Cysteinyl-flavan-3-ol conjugates from grape procyanidins. Antioxidant and antiproliferative properties.
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.
Torres
J L
JL
Department of Peptide and Protein Chemistry, Institute for Chemical and Environmental Research (IIQAB-CSIC), Jordi Girona 18-26, 08034 Barcelona, Spain. jltqbp@liqab.csic.es
Lozano
C
C
Julià
L
L
Sánchez-Baeza
F J
FJ
Anglada
J M
JM
Centelles
J J
JJ
Cascante
M
M
D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000302:isolation & purification / Q000494:pharmacology; D000975:Antioxidants / Q000138:chemical synthesis* / Q000302:isolation & purification / Q000494:pharmacology; D044946:Biflavonoids; D001713:Biphenyl Compounds; D002392:Catechin / Q000737:chemistry* / Q000302:isolation & purification; D002455:Cell Division / Q000187:drug effects; D003545:Cysteine / Q000737:chemistry; D005419:Flavonoids / Q000737:chemistry; D016166:Free Radical Scavengers / Q000138:chemical synthesis / Q000302:isolation & purification / Q000494:pharmacology; D006801:Humans; D010851:Picrates; D044945:Proanthocyanidins; D013329:Structure-Activity Relationship; D014407:Tumor Cells, Cultured; D027843:Vitis / Q000737:chemistry*
D000970:Antineoplastic Agents; D000975:Antioxidants; D044946:Biflavonoids; D001713:Biphenyl Compounds; D005419:Flavonoids; D016166:Free Radical Scavengers; D010851:Picrates; D044945:Proanthocyanidins; C404987:flavan-3-ol; C017674:procyanidin; D002392:Catechin; C004931:1,1-diphenyl-2-picrylhydrazyl; D003545:Cysteine