Phloroglucinols with prooxidant activity from Garcinia subelliptica.
A new phloroglucinol, garcinielliptone HF ( 1), possessing an unprecedented skeleton, and the tautomeric pair of garcinielliptone FC ( 2/ 2a) were isolated from the heartwood and pericarp of Garcinia subelliptica, respectively. Their structures, including relative configurations, were elucidated by means of spectroscopic methods. The ability of compounds 1 and 2/ 2a to induce DNA-cleavage activity was examined using supercoiled plasmid pBR322 DNA. In the presence of Cu(II), compounds 1 and 2/ 2a caused significant breakage of pBR322 DNA. The involvement of H2O2 and O2 (*-), and H2O2, O2 (*-), and OH (*) in 1- and 2/ 2a-mediated scission, respectively, was established by inhibition or no protection of DNA breakage by various oxygen radical scavengers. Thus, in the presence Cu(II), 1 and 2/ 2a may show a prooxidant effect on DNA and induce cell death.
Wu
Chien-Chang
CC
School of Pharmacy, Kaohsiung Medical University, Kaohsiung 807, Taiwan, Republic of China.
Lu
Yi-Huang
YH
Wei
Bai-Luh
BL
Yang
Shyh-Chyun
SC
Won
Shen-Jen
SJ
Lin
Chun-Nan
CN
D001577:Benzophenones / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D016923:Cell Death / Q000187:drug effects; D003300:Copper / Q000494:pharmacology; D004247:DNA / Q000187:drug effects; D016166:Free Radical Scavengers / Q000494:pharmacology; D029760:Garcinia / Q000737:chemistry*; D015394:Molecular Structure; D016877:Oxidants / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D010084:Oxidation-Reduction; D010696:Phloroglucinol / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D010946:Plants, Medicinal / Q000737:chemistry*; D010957:Plasmids / Q000187:drug effects; D013237:Stereoisomerism
D001577:Benzophenones; D016166:Free Radical Scavengers; D016877:Oxidants; C528162:garcinielliptone HF; D003300:Copper; D004247:DNA; D010696:Phloroglucinol