Chobot V, Hadacek F
Department of Chemical Ecology and Ecosystem Research, Faculty of Life Sciences, University of Vienna, 1090 Vienna, Austria.
J Chem Ecol. 2009 Mar;35(3):383-90. doi: 10.1007/s10886-009-9609-5. Epub 2009 Mar 5.
Juglone, 5-hydroxy-1,4-naphthoquinone, is known for its wide range of biological activities. It has been suggested that juglone's excellent redox cycling properties contribute to this reputation. Many biological activities are nonlinear with low concentrations exerting stimulating effects, whereas only higher concentrations cause inhibition. Here, we corroborate studies on the nematode Caenorhabditis elegans that point out hormetic effects by showing that juglone may cause a nonlinear effect on postgerminative shoot and root growth of Sinapis alba. This effect was only significantly visible, however, when seedlings were stressed with methanol. Classic and modified versions of the deoxyribose assay were applied successfully to characterize antioxidative (purposeful generation of hydroxyl radicals) and prooxidative (no purposeful generation of hydroxyl radicals) activities. Variants of the assay with and without the addition of the iron chelator EDTA showed that the antioxidant activity is independent on chelation of iron ions by juglone; by contrast, the strength of the prooxidative activity depended on the chelation of iron ions by juglone. The hormetic effects of lower concentrations on germination of Sinapis alba, thus, may be caused by the antioxidant activities of this compound, which are especially effective when the test organism is subjected to higher oxidative challenge. The present study suggests that pronounced prooxidative activities, which are considerably accelerated by chelation of iron ions, may contribute to the toxic effects of juglone at higher concentrations.
胡桃醌,即5-羟基-1,4-萘醌,以其广泛的生物活性而闻名。有人认为,胡桃醌出色的氧化还原循环特性促成了这一声誉。许多生物活性呈非线性,低浓度时发挥刺激作用,而只有高浓度时才会产生抑制作用。在此,我们通过证明胡桃醌可能对白芥发芽后的地上部和根部生长产生非线性影响,证实了对线虫秀丽隐杆线虫的研究中指出的 hormetic 效应。然而,只有当幼苗用甲醇处理时,这种效应才会明显显现。成功应用经典和改良版的脱氧核糖测定法来表征抗氧化(有意产生羟基自由基)和促氧化(无意产生羟基自由基)活性。添加和不添加铁螯合剂乙二胺四乙酸(EDTA)的测定法变体表明,抗氧化活性与胡桃醌对铁离子的螯合作用无关;相比之下,促氧化活性的强度取决于胡桃醌对铁离子的螯合作用。因此,较低浓度对白芥发芽的 hormetic 效应可能是由该化合物的抗氧化活性引起的,当受试生物受到更高的氧化挑战时,这种抗氧化活性尤其有效。本研究表明,明显的促氧化活性,因铁离子螯合而显著加速,可能导致胡桃醌在高浓度时产生毒性作用。