa polyphenols, processes for producing the cocoa components while conserving a significant amount of the cocoa polyphenols, compositions containing the cocoa components or the cocoa polyphenols, and methods of using the cocoa components or the cocoa polyphenols for improving the health of a mammal are described. The cocoa components include partially and fully defatted cocoa solids, cocoa nibs and fractions derived therefrom, cocoa polyphenol extracts, cocoa butter, chocolate liquors, and mixtures thereof. The invention provides processes for extracting fat from cocoa beans and for otherwise processing cocoa beans to yield a cocoa component having conserved concentrations of polyphenols relative to the starting materials.

Abstract: Processes for preparing racemic mixtures of 5,7,3?,4?-tetra-O-benzyl-(±)-catechin and (±)-epicatechin involves (i) condensing 2-hydroxy-4,6-bis(benzyloxy)-acetophenone and 3,4-bis(benzyloxy)benzaldehyde, cyclizing the resulting compound, oxidizing the resulting compound; (ii) dihydroxylating (E)-3-(3?,4?-bis(benzyloxy)phenyl)prop-2-ene-1-ol and reducing the 1,2-diol; or (iii) coupling 3,5-bis(benzyloxy)phenol with (E)-3,5-bis(benzyloxy)-2-(3?,4?-bis(benzyloxy)phenyl)allyl)phenol and cyclizing the resulting chalcone. A process for preparing the benzylated epimers of catechin and epicatechin involves seven steps. 3,4-Bis(benzyloxy)benzaldehyde is coupled with 2-hydroxy-4,6-benzyloxy-acetophenone to form a chalcone. The chalcone is selectively reduced to an alkene. The phenolic group of the alkene is protected. The protected alkene is asymetrically dihydroxylated. The resulting compound is deprotected, cyclized, and finally hydrolyzed.

Abstract: This invention relates to a method of therapeutic or prophylactic treatment of periodontal disease comprising administering to a subject in need thereof epicatechin and/or catechin and/or a polymeric compound of formula An. Also disclosed and claimed is an article of manufacture comprising the above compounds packaged within a container with instructions for use thereof.

Abstract: Various processes are disclosed for preparing protected epicatechin oligomers having (4?,8)-interflavan linkages. In one process, a tetra-O-protected epicatechin monomer or oligomer is coupled with a protected, C-4 activated epicatechin monomer in the presence of an acidic clay such as a mortmorillonite clay. In another process, a 5,7,3?,4?-benzyl protected or a 3 -acetyl-, 5,7,3?,4?-benzyl protected epicatechin or catechin monomer or oligomer is reacted with 3 -O-acetyl-4-[(2-benzothiazolyl)thio]-5,7,3?,4?-tetra-O-benzylepicatechin in the presence of silver tetrafluoroborate. In another process, two 5,7,3?,4?-benzyl protected epicatechin monomers activated with 2-(benzothiazolyl)thio groups at the C-4 positions are cross-coupled in the presence of silver tetrofluoroborate. A process is also disclosed for reacting an unprotected epicatechin or catechin monomer with 4-(benzylthio) epicatechin or catechin.

Abstract: This invention relates to compositions comprising epicatechin and method of use of such compositions for inducing vasodilation of blood vessels in humans and veterinary animals.

Abstract: This invention relates to methods of inducing dephosphorylation of a hyperphosphorylated cell cycle regulatory protein in a tumor cell in which hyperphosphorylation of said protein contributed to cell transformation, the method comprising contacting the tumor cell with a procyanidin oligomer of five monomeric units connected via a C-4?C-8 linkage. Examples of such compounds are [EC-(4??8)]4-EC, and [EC-(4??8)]3-EC-(4??8)-C, wherein EC is epicatcchin and C is catechin.

Abstract: Processes are disclosed for the production of linear and branched procyanidin oligomers having “n” procyanidin monomeric units where n is 2 to 18. The processes include coupling protected, activated monomers with an unprotected monomer to produce a partially protected (4?8) dimer. The dimer is optionally blocked, coupled with an activated protected monomer to produce a partially protected, optionally blocked trimer, and deprotected. The steps can be repeated to produce higher oligomers. Processes are also provided for producing (8?8), (8?6), and (6?6) dimers and doubly branched oligomers. Crystalline 8-bromo tetra-O-benzyl (?)-epicatechin is produced under certain conditions.

Abstract: A process is disclosed for the production of polyphenol oligomers having n polyphenol monomeric units, n being an integer from 2-18. The process includes coupling of a protected polyphenol, having protected phenolic hydroxyl groups, with a C-4 functionalized polyphenol monomer. The protected polyphenol may be a protected polyphenol monomer or a protected polyphenol oligomer having 2-17 monomeric units. Advantageously, polyphenol monomeric units forming the polyphenol oligomers may be the same or different flavanoid compounds.

Abstract: Various processes are disclosed for preparing procyanidin oligomers having (4,8)-interflavan linkages. In an improved process, a tetra-O-protected-epicatechin or -catechin monomer or oligomer is coupled with a protected, C-4 alkoxy-activated-epicatechin or -catechin monomer in the presence of an acidic clay instead of a Lewis acid. In a second process, a 5,7,3?,4?-tetra-O-protected or preferably penta-O-protected-epicatechin or -catechin monomer or oligomer is reacted with a tetra-O-protected or preferably penta-O-protected-epicatechin or -catechin monomer having a thio activating group at the C-4 position; the coupling is carried out in the presence of silver tetrafluoroborate. In third process, two molecules of a penta-O-protected-epicatechin or -catechin monomer activated with a 2-(benzothiazolyl)thio group at the C-4 position are self-condensed in the presence of silver tetrafluoroborate.

Abstract: Oligomeric procyanidins containing 4?-linked epicatechin units are rare in nature and have hitherto not been accessible through stereoselective synthesis. Provided herein is the preparation of the prototypical dimer, epicatechin-4?,8-epicatechin, by reaction of the protected 4-ketones with aryllithium reagents derived by halogen/metal exchange from the aryl bromides. Removal of the 4-hydroxyl group from the resulting tertiary benzylic alcohols is effected by tri-n-butyltin hydride and trifluoroacetic acid in a completely stereoselective manner, resulting in hydride delivery exclusively from the ? face.

Abstract: Polyphenol-containing compositions, for example procyanidins and derivatives thereof, and their use for treating hypertension are disclosed. Compositions may be used for human and veterinary use, and may be, for example, in a form of a food, a dietary supplement or a pharmaceutical.