Abstract
New bio-based antioxidant compounds have been obtained by depolymerisation of grape polymeric flavanols in the presence of cysteine. Their preparation and purification, as well as their antiradical/antioxidant and antiproliferative properties are reported. 4beta-(S-cysteinyl)epicatechin 5, 4beta-(S-cysteinyl)catechin 6 and 4beta-(S-cysteinyl)epicatechin 3-O-gallate 7 were efficiently purified from the crude depolymerised mixture by cation-exchange chromatography and preparative reversed-phase chromatography. The new compounds were more efficient than the underivatised (-)-epicatechin 1 as scavengers of the 1,1-diphenyl-2-picrylhydrazyl free radical (DPPH) and weak growth inhibitors of human colon carcinoma HT29 cells. The order of antiradical and antiproliferative efficiency was 7 >5 approximately 6 >1, the same for both assays.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Antineoplastic Agents / chemical synthesis*
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Antineoplastic Agents / isolation & purification
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Antineoplastic Agents / pharmacology
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Antioxidants / chemical synthesis*
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Antioxidants / isolation & purification
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Antioxidants / pharmacology
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Biflavonoids*
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Biphenyl Compounds
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Catechin / chemistry*
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Catechin / isolation & purification
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Cell Division / drug effects
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Cysteine / chemistry
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Flavonoids / chemistry
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Free Radical Scavengers / chemical synthesis
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Free Radical Scavengers / isolation & purification
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Free Radical Scavengers / pharmacology
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Humans
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Picrates
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Proanthocyanidins*
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Structure-Activity Relationship
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Tumor Cells, Cultured
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Vitis / chemistry*
Substances
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Antineoplastic Agents
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Antioxidants
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Biflavonoids
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Biphenyl Compounds
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Flavonoids
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Free Radical Scavengers
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Picrates
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Proanthocyanidins
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flavan-3-ol
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procyanidin
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Catechin
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1,1-diphenyl-2-picrylhydrazyl
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Cysteine