Chalcones: structural requirements for antioxidant, estrogenic and antiproliferative activities.
Flavonoids are largely studied for their biological properties and particularly for their scavenging and antioxidant activities. In the present study, we first evaluated the antioxidant and the estrogenic actions of chalcones, then we tested their effects on MCF-7 cell proliferation. Chalcones are unique in the flavonoids family in lacking a heterocyclic C ring. We tested substituted chalcones with different numbers and different positions of the hydroxy groups: 2'-hydroxychalcone, 4'-hydroxychalcone, 4-hydroxychalcone, 2',4-dihydroxychalcone, isoliquiritigenin, 2',4'-dihydroxychalcone, phloretin and naringenin chalcone. For the antioxidant tests we established the importance of the alpha-beta double bond and the 6'-hydroxy group. The establishment of the structure-activity relationship for the estrogenic properties showed a correlation between the antioxidant and the estrogenic properties. The importance of conformation and hydroxy group positions observed for chalcones, having antioxidant and estrogenic properties, was also observed on MCF-7 cell growth with the same structure-activity relationship. The role of electron and hydrogen transfer in the correlation between these three biological activities was discussed.
Calliste
C A
CA
UPRES EA 1085, Biomolécules et cibles cellulaires tumorales-Prolifération cellulaire et inhibition enzymatique, Laboratoire de Biophysique, Faculté de Pharmacie, Limoges, France.
Le Bail
J C
JC
Trouillas
P
P
Pouget
C
C
Habrioux
G
G
Chulia
A J
AJ
Duroux
J L
JL
D000975:Antioxidants / Q000737:chemistry* / Q000494:pharmacology; D015764:Bepridil / Q000031:analogs & derivatives* / Q000737:chemistry; D001713:Biphenyl Compounds; D001943:Breast Neoplasms / Q000188:drug therapy / Q000473:pathology; D002455:Cell Division / Q000187:drug effects; D002599:Chalcone / Q000031:analogs & derivatives* / Q000737:chemistry / Q000494:pharmacology; D003497:Cyclic N-Oxides / Q000737:chemistry; D004578:Electron Spin Resonance Spectroscopy; D004968:Estrogens, Non-Steroidal / Q000737:chemistry* / Q000494:pharmacology; D016166:Free Radical Scavengers / Q000737:chemistry / Q000494:pharmacology; D006131:Growth Inhibitors / Q000737:chemistry* / Q000494:pharmacology; D006801:Humans; D017665:Hydroxyl Radical / Q000737:chemistry; D009376:Neoplasms, Hormone-Dependent / Q000188:drug therapy / Q000473:pathology; D010851:Picrates; D013329:Structure-Activity Relationship; D014407:Tumor Cells, Cultured
D000975:Antioxidants; D001713:Biphenyl Compounds; D003497:Cyclic N-Oxides; D004968:Estrogens, Non-Steroidal; D016166:Free Radical Scavengers; D006131:Growth Inhibitors; D010851:Picrates; D017665:Hydroxyl Radical; D002599:Chalcone; C017245:5,5-dimethyl-1-pyrroline-1-oxide; D015764:Bepridil; C004931:1,1-diphenyl-2-picrylhydrazyl