Crockett Sara L, Wenzig Eva-Maria, Kunert Olaf, Bauer Rudolf
Institute for Pharmaceutical Sciences, Department of Pharmacognosy, Karl-Franzens-University-Graz, 8010 Graz, Austria.
Phytochem Lett. 2008 Apr 15;1(1):37-43. doi: 10.1016/j.phytol.2007.12.003.
Phytochemical investigation of Hypericum empetrifolium Willd. (Clusiaceae), a species native to Greece and Turkey has led to the bioassay-guided identification of two acylphloroglucinol derivatives with potent in vitro anti-inflammatory activity. Using NMR spectroscopy and mass spectrometry, the acylphloroglucinol derivatives were characterized as 3-geranyl-1-(2'-methylpropanoyl)phloroglucinol (1) and 3-geranyl-1-(2'-methylbutanoyl)phloroglucinol (2). Hypotheses are proposed regarding the biosynthetic origin of these and similar acylphloroglucinols from related Hypericum species. Compounds 1 and 2 were evaluated for in vitro inhibitory activity against COX-1, COX-2 and 5-LOX catalyzed LTB(4) formation. Compound 1 displayed good activity (IC(50) values: 6.0, 29.9, and 2.2 μM, respectively) in all three assays. Compound 2 showed good activity (IC(50) value: 5.8 μM) against LTB(4) formation and moderate activity (IC(50) value: 26.2 μM) against COX-1.
对原产于希腊和土耳其的金丝桃属植物（藤黄科）进行植物化学研究，通过生物测定导向法鉴定出两种具有强大体外抗炎活性的酰基间苯三酚衍生物。利用核磁共振光谱和质谱分析，将这两种酰基间苯三酚衍生物分别鉴定为3-香叶基-1-(2'-甲基丙酰基)间苯三酚（1）和3-香叶基-1-(2'-甲基丁酰基)间苯三酚（2）。针对这些以及相关金丝桃属植物中类似酰基间苯三酚的生物合成起源提出了假设。对化合物1和2进行了体外抑制COX-1、COX-2以及5-LOX催化LTB(4)生成的活性评估。化合物1在所有三项测定中均表现出良好活性（IC(50)值分别为：6.0、29.9和2.2 μM）。化合物2对LTB(4)生成表现出良好活性（IC(50)值：5.8 μM），对COX-1表现出中等活性（IC(50)值：26.2 μM）。
