Institute of Organic Chemistry , Technische Universität Braunschweig , Hagenring 30 , 38106 Braunschweig , Germany.
BASF SE , Speyerer Strasse 2 , 67117 Limburgerhof , Germany.
J Nat Prod. 2020 Feb 28;83(2):468-472. doi: 10.1021/acs.jnatprod.9b01013. Epub 2020 Feb 12.
Sigillins are highly chlorinated natural products from the springtail (Collembola) that are used to deter arthropod predators. We report here the isolation and structure elucidation of sigillin F, a hydrogenated benzopyranone compound bearing two trichloromethyl groups, and the synthesis of trideoxysigillin (), a non-natural compound representing the basic scaffold of the sigillins. Sigillins A and F showed insecticidal activity toward various insects, similar to the commercial insecticide imidacloprid, whereas was inactive. The highest mortality was observed for the aphids and , but other insect species were also susceptible. Sigillins act as noncompetitive antagonists of the GABA receptor. This mode of action is identical to that of known insecticides with high chlorine content such as dieldrin or endosulfan. The high content of sigillins in , more than 4 mM in concentration, indicates self-resistance. Strikingly, the Collembola and humans have both arrived at the same target with related types of compounds to combat insects.
Sigillins 是一种高度氯化的天然产物，来自跳虫（弹尾目），用于抵御节肢动物捕食者。我们在这里报告了 sigillin F 的分离和结构阐明，它是一种带有两个三氯甲基的氢化苯并吡喃酮化合物，以及 trideoxysigillin（）的合成，它是非天然化合物，代表了 sigillins 的基本支架。Sigillins A 和 F 对各种昆虫表现出杀虫活性，类似于商业杀虫剂吡虫啉，而 则没有活性。最高的死亡率观察到蚜虫 和 ，但其他昆虫物种也易感。Sigillins 作为 GABA 受体的非竞争性拮抗剂起作用。这种作用模式与具有高氯含量的已知杀虫剂如狄氏剂或硫丹相同。在 中含有高含量的 sigillins，浓度超过 4mM，表明具有自我抗性。引人注目的是，跳虫和人类都以相同的目标为目标，使用相关类型的化合物来对抗昆虫。
