Alanko J, Riutta A, Holm P, Mucha I, Vapaatalo H, Metsä-Ketelä T
Department of Internal Medicine, Tampere University Hospital, Finland.
Free Radic Biol Med. 1999 Jan;26(1-2):193-201. doi: 10.1016/s0891-5849(98)00179-8.
The effects of substituted catechols (3-methylcatechol, 4-methylcatechol, 4-nitrocatechol, and guaiacol) and trihydroxybenzenes (pyrogallol, propyl gallate, 1,2,4-trihydroxybenzene, and 1,3,5-trihydroxybenzene) on the synthesis of prostaglandin (PG)E2 and leukotriene (LT)B4 were tested in human A23187-stimulated polymorphonuclear leukocytes. The effects were related to their peroxyl-radical-scavenging (antioxidant), superoxide-scavenging (antioxidant), and superoxide-generating (prooxidant) properties. In general, compounds with hydroxyl groups in the ortho position increased PGE2/LTB4 ratio, and compounds with hydroxyl groups in the meta position decreased PGE2/LTB4 ratio. Catechols, which have hydroxyl groups in the ortho position, were the most potent peroxyl radical and superoxide anion scavengers. Trihydroxybenzenes (pyrogallol, 1,2,4-trihydroxybenzene, and 1,3,5-trihydroxybenzene) generated superoxide, whereas dihydroxybenzenes did not. Thus, the positions and number of hydroxyl groups seem to be the most important properties determining the action of phenolic compounds on PGE2/LTB4 ratio and their antioxidant/prooxidant activities.
在人A23187刺激的多形核白细胞中测试了取代儿茶酚（3-甲基儿茶酚、4-甲基儿茶酚、4-硝基儿茶酚和愈创木酚）和三羟基苯（连苯三酚、没食子酸丙酯、1,2,4-三羟基苯和1,3,5-三羟基苯）对前列腺素（PG）E2和白三烯（LT）B4合成的影响。这些影响与它们的过氧自由基清除（抗氧化）、超氧阴离子清除（抗氧化）和超氧阴离子生成（促氧化）特性有关。一般来说，邻位带有羟基的化合物会增加PGE2/LTB4比值，间位带有羟基的化合物会降低PGE2/LTB4比值。邻位带有羟基的儿茶酚是最有效的过氧自由基和超氧阴离子清除剂。三羟基苯（连苯三酚、1,2,4-三羟基苯和1,3,5-三羟基苯）会生成超氧阴离子，而二羟基苯则不会。因此，羟基的位置和数量似乎是决定酚类化合物对PGE2/LTB4比值的作用及其抗氧化/促氧化活性的最重要特性。
