Proksa B, Uhrín D, Adamacová J, Múcková M, Fuska J
Department of Biochemical Technology, Faculty of Chemistry, Technical University, Modra, Slovakia.
Pharmazie. 1993 Oct;48(10):738-40.
Hydrogenation of the macrodiolide antibiotic vermiculin (1) over Adams catalyst afforded [8S, 16S]-8,16-bis(2'-oxopropyl)-1,9- dioxyacyclohexadeca-2,5,10,13-tetrone (2), [8S, 16S]-8,16-bis(2'-oxopropyl)-13-hydroxy-1,9-dioxacyclohexadeca- 2,5,10-trione (3), [8S,16S]-8,16-bis(2' oxopropyl)-1,9- dioxacyclohexadeca-2,5,10-trione (4) together with [7S]-4,9-dioxo-7-(4',9'-dioxodecanoyloxy)decanoic acid (5). Hydrogenation of diolide 1 over Pd/C gave tetrahydrovermiculin (2) only. The prepared compounds showed lower antibacterial and cytotoxic activities than vermiculin (1).
在亚当斯催化剂作用下，大环双内酯抗生素vermiculin（1）进行氢化反应，得到了[8S, 16S]-8,16-双(2'-氧代丙基)-1,9-二氧杂环十六烷-2,5,10,13-四酮（2）、[8S, 16S]-8,16-双(2'-氧代丙基)-13-羟基-1,9-二氧杂环十六烷-2,5,10-三酮（3）、[8S,16S]-8,16-双(2'-氧代丙基)-1,9-二氧杂环十六烷-2,5,10-三酮（4）以及[7S]-4,9-二氧代-7-(4',9'-二氧代癸酰氧基)癸酸（5）。在Pd/C作用下，双内酯1进行氢化反应仅得到四氢vermiculin（2）。所制备的化合物显示出比vermiculin（1）更低的抗菌和细胞毒性活性。
