二氢沉香呋喃醚类衍生物的合成及其杀虫活性

Synthesis and Insecticidal Activity of the Dihydroagarofuran Ether Analogues

摘要: 以苦皮藤Celastrus angulatus Max.提取物水解产物中的1β,2β,4α, 6α,8β,9α,13-七羟基-β-二氢沉香呋喃为起始原料,先经过甲基磺酸酯保护后再用氢化铝锂还原,得到一结构新颖的双呋喃二氢沉香呋喃倍半萜(化合物 S ),并以此为原料设计合成了7个未见文献报道的双呋喃二氢沉香呋喃醚类衍生物 (a~g ),其结构经核磁共振谱、红外光谱、高分辨质谱等方法确证。初步的杀虫活性测定结果表明:目标化合物对3龄粘虫Mythimna separate幼虫具有一定的杀虫活性,其中二烯丙基醚和三丁基醚衍生物(化合物 d和f )在10 mg/mL的浓度下该幼虫的死亡率分别为86.2% 和 82.7%。

Abstract: In order to find new active compounds,the structure of 1β,2β,4α,6α,8β,9α,13-hepthydroxy-β-dihydroagarofuran was simplified to be 1β,4α,6α,9α-tetrahydroxy-2β,12-ether-β-dihydroagarofuran,and seven new dihydroagarofuran ether analogues were synthesized using 1β,4α,6α,9α-tetrahydroxy-2β,12-ether-β-dihydroagarofuran as staring materials. Their structures were confirmed by NMR,IR and HRMS spectral data. Bioassay results indicated that diallyl ether and tributyl ether analogues exhibited higher insecticidal activity than Celangulin V against 3rd-instar larvae of Mythimna separata at the concentration of 10 mg/mL.