Socolsky Cecilia, Borkosky Susana, Bardón Alicia
INQUINOA - CONICET, Ayacucho 471, San Miguel de Tucumán, Tucumán 4000, Argentina.
Nat Prod Commun. 2011 Mar;6(3):387-91.
The molluscicidal activity of 12 phloroglucinol derivatives previously isolated from Elaphoglossum piloselloides, E. gayanum, E. yungense, and E. lindbergii, as well as 3 known acylphloroglucinols, now reported from an Argentine collection of Dryopteris wallichiana, was evaluated against the schistosomiasis vector snail Biomphalaria peregrina. Molluscicidal effects were analyzed and compared with those previously observed for 4 acylphloroglucinols from E. piloselloides and their corresponding peracetylated derivatives, in order to draw structure-activity relationships. The most active compounds were the prenylated desaspidins elaphogayanin B and elaphopilosins A and B (LD50 = 1.90, 2.90, and 0.94 ppm, respectively), together with the only evaluated prenylated para-aspidin, elaphopilosin C (LD50 = 2.15 ppm). Quantitative structure-activity relationships (QSAR) were studied by means of a semiempirical method (PM3) for the 24 natural phloroglucinol derivatives included in this paper. The descriptor molecular volume was found to have good correlation with the observed molluscicidal activity (r2 = 0.77). The derived equation can be considered useful to predict the molluscicidal activity of bi and tricyclic acylphloroglucinols. The QSAR analysis showed that there is an optimum volume for high activity, probably related to the size of a receptor's active site. Bigger molecules display lower activity.
此前从毛叶舌蕨、盖氏舌蕨、永德舌蕨和林氏舌蕨中分离得到的12种间苯三酚衍生物，以及从阿根廷采集的瓦氏鳞毛蕨中发现的3种已知的酰基间苯三酚，对血吸虫病传播媒介福寿螺的杀螺活性进行了评估。分析了杀螺效果，并与之前观察到的来自毛叶舌蕨的4种酰基间苯三酚及其相应的全乙酰化衍生物的杀螺效果进行比较，以得出构效关系。活性最高的化合物是异戊烯基去阿斯皮定类的盖氏舌蕨宁B、毛叶舌蕨素A和B（LD50分别为1.90、2.90和0.94 ppm），以及唯一评估的异戊烯基对阿斯皮定类的毛叶舌蕨素C（LD50 = 2.15 ppm）。采用半经验方法（PM3）对本文中包含的24种天然间苯三酚衍生物进行了定量构效关系（QSAR）研究。发现描述符分子体积与观察到的杀螺活性具有良好的相关性（r2 = 0.77）。推导的方程可被认为有助于预测双环和三环酰基间苯三酚的杀螺活性。QSAR分析表明，存在一个高活性的最佳体积，这可能与受体活性位点的大小有关。分子越大，活性越低。
