Snijman Petra W, Swanevelder Sonja, Joubert Elizabeth, Green Ivan R, Gelderblom Wentzel C A
Department of Chemistry and Polymer Science, University of Stellenbosch, Private Bag X1, Matieland 7602, South Africa.
Mutat Res. 2007 Jul 28;631(2):111-23. doi: 10.1016/j.mrgentox.2007.03.009. Epub 2007 Apr 21.
The antimutagenic properties of the most prevalent flavonoids in rooibos (Aspalathus linearis) were compared in the Salmonella typhimurium mutagenicity assay using tester strains TA98 and TA100 with, respectively, 2-acetamido-fluorene (2-AAF) and aflatoxin B(1) (AFB(1)) as mutagens in the presence of metabolic activation. The flavonoids included the dihydrochalcones aspalathin and nothofagin and their flavone analogues, orientin and isoorientin, and vitexin and isovitexin, respectively, as well as luteolin, chrysoeriol, (+)-catechin, quercetin, isoquercitrin, hyperoside and rutin. Flavonoid-mutagen interactions ranged from antimutagenic, comutagenic and promutagenic to mutagenic, while dose-response effects were mutagen-specific and ranged from typical to atypical including biphasic and threshold effects. Aspalathin and nothofagin and their structural flavonoid analogues displayed moderate antimutagenic properties while luteolin and to some extent, chrysoeriol, showed activities comparable to those of the green tea flavonoid (-) epigallocatechin gallate (EGCG). Apart from their mutagenic and promutagenic properties, quercetin and isoquercitrin exhibited concentration-dependent comutagenic and/or antimutagenic effects against 2-AAF- and AFB(1)-induced mutagenesis. Different structural parameters known to affect the antimutagenic properties of flavonoids include their hydrophilic or lipophilic nature due to the extent of hydroxylation and O-methylation, glycosylation on the A and B rings, the C4-keto group and the C2-C3 double bond. The C ring does not appear to be a prerequisite when comparing for the antimutagenic activity of the dihydrochalcones when compared of the dihydrochalcones with the structural flavone analogues.
在鼠伤寒沙门氏菌致突变性试验中，以2-乙酰氨基芴（2-AAF）和黄曲霉毒素B1（AFB1）分别作为诱变剂，在代谢活化存在的情况下，使用测试菌株TA98和TA100，比较了路易波士茶（Aspalathus linearis）中最常见的黄酮类化合物的抗诱变特性。这些黄酮类化合物包括二氢查耳酮阿扎拉亭和诺托法金及其黄酮类似物，分别为荭草素和异荭草素，以及牡荆素和异牡荆素，还有木犀草素、 Chrysoeriol、（+）-儿茶素、槲皮素、异槲皮苷、金丝桃苷和芦丁。黄酮类化合物与诱变剂的相互作用范围从抗诱变、协同诱变、促诱变到诱变，而剂量反应效应是诱变剂特异性的，范围从典型到非典型，包括双相和阈值效应。阿扎拉亭和诺托法金及其结构黄酮类似物表现出中等的抗诱变特性，而木犀草素以及在一定程度上的Chrysoeriol，显示出与绿茶黄酮（-）表没食子儿茶素没食子酸酯（EGCG）相当的活性。除了它们的诱变和促诱变特性外，槲皮素和异槲皮苷对2-AAF和AFB1诱导的诱变表现出浓度依赖性的协同诱变和/或抗诱变作用。已知影响黄酮类化合物抗诱变特性的不同结构参数包括由于羟基化和O-甲基化程度导致的亲水性或亲脂性、A环和B环上的糖基化、C4-酮基和C2-C3双键。当比较二氢查耳酮与结构黄酮类似物的抗诱变活性时，C环似乎不是必需的。
