Department of Pharmaceutical and Biological Chemistry, The School of Pharmacy, University of London, 29-39 Brunswick Square, London WC1N 1AX, UK.
J Nat Prod. 2012 Mar 23;75(3):336-43. doi: 10.1021/np2003319. Epub 2011 Sep 7.
New antibacterial acylphloroglucinols (1-5) were isolated and characterized from the aerial parts of the plant Hypericum olympicum L. cf. uniflorum. The structures of these compounds were confirmed by extensive 1D- and 2D-NMR experiments to be 4,6-dihydroxy-2-O-(3″,7″-dimethyl-2″,6″-octadienyl)-1-(2'-methylbutanoyl)benzene (1), 4,6-dihydroxy-2-O-(7″-hydroxy-3″,7″-dimethyl-2″,5″-octadienyl)-1-(2'-methylbutanoyl)benzene (2), 4,6-dihydroxy-2-O-(6″-hydroxy-3″,7″-dimethyl-2″,7″-octadienyl)-1-(2'-methylbutanoyl)benzene (3), 4,6-dihydroxy-2-O-(6″-hydroperoxy-3″,7″-dimethyl-2″,7″-octadienyl)-1-(2'-methylbutanoyl)benzene (4), and 4,6-dihydroxy-2-O-(6″,7″-epoxy-3″,7″-dimethyloct-2″-enyl)-1-(2'-methylbutanoyl)benzene (5). These new natural products have been given the trivial names olympicins A-E (1-5). All compounds were evaluated against a panel of methicillin-resistant Staph. aureus and multidrug-resistant strains of Staph. aureus. Compound 1 exhibited minimum inhibitory concentrations (MICs) of 0.5-1 mg/L against the tested Staph. aureus strains. Compounds 2 to 5 were also shown to be active, with MICs ranging from 64 to 128 mg/L. Compound 1 was synthesized using a simple four-step method that can be readily utilized to give a number of structural analogues of 1.
从药用植物贯叶金丝桃（Hypericum olympicum L. cf. uniflorum）的地上部分分离得到了五个新的具有抗菌活性的酰基间苯三酚（1-5）。通过广泛的 1D 和 2D-NMR 实验确定了这些化合物的结构，它们分别为 4,6-二羟基-2-O-(3″,7″-二甲基-2″,6″-辛二烯基)-1-(2'-甲基丁酰基)苯（1）、4,6-二羟基-2-O-(7″-羟基-3″,7″-二甲基-2″,5″-辛二烯基)-1-(2'-甲基丁酰基)苯（2）、4,6-二羟基-2-O-(6″-羟基-3″,7″-二甲基-2″,7″-辛二烯基)-1-(2'-甲基丁酰基)苯（3）、4,6-二羟基-2-O-(6″-过氧基-3″,7″-二甲基-2″,7″-辛二烯基)-1-(2'-甲基丁酰基)苯（4）和 4,6-二羟基-2-O-(6″,7″-环氧-3″,7″-二甲氧基-2″-辛烯基)-1-(2'-甲基丁酰基)苯（5）。这些新的天然产物被赋予了俗名 olympicins A-E（1-5）。所有化合物都针对耐甲氧西林金黄色葡萄球菌和耐多种药物的金黄色葡萄球菌进行了评估。化合物 1 对测试的金黄色葡萄球菌菌株的最低抑菌浓度（MIC）为 0.5-1 mg/L。化合物 2 至 5 也显示出活性，MIC 范围为 64 至 128 mg/L。化合物 1 采用简单的四步合成方法合成，可方便地用于制备 1 的多种结构类似物。
