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.fwdarw.C-8 linkage. Examples of such compounds are [EC-(4.beta..fwdarw.8)].sub.4-EC, and [EC-(4.beta..fwdarw.8)].sub.3-EC-(4.beta..fwdarw.8)-C, wherein EC is epicatcchin and C is catechin.

Mars, Incorporated

Methods and compositions for treating cancer

A pharmaceutical composition for prevention and treatment of cancer, cardiovascular disease and antioxidation contains resveratol. The new method of process for producing resveratol is extracted resveratol from oil residue and stems of peanuts or stems of other cheap herbs. Derivates of resveratol include procyanidins, polydatin, peceid, anthraglycoside, emodin, chrysophanol and quercetin.

Method for producing antioxidant and prevention of cancer

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. An improved two-step process for preparing a C-4 alkoxy activated tetra-O-benzyl-protected, 8-bromo-blocked-epicatechin or -catechin monomer is also provided. The use of naturally-derived and synthetically-prepared procyanidin (4.beta.,8).sub.4-pentamers to treat cancer is also disclosed.

Mars, Inc.

Synthesis of oligomeric epicatechin and catechin-derived procyanidins

Various processes are disclosed for preparing protected epicatechin oligomers having (4.beta.,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. The use of naturally-derived and synthetically-prepared procyanidin (4.beta.,8).sub.4-pentamers to treat cancer is also disclosed.

procyanidin a 4/悪性腫瘍

Methods and compositions for treating cancer

Method for producing antioxidant and prevention of cancer

Synthesis of oligomeric epicatechin and catechin-derived procyanidins

Tetra- and penta-o-benzyl-protected, C-4 activated-epicatechin and -catechin monomers and processes for their preparation and use

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