DNA strand-scission by phloroglucinols and lignans from heartwood of Garcinia subelliptica Merr. and Justicia plants.
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.
School of Pharmacy, Kaohsiung Medical University, Kaohsiung 807, Taiwan.
Yi-Huang
YH
Lu
Bai-Luh
BL
Wei
Horng-Huey
HH
Ko
Chun-Nan
CN
Lin
D027901:Acanthaceae / Q000737:chemistry*; D003300:Copper / Q000737:chemistry; D053837:DNA Cleavage / Q000187:drug effects*; D004249:DNA Damage / Q000187:drug effects; D004270:DNA, Circular / Q000187:drug effects / Q000378:metabolism; D004278:DNA, Superhelical / Q000187:drug effects / Q000378:metabolism; D004587:Electrophoresis, Agar Gel; D029760:Garcinia / Q000737:chemistry*; D017705:Lignans / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D009682:Magnetic Resonance Spectroscopy; D010618:Phenanthrolines / Q000494:pharmacology; D010696:Phloroglucinol / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D017382:Reactive Oxygen Species / Q000378:metabolism; D013055:Spectrophotometry, Infrared; D014934:Wood / Q000737:chemistry*
D004270:DNA, Circular; D004278:DNA, Superhelical; D017705:Lignans; D010618:Phenanthrolines; D017382:Reactive Oxygen Species; D003300:Copper; C002701:neocuproine; D010696:Phloroglucinol