27856-66-2Relevant articles and documents
Alkaloids from Alangium javanicum and Alangium grisolleoides that mediate Cu2+-dependent DNA strand scission
Pham, Van Cuong,Ma, Ji,Thomas, Shannon J.,Xu, Zhidong,Hecht, Sidney M.
, p. 1147 - 1152 (2005)
Crude CH2Cl2-MeOH extracts prepared from Alangium javanicum and A. grisolleoides were found to induce DNA strand breakage in the presence of Cu2+ and were subjected to bioassay-guided fractionation to permit identification of the active principle(s). Javaniside (1), a novel alkaloid possessing an unusual monoterpenoid oxindole skeleton, was identified as an active principle contributing to the DNA cleavage activity observed for the crude extract of A. javanicum. Alangiside (2), a tetrahydroisoquinoline monoterpene glucoside widely distributed in the genus Alangium, was also isolated from A. grisolleoides as a new type of Cu2+-dependent DNA cleavage agent. The relative configuration of the asymmetric centers in javaniside was established by analysis of 1H-1H coupling constants and NOESY correlations. Semisynthesis of javaniside from secologanin (3) established the absolute stereochemistry of javaniside.
Souzu,Mitsuhashi
, p. 191 (1970)
Guarnaccia et al.
, p. 7079,7080, 7082 (1974)
Total Syntheses of (?)-Secologanin, (?)-5-Carboxystrictosidine, and (?)-Rubenine
Rakumitsu, Kenta,Sakamoto, Jukiya,Ishikawa, Hayato
supporting information, p. 8996 - 9000 (2019/06/25)
The first enantioselective total syntheses of (?)-secologanin (1), (?)-5-carboxystrictosidine (2), and (?)-rubenine (3) were accomplished in 10, 9, and 14 steps, respectively. The key transformation in the synthesis of 1 was a sequential anti-selective or
