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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.