DNA strand-scission by phloroglucinols and lignans from heartwood of Garcinia subelliptica Merr. and Justicia plants

Phloroglucinols, garcinielliptones HA ( 1), HB ( 2), HC ( 3), HD ( 4) and HE ( 5), isolated from the heartwood of Garcinia subelliptica, were identified by extensive analysis of spectroscopic data. In the presence of Cu(II), compound 3 and lignans, isolated from Justicia plants, 8, 10 and 11 caused significant breakage of supercoiled plasmid pBR322. Five 2,4,6-prenylated phloroglucinols, garcinielliptones HA ( 1), HB ( 2), HC ( 3), HD ( 4) and HE ( 5), were isolated from the heartwood of Garcinia subelliptica Merr. Their structures, including relative configurations, were elucidated by means of spectroscopic data analysis. The ability of phloroglucinols, 1– 5 and lignans, tuberculatin ( 8), justicidin A ( 9), procumbenoside A ( 10) and ciliatosides A ( 11) and B ( 12), isolated from Justicia ciliata and Justicia procumbens, to induce DNA-cleavage activity was examined using pBR322, a supercoiled, covalently closed circular DNA, and it was analyzed by agarose gel electrophoresis. In the presence of Cu (II), compounds 3, 8, 10 and 11 caused significant breakage of supercoiled plasmid pBR322. The products were relaxed circles with no detectable linear forms. In the Cu(II)-mediated DNA damage of 3 and selective compound 8, Cu(I) was shown not to be an essential intermediate by using the Cu(I)-specific sequestering reagent neocuproine.