Natural Products Synthesis and Bioorganic Chemistry Laboratory, Institute of Advanced Materials, Physicochemical Processes, Nanotechnology and Microsystems, NCSR "Demokritos" 15310 Ag. Paraskevi, Attiki, POB 60228, Athens, Greece; Chemistry Laboratories, Agricultural University of Athens, 75 Iera Odos Str., 11855 Athens, Greece.
Natural Products Synthesis and Bioorganic Chemistry Laboratory, Institute of Advanced Materials, Physicochemical Processes, Nanotechnology and Microsystems, NCSR "Demokritos" 15310 Ag. Paraskevi, Attiki, POB 60228, Athens, Greece.
Chemosphere. 2014 Apr;100:124-9. doi: 10.1016/j.chemosphere.2013.11.073. Epub 2013 Dec 28.
The larvicidal effect of hyperforin (1), a bioactive compound of Hypericum perforatum, and deoxycohumulone (2) (biosynthetic precursor of hyperforin) were evaluated against Culex pipiens (Diptera: Culicidae) for the first time. All the acetate analogues (3-6) of hyperforin (1) and deoxycohumulone (2) were also synthesized and bioassayed to provide information on structural requirements for the tested compounds. Larvicidal results revealed that hyperforin (1) and deoxycohumulone (2) exhibited potent activity with LC50 value of 26.72 and 51.03 mg L(-1), respectively. The monoacetyl-deoxycohumulone (4) displayed lower activity with LC50 value of 135.92 mg L(-1), while all other acetate analogues were inactive at concentrations even as high as 150 mg L(-1), indicating that the free hydroxyl groups are essential for the larvicidal activity. The mortality values were increased, more than 80%, when 10 mg L(-1) piperonyl butoxide were added in hyperforin (1) or deoxycohumulone (2) bioassays. Finally, sub-lethal survival analysis is conducted for three doses of hyperforin (1) and deoxycohumulone (2) and results are discussed.
首次评估了贯叶金丝桃（Hypericum perforatum）中的生物活性化合物贯叶金丝桃素（1）和脱氧瓜氨酸（2）（贯叶金丝桃素的生物合成前体）对库蚊（双翅目：蚊科）的杀幼虫效果。还合成了贯叶金丝桃素（1）和脱氧瓜氨酸（2）的所有乙酸酯类似物（3-6），并进行了生物测定，以提供有关测试化合物结构要求的信息。杀幼虫结果表明，贯叶金丝桃素（1）和脱氧瓜氨酸（2）表现出很强的活性，LC50 值分别为 26.72 和 51.03 mg L(-1)。单乙酰脱氧瓜氨酸（4）的活性较低，LC50 值为 135.92 mg L(-1)，而其他所有乙酸酯类似物在浓度高达 150 mg L(-1)时均无活性，表明游离羟基对杀幼虫活性至关重要。当在贯叶金丝桃素（1）或脱氧瓜氨酸（2）的生物测定中添加 10 mg L(-1)增效醚时，死亡率增加了 80%以上。最后，对三种剂量的贯叶金丝桃素（1）和脱氧瓜氨酸（2）进行了亚致死生存分析，并对结果进行了讨论。
