Muhammad Ilias, Takamatsu Satoshi, Walker Larry A, Mossa Jaber S, Fong Harry H S, El-Feraly Farouk S
National Center for Natural Products Research, Research Institute of Pharmaceutical Sciences, School of Pharmacy, University of Mississippi, University, MS 38677, USA.
Phytother Res. 2003 Sep;17(8):887-91. doi: 10.1002/ptr.1237.
The natural and semi-synthetic analogs of substituted 1,4-benzoquinones were evaluated for in vitro cytotoxic and antioxidant activities. Maesanin, dihydromaesanin, maesanin dimethyl ether and isomeric mixtures of 3-[(Z)-10'-pentadecenyl]-benzoquinone derivatives exhibited cytotoxic activity against HL-60 cell line (IC50 values 4.5, 2.2, 0.43 and 2.8 microg/mL, respectively), while it was found to be inactive against ROS (Reactive Oxygen Species) generation in HL-60. In contrast, the isomeric acylated benzoquinones with shorter alkyl substituents, namely, 2-acetoxy-5-hydoxy-6-methyl-3-tridecyl-1,4-benzoquinone and 2-hydoxy-5-acetoxy-6-methyl-3-tridecyl-1,4-benzoquinone showed most prominent antioxidant and antiproliferative effect on HL-60 (IC50 values 6.2 and 2.2 microg/mL, respectively), as well as cytotoxicities against SK-MEL, KB, BT-549 and SK-OV-3 carcinomas (IC50 values <1.1-4.2 microg/mL). All benzoquinones were found to be inactive against cell aggregation and cell adhesion assays, thus showing no effect on immune responses and inflammation.
对取代的1,4 - 苯醌的天然和半合成类似物进行了体外细胞毒性和抗氧化活性评估。桑色素、二氢桑色素、桑色素二甲醚以及3 - [(Z)-10'-十五碳烯基]-苯醌衍生物的异构体混合物对HL - 60细胞系表现出细胞毒性活性（IC50值分别为4.5、2.2、0.43和2.8μg/mL），而在HL - 60中对活性氧（ROS）生成无活性。相比之下，具有较短烷基取代基的异构酰化苯醌，即2 - 乙酰氧基 - 5 - 羟基 - 6 - 甲基 - 3 - 十三烷基 - 1,4 - 苯醌和2 - 羟基 - 5 - 乙酰氧基 - 6 - 甲基 - 3 - 十三烷基 - 1,4 - 苯醌对HL - 60表现出最显著的抗氧化和抗增殖作用（IC50值分别为6.2和2.2μg/mL），以及对SK - MEL、KB、BT - 549和SK - OV - 3癌细胞的细胞毒性（IC50值<1.1 - 4.2μg/mL）。所有苯醌在细胞聚集和细胞黏附试验中均无活性，因此对免疫反应和炎症无影响。
