93(P10) CHEMICAL REACTIONS OF ACRONYCINE AND RELATED COMPOUNDS

Funayama Shinji, Noshita Toshiro, Aoyagi Tomoko, Tadauchi Kaori, Pan Tzu-Yun, Nozoe Shigeo, Chai Hee-Byung, Pezzuto John M., Cordell Geoffrey A.

doi:10.24496/tennenyuki.38.0_553

Acronycine (1) is an alkaloid isolated from the bark of the Australian scrub ash Baurella simplicifolia (ENDL.) Hartley (syn. Acronychia baueri SCOTT) (Rutaceae). When 1 was treated with hot methanolic HCl, two dimers (3,4), a trimer(6), two tetramers (7, 9) and two pentamers (8, 10) of noracronycine (2) were obtained.Two of these seven compounds (4, 9) possessed a rearranged partial structure. The dimeric compound (3) was obtained selectively in 41% yield when 2 was treated with conc. H_2SO_4-MeOH (1:1) at r.t. On the other hand, when norisoacronycine (5) was treated with hot methanolic HCl, a dimeric compound (17) was obtained. The structure of this compound was elucidated by comparison of the ^1H and ^<13>C NMR spectra of this compound with those of 3 and 4. By treatment of dihydronoracronycine (11) with conc. H_2SO_4 at r.t., dihydronorisoacronycine (12) and dihydronoralloacronycine (14) were obtained together with 1,3-dihydroxy-10-methylacridone (13) and 15. It was reported that noracronycine (2) was obtained in quantitative yield when the HCl salt of acronycine was heated at 140℃. On the other hand, when it was heated at 250℃, various acridone derivatives were obtained and one of the main products was dihydronorisoacronycine (12). In this reaction, four novel acridone derivatives 20-23 were obtained. Cytotoxic activities of 16 acridone derivatives obtained through these experiments were evaluated and it was found that 1,3-dihydroxy-10-methylacridone (13) and 1,3-dihydroxy-2,10-dimethylacridone (20) showed activity against VLB resistant KB cells (KB-VI).

93(P10) CHEMICAL REACTIONS OF ACRONYCINE AND RELATED COMPOUNDS

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