Trewia nudiflora Maytansinoids

The crystal and molecular structure and the absolute configuration of maytansine (73) were studied using its 3-bromopropyl ether [121] and the cytotoxicity of 73 [122] was reported. Several other maytansinoids, such as colubrinol (74), normaytancyprine (75) [123], 10-epitrewiasine (76), trewiasine (77) and nortrewiasine (78) [124], were isolated from Putterlickia verrucosa and Trewia nudiflora, respectively, and the structure elucidation, and the structural requirements for antileukemic activity of natural and semisynthetic maytansinoids were reported [120, 125]. As described above, maytansine (73) was isolated initially from a higher plant, although it was evident that the content of this compound was extremely low. 

Four maytansinoids, trewiasine (158), treflorine, trenudine, and trenudine diacetate, have been isolated from the seeds of Trewia nudiflora and showed... 

Trewia nudiflora (Powell et al, 1981,1983). Several include an ususual second macrocyclic ring attached to the macrocy-clic ring found in most maytansinoids (Powell et al., 1981, 1982). 

Extracts of Trewia nudiflora (Euphorbiaceae) that contain maytansanoids have been shown to have insect antifeedant activity and produce several other effects in insects that may limit herbivory (Powell et al., 1982, 1983 Reider and Roland, 1984 Smith and Powell, 1984). Several maytansinoids were antifeedant to larvae of Ostrinia nubilalis, the European com borer, whereas others significantly retarded development of the larvae (Madrigal et al., 1985). 

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