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Acute Larvicidal Activity against Mosquitoes and Oxygen Consumption Inhibitory Activity of Dihydroguaiaretic Acid Derivatives

Nishiwaki, Hisashi, Tabara, Yoshimi, Kishida, Taro, Nishi, Kosuke, Shuto, Yoshihiro, Sugahara, Takuya, Yamauchi, Satoshi
Journal of agricultural and food chemistry 2015 v.63 no.9 pp. 2442-2448
Culex pipiens, insect larvae, larvicides, lethal concentration 50, mitochondria, oxygen, oxygen consumption, toxicity
(−)-Dihydroguaiaretic acid (DGA) and its derivatives having 3-hydroxyphenyl (3-OH-DGA) and variously substituted phenyl groups instead of 3-hydroxy-4-methoxyphenyl groups were synthesized to measure their larvicidal activity against the mosquito Culex pipiens Linnaeus, 1758 (Diptera: Culicidae). Compared with DGA and 3-OH-DGA (LC50 (M), 3.52 × 10(–5) and 4.57 × 10(–5), respectively), (8R,8′R)-lignan-3-ol (3) and its 3-Me (10), 2-OH (12), 3-OH (13), and 2-OMe (15) derivatives showed low potency (ca. 6–8 × 10(–5) M). The 4-Me derivative (11) showed the lowest potency (12.1 × 10(–5) M), and the 2-F derivative (4) showed the highest (2.01 × 10(–5) M). All of the synthesized compounds induced an acute toxic symptom against mosquito larvae, with potency varying with the type and position of the substituents. The 4-F derivative (6), which killed larvae almost completely within 45 min, suppressed the O2 consumption of the mitochondrial fraction, demonstrating that this compound inhibited mitochondrial O2 consumption contributing to a respiratory inhibitory activity.