Calliste C A, Le Bail J C, Trouillas P, Pouget C, Habrioux G, Chulia A J, Duroux J L
UPRES EA 1085, Biomolécules et cibles cellulaires tumorales-Prolifération cellulaire et inhibition enzymatique, Laboratoire de Biophysique, Faculté de Pharmacie, Limoges, France.
Anticancer Res. 2001 Nov-Dec;21(6A):3949-56.
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.
黄酮类化合物因其生物学特性，特别是其清除自由基和抗氧化活性而受到广泛研究。在本研究中，我们首先评估了查耳酮的抗氧化和雌激素作用，然后测试了它们对MCF-7细胞增殖的影响。查耳酮在黄酮类化合物家族中独一无二，它缺少一个杂环C环。我们测试了具有不同羟基数量和位置的取代查耳酮：2'-羟基查耳酮、4'-羟基查耳酮、4-羟基查耳酮、2',4-二羟基查耳酮、异甘草素、2',4'-二羟基查耳酮、根皮素和柚皮素查耳酮。对于抗氧化测试，我们确定了α-β双键和6'-羟基的重要性。雌激素特性的构效关系研究表明抗氧化特性与雌激素特性之间存在相关性。在具有抗氧化和雌激素特性的查耳酮中观察到的构象和羟基位置的重要性，在MCF-7细胞生长中也观察到了相同的构效关系。讨论了电子和氢转移在这三种生物学活性相关性中的作用。
