Department of Medicinal Chemistry and Pharmacognosy and Program for Collaborative Research in the Pharmaceutical Sciences College of Pharmacy, University of Illinois at Chicago, 833 S. Wood Street, 60612, Chicago, Illinois.
J Chem Ecol. 1985 Feb;11(2):191-206. doi: 10.1007/BF00988202.
Twenty esters, representing the biogenetically related tigliane, daphnane, ingenane, and lathyrane series of diterpenes, were screened for growth-inhibitory and insecticidal effects on newly hatched larvae of the North American cotton pest,Pectinophora gossypiella (pink bollworm). Among the tigliane derivatives tested, only 12-O-tetradecanoylphorbol-13-acetate and 12-O-(2-methyl)butyrylphorbol-13-decanoate, of seven phorbol diesters isolated from croton oil by a new procedure involving droplet countercurrent chromatography, were active againstP.gossypiella as both growth inhibitors and insecticides. The effects of the former compound were not significantly diminished by acetylation of its C-20 primary hydroxy group. Three other croton oil phorbol diester constituents, as well as daphnetoxin and daphnetoxin-5,20-diacetate, exhibited activity as growth inhibitors, but not as insecticidal agents, at the doses used. None of the ingenane or lathyrane derivatives investigated was active in either respect. 12-0-Tetradecanoylphorbol-13-acetate was found to cause 100% mortality on second-stadium larvae ofCulex pipiens at 0.6 ppm, but exhibited less significant effects onOncopeltus fasciatus (second-stadium nymphs) andTribolium confusion (adults) when applied at higher doses.
二十种酯类化合物,代表了生物相关的贝壳杉烷、贝壳杉烷、依兰烷和拉坦烷二萜系列,被筛选出对北美棉花害虫 Pectinophora gossypiella(粉斑螟)刚孵化的幼虫具有生长抑制和杀虫作用。在所测试的贝壳杉烷衍生物中,只有 12-O-十四烷酰佛波醇-13-乙酸酯和 12-O-(2-甲基)丁酰佛波醇-13-癸酸酯,这两种是通过涉及液滴逆流色谱的新程序从巴豆油中分离出的七种佛波酯二酯,对 P.gossypiella 具有生长抑制和杀虫剂的双重活性。该化合物的 C-20 伯羟基乙酰化后,其作用并没有明显减弱。巴豆油中的另外三种佛波酯二酯成分,以及瑞香毒素和瑞香毒素-5,20-二乙酸酯,在使用的剂量下作为生长抑制剂表现出活性,但不是杀虫剂。所研究的依兰烷和拉坦烷衍生物均无活性。12-O-十四烷酰佛波醇-13-乙酸酯在 0.6ppm 时可使 Culex pipiens 的第二代幼虫 100%死亡,但在更高剂量下对 Oncopeltus fasciatus(第二代若虫)和 Tribolium confusion(成虫)的影响较小。