Tikkanen L, Matsushima T, Natori S, Yoshihira K
Mutat Res. 1983 Oct;124(1):25-34. doi: 10.1016/0165-1218(83)90182-9.
The mutagenicities of naturally occurring naphthoquinones and benzoquinones were tested by the pre-incubation method with Salmonella typhimurium strains TA98, TA100 and TA2637, which all contain plasmid pKM101. 6 of the 16 naphthoquinones tested, i.e., plumbagin, naphthazarin, 2-hydroxy-naphthoquinone, vitamin K3 (menadione), juglone and 7-methyljuglone, were mutagenic to strain TA2637 with metabolic activation. Except for juglone and 7-methyl-juglone, these compounds also had slight mutagenic effects on strain TA98 with S9 mix. All the mutagenic naphthoquinones contain one or two hydroxyl and/or methyl substituents. The naphthoquinone mompain, which has four hydroxyl groups, was not mutagenic. Unsubstituted beta-naphthoquinone, naphthoquinones with a prenyl side chain and all bi-naphthoquinone derivatives tested were non-mutagenic. None of the 13 benzoquinones examined was mutagenic to any of the strains used with or without metabolic activation. These results show that natural naphthoquinones are mutagenic when they have only one or two hydroxyl and/or methyl substituents.
采用预孵育法，以均含有质粒pKM101的鼠伤寒沙门氏菌TA98、TA100和TA2637菌株，对天然存在的萘醌和苯醌的致突变性进行了测试。在测试的16种萘醌中，有6种，即紫草素、萘茜、2-羟基萘醌、维生素K3（甲萘醌）、胡桃醌和7-甲基胡桃醌，在代谢活化条件下对TA2637菌株具有致突变性。除胡桃醌和7-甲基胡桃醌外，这些化合物在加入S9混合物的情况下对TA98菌株也有轻微的致突变作用。所有具有致突变性的萘醌都含有一个或两个羟基和/或甲基取代基。具有四个羟基的萘醌莫姆平没有致突变性。未取代的β-萘醌、带有异戊二烯侧链的萘醌以及所测试的所有联萘醌衍生物均无致突变性。在所检测的13种苯醌中，无论有无代谢活化，对所使用的任何菌株均无致突变性。这些结果表明，天然萘醌在仅含有一个或两个羟基和/或甲基取代基时具有致突变性。
