Czeczot H, Tudek B, Kusztelak J, Szymczyk T, Dobrowolska B, Glinkowska G, Malinowski J, Strzelecka H
Department of Biochemistry, Warsaw Medical School, Poland.
Mutat Res. 1990 Mar;240(3):209-16. doi: 10.1016/0165-1218(90)90060-f.
Quercetin, rhamnetin, isohamnetin, apigenin and luteolin were isolated from medicinal herbs: Erigeron canadensis L., Anthyllis vulneraria L. and Pyrola chloranta L. The mutagenicity of these naturally occurring flavonoids was tested by the Ames method with S. typhimurium strains TA1535, TA1538, TA97, TA98, TA100 and TA102 in the presence and absence of metabolic activation. Of the above flavonoids only quercetin and rhamnetin revealed mutagenic activity in the Ames test. Quercetin induced point mutations in strains TA97, TA98, TA100 and TA102 of S. typhimurium. The presence of S9 rat liver microsome fraction markedly enhanced the mutagenic activity of quercetin in these strains. Rhamnetin appeared to be a much weaker mutagen in the Ames test. The compound induced mutations in strains TA97, TA98 and TA100 of S. typhimurium but only in the presence of metabolic activation. Comparison of the structure of the studied flavonoids with their mutagenic activity indicates that the mutagenicity of flavonoids is dependent on the presence of hydroxyl groups in the 3' and 4' positions of the B ring, and that the presence of a free hydroxy or methoxy group in the 7 position of the A ring also probably contributes to the appearance of mutagenic activity of flavonoids in the Ames test. It also appeared that the presence of methoxy groups, particularly in the B ring of the flavonoid molecule, markedly decreases the mutagenic activity of the compound.
槲皮素、鼠李素、异鼠李素、芹菜素和木犀草素是从药用植物加拿大飞蓬、 vulneraria 岩黄芪和绿花鹿蹄草中分离得到的。采用艾姆斯试验，在有和没有代谢活化的情况下，用鼠伤寒沙门氏菌菌株TA1535、TA1538、TA97、TA98、TA100和TA102测试了这些天然存在的黄酮类化合物的致突变性。在上述黄酮类化合物中，只有槲皮素和鼠李素在艾姆斯试验中显示出致突变活性。槲皮素在鼠伤寒沙门氏菌的TA97、TA98、TA100和TA102菌株中诱导点突变。S9大鼠肝微粒体组分的存在显著增强了槲皮素在这些菌株中的致突变活性。鼠李素在艾姆斯试验中似乎是一种弱得多的诱变剂。该化合物在鼠伤寒沙门氏菌的TA97、TA98和TA100菌株中诱导突变，但仅在有代谢活化的情况下。将所研究的黄酮类化合物的结构与其致突变活性进行比较表明，黄酮类化合物的致突变性取决于B环3'和4'位羟基的存在，并且A环7位游离羟基或甲氧基的存在也可能有助于黄酮类化合物在艾姆斯试验中出现致突变活性。还发现甲氧基的存在，特别是在黄酮类分子的B环中，显著降低了该化合物的致突变活性。
