title: Acute larvicidal activity against mosquitoes and oxygen consumption inhibitory activity of dihydroguaiaretic acid derivatives.
abstract: (-)-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.
authors: Faculty of Agriculture, Ehime University , 3-5-7 Tarumi, Matsuyama, Ehime 790-8566, Japan.
authors: Hisashi
authors: H
authors: Nishiwaki
authors: Yoshimi
authors: Y
authors: Tabara
authors: Taro
authors: T
authors: Kishida
authors: Kosuke
authors: K
authors: Nishi
authors: Yoshihiro
authors: Y
authors: Shuto
authors: Takuya
authors: T
authors: Sugahara
authors: Satoshi
authors: S
authors: Yamauchi
mesh_terms: D000818:Animals; D003465:Culex / Q000187:drug effects* / Q000254:growth & development / Q000378:metabolism; D006139:Guaiacol / Q000031:analogs & derivatives* / Q000737:chemistry / Q000633:toxicity; D007306:Insecticides / Q000737:chemistry / Q000633:toxicity*; D007814:Larva / Q000187:drug effects / Q000254:growth & development / Q000378:metabolism*; D017705:Lignans / Q000737:chemistry / Q000633:toxicity*; D015394:Molecular Structure; D010100:Oxygen / Q000378:metabolism*
chemical_list: D007306:Insecticides; D017705:Lignans; C015816:dihydroguaiaretic acid; D006139:Guaiacol; D010100:Oxygen
keywords: Culex pipiens; acute toxicity; dihydroguaiaretic acid; larvicides; lignans