• Archives of Pharmacal Research
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• v.18 no.6
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• pp.415-422
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• 1995

Twenty-four flavones were synthesized with various hydroxyl and/or methoxyl groups on A and B rings. Their antimutagenic properties were evaluated against ben:w(a)pyrene (BaP) and a pool of mutagenic urine concentrate (U) using a modified liquid incubation method of Ames test. The tester strain was Salmonella typhimurium TA98+S9 Mix. The antimutagenic activities were calculated by non linear regression analysis and the doses of flavones (in nmoles) required for a 50% reduction of induced revertants with BaP and U were defined as the inhibition doses (TEX>$ID_{508}{\;}and{\;}ID_{508}$ respectively). Seventeen flavones possessed significant antimutagenic activity against BaP. $ID_{508}$ ranged from 15.1 nmoles (F22) to 1000.6 nmoles (F13). Eighteen f1avones showed significant antimutagenic activity against U. $ID_{50U}$ ranged from 23.5 nmoles (F22) to 354.6 nmoles (F3). The 2',3',4'-trihydroxyflavone (F22, $ID_{508}=15.1$ nmoles, $ID_{50U}=23.5$ nmoles) and the 2',3',4',7-tetrahydroxyflavone (F20, $ID_{508}=37.8$ nmoles; $ID_{50U}=62.3$ nmoles) had antimutagenic activities similar to those of chlorophyllin ($ID_{508}=19.6$ nmoles and $ID_{50U}=44.2$ nmoles) and were evaluated against B(alP 7,8-dihydrodiol-9,10-epoxide. Against this last mutagen, the flavones which included three OH in B ring showed the highest activity and this property seemed independent of the substituent groups on A ring.